Α-Tocopheryl acetate

Vitamin

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| Name = α Tocopheryl acetate
| verifiedrevid = 470611314
| ImageFile1 = Tocopheryl acetate. png
| ImageAlt1 = RRR α Tocopheryl acetate
| ImageFile2= Tocopheryl acetate 3d structure. png
| ImageAlt2 = RRR α Tocopheryl acetate
| PIN = (2R) 2,5,7,8 Tetramethyl 2 [(4R,8R) 4,8,12 trimethyltridecyl] 3,4 dihydro 2H 1 benzopyran 6 yl acetate
| OtherNames = α Tocopherol acetateVitamin E acetate
|Section1=
|Section2=Chembox Properties
| Formula = C31H52O3
| MolarMass = 472.743 g/mol
| Appearance =pale yellow, viscous liquid α 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. Tocopheryl acetate was first synthesized in 1963 by workers at Hoffmann La Roche. Although there is widespread use of tocopheryl acetate as a topical medication, with claims for improved wound healing and reduced scar tissue, reviews have repeatedly concluded that there is insufficient evidence to support these claims. 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.

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 which had been used as a thickening agent by illicit THC vape cartridge manufacturers. 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. Research suggests when vitamin E acetate is inhaled, it may interfere with normal lung functioning. 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.

At room temperature, α tocopheryl acetate is a fat soluble liquid. It has 3 chiral centers and thus 8 stereoisomers. It is made by esterifying 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. α Tocopherol acetate does not boil at atmospheric pressure and begins to degrade at 240 °C. α Tocopherol acetate is hydrolyzed to α tocopherol and acetic acid under suitable conditions or when ingested by people.