58 SKIN CARE
Synthetic Vitamin E
all-rac-α-tocopherol corresponds to all-racemic mixture which includes eight stereoisomers.
50% of the synthetic vitamin E contain isomers that are not bioavailable.
Other isomers (RSR, RRS, RSS) have limited activity and bioavailability.
Only 12.5% contains the active RRR isomer.
2 1 4 R configuration
clockwise 3
3 counterclockwise 1 4 S configuration
Figure 3: Synthetic and natural plant-based α-tocopherol stereochemistry comparison and migration.13
Vitamin E serves as a peroxyl
radical scavenger that protects polyunsaturated fatty acids (PUFAs) in membranes and lipoproteins from oxidative damage. Consequences of the peroxidation of
membrane-unsaturated fatty acids induced enzyme inactivation and modify physical properties of membranes including ion transport and fluidity. The antioxidant properties of vitamin E are exerted through its phenolic hydroxyl group, which donates hydrogen to peroxyl radicals, resulting in the formation of stable lipid species. Vitamin E scavenges peroxyl radicals and
terminates the oxidation of polyunsaturated fatty acids.14
In the presence of vitamin E,
peroxyl radicals react with α-tocopherol instead of lipid hydroperoxide, the chain reaction of peroxyl radical; vitamin sacrifices itself to protect the plasma membrane (Figure 1). Without vitamin E activity, a single initiating
event could potentially lead to the production of thousands of lipid peroxides which would have a deleterious effect on the biological membrane and its function but also on DNA mutation that may lead to many structural, functional and morphological changes in the skin, accelerating ageing and initiating the development of many diseases including erythema, hyperplasia, sunburn cell formation and photocarcinogenesis. Indeed, Vitamin E prevents sun burn cells Sunburn cells are keratinocytes
formation.15
undergoing apoptosis after they have received a physiological UVB dose that irreversibly and severely damaged their DNA or other chromophores. But also, UVA and UVB lead to the activation
of the transcription factor AP1 that induces the expression of metalloproteinases 1, which degrade collagen and alter the density of the dermis.16
All this cellular damage can be
grouped together under the term oxy-ageing, and vitamin E appears to be the reference physiological molecule for fighting against oxy- ageing in the skin.
Conclusion In conclusion, it appears that vitamin E is not ‘just
PERSONAL CARE May 2025 Figure 4: Vitamin E gradient and α/δ ratio in skin 2
Synthetic Vitamin E
Plant-based Vitamin E
RRR-a Tocopherol is 2x more biologically active than synthetic vitamin E
Natural Plant-based Vitamin E
Contains 100% of the active
RRR-α-tocopherol natural isomer and is more bioavailable.
RRR corresponds to the perfect alignment of CH3 methyl groups.
CH3 CH3 CH3
a single molecule’; it is a family of eight vitamers due to the three chiral carbons. Depending on the stereochemistry, the eight isomers have different level of biological activity in the body and different antioxidant power in skincare. Vitamin E could be used either as a functional
ingredient to protect cosmetic formulations or in the form of RRR-α-tocopherol as an active ingredient for protecting the skin cell plasma membranes. Vitamin E in its RRR-α-tocopherol form is a core protective skin care active ingredient that is suitable for dermatology and cosmetology topical products. Respectively, topical application of RRR-α-
tocopherol can protect the skin from oxidative stress induced by radiotherapy and by exposome leading to oxy-ageing and premature skin ageing. For all these reasons, RRR-α-tocopherol is the ‘vitamin E superstar’, which needs to regain its credentials and take its place on the vitamin podium alongside vitamins A and C.
References 1. Evans HM, Bishop KS. On the existence of a hitherto unrecognized dietary factor essential for reproduction. Science. 1922; 56: 650 – 651
2. Barnett S. Dietary requirements for reproduction: ii. The existence of a specific vitamin for reproduction. J Biol Chem. 1924; 58, 693–710
3. Evans HM, Emerson OH, Emerson GA. The isolation from wheat germ oil of an alcohol, a
tocopherol having the properties of vitamin E. J Biol Chem. 1936; 319-323
4. Toyokuni S, Noguchi N, Niki E. Editorial: Centennial anniversary of vitamin E discovery. Free Radical Biology and Medicine. April 2022; Volume 183, Pages 125-126
5. Khadangui , Azzi A. Vitamin E. The next 100 years, IUBMM Life. 2019; 71, 4, 2019, 411-415
6. Azzi A. Many tocopherols, one vitamin. Mol Aspects Med. 2018; 61, 92-103
7. Blaner WS. Vitamin E: the enigmatic one! Journal of Lipid Research. 2013; Volume 54
8. Sontag TJ, Parker RS. Cytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. J Biol Chem. 2002 ; 277: 25290 – 25296
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9. Thiele JJ, Traber MG, Packer L. Depletion of human stratum corneum vitamin E: an early and sensitive in vivo marker of UV induced photo-oxidation. J Invest Dermatol. 1998 ; 110, 756-761
10. Thiele JJ, Weber U, Packer L. Sebaceous gland secretion is a major physiologic route of vitamin E delivery to skin. J Invest Dermatol. 1999; 113, 1006-1010
11. Thiele JJ, Traber MG, Packer L. Depletion of human stratum corneum vitamin E. An early and sensitive in vivo marker of UV-induced photooxidation. J Invest Dermatol. 1998; 110, 1998, 756-761
12. Thiele JJ, Traber MG, Polefka TG, Cross CE, Packer LP. Ozone exposure depletes vitamin E and induced lipid peroxidation in murine stratum corneum. J Invest Dermatol. 108, 1997, 753-757
13. Maxfield F, Tabas I. Role of cholesterol and lipid organization in Disease. Nature. 2005; Vol 438(1)
14. Miyazawa T et al. Vitamin E: Regulatory Redox Interactions. IUBMB Life. 2019; Apr;71(4):430-441
15. Lin et al. UV photoprotection by combination topical antioxidants vitamin C and vitamin E. J Am Acad Dermatol. 2003; Jun;48(6):866-74
16. Stojiljković D et al. Oxidative Stress, Skin Aging and Antioxidant Therapy. Scientific Journal of the Faculty of Medicine in Niš. 2014;31(4): 207-217
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