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Α-Tocopheryl acetate

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Α-Tocopheryl acetate
Names
IUPAC name
[(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]chroman-6-yl] acetate
Other names
Tocopherol acetate
Vitamin E acetate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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
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 ?)

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. Tocopheryl acetate is not oxidized and can penetrate through the skin to the living cells, where about 5% is converted to free tocopherol. Claims are made for beneficial antioxidant effects.[1] 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 after it is absorbed into the skin, regenerating tocopherol and providing protection against the sun's ultraviolet rays.[2] Tocopheryl acetate was first synthesized in 1963 by workers at Hoffmann-La Roche.[3]

Although there is widespread use of tocopheryl acetate as a topical medication, with claims for improved wound healing and reduced scar tissue,[4] reviews have repeatedly concluded that there is insufficient evidence to support these claims.[5][6] 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.[7]

On September 5th, 2019, the United States Food and Drug Administration (US FDA) announced that 10 out of 18, or 55.56% of the samples of cannabis-containing vape liquids sent in by states, linked to recent vaping related lung disease outbreak in the United States, tested positive for vitamin E acetate[8] which is being used as a thickening agent by some manufacturers.[9] The FDA announced that some state labs have found vitamin E acetate, but stressed that "[a]t this time, no one device, product, or substance has been linked to all cases."[10]


References

  1. ^ Linus Pauling Institute Research Report: All About E at the Wayback Machine (archived 2015-02-23)
  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.
  3. ^ Mayer, H.; Schudel, P.; Rüegg, R.; Isler, O. (1963). "Über die Chemie des Vitamins E. 3. Mitteilung. Die Totalsynthese von (2R, 4′R, 8′R)- und (2S, 4′R, 8′R)-α-Tocopherol". Helvetica Chimica Acta. 46 (2): 650–671. doi:10.1002/hlca.19630460225. ISSN 0018-019X.
  4. ^ Panin G, Strumia R, Ursini F (2004). "Topical alpha-tocopherol acetate in the bulk phase: eight years of experience in skin treatment". Ann. N. Y. Acad. Sci. 1031: 443–447. Bibcode:2004NYASA1031..443P. doi:10.1196/annals.1331.069. PMID 15753192.
  5. ^ Sidgwick GP, McGeorge D, Bayat A (2015). "A comprehensive evidence-based review on the role of topicals and dressings in the management of skin scarring". Arch. Dermatol. Res. 307 (6): 461–477. doi:10.1007/s00403-015-1572-0. PMC 4506744. PMID 26044054.
  6. ^ Tanaydin V, Conings J, Malyar M, van der Hulst R, van der Lei B (2016). "The Role of Topical Vitamin E in Scar Management: A Systematic Review". Aesthet Surg J. 36 (8): 959–965. doi:10.1093/asj/sjw046. PMID 26977069.
  7. ^ Kosari P, Alikhan A, Sockolov M, Feldman SR (2010). "Vitamin E and allergic contact dermatitis". Dermatitis. 21 (3): 148–153. PMID 20487657.
  8. ^ Sun, Lena (September 6, 2019). "Contaminant found in marijuana vaping products linked to deadly lung illnesses, tests show". Washington Post. Retrieved 2019-09-09.{{cite web}}: CS1 maint: url-status (link)
  9. ^ "Vague Warning to Stop Vaping E-Cigarettes is Incorrect and Irresponsible". The Globe Post. September 12, 2019.{{cite web}}: CS1 maint: url-status (link)
  10. ^ Centers for Disease Control and Prevention (September 6, 2019). "Transcript of September 6, 2019, Telebriefing: Investigation of Pulmonary Disease Among People Who Use E-cigarettes". www.cdc.gov. Retrieved 2019-09-09.{{cite web}}: CS1 maint: url-status (link)
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