α-Tocopheryl acetate

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α-Tocopheryl acetate
RRR-α-Tocopheryl acetate
RRR-α-Tocopheryl acetate
Names
Preferred IUPAC name
(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-yl acetate
Other names
α-Tocopherol acetate
Vitamin E acetate
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.000.369 Edit this at Wikidata
UNII
  • 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/s1 checkY
    Key: ZAKOWWREFLAJOT-CEFNRUSXSA-N checkY
  • 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/s1
    Key: ZAKOWWREFLAJOT-CEFNRUSXBQ
  • O=C(Oc2c(c(c1O[C@](CCc1c2C)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)C)C
Properties
C31H52O3
Molar mass 472.743 g/mol
Appearance pale yellow, viscous liquid[1]
Melting point –27.5 °C[1]
Boiling point 240 °C decays without boiling[2]
insoluble[1]
Solubility soluble in acetone, chloroform, diethyl ether; poorly soluble in ethanol[1]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

α-Tocopheryl acetate (alpha-tocopherol acetate), also known as vitamin E acetate, is a form of

α-tocopherol.[2]

The

2019 outbreak of vaping-associated pulmonary injury (VAPI),[3] but there is not yet sufficient evidence to rule out contributions from other chemicals.[4][5] Vaporization of this ester produces toxic pyrolysis products.[6]

Use in cosmetics

α-Tocopheryl acetate is often used in

Hoffmann-La Roche.[9]

Although there is widespread use of tocopheryl acetate as a topical medication, with claims for improved wound healing and reduced scar tissue,[10] reviews have repeatedly concluded that there is insufficient evidence to support these claims.[11][12] There are reports of vitamin E-induced allergic contact dermatitis from use of vitamin E derivatives such as tocopheryl linoleate and tocopherol acetate in skin care products. Incidence is low despite widespread use.[13]

Misuse

Ingredient in vape liquids

See also:
2019–20 vaping lung illness outbreak, Vaping-associated pulmonary injury, and Lacing (drugs) § Cannabis

On September 5, 2019, the United States

alkenes and benzene, but also exceptionally toxic ketene gas, which may be a contributing factor to the pulmonary injuries.[6]

Chemistry

At room temperature, α-tocopheryl acetate is a fat-soluble liquid. It has 3

α-tocopherol with acetic acid. 2R,4R,8R-isomer, also known as RRR-α-tocopheryl acetate, is the most common isomer used for various purposes. This is because α-tocopherol occurs in nature primarily as RRR-α-tocopherol.[2]

α-Tocopherol acetate does not boil at

UV-radiation. It has a refractive index of 1.4950–1.4972 at 20 °C.[1]

α-Tocopherol acetate is

hydrolyzed to α-tocopherol and acetic acid under suitable conditions or when ingested by people.[2]

References

  1. ^
    ISBN 9780911910124
    .
  2. ^
    doi:10.2903/j.efsa.2016.4412
    .
  3. ^ a b c "Transcript of CDC Telebriefing: Update on Lung Injury Associated with E-cigarette Use, or Vaping". Centers for Disease Control and Prevention. November 8, 2019.Public Domain This article incorporates text from this source, which is in the public domain.
  4. S2CID 218878143
    .
  5. ^ a b "Outbreak of Lung Injury Associated with E-Cigarette Use, or Vaping". Centers for Disease Control and Prevention. November 8, 2019.Public Domain This article incorporates text from this source, which is in the public domain.
  6. ^
    PMID 32156732
    .
  7. ^ Linus Pauling Institute Research Report: All About E at the Wayback Machine (archived February 23, 2015)
  8. PMID 7472802
    .
  9. ISSN 0018-019X
    .
  10. S2CID 45771699
    .
  11. PMID 26044054
    .
  12. PMID 26977069
    .
  13. S2CID 38212099
    .
  14. ^ Sun L (September 6, 2019). "Contaminant found in marijuana vaping products linked to deadly lung illnesses, tests show". Washington Post. Retrieved September 9, 2019.
  15. ^ "Three Companies Subpoenaed in Weed Vape Illness Investigation". Rolling Stone. September 10, 2019.
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