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Revision as of 13:40, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 459240436 of page Tocopheryl_acetate for the Chem/Drugbox validation project (updated: '').		Latest revision as of 15:17, 19 November 2024 edit 71.255.141.126 (talk)No edit summary
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			{{Short description|Vitamin}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			{{cs1 config|name-list-style=vanc}}
			{{lowercasetitle}}
			{{Use mdy dates|date=February 2024}}
	{{chembox		{{chembox
			| Name = α-Tocopheryl acetate
	| verifiedrevid = 419011964		| verifiedrevid = 470611314
	| ImageFile1 = Tocopheryl acetate.png		| ImageFile1 = Tocopheryl acetate.png
			| ImageAlt1 = RRR-α-Tocopheryl acetate
	| ImageSize1 = 200px
	| ImageFile2= Tocopheryl_acetate_3d_structure.png		| ImageFile2= Tocopheryl_acetate_3d_structure.png
			| ImageAlt2 = RRR-α-Tocopheryl acetate
	| ImageSize2 = 200px
	| IUPACName = chroman-6-yl] acetate		| PIN = (2''R'')-2,5,7,8-Tetramethyl-2--3,4-dihydro-2''H''-1-benzopyran-6-yl acetate
	| OtherNames = Tocopherol acetate <br>Vitamin E acetate		| OtherNames = α-Tocopherol acetate<br>Vitamin E acetate
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 77987		| ChemSpiderID = 77987
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
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	| StdInChIKey = ZAKOWWREFLAJOT-CEFNRUSXSA-N		| StdInChIKey = ZAKOWWREFLAJOT-CEFNRUSXSA-N
	| CASNo = 58-95-7		| CASNo = 58-95-7
			| CASNo_Comment =RRR-α-isomer
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| PubChem = 86472		| PubChem = 86472
⚫	| SMILES = O=C(Oc2c(c(c1O(CCc1c2C)(C)CCC(C)CCC(C)CCCC(C)C)C)C)C
			| DrugBank = DB14003
		⚫	| SMILES = O=C(Oc2c(c(c1O(CCc1c2C)(C)CCC(C)CCC(C)CCCC(C)C)C)C)C
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>31</sub>H<sub>52</sub>O<sub>3</sub>		| Formula = C<sub>31</sub>H<sub>52</sub>O<sub>3</sub>
	| MolarMass = 472.743 g/mol		| MolarMass = 472.743 g/mol
	| Appearance =		| Appearance =pale yellow, viscous liquid<ref name=m/>
	| Density =		| Density =
	| MeltingPt =		| MeltingPt =–27.5 °C
			| MeltingPt_ref =<ref name=m/>
	| BoilingPt =
	| Solubility =		| BoilingPt =240 °C
			| BoilingPt_notes =decays without boiling<ref name=eu/>
			| Solubility =insoluble<ref name=m/>
			| SolubleOther =soluble in ], ], ]; poorly soluble in ]<ref name=m/>
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards =		| NFPA-H = 1
	| FlashPt =		| NFPA-F = 1
	| Autoignition =		| NFPA-R = 0
			| MainHazards =
			| FlashPt =
			| AutoignitionPt =
	}}		}}
	}}		}}
			'''α-Tocopheryl acetate''' ('''''alpha''-tocopherol acetate'''), also known as '''vitamin E acetate''', is a form of ] with D-Alpha Tocopheryl Acetate as the natural form and DL-Alpha Tocopheryl Acetate as the synthetic form. DL-indicates the synthetic form where as D- indicates the natural form. It is the ] of ] and {{nowrap|]}}.<ref name=eu/>
			The ] says that vitamin E acetate is a very strong culprit of concern in the ] of ] (VAPI),<ref name=CDC----2019/> but there is not yet sufficient evidence to rule out contributions from other chemicals.<ref>{{cite journal|last1=Feldman|first1=Ryan|last2=Meiman|first2=Jonathan|last3=Stanton|first3=Matthew|last4=Gummin|first4=David D.|date=June 2020|title=Culprit or correlate? An application of the Bradford Hill criteria to Vitamin E acetate|journal=Archives of Toxicology|volume=94|issue=6|pages=2249–2254|doi=10.1007/s00204-020-02770-x|issn=1432-0738|pmid=32451600|s2cid=218878143}}</ref><ref name=CDC2019/> Vaporization of this ester produces toxic ] products.<ref name=pmid32156732/>
