
[Medieval Latin, fine metallic powder, especially of antimony, from Arabic al-kuḥl : al-, the + kuḥl, powder of antimony.]
WORD HISTORY The al- in alcohol may alert some readers to the fact that this is a word of Arabic descent, as is the case with algebra and alkali, al- being the Arabic definite article corresponding to the in English. The origin of -cohol is less obvious, however. Its Arabic ancestor was kuḥl, a fine powder most often made from antimony and used by women to darken their eyelids; in fact, kuḥl has given us the word kohl for such a preparation. Arabic chemists came to use al-kuḥl to mean "any fine powder produced in a number of ways, including the process of heating a substance to a gaseous state and then recooling it." The English word alcohol, derived through Medieval Latin from Arabic, is first recorded in 1543 in this sense. Arabic chemists also used al-kuḥl to refer to other substances such as essences that were obtained by distillation, a sense first found for English alcohol in 1672. One of these distilled essences, known as "alcohol of wine," is the constituent of fermented liquors that causes intoxication. This essence took over the term alcohol for itself, whence it has come to refer to the liquor that contains this essence as well as to a class of chemical compounds such as methanol.
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A member of a class of organic compounds composed of carbon, hydrogen, and oxygen. They can be considered as hydroxyl derivatives of hydrocarbons produced by the replacement of one or more hydrogens by one or more hydroxyl (SOH) groups.
Classification
Alcohols may be mono-, di-, tri-, or polyhydric, depending upon the number of hydroxyl groups they possess. They are classified as primary (RCH2OH), secondary (R2CHOH), or tertiary (R3COH), depending on the number of hydrogen atoms attached to the carbon atom bearing the hydroxyl group. Alcohols can also be characterized by the molecular configuration of the hydrocarbon portion (aliphatic, cyclic, heterocyclic, or unsaturated). There are two systems in use for alcohol nomenclature, the common naming system and the IUPAC (International Union of Pure and Applied Chemistry) naming system. The common name is sometimes associated with the natural source of the alcohol or with the hydrocarbon portion (for example, methyl alcohol, ethyl alcohol). The IUPAC method is a systematic procedure with agreed-upon rules. The name of the alcohol is derived from the parent hydrocarbon which corresponds to the longest carbon chain in the alcohol. The final “e” in the hydrocarbon name is dropped and replaced with “ol”; and a number before the name indicates the position of the hydroxyl. Examples of these two systems are given in the table.
Name | ||
|---|---|---|
Common | IUPAC | Formula |
Methyl alcohol | Methanol | CH3OH |
Ethyl alcohol | Ethanol | CH3CH2OH |
n-Propyl alcohol | 1-Propanol | CH3CH2CH2OH |
Isopropyl alcohol | 2-Propanol | (CH3)2CHO |
n-Butyl alcohol | 1-Butanol | CH3(CH2)2CH2OH |
sec-Butyl alcohol | 2-Butanol | CH3CH2CHOHCH3 |
tert-Butyl alcohol | 2-Methyl-2-propanol | (CH3)3COH |
Isobutyl alcohol | 2-Methyl-1-propanol | (CH3)2CHCH2OH |
n-Amyl alcohol | 1-Pentanol | CH3(CH2)3CH2OH |
n-Hexyl alcohol | 1-Hexanol | CH3(CH2)4CH2OH |
Allyl alcohol | 2-Propen-1-ol | CH2&dbnd;CHCH2OH |
Crotyl alcohol | 2-Buten-1-ol | CH3CH&dbnd;CHCH2OH |
Ethylene glycol | 1,2-Ethanediol | HOCH2CH2OH |
Propylene glycol | 1,2-Propanediol | CH3CHOHCH2OH |
Trimethylene glycol | 1,3-Propanediol | HOCH2CH3CH2OH |
Glycerol | 1,2,3-Propanetriol | CH2OHCHOHCH2OH |
Oxidation of primary alcohols produces aldehydes (RCHO) and carboxylic acids (RCO2H); oxidation of secondary alcohols yields ketones (RCOR′). Dehydration of alcohols produces alkenes and ethers (ROR). Reaction of alcohols with carboxylic acids results in the formation of esters (ROCOR′), a reaction of great industrial importance. The hydroxyl group of an alcohol is readily replaced by halogens or pseudohalogens. See also Aldehyde; Alkene; Carboxylic acid; Ester; Ether; Ketone.
Uses
Industrially, the monohydric aliphatic alcohols are classified according to their uses as the lower alcohols (1–5 carbon atoms), the plasticizer-range alcohols (6–11 carbon atoms), and the detergent-range alcohols (12 or more carbon atoms). The lower alcohols are employed as solvents, extractants, and antifreezes. Esters of the lower alcohols are employed extensively as solvents for lacquers, paints, varnishes, inks, and adhesives. The plasticizer-range alcohols find their primary use in the form of esters as plasticizers and also as lubricants in high-speed applications such as jet engines. The detergent-range alcohols are used in the form of sulfate and ethoxysulfate esters in detergents and surfactants.
Alcohols are derived either from natural-product processing, such as the fermentation of carbohydrates and the reductive cleavage of natural fats and oils, or by chemical synthesis based on the hydrocarbons derived from petroleum or the synthesis gas from coal.
The fermentation of sugars and starches (carbohydrates) to produce alcoholic beverages has been employed at least since history has been recorded. The industrial fermentation process is the biological transformation of a carbohydrate by a highly specialized strain of yeast to produce the desired product, such as ethanol, or 1-butanol and acetone. Fermentation is no longer the major source of 1-butanol, but still accounts for all potable ethanol and a large proportion of the ethanol used industrially worldwide. As sources of hydrocarbons based on petroleum continue to be depleted, fermentation processes based on renewable raw materials are likely to become more important.
Chemically alcohols are compounds with the general formula CnH (2n+1)OH. The alcohol in alcoholic beverages is ethyl alcohol (ethanol, C2H5OH); pure ethyl alcohol is also known as absolute alcohol. The energy yield of alcohol is 7 kcal (29 kJ)/gram.
The strength of alcoholic beverages is most often shown as the percentage of alcohol by volume (sometimes shown as % v/v or % ABV). This is not the same as the percentage of alcohol by weight (% w/v) since alcohol is less dense than water: 5% v/v alcohol = 3.96% by weight (w/v); 10% v/v = 7.93% w/v and 40% v/v = 31.7% w/v. See also proof spirit.
Alcohol (or more precisely ethanol) is a colourless, tasteless, flammable liquid, formed during the fermentation of yeasts. In medicine, it is used as a tincture and antiseptic but its greatest use is in drinks. It is quickly absorbed into the bloodstream from the mouth cavity and stomach. After absorption, it acts as a depressant on the central nervous system. This may have the beneficial effect of reducing feelings of fatigue but it also reduces judgement, self-control, and concentration. Reactions are slowed by alcohol and muscular coordination is impaired. Alcohol also acts as a diuretic, stimulating the kidneys to eliminate more urine which can result in dehydration.
Alcohol can lessen hand tremor and improve performance in ‘aiming’ sports such as archery, fencing, and shooting, but because of its potentially harmful effects, its use is restricted by some sports federations.
Alcohol and its after-effects decrease aerobic fitness. Tests of rugby players showed that those suffering from a hangover 16 hours after drinking alcohol performed on average almost 12 per cent worse than when they had no hangover.
Alcohol is no great friend to the athlete, nor is it to those on a weight-loss diet. Each gram of pure alcohol provides 7 Calories (7000 calories) of energy. In addition, alcoholic beverages often contain sugar and other nutrients, increasing their calorific value. A single measure of spirits contains about 50 Calories, and one pint of lager contains about 170 Calories. Drinking too much alcohol can lead to obesity because some is converted to fat. Despite its relatively high energy content, alcohol is a poor energy source compared with carbohydrate because it cannot be used directly by muscles, and because of its adverse effects. Before it can be used by heart muscle and skeletal muscle, alcohol has to be broken down in the liver to acetate or acetaldehydes. The breakdown is relatively slow which is why alcohol can remain in the bloodstream for several hours. Alcohol can also inhibit the conversion of glycogen to glucose in the liver. If it is ingested during prolonged exercise it can increase the likelihood of hypoglycaemia (abnormally low blood sugar).
