Alpha-Tocopherol Acetate

Alpha-Tocopherol Acetate

Cat Number
API0231523
CAS Number
7695-91-2

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CAS Number
7695-91-2
EINECS
231-710-0
Storage
Store at room temperature
Synonyms
Alfacol; Ecofrol; Contopheron; Tofaxin; Tocopherol acetate; Combinal E; Tokoferol acetate; (2R,4'R,8'R)-alpha-Tocopheryl acetate; 9E8X80D2L0; [(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] acetate
Molecular Formula
C31H52O3
Molecular Weight
472.7
Smiles
CC1=C(C(=C(C2=C1O[C@](CC2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)OC(=O)C)C
Appearance
Light yellow oily liquid
Boiling Point
485.3℃
General Description
Alpha-tocopherol acetate is the esterified, stabilized form of vitamin E, a fat-soluble antioxidant essential for human health. It is the most biologically active form of vitamin E and is commonly used in oral supplements and topical preparations. The acetate ester protects the active tocopherol from oxidation during storage and is hydrolyzed to free alpha-tocopherol following absorption.
Mechanism of Action
Following de-esterification in the small intestine, free alpha-tocopherol is incorporated into lipoproteins and functions as a chain-breaking antioxidant within cell membranes. It scavenges reactive oxygen species and prevents lipid peroxidation by donating a hydrogen atom to peroxyl radicals, thereby terminating free radical chain reactions. This activity preserves membrane integrity and protects polyunsaturated fatty acids, red blood cells, and neural tissues from oxidative damage.
Application
It is indicated for the treatment and prevention of vitamin E deficiency resulting from malabsorption syndromes such as cystic fibrosis, chronic cholestasis, and short bowel syndrome. It is also used as a nutritional supplement in patients with abetalipoproteinemia, where it helps prevent the progressive neurologic deterioration associated with this disorder. Topical formulations are employed for their moisturizing and antioxidant properties in cosmetic and dermatologic applications.

Antioxidant supplementation (alpha‑tocopherol acetate 2,000 IU/d plus crystalline ascorbate 500 mg/d) was compared to control (alpha‑tocopherol acetate 200 IU/d) in 392 feedlot heifers over 94 days. Supplementation tended to decrease dry matter intake (P=0.08) and improve feed efficiency (P=0.12) but did not affect average daily gain, liver abscess incidence (25.6% vs. 23.5%), hot carcass weight, or other carcass traits. The authors conclude that feeding these antioxidants at the tested doses is not a viable alternative to antibiotics for controlling liver abscesses in finishing cattle.

Fig. 1 Effect of liver abscess severity on HCW gain. (Müller HC, <i>et al</i>., 2018) Fig. 1 Effect of liver abscess severity on HCW gain. (Müller HC, et al., 2018)

References

  1. Müller HC, et al. Effect of alpha-tocopherol acetate and ascorbic acid on performance, carcass traits, and incidence and severity of liver abscesses in feedlot cattle. J Anim Sci. 2018; 96(9):3878-3883.

Interindividual variability of α‑tocopherol (vitamin E) metabolites was studied in 17 healthy volunteers before and after one week of supplementation with 800 IU/day RRR‑α‑tocopherol using LC‑MS/MS. Enzymatic metabolite levels showed marked interindividual variability that increased with supplementation. Most metabolites, except α‑CEHC and the long‑chain metabolites M1 and α‑13'OH, were not reliable as sensitive indicators of α‑tocopherol intake due to this variability. The free radical‑derived metabolite α‑tocopheryl quinone significantly correlated with post‑supplementation α‑tocopherol levels. Supplementation stimulated PXR expression in leukocytes, and baseline α‑tocopherol correlated with PXR. These findings provide critical analytical and molecular information on vitamin E metabolism and its intrinsic variability, which should be considered in future nutrigenomics and intervention studies.

Fig. 2 Chemical structure of the vitamin E compounds included in this metabolomics investigation. (Bartolini D, <i>et al</i>., 2021) Fig. 2 Chemical structure of the vitamin E compounds included in this metabolomics investigation. (Bartolini D, et al., 2021)

References

  1. Bartolini D, et al. Alpha-Tocopherol Metabolites (the Vitamin E Metabolome) and Their Interindividual Variability during Supplementation. Antioxidants (Basel). 2021; 10(2):173.

Does Alpha-Tocopherol Acetate require protection from light and oxygen?

Yes, while more stable than the free tocopherol, it can still undergo oxidative degradation upon prolonged exposure to light and air. Store in light-resistant, airtight containers.

What is the recommended storage temperature for Alpha-Tocopherol Acetate?

Store at controlled room temperature, between 15°C and 25°C. Avoid excessive heat, which can accelerate oxidation and cause color changes.

Is Alpha-Tocopherol Acetate stable in liquid-filled capsules?

Yes, it is commonly formulated in soft gelatin capsules. We provide compatibility data for various oils and recommend the use of antioxidants for extended shelf life.

How is the purity of Alpha-Tocopherol Acetate verified for dietary supplement use?

We use a validated HPLC method to monitor for related tocopherols and degradation products, ensuring compliance with USP specifications for potency and purity.
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