			==Use in cosmetics==
			α-Tocopheryl acetate is often used in ] ] 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 ]. Claims are made for beneficial antioxidant effects.<ref>{{webarchive |url=https://web.archive.org/web/20150223105720/http://lpi.oregonstate.edu/fw04/allaboute.html|date=February 23, 2015|title=Linus Pauling Institute Research Report: All About E }}</ref> α-Tocopheryl acetate is used as an alternative to tocopherol itself because the ]ic ] is blocked, providing a less acidic product with a longer shelf life. It is believed that the acetate is slowly ] after it is absorbed into the skin, regenerating tocopherol and providing protection against the sun's ] rays.<ref>{{cite journal |vauthors=Beijersbergen van Henegouwen G, Junginger H, de Vries H |title=Hydrolysis of RRR-alpha-tocopheryl acetate (vitamin E acetate) in the skin and its UV protecting activity (an in vivo study with the rat) |journal=J Photochem Photobiol B |volume=29 |issue=1 |pages=45–51 |year=1995 |pmid=7472802 |doi=10.1016/1011-1344(95)90251-1}}</ref> Tocopheryl acetate was first synthesized in 1963 by workers at ].<ref name="MayerSchudel1963">{{cite journal|last1=Mayer|first1=H.|last2=Schudel|first2=P.|last3=Rüegg|first3=R.|last4=Isler|first4=O.|title=Über die Chemie des Vitamins E. 3. Mitteilung. Die Totalsynthese von (2''R'', 4''′R'', 8''′R'')- und (2''S'', 4''′R'', 8''′R'')-α-Tocopherol|journal=Helvetica Chimica Acta|volume=46|issue=2|year=1963|pages=650–671|issn=0018-019X|doi=10.1002/hlca.19630460225}}</ref>
			Although there is widespread use of tocopheryl acetate as a ], with claims for improved ] and reduced ] tissue,<ref>{{cite journal |vauthors=Panin G, Strumia R, Ursini F |title=Topical alpha-tocopherol acetate in the bulk phase: eight years of experience in skin treatment |journal=Ann. N. Y. Acad. Sci. |volume=1031 |pages=443–447 |date=2004 |issue=1 |pmid=15753192 |doi=10.1196/annals.1331.069 |bibcode=2004NYASA1031..443P |s2cid=45771699 |s2cid-access=free |url=https://images-na.ssl-images-amazon.com/images/I/B2tgqw5FeaS.pdf }}</ref> reviews have repeatedly concluded that there is insufficient evidence to support these claims.<ref>{{cite journal |vauthors=Sidgwick GP, McGeorge D, Bayat A |title=A comprehensive evidence-based review on the role of topicals and dressings in the management of skin scarring |journal=Arch. Dermatol. Res. |volume=307 |issue=6 |pages=461–477 |year=2015 |pmid=26044054 |pmc=4506744 |doi=10.1007/s00403-015-1572-0 |doi-access=free }}</ref><ref>{{cite journal |vauthors=Tanaydin V, Conings J, Malyar M, van der Hulst R, van der Lei B |title=The Role of Topical Vitamin E in Scar Management: A Systematic Review |journal=Aesthet Surg J |volume=36 |issue=8 |pages=959–965 |date=2016 |pmid=26977069 |doi=10.1093/asj/sjw046|doi-access=free }}</ref> There are reports of vitamin E-induced allergic contact dermatitis from use of vitamin E derivatives such as ] and tocopherol acetate in skin care products. Incidence is low despite widespread use.<ref>{{cite journal |vauthors=Kosari P, Alikhan A, Sockolov M, Feldman SR |title=Vitamin E and allergic contact dermatitis |journal=Dermatitis |volume=21 |issue=3 |pages=148–153 |date=2010 |pmid=20487657 |doi=10.2310/6620.2010.09083|s2cid=38212099 }}</ref>
			==Misuse==
			===Ingredient in vape liquids===
			{{also|2019–20 vaping lung illness outbreak|Vaping-associated pulmonary injury|Lacing (drugs)#Cannabis}}
