Tocopheryl acetate

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Structural formula
Structure of (R, R, R) -tocopheryl acetate
( R , R , R ) -isomer (structural formula of one of eight isomers)
General
Common name Vitamin E acetate
other names
  • Tocopheryl acetate
  • Tocopherol acetate
  • all rac -α-tocopheryl acetate
  • DL -α-tocopheryl acetate
Molecular formula C 31 H 52 O 3
CAS number
  • 7695-91-2 (racemate)
  • 58-95-7 (D-shape)
PubChem 86472
ATC code

A11 HA03

Brief description
  • crystalline, odorless substance (D-form)
  • colorless to yellow, odorless oil ( racemate )
Occurrence only synthetic
physiology
function antioxidant
Daily need Vitamin E equivalent
Consequences in case of deficiency see vitamin E.
Overdose > 300 mg / day
properties
Molar mass 472.76 g mol −1
Physical state
  • fixed (D-shape)
  • liquid (racemate)
density 0.9533 g cm −3
Melting point
  • 25 ° C (D-shape)
  • −27.5 ° C (racemate)
boiling point

Bp. 184 ° C at 0.01 mmHg (racemate)

solubility
safety instructions
Please note the restricted labeling requirements for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

α -Tocopheryl acetate ( vitamin E acetate ) is a synthetic vitamin E derivative . In the body it is converted to vitamin E and is therefore one of the provitamins .

structure

α-tocopheryl acetate is a Essigsäureester of Vitamin E . It contains three stereocenters , so there are eight stereoisomeric α-tocopheryl acetates. The commercially available α-tocopheryl acetate is a mixture of these isomers. This is usually referred to as all-rac -α-tocopheryl acetate, also outdated as DL - α -tocopheryl acetate .

In addition, there are three other derivatives (β, γ and δ) that differ in the methylation of the chroman ring . There are also eight stereoisomers of β-, γ- and δ-tocopheryl acetate.

Structure of the ( RRR ) isomers
Structural formula
Surname R 1 R 2
α-tocopheryl acetate CH 3 CH 3
β-tocopheryl acetate CH 3 H
γ-tocopheryl acetate H CH 3
δ-tocopheryl acetate H H

Manufacturing

The production of vitamin E acetate is a multi-step process. A possible synthetic chain based on 2,3,6-trimethylphenol is:

Vitamin E acetate is u. a. manufactured by BASF , E. Merck (India) and DSM Nutritional Products .

The synthetic provitamin E is also often used as a feed additive and an additive for cosmetics.

properties

α-Tocopheryl acetate is an oily, odorless, water-insoluble liquid. Since it is synthesized with a high degree of purity, it can also be used for the production of medicines. In contrast to natural vitamin E, α-tocopheryl acetate is relatively stable and can be stored for a longer period of time.

pharmacology

The provitamin itself has no effect as a fat-soluble antioxidant . The hydroxyl group required for this task is esterified in tocopheryl acetate and is therefore inaccessible. In the body, however, it is quickly converted into the active vitamin E by esterases . This also happens when it is absorbed through the skin. Here, however, the type of preparation plays a decisive role: with aqueous preparations, up to 50% can be absorbed, with oily preparations only less than 5%, where it can be converted into vitamin E.

In the USA in 2019, tocopherol acetate was added en masse in exclusively illegal cannabis products for e-cigarettes (so-called e-joints) as a blending agent and caused severe lung damage in a number of cases when inhaled.

Analytics

For a reliable qualitative and quantitative determination of tocopheryl acetate may for adequate sample preparation the gas chromatography or thin-layer chromatography may be used.

literature

Individual evidence

  1. a b c d e f g Michael Ash, Irene Ash: Handbook of preservatives. Synapse Information Resources, 2004, ISBN 1-890595-66-7 , p. 569.
  2. ^ A b David R. Lide: CRC Handbook of Chemistry and Physics . 87th edition, CRC Press, 2006, ISBN 0-8493-0487-3 , chap. 3, p. 520.
  3. Data sheet Vitamin E acetate from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
  4. a b Entry on tocopheryl acetate in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on May 14, 2017.
  5. a b Gekkan Yakuji. ( Pharmaceuticals Monthly. ) Vol. 9, Pg. 759, 1967.
  6. Data sheets for evaluating the effectiveness of active ingredients in cosmetic products - Vitamin E (PDF; 148 kB), Lebensmittelchemische Gesellschaft.
  7. ^ New York State Department of Health Announces Update on Investigation into Vaping-Associated Pulmonary Illnesses. New York State Department of Health press release, September 5, 2019 (accessed November 10, 2019)
  8. W. Wachs, H.-U. Melchert: A new method for the quantitative determination of tocopherols in vegetable oils . In: Deutsche Lebensmittel-Rundschau , 67 (7), 1971, pp. 221-225.
  9. Trevithick JR, Mitton KP: Topical application and uptake of vitamin E acetate by the skin and conversion to free vitamin E . In: Biochem Mol Biol Int. , 1993 Dec; 31 (5), pp. 869-878, PMID 8136705 .