Pristane
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(′pri′stān)
(organic chemistry) C19H40 A liquid soluble in such organic solvents as ether, petroleum ether, benzene, chloroform, and carbon tetrachloride; used as a lubricant, as an oil in transformers, and as an anticorrosion agent. Also known as norphytane.
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Pristane
| Pristane | |
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2,6,10,14-Tetramethylpentadecane[1] |
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Other names
Norphytane[citation needed] |
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| Identifiers | |
| CAS number | 1921-70-6  |
| PubChem | 15979 |
| ChemSpider | 15182 , 24531975 6R,10R , 21428537 6R,10S , 24531981 6S,10S |
| EC number | 217-650-8 |
| MeSH | pristane |
| ChEBI | CHEBI:53181 |
| RTECS number | RZ1880000 |
| Beilstein Reference | 1720538 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C19H40 |
| Molar mass | 268.52 g mol−1 |
| Appearance | Colourless, transparent liquid |
| Odor | Odourless |
| Density | 783 mg mL−1 |
| Melting point |
-100 °C, 173.2 K, -148 °F |
| Boiling point |
296 °C, 569 K, 565 °F |
| Refractive index (nD) | 1.438 |
| Thermochemistry | |
| Specific heat capacity, C | 569.76 J K−1 mol−1 |
| Hazards | |
| GHS pictograms |  |
| GHS signal word | WARNING |
| GHS hazard statements | H315 |
| EU classification |  Xi |
| R-phrases | R36/38 |
| S-phrases | S26, S36 |
| Flash point | >110 °C |
| Related compounds | |
| Related alkanes | |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Pristane is a natural saturated terpenoid alkane obtained primarily from shark liver oil, from which its name is derived (Latin pristis, "shark"). It is also found in mineral oil and some foods.[2] It is a transparent oily liquid that is immiscible with water, but soluble in diethyl ether, benzene, chloroform and carbon tetrachloride.
Pristane is known to induce autoimmune diseases in rodents. It is used in research to understand the pathogenesis of rheumatoid arthritis and lupus.[3][4] The fact that it is used in many products, raises the possibility that it may be a possible environmental exposure that triggers diseases such as lupus and rheumatoid arthritis.[5]
It is used as a lubricant, a transformer oil, an immunologic adjuvant, and an anti-corrosion agent, biological marker, plasmocytomas inducer and in production of monoclonal antibodies.
Biosynthetically, pristane is derived from phytol and is used as a biomarker in petroleum studies.[6]
References
- ^ "pristane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=15979&loc=ec_rcs#x291.
- ^ Chung, J. G., L. R. Garrett, P. E. Byers, and M. A. Cuchens (1989). "A survey of the amount of pristane in common fruits and vegetables". J. Food Comp. Anal. 2 (22): 22. doi:10.1016/0889-1575(89)90058-6.
- ^ Anderson, P. N., and M. Potter (1969). "Induction of plasma cell tumours in BALB-c mice with 2,6,10,14-tetramethylpentadecane (pristane)". Nature 222 (5197): 994. doi:10.1038/222994a0. PMID 5789334.
- ^ Hazani R, Engineer N. (Nov 2008). "Surreptitious injection of mineral oil: a case report of sclerosing lipogranulomatosis". Ann Plast Surg 61 (5): 555–8. doi:10.1097/SAP.0b013e31816d8316. PMID 18948786.
- ^ Frederick W Miller (2006). "Is occupational exposure to mineral oil a risk factor for rheumatoid arthritis?". Nature Clinical Practice Rheumatology 2 (3): 130–131. doi:10.1038/ncprheum0137. PMID 16932671.
- ^ Hunt, J. (2002). "Early developments in petroleum geochemistry". Organic Geochemistry 33: 1025–1052. doi:10.1016/S0146-6380(02)00056-6.
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