			On September 5, 2019, the United States ] (US FDA) announced that 10 out of 18, or 56% of the samples of vape liquids sent in by states, linked to ], tested positive for vitamin E acetate<ref>{{cite news|url=https://www.washingtonpost.com/health/2019/09/05/contaminant-found-vaping-products-linked-deadly-lung-illnesses-state-federal-labs-show/|title=Contaminant found in marijuana vaping products linked to deadly lung illnesses, tests show|last=Sun|first=Lena|date=September 6, 2019|newspaper=Washington Post|language=en|access-date=September 9, 2019}}</ref> which had been used as a thickening agent by ] THC vape cartridge manufacturers.<ref>{{cite magazine|url=https://www.rollingstone.com/culture/culture-features/vaping-honey-cut-mystery-thickener-vitamin-e-acetate-vapes-881896/|title=Three Companies Subpoenaed in Weed Vape Illness Investigation|date=September 10, 2019|magazine=Rolling Stone|language=en}}</ref> On November 8, 2019, the ] (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.<ref name=CDC----2019/> The CDC's findings were based on fluid samples from the lungs of 29 patients with ], which provided direct evidence of vitamin E acetate at the primary site of injury in all the 29 lung fluid samples tested.<ref name=CDC----2019>{{cite web|url=https://www.cdc.gov/media/releases/2019/t1108-telebriefing-vaping.html|title=Transcript of CDC Telebriefing: Update on Lung Injury Associated with E-cigarette Use, or Vaping|publisher=Centers for Disease Control and Prevention|date=November 8, 2019}}{{PD-notice}}</ref> Research suggests when vitamin E acetate is inhaled, it may interfere with normal lung functioning.<ref name=CDC2019>{{cite web|url=https://www.cdc.gov/tobacco/basic_information/e-cigarettes/severe-lung-disease.html|title=Outbreak of Lung Injury Associated with E-Cigarette Use, or Vaping|publisher=]|date=November 8, 2019}}{{PD-notice}}</ref> A 2020 study found that vaporizing vitamin E acetate produced carcinogenic ] and ], but also exceptionally toxic ] gas, which may be a contributing factor to the pulmonary injuries.<ref name=pmid32156732>{{cite journal|last1=Wu|first1=D|last2=O'Shea|first2=DF|date=March 24, 2020|title=Potential for release of pulmonary toxic ketene from vaping pyrolysis of vitamin E acetate|journal=Proceedings of the National Academy of Sciences of the United States of America|volume=117|issue=12|pages=6349–6355|doi=10.1073/pnas.1920925117|pmc=7104367|pmid=32156732|doi-access=free|bibcode=2020PNAS..117.6349W}}</ref>
			==Chemistry==
			At room temperature, α-tocopheryl acetate is a fat-soluble liquid. It has 3 ] and thus 8 ]. It is made by ]ifying ] with ]. 2''R'',4''R'',8''R''-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.<ref name=eu>{{cite journal|date=2016|title=Safety assessment of the substance α-tocopherol acetate for use in food contact materials|journal=EFSA Journal|volume=14|issue=3|pages=4412|doi=10.2903/j.efsa.2016.4412|doi-access=free}}</ref>
			α-Tocopherol acetate does not boil at ] and begins to degrade at 240&nbsp;°C.<ref name=eu/> It can be ]: it boils at 184&nbsp;°C at 0.01&nbsp;], at 194&nbsp;°C (0.025&nbsp;mmHg) and at 224&nbsp;°C (0.3&nbsp;mmHg). In practice, it is not degraded notably by ], ] or ]. It has a ] of 1.4950–1.4972 at 20&nbsp;°C.<ref name=m>{{cite book|title=The Merck index|date=1996|publisher=Merck|isbn=9780911910124|edition=12th|pages=1580|display-authors=et al}}</ref>
			α-Tocopherol acetate is ] to α-tocopherol and acetic acid under suitable conditions or when ingested by people.<ref name=eu/>
			== References ==
			{{Reflist}}
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