Moderate drinking has not been linked to any significant health problems. On the contrary, several studies have shown that it can be beneficial and may reduce the risk of coronary heart disease by preventing platelets in the blood from sticking together. However, chronic, heavy drinking is a significant health risk: it can shrink the brain; it irritates the stomach and small intestine, resulting in malabsorption and deficiencies of vitamins and minerals; it can damage the liver and cause cirrhosis; and it can adversely affect the cardiovascular system, increasing the risk of heart attacks. Heavy drinking is not compatible with a healthy, active lifestyle.
As a general rule the following alcoholic drinks contain roughly the same amount of ethyl alcohol (about 8 grams):
• a single measure of whisky or other spirit (about 25 ml)
• a glass of wine (125 ml)
• a small glass of sherry or other fortified wine (about 80 ml)
• half a pint of cider, lager or beer (figure 4).

number of units = % alcohol/1000 × volume in mlFor example, a bottle of claret with 12 per cent alcohol has 9 units (12/1000 × 750). Assuming six glasses to the bottle, each glass will contain 1.5 units.
1. The only alcohol suitable for drinking is ethyl alcohol, a liquid produced by distilling (see distillation) the fermented juice of fruits or grains. Pure ethyl alcohol is clear, flammable and caustic. Water is therefore added to reduce its potency. In the United States, the average amount of alcohol in distilled spirits is about 40 percent (80 proof). Pure alcohol boils at 173°F, water at 212°F. A mixture of the two will boil somewhere between these two temperatures. When cooking with alcohol, remember that the old saw claiming that it "completely evaporates when heated" has been proven invalid by a USDA study. In truth, cooked food can retain from 5 to 85 percent of the original alcohol, depending on various factors such as how and at what temperature the food was heated, the cooking time and the alcohol source. Even the smallest trace of alcohol may be a problem for alcoholics and those with alcohol-related illnesses. Because alcohol freezes at a much lower temperature than water, the amount of alcohol used in a frozen dessert (such as ice cream) must be carefully regulated or the dessert won't freeze. Calorie-wise, a one-and-a-half-ounce jigger of 80-proof liquor (such as Scotch or vodka) equals almost 100 calories, a four-ounce glass of dry wine costs in the area of 85 to 90 calories and a twelve-ounce regular (not light) beer contributes about 150 calories. 2. A general term for any alcoholic liquor.
Chemical formula:

Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
The Cavalier poet Richard Lovelace testifies to the connection between military life and alcohol.
Let others glory follow
In their false riches wallow
And in their grief be merry,
Leave me but love and sherry.
— Richard Holmes
Any of a large group of organic compounds derived from hydrocarbons in which a hydrogen atom has been replaced by a hydroxyl (-OH) group. The alcohol commonly used in drinks is ethyl alcohol or ethanol (C2H5OH), a colourless, tasteless liquid, formed during the fermentation of yeast. In medicine, alcohol is used as a solvent and an antiseptic. As a drink, it is rapidly absorbed into the bloodstream from the buccal cavity and stomach. After absorption, alcohol acts as a depressant of the central nervous system, reducing feelings of fatigue, but also adversely affecting judgement, self-control, and concentration. Reactions are slowed and muscular coordination impaired. Alcohol is broken down in the liver to acetate, a potential source of fuel for cardiac and skeletal muscle, which has an energy value of about 7 kcal g−1. Alcohol interacts harmfully with some drugs, including antihistamines and many analgesics. A moderate intake of alcohol may reduce the risk of coronary heart disease, but excessive chronic use may result in cirrhosis of the liver, and damage to the kidneys and heart. In sport, alcohol has been used as a mild tranquillizer by archers and as an energy source for cyclists. However, it interferes with the release of antidiuretic hormone, causing the body to excrete more urine and increasing the risk of dehydration when exercising in hot environments. In cold environments, alcohol may increase the risk of hypothermia by causing blood vessels in the skin to dilate. It is generally accepted that heavy drinking is not compatible with serious sport participation. Alcohol (ethanol) is on the World Anti-Doping Agency's 2005 Prohibited List. It is considered prohibited when in-competition blood levels exceed the doping violation threshold of the relevant sports Federation. The following lists the doping threshold for each Federation aeronautic, FAI (0.20 g l−1); archery, FITA (0.10 g l−1), automobile, FIA (0.10 g l−1) billiards, WCBS (0.20 g l−1); boules, CMSB (0.20 g l−1); karate, WKF (0.10 g l−1); modern pentathlon, UIPM (0.10 g l−1) for disciplines involving shooting; motorcycling, FIM (0.00 g l−1); skiing, FLS (0.10 g l−1). Alcohol is classified in the Prohibited List as a ‘specified substance'. Specified substances are so generally available that it is easy for an athlete to unintentionally violate anti-doping rules. Doping violations involving a specified substance, such as a alcohol, may result in a reduced sanction if the athlete can establish that its use was not intended to enhance sport performance. Use of alcohol is banned at some sports venues (such as Scottish soccer grounds) because of its association with crowd violence.
The word "alcohol" is derived from the Arabic word al kuhul, meaning 'essence'. The favorite mood-altering drug in the United States, as in almost every human society, continues to be alcohol. One of the reasons for the significant use of alcohol and its health impact is its feature of being (along with nicotine) a legally available drug of abuse and dependence.
Our knowledge of alcohol rests on a heritage of myth and speculation. Many health benefits have been attributed to alcohol by ancient healers who saw ethanol as the elixir of life, but almost none of its positive benefits have stood the test of time. Alcoholic beverages have been revered, more than any other substance, as mystical and medicinal agents. In recent years, however, we have stripped away much of the mystery surrounding alcohol and now recognize it as a drug with distinct pharmacological effects. However, one of the reasons that beverages containing alcohol continue to be consumed is related to the folklore and history that surround its many combinations with other flavors and its many sources of fermentation and distillation.
Chemist's View
Today one thinks of alcohol and alcoholic spirits as being synonymous, yet to a chemist an alcohol is any of an entire class of organic compounds containing a hydroxyl (OH) group or groups. The first member of its class, methyl alcohol or methanol, is used commercially as a solvent. Isopropyl alcohol, also known as rubbing alcohol, serves as a drying agent and disinfectant. Ethyl alcohol or ethanol shares these functions but differs from other alcohols in also being suitable as a beverage ingredient and intoxicant. Ethanol also differs from other alcohols in being a palatable source of energy and euphoria. It is a small, un-ionized molecule that is completely miscible with water and also somewhat fat-soluble. The remainder of this article pertains to ethanol, but refers to it simply as alcohol.
Biology of Production
Making alcoholic beverages dates back at least eight thousand years; for example, beer was made from cereal mashes in Mesopotamia in 6000 B.C.E. and wine in Egypt in 3700 B.C.E.
Ethyl alcohol is actually a by-product of yeast metabolism. Yeast is a fungus that feeds on carbohydrates. Yeasts are present ubiquitously. For example, the white waxy surface of a grape is almost entirely composed of yeast. When, for example, the skin of a berry is broken, the yeast acts quickly and releases an enzyme that, under anaerobic conditions, converts the sugar (sucrose, C12H22O11) in the berry into carbon dioxide (CO2) and alcohol (C2H5OH). This process is known as fermentation (if the mixture is not protected from air, alcohol turns into acetic acid, producing vinegar). When cereal grains and potatoes are used, each requires a sprouting pretreatment (malting) to hydrolyze starch, during which diastase enzymes are produced that break down starches to simple sugars that the yeast, which lacks these enzymes, can anaerobically convert to alcohol. This process makes the sugar available for the fermentation process. The yeast then continues to feed on the sugar until it literally dies of acute alcohol intoxication.
