[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/%ce%b1-tocopheryl-acetate-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki24\/%ce%b1-tocopheryl-acetate-wikipedia\/","headline":"\u03b1-Tocopheryl acetate – Wikipedia","name":"\u03b1-Tocopheryl acetate – Wikipedia","description":"before-content-x4 From Wikipedia, the free encyclopedia \u03b1-Tocopheryl acetate Names Preferred IUPAC name after-content-x4 (2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-yl acetate after-content-x4 Other names \u03b1-Tocopherol acetateVitamin","datePublished":"2018-09-04","dateModified":"2018-09-04","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki24\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/c\/c2\/Tocopheryl_acetate.png\/220px-Tocopheryl_acetate.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/c\/c2\/Tocopheryl_acetate.png\/220px-Tocopheryl_acetate.png","height":"52","width":"220"},"url":"https:\/\/wiki.edu.vn\/en\/wiki24\/%ce%b1-tocopheryl-acetate-wikipedia\/","about":["Wiki"],"wordCount":5398,"articleBody":"     (adsbygoogle = window.adsbygoogle || []).push({});before-content-x4From Wikipedia, the free encyclopedia\u03b1-Tocopheryl acetateNamesPreferred IUPAC name       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4(2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-yl acetate       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4Other names\u03b1-Tocopherol acetateVitamin E acetateIdentifiersChEMBLChemSpiderDrugBankECHA InfoCard100.000.369 UNIIInChI=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\u00a0YKey:\u00a0ZAKOWWREFLAJOT-CEFNRUSXSA-N\u00a0YInChI=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:\u00a0ZAKOWWREFLAJOT-CEFNRUSXBQ       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4O=C(Oc2c(c(c1O[C@](CCc1c2C)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)C)CPropertiesC31H52O3Molar mass472.743 g\/molAppearancepale yellow, viscous liquid[1]Melting point\u201327.5 \u00b0C[1]Boiling point240 \u00b0C decays without boiling[2]insoluble[1]Solubilitysoluble in acetone, chloroform, diethyl ether; poorly soluble in ethanol[1]HazardsNFPA 704 (fire\u00a0diamond)Except where otherwise noted, data are given for materials in their standard state (at 25\u00a0\u00b0C [77\u00a0\u00b0F], 100\u00a0kPa).Chemical compound\u03b1-Tocopheryl acetate (alpha-tocopherol acetate), also known as vitamin E acetate, is a synthetic form of vitamin E. It is the ester of acetic acid and \u03b1-tocopherol.[2]The U.S. Centers for Disease Control and Prevention says that vitamin E acetate is a very strong culprit of concern in 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]Table of ContentsUse in cosmetics[edit]Ingredient in vape liquids[edit]Chemistry[edit]References[edit]Use in cosmetics[edit]\u03b1-Tocopheryl acetate is often used in dermatological products such as skin creams. It 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.[7] \u03b1-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.[8] Tocopheryl acetate was first synthesized in 1963 by workers at 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]Ingredient in vape liquids[edit]On September 5, 2019, the United States Food and Drug Administration (US FDA) announced that 10 out of 18, or 56% of the samples of vape liquids sent in by states, linked to the recent vaping-related lung disease outbreak in the United States, tested positive for vitamin E acetate[14] which had been used as a thickening agent by illicit THC vape cartridge manufacturers.[15] On November 8, 2019, the Centers for Disease Control and Prevention (CDC) identified vitamin E acetate as a very strong culprit of concern in the vaping-related illnesses, but has not ruled out other chemicals or toxicants as possible causes.[3] The CDC’s findings were based on fluid samples from the lungs of 29 patients with vaping-associated pulmonary injury, which provided direct evidence of vitamin E acetate at the primary site of injury in all the 29 lung fluid samples tested.[3] Research suggests when vitamin E acetate is inhaled, it may interfere with normal lung functioning.