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
SMILES	OC([C@]([C@@H](O)COC(CCCCCCCCCCCCCCC)=O)([H])O1)=C(O)C1=O
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 (what is this?)  (verify) 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). Oral supplements of ascorbyl palmitate are less effective, due to the substance breaking down again into its components before being digested^[1]. Ascorbyl palmitate is also marketed as "vitamin C ester. The Linus Pauling Institute notes the following: Ascorbyl palmitate is a fat-soluble antioxidant used to increase the shelf life of vegetable oils and potato chips (8). It is an amphipathic molecule, meaning one end is water-soluble and the other end is fat-soluble. This dual solubility allows it to be incorporated into cell membranes. When incorporated into the cell membranes of human red blood cells, ascorbyl palmitate has been found to protect them from oxidative damage and to protect alpha-tocopherol (a fat-soluble antioxidant) from oxidation by free radicals (9). However, the protective effects of ascorbyl palmitate on cell membranes have only been demonstrated in the test tube. Taking ascorbyl palmitate orally probably doesn't result in any significant incorporation into cell membranes because most of it appears to be hydrolyzed (broken apart into palmitate and ascorbic acid) in the human digestive tract before it is absorbed. The ascorbic acid released by the hydrolysis of ascorbyl palmitate appears to be as bioavailable as ascorbic acid alone (10). The presence of ascorbyl palmitate in oral supplements contributes to the ascorbic acid content of the supplement and probably helps protect fat-soluble antioxidants in the supplement. The role of vitamin C in promoting collagen synthesis and its antioxidant properties have generated interest in its use on the skin. Ascorbyl palmitate is frequently used in topical preparations because it is more stable than some aqueous (water-soluble) forms of vitamin C (11). Ascorbyl palmitate is also marketed as, "vitamin C ester," which should not be confused with Ester-C®.

See also

• Ascorbyl stearate
• Vitamin C

External links

• Information from the Linus Pauling Institute

References

1. ^ DeRitter E. Physiologic availability of dehydro-L-ascorbic acid and palmitoyl-L-ascorbic acid. Science. 1951;113:628-631.

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