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Α-Tocopheryl acetate

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Α-Tocopheryl acetate
Names
IUPAC name chroman-6-yl] acetate
Other names Tocopherol acetate
Vitamin E acetate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.369 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C31H52O3/c1-21(2)13-10-14-22(3)15-11-16-23(4)17-12-19-31(9)20-18-28-26(7)29(33-27(8)32)24(5)25(6)30(28)34-31/h21-23H,10-20H2,1-9H3/t22-,23-,31-/m1/s1Key: ZAKOWWREFLAJOT-CEFNRUSXSA-N
  • InChI=1/C31H52O3/c1-21(2)13-10-14-22(3)15-11-16-23(4)17-12-19-31(9)20-18-28-26(7)29(33-27(8)32)24(5)25(6)30(28)34-31/h21-23H,10-20H2,1-9H3/t22-,23-,31-/m1/s1Key: ZAKOWWREFLAJOT-CEFNRUSXBQ
SMILES
  • O=C(Oc2c(c(c1O(CCc1c2C)(C)CCC(C)CCC(C)CCCC(C)C)C)C)C
Properties
Chemical formula C31H52O3
Molar mass 472.743 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Tocopheryl acetate, also known as vitamin E acetate, is a common vitamin supplement with the molecular formula C31H52O3 (for 'α' form). It is the ester of acetic acid and tocopherol (vitamin E). It is often used in dermatological products such as skin creams. Tocopherol acetate is not oxidized and can penetrate through the skin to the living cells, where about 5% is converted to free tocopherol and provides beneficial antioxidant effects.

Tocopheryl acetate is used as an alternative to tocopherol itself because the phenolic hydroxyl group is blocked, providing a less acidic product with a longer shelf life. It is believed that the acetate is slowly hydrolyzed once it is absorbed into the skin, regenerating tocopherol and providing protection against the sun's ultraviolet rays.

References

  1. Linus Pauling Institute Research Report: All About E
  2. Beijersbergen van Henegouwen G, Junginger H, de Vries H (1995). "Hydrolysis of RRR-alpha-tocopheryl acetate (vitamin E acetate) in the skin and its UV protecting activity (an in vivo study with the rat)". J Photochem Photobiol B. 29 (1): 45–51. doi:10.1016/1011-1344(95)90251-1. PMID 7472802.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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