Because yeast expires when the alcohol concentration reaches 12 to 15 percent, natural fermentation stops at this point. In beer, which is made of barley, rice, corn, and other cereals, the fermentation process is artificially halted somewhere between 3 and 6 percent alcohol. Table wine contains between 10 and 14 percent alcohol, the limit of yeast's alcohol tolerance. This amount is insufficient for complete preservation, and thus a mild pasteurization is applied.
Distillation, which was discovered about 800 C.E.in Arabia, is the man-made process designed to take over where the vulnerable yeast fungus leaves off. The distilled, or hard, liquors, including brandy, gin, whiskey, scotch, bourbon, rum, and vodka, contain between 40 and 75 percent pure alcohol. Dry wines result when nearly all the available sugar is fermented. Sweet wines still have unfermented sugar. Pure alcohol also is added to fortify wines such as port and sherry. This addition boosts their percentage of alcohol to 18 or 20 percent (such wines do not require further pasteurization). "Still wines" are bottled after complete fermentation takes place. Sparkling wines are bottled before fermentation is complete so that the formed CO2 is retained. "White" wines are made only from the juice of the grapes; "reds" contain both the juice and pigments from skins.
The percentage of alcohol in distilled liquors commonly is expressed in degrees of "proof" rather than as a percentage of pure alcohol. This measure developed from the seventeenth-century English custom of "proving" an alcoholic drink was of sufficient strength. This was accomplished by mixing it with gunpowder and attempting to ignite it. If the drink contained 49 percent alcohol by weight (or 57 percent by volume), it could be ignited. Thus, proof is approximately double the percentage of pure alcohol (an 86 proof whiskey is 43 percent pure alcohol).
Pure alcohol is a colorless, somewhat volatile liquid with a harsh, burning taste, which is used widely as a fuel or as a solvent for various fats, oils, and resins. This simple and unpalatable chemical is made to look, taste, and smell appetizing by combining it with water and various substances called congeners (pharmacologically active molecules other than ethanol, including higher alcohols and benzene). Congeners make bourbon whiskey taste different from Scotch whiskey, distinguish one brand of beer from another, give wine its "nose" and sherry its golden glow. In trace amounts, most congeners are harmless, but their consumption has been linked to the severity of hangovers and other central nervous system symptoms that include sleepiness.
Use in Food Products
Wines, liqueurs, and distilled spirits are used to prepare main dishes, sauces, and desserts, creating new and interesting flavors. The presence of alcohol in significant amounts affects the energy value of a food. Alcohol is rich in energy (29 kJ/g, or 7.1 kcal/g). It is assumed that, because of its low boiling point, alcohol is evaporated from foods during cooking. However, almost 4 to 85 percent of alcohol can be retained in foods. Foods that require heating for prolonged periods (over two hours—for example, pot roast), retain about 4–6 percent; foods like sauces (where alcohol is typically added after the sauce has been brought to a boil) may retain as much as 85 percent.
Alcohol and Malnutrition
Alcoholism is a major cause of malnutrition. The reasons are threefold. First, alcohol interferes with central mechanisms that regulate food intake and causes food intake decreases. Second, alcohol is rich in energy (7.1 kcal/g), and like pure sugar most alcoholic beverages are relatively empty of nutrients. Increasing amounts of alcohol ingested lead to the consumption of decreasing amounts of other foods, making the nutrient content of the diet inadequate, even if total energy intake is sufficient. Thus chronic alcohol abuse causes primary malnutrition by displacing other dietary nutrients. Third, gastrointestinal and liver complications associated with alcoholism also interfere with digestion, absorption, metabolism, and activation of nutrients, and thereby cause secondary malnutrition.
It is important to note that although ethanol is rich in energy, its chronic consumption does not produce the expected gain in body weight. This may be attributed, in part, to damaged mitochondria and the resulting poor coupling of oxidation of fat metabolically utilizable with energy production. The microsomal pathways that oxidize ethanol may be partially responsible. These pathways produce heat rather than adenosine triphosphate (ATP) and thereby fail to couple ethanol oxidation to useful energy-rich intermediates such as ATP. Thus, perhaps because of these energy considerations, alcoholics with higher total caloric intake do not experience expected weight gain despite physical activity levels similar to those of the non-alcohol-consuming overweight population.
Absorption and Metabolism
Unlike foods, which require time for digestion, alcohol needs no digestion and is absorbed quickly. The presence of food in the stomach delays emptying, slowing absorption that occurs mainly in the upper small intestine.
Only 2 to 10 percent of absorbed ethanol is eliminated through the kidneys and lungs; the rest is metabolized, principally in the liver. A small amount of ethanol also is metabolized by gastric alcohol dehydrogenase (ADH) [first-pass metabolism (FPM)]. This FPM explains why, for any given dose of ethanol, blood levels are usually higher after an intravenous dose than following a similar amount taken orally. FPM is partly lost in the alcoholic.This lost function is due to decreased gastric ADH activity. Premenopausal women also have less of this gastric enzyme than do men. This difference partially explains why women become more intoxicated than men when each consume similar amounts of alcohol.
Hepatocytes are the primary cells that oxidize alcohol at significant rates. This hepatic specificity for ethanol oxidation, coupled with ethanol's high energy content and the lack of effective feedback control of alcohol hepatic metabolism, results in the displacement of up to 90 percent of the liver's normal metabolic substrates.
Oxidation. Hepatocytes contain three main pathways for ethanol metabolism. Each pathway is localized to a different subcellular compartment: (1) the alcohol dehydrogenase (ADH) pathway (soluble fraction of the cell); (2) the microsomal ethanol oxidizing system (MEOS) located in the endoplasmic reticulum; and (3) catalase located in the peroxisomes. Each of these pathways produces specific toxic and nontoxic metabolites. All three result in the production of acetaldehyde (CH3CHO), a highly toxic metabolite. The MEOS may account for up to 40 percent of ethanol oxidation. Normally, the role of catalase is small. It is not discussed further here.
Physiological Effects At Different Levels
Beneficial effects. A large variety of alcoholic beverages are available, and most people can find at least one that provides gustatory and other pleasures. Alcohol is said to reduce tension, fatigue, anxiety, and pressure and to increase feelings associated with relaxation. It also has been claimed that drinking in moderation may lower the risk of coronary heart disease (mainly among men over 45 and women over age 55), but whether that putative protection is due primarily to the alcohol or some other associated factors, such as lifestyle, remains controversial. Moderate alcohol consumption provides no health benefit for younger people, and in fact may increase risks to alcohol's ill effects because the potential for alcohol abuse increases when drinking starts at an early age.
Harmful effects. The problems of individuals who occasionally become drunk differ from those who experience drinking binges at regular intervals.
"Acute" harmful effects of alcohol intoxication: Occasional excess drinking can cause nausea, vomiting, and hangovers (especially in inexperienced drinkers). The acute neurological effects of alcohol intoxication are dose-related. These progress from euphoria, relief from anxiety, and removal of inhibitions to ataxia, impaired vision, judgment, reasoning, and muscle control. When alcohol intakes continue after the appearance of these signs and symptoms, progress to lethal levels occurs very quickly, resulting in the anesthetization of the brain's circulatory and respiratory centers.
"Chronic" harmful effects of alcohol excess: Chronic excessive alcohol consumption can affect adversely virtually all tissues. Alcoholics have a mortality and suicide rate 2½ times greater, and an accident rate 7 times greater than average. Some of the dire consequences that are associated with alcohol abuse are:
Treatment
There are two major approaches that are used in the treatment of alcohol abuse: (1) correction of the medical, nutritional, and psychological problems; and (2) the alleviation of dependency on alcohol. Many sedatives or tranquilizers (for example, chlordiazepoxide) are effective in controlling minor withdrawal symptoms such as tremors. More serious symptoms include delirium tremens and seizures. For treatment of alcohol dependence, the anticraving agent naltrexone has shown promising results. Nutritional deficiency, such as lack of thiamine or magnesium, when present, must be corrected. Psychological approaches such as the twelve steps of Alcoholics Anonymous are also effective in achieving more sustained abstinence. These approaches, although helpful, too often come too late to revert the liver to its normal state. Other approaches, such as those focusing on prevention (utilizing biochemical markers), screening (through use of improved blood tests), and early detection are needed to impact on the prevalence of liver disease. The correction of nutritional deficiencies and supplementation with other substrates that may be produced in abnormally low quantities by affected patients, for example, S-adenosylmethionine (SAMe) and polyunsaturated lecithin have been shown to offset some of the adverse manifestations of alcohol's toxic effects. These and others are now being tested in humans.