[5] A 2020 study found that vaporizing vitamin E acetate produced carcinogenic alkenes and benzene, but also exceptionally toxic ketene gas, which may be a contributing factor to the pulmonary injuries.[6]Chemistry[edit]At room temperature, \u03b1-tocopheryl acetate is a fat-soluble liquid. It has 3 chiral centers and thus 8 stereoisomers. It is made by esterifying \u03b1-tocopherol with acetic acid. 2R,4R,8R-isomer, also known as RRR-\u03b1-tocopheryl acetate, is the most common isomer used for various purposes. This is because \u03b1-tocopherol occurs in nature primarily as RRR-\u03b1-tocopherol.[2]\u03b1-Tocopherol acetate does not boil at atmospheric pressure and begins to degrade at 240\u00a0\u00b0C.[2] It can be vacuum distilled: it boils at 184\u00a0\u00b0C at 0.01\u00a0mmHg, at 194\u00a0\u00b0C (0.025\u00a0mmHg) and at 224\u00a0\u00b0C (0.3\u00a0mmHg). In practice, it is not degraded notably by air, visible light or UV-radiation. It has a refractive index of 1.4950\u20131.4972 at 20\u00a0\u00b0C.[1]\u03b1-Tocopherol acetate is hydrolyzed to \u03b1-tocopherol and acetic acid under suitable conditions or when ingested by people.[2]References[edit]^ a b c d e The Merck index (12th\u00a0ed.). Merck. 1996. p.\u00a01580. ISBN\u00a09780911910124.^ a b c d e “Safety assessment of the substance \u03b1-tocopherol acetate for use in food contact materials”. EFSA Journal. 14 (3): 4412. 2016. doi:10.2903\/j.efsa.2016.4412.^ a b c “Transcript of CDC Telebriefing: Update on Lung Injury Associated with E-cigarette Use, or Vaping”. Centers for Disease Control and Prevention. 8 November 2019. This article incorporates text from this source, which is in the public domain.^ Feldman, Ryan; Meiman, Jonathan; Stanton, Matthew; Gummin, David D. (June 2020). “Culprit or correlate? An application of the Bradford Hill criteria to Vitamin E acetate”. Archives of Toxicology. 94 (6): 2249\u20132254. doi:10.1007\/s00204-020-02770-x. ISSN\u00a01432-0738. PMID\u00a032451600. S2CID\u00a0218878143.^ a b “Outbreak of Lung Injury Associated with E-Cigarette Use, or Vaping”. Centers for Disease Control and Prevention. 8 November 2019. This article incorporates text from this source, which is in the public domain.^ a b Wu, D; O’Shea, DF (24 March 2020). “Potential for release of pulmonary toxic ketene from vaping pyrolysis of vitamin E acetate”. Proceedings of the National Academy of Sciences of the United States of America. 117 (12): 6349\u20136355. doi:10.1073\/pnas.1920925117. PMC\u00a07104367. PMID\u00a032156732.^ Linus Pauling Institute Research Report: All About E at the Wayback Machine (archived February 23, 2015)^ 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\u201351. doi:10.1016\/1011-1344(95)90251-1. PMID\u00a07472802.^ Mayer, H.; Schudel, P.; R\u00fcegg, R.; Isler, O. (1963). “\u00dcber die Chemie des Vitamins E. 3. Mitteilung. Die Totalsynthese von (2R, 4\u2032R, 8\u2032R)- und (2S, 4\u2032R, 8\u2032R)-\u03b1-Tocopherol”. Helvetica Chimica Acta. 46 (2): 650\u2013671. doi:10.1002\/hlca.19630460225. ISSN\u00a00018-019X.^ 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 (1): 443\u2013447. Bibcode:2004NYASA1031..443P. doi:10.1196\/annals.1331.069. PMID\u00a015753192. S2CID\u00a045771699.^ 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\u2013477. doi:10.1007\/s00403-015-1572-0. PMC\u00a04506744. PMID\u00a026044054.^ 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\u2013965. doi:10.1093\/asj\/sjw046. PMID\u00a026977069.^ Kosari P, Alikhan A, Sockolov M, Feldman SR (2010). “Vitamin E and allergic contact dermatitis”. Dermatitis. 21 (3): 148\u2013153. doi:10.2310\/6620.2010.09083. PMID\u00a020487657. S2CID\u00a038212099.^ Sun, Lena (September 6, 2019). “Contaminant found in marijuana vaping products linked to deadly lung illnesses, tests show”. Washington Post. Retrieved 2019-09-09.^ “Three Companies Subpoenaed in Weed Vape Illness Investigation”. Rolling Stone. September 10, 2019.       (adsbygoogle = window.adsbygoogle || []).push({});after-content-x4"},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/%ce%b1-tocopheryl-acetate-wikipedia\/#breadcrumbitem","name":"\u03b1-Tocopheryl acetate – Wikipedia"}}]}]