Ascorbyl palmitate

Ascorbyl palmitate
IUPAC name [(2S)-2-[(2R)-4,5-Dihydroxy-3-oxo-2-furyl]-2-hydroxy-ethyl] hexadecanoate
Other names Ascorbyl palmitate L-Ascorbic acid 6-hexadecanoate 6-O-Palmitoylascorbic acid
Identifiers
Abbreviations	E304
CAS number	137-66-6 Y
PubChem	5282506
ChemSpider	16736579 Y
UNII	QN83US2B0N Y
ChEMBL	CHEMBL220190 Y
Jmol-3D images	Image 1
SMILES OC=1[C@H](OC(=O)C=1O)[C@@H](O)COC(=O)CCCCCCCCCCCCCCC
InChI InChI=1S/C22H38O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(24)28-16-17(23)21-19(25)20(26)22(27)29-21/h17,21,23,25-26H,2-16H2,1H3/t17-,21+/m0/s1 Y Key: QAQJMLQRFWZOBN-LAUBAEHRSA-N Y InChI=1/C22H38O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(24)28-16-17(23)21-19(25)20(26)22(27)29-21/h17,21,23,25-26H,2-16H2,1H3/t17-,21+/m0/s1 Key: QAQJMLQRFWZOBN-LAUBAEHRBD
Properties
Molecular formula	C22H38O7
Molar mass	414.533 g/mol
Appearance	White to yellowish colored powder
Melting point	116–117 °C
Solubility in water	Very slightly soluble in water; freely soluble in ethanol
Hazards
Flash point	178.1 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ascorbyl palmitate is an ester formed from ascorbic acid and palmitic acid creating a fat-soluble form of vitamin C. In addition to its use as a source of vitamin C, it is also used as an antioxidant food additive (E number E304). It is approved for use as a food additive in the EU^[1], USA ^[2] and Australia and New Zealand.^[3]

Ascorbyl palmitate taken orally is, in all probability, far less effective than the claims made by advertisers and marketers. This is due to the fact that ascorbyl palmitate is known to be broken down (through the digestive process) into ascorbic acid and palmitic acid (a saturated fatty acid) before being absorbed into the bloodstream. ^[4] Ascorbyl palmitate is also marketed as "vitamin C ester".

See also

• Ascorbyl stearate
• Vitamin C
• Mineral ascorbates

External links

• Bioavailability of Different Forms of Vitamin C (Ascorbic Acid)
• Information from the Linus Pauling Institute
• Record in the Household Products Database of NLM

References

1. ^ UK Food Standards Agency: "Current EU approved additives and their E Numbers". http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist. Retrieved 2011-10-27. 
2. ^ US Food and Drug Administration: "Listing of Food Additives Status Part I". http://www.fda.gov/Food/FoodIngredientsPackaging/FoodAdditives/FoodAdditiveListings/ucm091048.htm. Retrieved 2011-10-27. 
3. ^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". http://www.comlaw.gov.au/Details/F2011C00827. Retrieved 2011-10-27. 
4. ^ DeRitter E.; Cohen, N; Rubin, SH (1951). "Physiologic availability of dehydro-L-ascorbic acid and palmitoyl-L-ascorbic acid". Science 113 (2944): 628–631. doi:10.1126/science.113.2944.628. PMID 14845692.