Conclusion
Alcoholism, an addiction to heavy and frequent alcohol consumption, is a major public health issue. However, many believe that this condition does not attract attention that it merits from either the public or the health professions. Alcoholism is a multifaceted problem that cannot be solved by any single approach. The "consumption control approach" is a worthwhile endeavor with proven efficacy, but consumption control efforts by themselves are not sufficient. Prevention of alcohol misuse before it occurs also can be beneficial. Another prevention strategy includes establishing standards and guidelines for advertising and emphasizing responsibility and moderation in the serving and consumption of alcohol. "Behavioral" approaches focus on recognition of social and psychological factors and their correction. Finally, the "disease-control" approach provides new insights. Continued research into the pathophysiology of alcohol-induced disorders increases understanding of the condition and provides prospects of earlier recognition, and improved efforts for its early prevention and treatment, prior to the medical and social disintegration of its victims. By combining all of these approaches, chances to alleviate the suffering of the alcoholic are multiplied in a positively synergistic manner and the public health impact of alcoholism on our society can be minimized.
Bibliography
Lieber, Charles S. Medical and Nutritional Complications of Alcoholism: Mechanisms and Management. New York: Plenum, 1992.
Lieber, Charles S. "Medical Disorders of Alcoholism." New England Journal of Medicine 333 (1995): 1058–1065.
Lieber, Charles S. "Alcohol: Its Metabolism and Interaction with Nutrients." Annual Reviews in Nutrition 20 (2000): 395–430.
—Khursheed P. Navder; Charles S. Lieber
A Congressman was once asked by a constituent to explain his attitude toward whiskey. "If you mean the demon drink that poisons the mind, pollutes the body, desecrates family life, and inflames sinners, then I'm against it," the Congressman said. "But if you mean the elixir of Christmas cheer, the shield against winter chill, the taxable potion that puts needed funds into public coffers to comfort little crippled children, then I'm for it. This is my position, and I will not compromise."
The legal history of alcohol in the United States closely parallels the economic and social trends that shaped the country. The libertarian philosophy that ignited the Whiskey Rebellion was born in the American Revolution. Shifting concerns about morality and family harmony that were characteristic of the industrial revolution inspired the temperance movement and brought about Prohibition, which began with the passage of the Eighteenth Amendment to the Constitution in 1919 and ended with its repeal in 1933. The return of legalized drinking in the United States led to renewed discussion of the many health and safety issues associated with alcohol consumption. Over the years, the states have addressed these issues through a variety of laws, such as those dealing with a minimum age for the purchase or consumption of alcohol, the labeling of alcoholic beverages, and drunk driving. Private litigants have expanded protections against harm from alcohol through tort actions, and various groups, both national and local, continue to lobby for increased legislation and higher penalties for alcohol-related acts that lead to injury.
Historical Background of Alcohol in the United States
Drink is in itself a good creature of God, and to be received with thankfulness, but the abuse of drink is from Satan, the wine is from God, but the Drunkard is from the Devil. (Increase Mather, Puritan clergyman, Wo to Drunkards [1673])
Alcoholic beverages have been consumed in the United States since the days of Plymouth Rock. Beer and wine were staples on the ships carrying settlers to the New World. However, debate and controversy have surrounded alcohol consumption throughout the nation's history.
In colonial times, water and milk were scarce and susceptible to contamination or spoilage, and tea and coffee were expensive. The Pilgrims turned to such alternatives as cider and beer, and, less frequently, whiskey, rum, and gin. In 1790, per capita consumption of pure alcohol, or absolute alcohol, was just under six gallons a year. (Pure alcohol constitutes only a small percentage of an alcoholic drink. For example, if a beverage contains 10 percent alcohol by volume, one would have to drink ten gallons of it to consume one gallon of pure alcohol.)
Although the majority of the colonists drank alcohol regularly, strong community social strictures curbed any tendency toward immoderation. Drunken behavior was dealt with by emphasizing the need to restore community harmony and stability, rather than by imposing punishment.
Alcohol consumption continued without much controversy until after the Revolutionary War when whiskey and other distilled spirits became valuable commercial commodities. When Congress imposed an excise tax on the farmers who produced liquor in the 1790s, they resisted paying the tax. Their resistance became known as the Whiskey Rebellion, a protest movement of farmers who felt the tax placed an undue burden on their commercial activities.
Before the nineteenth century, farming was the predominant occupation, and although it involved grueling work, it did not demand precision or speed. The industrial revolution brought millions of workers into factories where efficiency, dexterity, and rigid scheduling were necessary. With these economic changes came a shift in societal attitudes toward alcohol. Gone was the time when people considered the midday liquor break a benign diversion.
The Temperance Movement
'Mid pleasures and palaces, though we may roam, Be it ever so humble, there's no place like home. But there is the father lies drunk on the floor, The table is empty, the wolf's at the door, And mother sobs loud in her broken-back'd chair, Her garments in tatters, her soul in despair. (Nobil Adkisson, Ruined by Drink [c. 1860])
As the United States entered the industrial age, attitudes about alcohol consumption gradually changed. A moralistic and punitive view of alcohol replaced the laissez-faire attitudes of earlier times. What had been the "good creature of God" in the eighteenth century became the "demon rum" of the nineteenth.
The U.S. temperance movement emerged around 1826 with the formation of the American Society for the Promotion of Temperance, later called the American Temperance Society. In the 1840s, the society began crusading for complete abstinence from alcohol. Dissemination of the temperance message caused a fall in per capita consumption of pure alcohol from a high of over seven gallons a year in 1830 to just over three in 1840, the largest ten-year drop in U.S. history. By the outbreak of the Civil War, thirteen states, beginning with Maine in 1851, had adopted some form of prohibition as law.
Other temperance organizations became prominent during the middle to late 1800s. In 1874, the Woman's Christian Temperance Union (WCTU) was founded. The only temperance organization still in operation, the WCTU has worked continuously since its inception to educate the public and to influence policies that discourage the use of alcohol and other drugs. In 1990, the group was nominated for a Nobel Peace Prize.
In 1869, the antialcohol movement created its own political party — the National Prohibition party — devoted to a single goal: to inspire legislation prohibiting the manufacture, transportation, and sale of alcoholic beverages. The party made modest showings in state elections through the 1860s and 1870s, and reached its peak of popular support in 1892 when John Bidwell won almost 265,000 votes in his bid for the presidency. The Prohibition party's main effect was its influence on public policy. It succeeded in placing Prohibition planks into many state party platforms and was a potent impetus behind passage of the Eighteenth Amendment.
One of the most powerful forces in the Prohibition movement was the Anti-Saloon League, a nonpartisan group founded in 1893 by representatives of temperance societies and evangelical Protestant churches. The Anti-Saloon League, unlike the Prohibition party, worked within established political parties to support candidates who were sympathetic to the league's goals. By 1916, the league, with the help of the Prohibition party and the WCTU, had sent enough sympathetic candidates to Congress to ensure action on a Prohibition amendment to the Constitution.
Prohibition
Prohibition is an awful flop. We like it. It can't stop what it's meant to stop. We like it. It's left a trail of graft and slime It don't prohibit worth a dime It's filled our land with vice and crime, Nevertheless, we're for it. (Franklin P. Adams, quoted in Era of Excess)
In December 1917, the temperance movement achieved its goal when Congress approved the Eighteenth Amendment, which prohibited the manufacture, sale, transportation, importation, or exportation of intoxicating liquors from or to the United States or its territories. The amendment was sent to the states, and by January 1919 it was ratified. In January 1920, the United States became officially dry.
