Ascorbyl palmitate

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] the U.S.,[2] Canada,[3] Australia, and New Zealand.[4]

Ascorbyl palmitate
Names
IUPAC name
L-threo-Hex-2-enono-1,4-lactone 6-hexadecanoate
Systematic IUPAC name
(2S)-2-[(2R)-3,4-Dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl hexadecanoate
Other names
Ascorbyl palmitate
L-Ascorbic acid 6-hexadecanoate
6-O-Palmitoylascorbic acid
Identifiers
3D model (JSmol)
Abbreviations E304
ChEMBL
ChemSpider
ECHA InfoCard 100.004.824
E number E304 (antioxidants, ...)
UNII
  • 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 checkY
    Key: QAQJMLQRFWZOBN-LAUBAEHRSA-N checkY
  • 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
  • OC=1[C@H](OC(=O)C=1O)[C@@H](O)COC(=O)CCCCCCCCCCCCCCC
Properties
C22H38O7
Molar mass 414.539 g·mol−1
Appearance White to yellowish colored powder
Melting point 116 to 117 °C (241 to 243 °F; 389 to 390 K)
Very slightly soluble in water; freely soluble in ethanol
Hazards
Flash point 178.1 °C (352.6 °F; 451.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ascorbyl palmitate is also marketed as "vitamin C ester". It is synthesized by acylation of vitamin C using different acyl donors.[5]

See also

References
  1. UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.
  2. US Food and Drug Administration: "Listing of Food Additives Status Part I". Food and Drug Administration. Archived from the original on 2012-01-17. Retrieved 2011-10-27.
  3. Health Canada: "Chemical Substance - Ascorbyl palmitate". 26 July 2004. Retrieved 2016-08-13.
  4. Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.
  5. Karmee SK (January 2009). "Biocatalytic synthesis of ascorbyl esters and their biotechnological applications". Applied Microbiology and Biotechnology. 81 (6 Suppl): 1013–1022. doi:10.1007/s00253-008-1781-y. PMID 19030854. S2CID 35465409.
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