The demand for liquor did not end with Prohibition, however. Those willing to violate the law saw an opportunity to fill that demand and become wealthy in the process. Illegal stills produced the alcohol needed to make "bathtub gin." Rum and other spirits from abroad were commonly smuggled into the country from the east and northwest coasts, and illegal drinking establishments, known as speakeasies or blind pigs, proliferated. The illicit production and distribution of alcohol, called bootlegging, spawned a multibillion-dollar underworld business run by a syndicate of criminals.
Perhaps the most famous of the bootleggers was Al Capone, who ran liquor, prostitution, and racketeering operations in Chicago — one of the wettest of the wet towns. At the height of his power in the mid-1920s, Capone made hundreds of millions of dollars a year. He employed nearly a thousand people and enjoyed the cooperation of numerous police officers and other corrupt public officials who were willing to turn a blind eye in return for a share of his profits. For years, Capone and others like him evaded attempts to shut down their operations. Capone's reign finally ended in 1931 when he was convicted of income tax evasion.
Historians differ about the success of Prohibition. Some feel that the effort was a ludicrous failure that resulted in more severe social problems than had ever been associated with alcohol consumption. Others point to ample evidence that Prohibition, although never succeeding in making the country completely dry, dramatically changed U.S. drinking habits. Per capita consumption at the end of Prohibition had fallen to just under a gallon of pure alcohol a year, and accidents and deaths attributable to alcohol had declined steeply.
Although Prohibition enjoyed widespread popular support, a substantial minority of U.S. citizens simply ignored the law. Also, although Prohibition unquestionably fostered unprecedented criminal activity, many people were concerned that the government's enforcement efforts unduly intruded into personal privacy. In cases such as Carroll v. United States, 267 U.S. 132, 45 S. Ct. 280, 69 L. Ed. 543 (1925), the Supreme Court indicated its willingness to stretch the limits of police power in order to enforce Prohibition. In Carroll, the Court held that federal agents were justified in conducting a warrantless search of an automobile, because they had probable cause to believe it contained illegal liquor.
Concerns over diminished liberties led to feelings that Prohibition was too oppressive a measure to impose upon an entire nation. This sentiment was bolstered by arguments that the production and sale of alcohol were profitable enterprises that could help bolster the nation's depressed economy. By the beginning of the 1930s, after little more than a decade as law, Prohibition lost its hold on the U.S. conscience. The promise of jobs and increased tax revenues helped the anti-Prohibition message recapture political favor. The Twenty-first Amendment, repealing Prohibition, swept through the necessary thirty-six-state ratification process, and the "noble experiment" ended on December 5, 1933.
Post-Prohibition Regulation and Control
The repeal of Prohibition forced states to address once more the dangers posed by excessive alcohol consumption. The risks are well documented: figures compiled in 1990 indicate that as many as 10.5 million U.S. citizens are alcohol dependent and an additional 7.2 million drink heavily enough to cause impaired health and social functioning. Mothers against Drunk Driving (MADD) reported in 1995 that over eighteen thousand alcohol-related traffic deaths occur each year in the United States. Alcohol is the most widely used drug among teenagers and is linked to juvenile crime, health problems, suicide, date rape, and unwanted pregnancy. Alcohol-related traffic accidents are the leading cause of death among fifteen- to twenty-four-year-olds.
In the face of rising concerns about liquor consumption and personal injury, many states chose to regulate alcohol through dramshop laws. A dramshop is any type of drinking establishment where liquor is sold for consumption on the premises. Dramshop statutes impose liability on sellers of alcoholic beverages for injuries caused by an intoxicated patron. Under such statutes, a person injured by a drunk patron sues the establishment where the patron was served. The purpose of dramshop laws is to hold responsible those who enjoy economic benefit from the sale of liquor, thereby ensuring that a loss is not borne solely by an innocent victim (as when the intoxicated person who caused the injuries has no assets and no insurance).
The first dramshop law, enacted in Wisconsin in 1849, required saloons or taverns to post a bond for expenses that might result from civil lawsuits against their patrons. Many states followed Wisconsin's lead, and dramshop laws were prominent until the 1940s, 1950s, and 1960s, when most were repealed. However, the 1980s brought renewed concern over the consequences of overindulgence in alcohol, and public pressure led to the passage of new dramshop statutes. By 1993, thirty-six states had imposed some form of liability on purveyors of alcoholic beverages for injuries caused by their customers.
All states and the District of Columbia also regulate the sale of liquor to minors or to individuals who are intoxicated. Challenges to the age restriction on equal protection grounds have been unsuccessful.
Along with statutory measures, most courts have also recognized a common-law cause of action against alcohol vendors for the negligent sale of alcohol. In Rappaport v. Nichols, 31 N.J. 188, 156 A.2d 1 (1959), the court held that a tavern could be held liable for the plaintiff's husband's death after the tavern served an intoxicated minor who caused the accident that killed the man. The court relied on the public policy concerns underlying liquor control laws. Such laws are intended to protect the general public as well as minors or intoxicated persons, the court reasoned, and therefore the tavern should be held liable if its negligence was a substantial factor in creating the circumstances that led to the husband's death. Under Rappaport, serving as well as consuming alcohol can be construed to be the proximate cause of an injury. A majority of jurisdictions now follow the Rappaport court's reasoning.
In determining the extent of an alcohol vendor's liability, a growing number of courts apply comparative negligence principles. Comparative negligence assesses partial liability to a plaintiff whose failure to exercise reasonable care contributes to his or her own injury. In Lee v. Kiku Restaurant, 127 N.J. 170, 603 A.2d 503 (1992), and Baxter v. Noce, 107 N.M. 48, 752 P.2d 240 (1988), the plaintiffs sued under dramshop statutes for injuries suffered when they rode with drunk drivers. The courts in both cases recognized the importance of dramshop statutes in protecting innocent victims of drunk behavior. However, they also recognized the need to hold individuals responsible to some degree for their own safety. Under comparative negligence, which divides liability among the parties in accordance with each party's degree of fault, both goals are achieved.
A few courts have extended liability for injuries to social hosts who serve a minor or an intoxicated guest. In Kelly v. Gwinnell, 96 N.J. 538, 476 A.2d 1219 (1984), the New Jersey Supreme Court found both the host and the guest jointly liable when the guest had an accident after drinking at the host's house. The court based the host's liability on his continuing to serve alcoholic beverages to the guest when he knew the guest was intoxicated and likely to drive a car. Similarly, in Koback v. Crook, 123 Wis.2d 259, 366 N.W.2d 857 (1985), the Wisconsin Supreme Court held that a social host was negligent for serving liquor to a minor guest at a graduation party. The guest was later involved in a motorcycle accident in which the plaintiff was injured. However, the Ohio Supreme Court refused to extend liability to the social host in Settlemyer v. Wilmington Veterans Post No. 49, 11 Ohio St. 3d 123, 464 N.E.2d 521 (1984). The court in Settlemyer held that assigning liability to a social host is a matter better left to the legislature.
All states and many local governments regulate the sale of alcohol through the issuance of licenses. These licenses limit the times and locations where liquor sales can take place. The government also regulates alcohol through taxation. Current taxes on liquor serve the same dual purpose as did the first excise tax on liquor when it was proposed by Alexander Hamilton in 1791: they provide a source of revenue for the government and, theoretically, discourage overindulgence. Enforcement of the laws regulating and taxing alcohol is carried out by the Bureau of Alcohol, Tobacco, and Firearms (ATF), an agency of the U.S. Department of the Treasury. The collection of alcohol revenues is important to the federal government: in 1993, liquor taxes exceeded $7.2 billion.
During the 1980s and 1990s, public awareness of the dangers of alcohol led to a number of changes in the law. Groups such as MADD and Students against Drunk Driving (SADD) pressured state legislatures to greatly increase enforcement and penalties for driving while intoxicated. Likewise, increased knowledge about the physical consequences of alcohol consumption led to the imposition of a duty on the part of liquor manufacturers to warn consumers that their product may be hazardous.
Before 1987, manufacturers of alcoholic beverages were immune from civil liability for injuries resulting from the use of liquor. Garrison v. Heublein, Inc., 673 F.2d 189 (7th Cir. 1982), held that the defendant did not have a duty to warn the plaintiff of the dangers of its product. The court stated that the dangers inherent in the use of alcohol are "common knowledge to such an extent that the product cannot objectively be considered to be unreasonably dangerous." Garrison was followed by other jurisdictions until 1987 when Hon v. Stroh Brewery, 835 F.2d 510 (3d Cir. 1987), signaled a shift in judicial sentiment. In Hon, the plaintiff's twenty-six-year-old husband died of pancreatitis attributable to his moderate consumption of alcohol over a six-year period. The plaintiff alleged that the defendant's products were "unreasonably dangerous" because consumers were not warned of the lesser-known dangers of consumption. The court, relying on the Restatement (Second) of Torts § 402A, held that a product is defective if it lacks a warning sufficient to make it safe for its intended purpose. Since the general public is unaware of all the health risks associated with liquor consumption, the court found the defendant liable for failing to warn the plaintiff. The reasoning in Hon has been followed in other cases, including Brune v. Brown-Forman Corp., 758 S.W.2d 827 (Tex. Ct. App. 1988), where the court found that the defendant's product was unreasonably dangerous because it bore no warning about the dangers of excessive consumption. The plaintiff's daughter, a college student, died after consuming fifteen shots of tequila over a short period of time.
The duty of liquor manufacturers to warn consumers of the hazards of drinking was codified when Congress passed the Alcoholic Beverage Labeling Act of 1988 (27 U.S.C.A. § 215). The act requires all alcoholic beverage containers to bear a clear and conspicuous label warning of the dangers of alcohol consumption.
The United States' long history of ambivalence toward the consumption of alcoholic beverages shows no sign of abating. At the same time that manufacturers are required to warn consumers about the health risks inherent in liquor, some medical studies indicate that some health benefits may be associated with moderate imbibing.
See: Alcohol, Tobacco and Firearms, Bureau of; Automobiles; Automobile Searches; Capone, Alphonse; Dramshop Acts; Eighteenth Amendment; Organized Crime; Product Liability; Prohibition; Temperance Movement; Twenty-First Amendment; Whiskey Rebellion.
[AL-kuh-hawl] Alcohol is the intoxicating element produced by the yeast fermentation of certain carbohydrates-the sugar in fruit, in the instance of wine. If a wine is fully fermented, from 40 to 45 percent of the grapes' sugar content is converted into carbon dioxide and from 55 to 60 percent is converted into ethyl alcohol (the only alcohol suitable for drinking). Therefore, a wine whose grapes were picked at 23° brix will end up with 12.6 to 13.8 percent alcohol if vinified completely dry. Ethyl alcohol, also known as ethanol, lends little if any flavor to wine but must be present in the right proportion to give wine a desirable balance. Wine with a low alcohol level might be too sweet because not enough of the grape's sugar was converted. This results in residual sugar an undesirable trait in some wines. Wines with excessive alcohol are characterized by a burning sensation in the mouth and are, in fact, referred to as hot. Wines with full, concentrated fruit flavors can withstand higher alcohol levels without becoming hot; more delicate wines don't fare as well. See also alcohol by volume.
1) A slang word meaning, "I'll call".
2) A beverage some players will consume while playing poker.
SoundPoker Says: 1. The slang term alcohol originated because of the similarities in the pronunciation sounds of "alcohol" and "I'll call".
2. It is not recommended to drink too much alcohol while playing poker as it can impair judgment and thus increase the chances of losing money.
See Also: Call
The restaurant did not serve alcohol.
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| ethyl, ethoxy, ethionine | |
| ethylene, ethylene receptor 1, ethylene-forming enzyme |
1. any organic compound containing the hydroxy (−OH) functional group except those in which the OH group is attached to an aromatic ring, which are called phenols. Alcohols are classified as primary, secondary or tertiary according to whether the carbon atom to which the OH group is attached is bonded to one, two or three other carbon atoms and as monohydric, dihydric or trihydric according to whether they contain one, two or three −OH groups; the latter two are called diols and triols, respectively.
2. common name for ethyl alcohol (ethanol). See also alcoholic.
A transparent, colorless liquid that is mobile and volatile. Alcohols are organic compounds formed from hydrocarbons by the substitution of hydroxyl radicals for the same number of hydrogen atoms.
In chemistry, an alcohol is an organic compound in which the hydroxyl functional group (-OH) is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms.[1]
An important class of alcohols are the simple acyclic alcohols, the general formula for which is CnH2n+1OH. Of those, ethanol (C2H5OH) is the type of alcohol found in alcoholic beverages, and in common speech the word alcohol refers specifically to ethanol.
Other alcohols are usually described with a clarifying adjective, as in isopropyl alcohol (propan-2-ol) or wood alcohol (methyl alcohol, or methanol). The suffix -ol appears in the IUPAC chemical name of all substances where the hydroxyl group is the functional group with the highest priority; in substances where a higher priority group is present the prefix hydroxy- will appear in the IUPAC name. The suffix -ol in non-systematic names (such as paracetamol or cholesterol) also typically indicates that the substance includes a hydroxyl functional group and, so, can be termed an alcohol. But many substances, particularly sugars (examples glucose and sucrose) contain hydroxyl functional groups without using the suffix.
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The most commonly used alcohol is ethanol, C2H5OH, with the ethane backbone. Ethanol has been produced and consumed by humans for millennia, in the form of fermented and distilled alcoholic beverages. It is a clear flammable liquid that boils at 78.4 °C, which is used as an industrial solvent, car fuel, and raw material in the chemical industry. In the US and some other countries, because of legal and tax restrictions on alcohol consumption, ethanol destined for other uses often contains additives that make it unpalatable (such as Bitrex) or poisonous (such as methanol). Ethanol in this form is known generally as denatured alcohol; when methanol is used, it may be referred to as methylated spirits or "surgical spirits".
The simplest alcohol is methanol, CH3OH, which was formerly obtained by the distillation of wood and, therefore, is called "wood alcohol". It is a clear liquid resembling ethanol in smell and properties, with a slightly lower boiling point (64.7 °C), and is used mainly as a solvent, fuel, and raw material. Unlike ethanol, methanol is extremely toxic: One sip (as little as 10 ml) can cause permanent blindness by destruction of the optic nerve and 30 ml (one fluid ounce) is potentially fatal.[2]
Two other alcohols whose uses are relatively widespread (though not so much as those of methanol and ethanol) are propanol and butanol. Like ethanol, they can be produced by fermentation processes. (However, the fermenting agent is a bacterium, Clostridium acetobutylicum, that feeds on cellulose, not sugars like the Saccharomyces yeast that produces ethanol.) Saccharomyces yeast are known to produce these higher alcohols at temperatures above 75 °F (24 °C). These alcohols are called fusel alcohols or fusel oils in brewing and tend to have a spicy or peppery flavor. They are considered a fault in most styles of beer.[3]
Simple alcohols, in particular, ethanol and methanol, possess denaturing and inert rendering properties, leading to their use as anti-microbial agents in medicine, pharmacy, and industry.[citation needed]
In the IUPAC system, the name of the alkane chain loses the terminal "e" and adds "ol", e.g., "methanol" and "ethanol".[4] When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the "ol": propan-1-ol for CH3CH2CH2OH, propan-2-ol for CH3CH(OH)CH3. Sometimes, the position number is written before the IUPAC name: 1-propanol and 2-propanol. If a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), then it is necessary to use the prefix "hydroxy",[4] for example: 1-hydroxy-2-propanone (CH3COCH2OH).[5]
The IUPAC nomenclature is used in scientific publications and where precise identification of the substance is important. In other less formal contexts, an alcohol is often called with the name of the corresponding alkyl group followed by the word "alcohol", e.g., methyl alcohol, ethyl alcohol. Propyl alcohol may be n-propyl alcohol or isopropyl alcohol, depending on whether the hydroxyl group is bonded to the 1st or 2nd carbon on the propane chain.
Alcohols are classified into primary, secondary (sec), and tertiary (tert), based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl group. The primary alcohols have general formulas RCH2OH; secondary ones are RR'CHOH; and tertiary ones are RR'R"COH, where R, R', and R" stand for alkyl groups. Ethanol and n-propyl alcohol are primary alcohols; isopropyl alcohol is a secondary one. The prefixes sec- (or s-) and tert- (or t-), conventionally in italics, may be used before the alkyl group's name to distinguish secondary and tertiary alcohols, respectively, from the primary one. For example, isopropyl alcohol is occasionally called sec-propyl alcohol, and the tertiary alcohol (CH3)3COH, or 2-methylpropan-2-ol in IUPAC nomenclature is commonly known as tert-butyl alcohol or tert-butanol.
| Chemical Formula | IUPAC Name | Common Name |
|---|---|---|
| Monohydric alcohols | ||
| CH3OH | Methanol | Wood alcohol |
| C2H5OH | Ethanol | Grain alcohol |
| C3H7OH | Isopropyl alcohol | Rubbing alcohol |
| C4H9OH | Butyl alcohol | Butanol |
| C5H11OH | Pentanol | Amyl alcohol |
| C16H33OH | Hexadecan-1-ol | Cetyl alcohol |
| Polyhydric alcohols | ||
| C2H4(OH)2 | Ethane-1,2-diol | Ethylene glycol |
| C3H5(OH)3 | Propane-1,2,3-triol | Glycerin |
| C4H6(OH)4 | Butane-1,2,3,4-tetraol | Erythritol |
| C5H7(OH)5 | Pentane-1,2,3,4,5-pentol | Xylitol |
| C6H8(OH)6 | Hexane-1,2,3,4,5,6-hexol | Mannitol, Sorbitol |
| C7H9(OH)7 | Heptane-1,2,3,4,5,6,7-heptol | Volemitol |
| Unsaturated aliphatic alcohols | ||
| C3H5OH | Prop-2-ene-1-ol | Allyl alcohol |
| C10H17OH | 3,7-Dimethylocta-2,6-dien-1-ol | Geraniol |
| C3H3OH | Prop-2-in-1-ol | Propargyl alcohol |
| Alicyclic alcohols | ||
| C6H6(OH)6 | Cyclohexane-1,2,3,4,5,6-hexol | Inositol |
| C10H19OH | 2 - (2-propyl)-5-methyl-cyclohexane-1-ol | Menthol |
The first alcohol (today known as ethyl alcohol) was discovered by the tenth-century Persian alchemist al-Razi.
kuḥl was originally the name given to the very fine powder, produced by the sublimation of the natural mineral stibnite to form antimony sulfide Sb2S3 (hence the essence or "spirit" of the substance), which was used as an antiseptic and eyeliner. Bartholomew Traheron in his 1543 translation of John of Vigo introduces the word as a term used by "barbarous" (Moorish) authors for "fine powder":
The word alcohol appears in English, as a term for a very fine powder, in the 16th century, loaned via French from medical Latin, ultimately from the Arabic الكحل (al-kuḥl, "the kohl, a powder used as an eyeliner"). Al- is the Arabic definitive article, equivalent to the in English.
William Johnson in his 1657 Lexicon Chymicum glosses the word as antimonium sive stibium. By extension, the word came to refer to any fluid obtained by distillation, including "alcohol of wine", the distilled essence of wine. Libavius in Alchymia (1594) has vini alcohol vel vinum alcalisatum. Johnson (1657) glosses alcohol vini as quando omnis superfluitas vini a vino separatur, ita ut accensum ardeat donec totum consumatur, nihilque fæcum aut phlegmatis in fundo remaneat. The word's meaning became restricted to "spirit of wine" (the chemical known today as ethanol) in the 18th century, and was extended to the class of substances so-called as "alcohols" in modern chemistry, after 1850.
The current Arabic name for alcohol is الكحول al-kuḥūl, re-introduced into that language from western usage.
Alcohols have an odor that is often described as “biting” and as “hanging” in the nasal passages. Ethanol has a slightly sweeter (or more fruit-like) odor than the other alcohols.
In general, the hydroxyl group makes the alcohol molecule polar. Those groups can form hydrogen bonds to one another and to other compounds (except in certain large molecules where the hydroxyl is protected by steric hindrance of adjacent groups[6]). This hydrogen bonding means that alcohols can be used as protic solvents. Two opposing solubility trends in alcohols are: the tendency of the polar OH to promote solubility in water, and the tendency of the carbon chain to resist it. Thus, methanol, ethanol, and propanol are miscible in water because the hydroxyl group wins out over the short carbon chain. Butanol, with a four-carbon chain, is moderately soluble because of a balance between the two trends. Alcohols of five or more carbons (pentanol and higher) are effectively insoluble in water because of the hydrocarbon chain's dominance. All simple alcohols are miscible in organic solvents.
Because of hydrogen bonding, alcohols tend to have higher boiling points than comparable hydrocarbons and ethers. The boiling point of the alcohol ethanol is 78.29 °C, compared to 69 °C for the hydrocarbon hexane (a common constituent of gasoline), and 34.6 °C for diethyl ether.
Alcohols, like water, can show either acidic or basic properties at the -OH group. With a pKa of around 16-19, they are, in general, slightly weaker acids than water, but they are still able to react with strong bases such as sodium hydride or reactive metals such as sodium. The salts that result are called alkoxides, with the general formula RO- M+.
Meanwhile, the oxygen atom has lone pairs of nonbonded electrons that render it weakly basic in the presence of strong acids such as sulfuric acid. For example, with methanol:
Alcohols can also undergo oxidation to give aldehydes, ketones, or carboxylic acids, or they can be dehydrated to alkenes. They can react to form ester compounds, and they can (if activated first) undergo nucleophilic substitution reactions. The lone pairs of electrons on the oxygen of the hydroxyl group also makes alcohols nucleophiles. For more details, see the reactions of alcohols section below.
As one moves from primary to secondary to tertiary alcohols with the same backbone, the hydrogen bond strength, the boiling point, and the acidity typically decrease.
Alcohols can be used as a beverage (ethanol only), as fuel and for many scientific, medical, and industrial utilities. Ethanol in the form of alcoholic beverages has been consumed by humans since pre-historic times. A 50% v/v solution of ethylene glycol in water is commonly used as an antifreeze.
Some alcohols, mainly ethanol and methanol, can be used as an alcohol fuel. Fuel performance can be increased in forced induction internal combustion engines by injecting alcohol into the air intake after the turbocharger or supercharger has pressurized the air. This cools the pressurized air, providing a denser air charge, which allows for more fuel, and therefore more power.
Alcohols have applications in industry and science as reagents or solvents. Because of its relatively low toxicity compared with other alcohols and ability to dissolve non-polar substances, ethanol can be used as a solvent in medical drugs, perfumes, and vegetable essences such as vanilla. In organic synthesis, alcohols serve as versatile intermediates.
Ethanol can be used as an antiseptic to disinfect the skin before injections are given, often along with iodine. Ethanol-based soaps are becoming common in restaurants and are convenient because they do not require drying due to the volatility of the compound. Alcohol is also used as a preservative for specimens.
Alcohol gels have become common as hand sanitizers.
In industry, alcohols are produced in several ways:
Several of the benign bacteria[which?] in the intestine use fermentation as a form of anaerobic metabolism. This metabolic reaction produces ethanol as a waste product, just like aerobic respiration produces carbon dioxide and water. Thus, human bodies contain some quantity of alcohol endogenously produced by these bacteria.[citation needed]
Several methods exist for the preparation of alcohols in the laboratory.
Primary alkyl halides react with aqueous NaOH or KOH mainly to primary alcohols in nucleophilic aliphatic substitution. (Secondary and especially tertiary alkyl halides will give the elimination (alkene) product instead). Grignard reagents react with carbonyl groups to secondary and tertiary alcohols. Related reactions are the Barbier reaction and the Nozaki-Hiyama reaction.
Aldehydes or ketones are reduced with sodium borohydride or lithium aluminium hydride (after an acidic workup). Another reduction by aluminiumisopropylates is the Meerwein-Ponndorf-Verley reduction. Noyori asymmetric hydrogenation is the asymmetric reduction of β-keto-esters.
Alkenes engage in an acid catalysed hydration reaction using concentrated sulfuric acid as a catalyst that gives usually secondary or tertiary alcohols. The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with NBS and water in halohydrin formation reaction. Amines can be converted to diazonium salts, which are then hydrolyzed.
The formation of a secondary alcohol via reduction and hydration is shown:
Alcohols can behave as weak acids, undergoing deprotonation. The deprotonation reaction to produce an alkoxide salt is performed either with a strong base such as sodium hydride or n-butyllithium or with sodium or potassium metal.
Water is similar in pKa to many alcohols, so with sodium hydroxide there is an equilibrium set-up, which usually lies to the left:
It should be noted, however, that the bases used to deprotonate alcohols are strong themselves. The bases used and the alkoxides created are both highly moisture-sensitive chemical reagents.
The acidity of alcohols is also affected by the overall stability of the alkoxide ion. Electron-withdrawing groups attached to the carbon containing the hydroxyl group will serve to stabilize the alkoxide when formed, thus resulting in greater acidity. On the other hand, the presence of electron-donating group will result in a less stable alkoxide ion formed. This will result in a scenario whereby the unstable alkoxide ion formed will tend to accept a proton to reform the original alcohol.
With alkyl halides alkoxides give rise to ethers in the Williamson ether synthesis.
The OH group is not a good leaving group in nucleophilic substitution reactions, so neutral alcohols do not react in such reactions. However, if the oxygen is first protonated to give R−OH2+, the leaving group (water) is much more stable, and the nucleophilic substitution can take place. For instance, tertiary alcohols react with hydrochloric acid to produce tertiary alkyl halides, where the hydroxyl group is replaced by a chlorine atom by unimolecular nucleophilic substitution. If primary or secondary alcohols are to be reacted with hydrochloric acid, an activator such as zinc chloride is needed. In alternative fashion, the conversion may be performed directly using thionyl chloride.[1]
Alcohols may, likewise, be converted to alkyl bromides using hydrobromic acid or phosphorus tribromide, for example:
In the Barton-McCombie deoxygenation an alcohol is deoxygenated to an alkane with tributyltin hydride or a trimethylborane-water complex in a radical substitution reaction.
Alcohols are themselves nucleophilic, so R−OH2+ can react with ROH to produce ethers and water in a dehydration reaction, although this reaction is rarely used except in the manufacture of diethyl ether.
More useful is the E1 elimination reaction of alcohols to produce alkenes. The reaction, in general, obeys Zaitsev's Rule, which states that the most stable (usually the most substituted) alkene is formed. Tertiary alcohols eliminate easily at just above room temperature, but primary alcohols require a higher temperature.
This is a diagram of acid catalysed dehydration of ethanol to produce ethene:
A more controlled elimination reaction is the Chugaev elimination with carbon disulfide and iodomethane.
To form an ester from an alcohol and a carboxylic acid the reaction, known as Fischer esterification, is usually performed at reflux with a catalyst of concentrated sulfuric acid:
In order to drive the equilibrium to the right and produce a good yield of ester, water is usually removed, either by an excess of H2SO4 or by using a Dean-Stark apparatus. Esters may also be prepared by reaction of the alcohol with an acid chloride in the presence of a base such as pyridine.
Other types of ester are prepared in a similar manner — for example, tosyl (tosylate) esters are made by reaction of the alcohol with p-toluenesulfonyl chloride in pyridine.
Primary alcohols (R-CH2-OH) can be oxidized either to aldehydes (R-CHO) or to carboxylic acids (R-CO2H), while the oxidation of secondary alcohols (R1R2CH-OH) normally terminates at the ketone (R1R2C=O) stage. Tertiary alcohols (R1R2R3C-OH) are resistant to oxidation.
The direct oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (R-CH(OH)2) by reaction with water before it can be further oxidized to the carboxylic acid.
Reagents useful for the transformation of primary alcohols to aldehydes are normally also suitable for the oxidation of secondary alcohols to ketones. These include Collins reagent and Dess-Martin periodinane. The direct oxidation of primary alcohols to carboxylic acids can be carried out using potassium permanganate or the Jones reagent.
Ethanol in alcoholic beverages has been consumed by humans since prehistoric times for a variety of hygienic, dietary, medicinal, religious, and recreational reasons. The consumption of large doses of ethanol causes drunkenness (intoxication), which may lead to a hangover as its effects wear off. Depending upon the dose and the regularity of its consumption, ethanol can cause acute respiratory failure or death. Because ethanol impairs judgment in humans, it can be a catalyst for reckless or irresponsible behavior. The LD50 of ethanol in rats is 10.3 g/kg.[9]
Ethanol's toxicity is largely caused by its primary metabolite; acetaldehyde[10][11] and secondary metabolite; acetic acid.[12][13][14][11] All primary alcohols are broken down into aldehydes then to carboxylic acids, and whose toxicities are similar to acetaldehyde and acetic acid. Metabolite toxicity is reduced in rats fed N-acetylcysteine[10][15] and thiamine[16].
Some secondary and tertiary alcohols are less poisonous than ethanol because the liver is unable to metabolise them into these toxic by-products. This makes them more suitable for recreational[17][18] and medicinal[19] use as the chronic harms are lower. Ethchlorvynol is a good example of a tertiary alcohol which saw both medicinal and recreational use.
Other alcohols are substantially more poisonous than ethanol, partly because they take much longer to be metabolized and partly because their metabolism produces substances that are even more toxic. Methanol (wood alcohol), for instance, is oxidized to formaldehyde and then to the poisonous formic acid in the liver by alcohol dehydrogenase and formaldehyde dehydrogenase enzymes, respectively; accumulation of formic acid can lead to blindness or death.[20] Likewise, poisoning due to other alcohols such as ethylene glycol or diethylene glycol are due to their metabolites, which are also produced by alcohol dehydrogenase.[21][22] An effective treatment to prevent toxicity after methanol or ethylene glycol ingestion is to administer ethanol. Alcohol dehydrogenase has a higher affinity for ethanol, thus preventing methanol from binding and acting as a substrate. Any remaining methanol will then have time to be excreted through the kidneys.[20][23][24]
Methanol itself, while poisonous, has a much weaker sedative effect than ethanol. Some longer-chain alcohols such as n-propanol, isopropanol, n-butanol and t-butanol do, however, have stronger sedative effects, but also have higher toxicity than ethanol.[25][26] These longer chain alcohols are found as contaminants in some alcoholic beverages and are known as fusel alcohols,[27][28] and are reputed to cause severe hangovers although it is unclear if the fusel alcohols are actually responsible.[29] Many longer chain alcohols are used in industry as solvents and are occasionally abused by alcoholics,[30][31] leading to a range of adverse health effects.[32]
Alcohol has been found outside the Solar System. It can be found in low densities in star and planetary system forming regions of space.[33]
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This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)
Dansk (Danish)
n. - alkohol, sprit
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Ελληνική (Greek)
n. - (χημ., μτφ.) αλκοόλ(η), οινόπνευμα
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Português (Portuguese)
n. - álcool (m) (Quím.)
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Русский (Russian)
спирт, алкоголь
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Español (Spanish)
n. - alcohol, bebida alcohólica
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Svenska (Swedish)
n. - alkohol
中文(简体)(Chinese (Simplified))
酒精, 含酒精饮料, 醇, 酒
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中文(繁體)(Chinese (Traditional))
n. - 酒精, 含酒精飲料, 醇, 酒
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日本語 (Japanese)
n. - アルコール, アルコール飲料, 酒類
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العربيه (Arabic)
(الاسم) كحول
עברית (Hebrew)
n. - אלכוהול, כוהל
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