3-O-Ethylascorbic acid
[CAS# 86404-04-8]

Identification

• Classification: Food additive >> Antioxidants
• Name: 3-O-Ethylascorbic acid
• Synonyms: (5R)-5-[(1S)-1,2-Dihydroxyethyl]-4-ethoxy-3-hydroxy-5H-furan-2-one; 3-O-Ethyl-L-ascorbic acid
• Molecular Formula: C₈H₁₂O₆
• Molecular Weight: 204.18
• CAS Registry Number: 86404-04-8
• EC Number: 617-849-3
• SMILES: CCOC1=C(C(=O)O[C@@H]1[C@H](CO)O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

3-O-Ethylascorbic acid, also known as ethyl ascorbic acid, is a stable derivative of vitamin C (ascorbic acid) that has garnered significant attention in the cosmetic and pharmaceutical industries. Its discovery and subsequent applications have highlighted its effectiveness in various skincare products and medical treatments.

3-O-Ethylascorbic acid is chemically modified to enhance the stability and efficacy of traditional vitamin C. Vitamin C is well-known for its antioxidant properties and its role in collagen synthesis, making it a vital ingredient in skincare and anti-aging products. However, pure vitamin C is highly unstable and prone to oxidation when exposed to air, light, and heat. To overcome these limitations, scientists developed 3-O-Ethylascorbic acid by attaching an ethyl group to the third carbon position of the ascorbic acid molecule. This modification significantly improves its stability without compromising its beneficial properties.

The discovery of 3-O-Ethylascorbic acid can be traced to ongoing research aimed at creating more stable and effective forms of vitamin C for topical applications. The ethyl group protects the ascorbic acid from premature oxidation, ensuring that it remains potent when applied to the skin. This innovation has allowed for the development of a wide range of skincare products that can deliver the full benefits of vitamin C.

In skincare, 3-O-Ethylascorbic acid is celebrated for its ability to brighten the skin, reduce hyperpigmentation, and protect against UV-induced damage. It works by inhibiting the enzyme tyrosinase, which plays a key role in melanin production, thereby helping to lighten dark spots and even out skin tone. Additionally, its antioxidant properties help to neutralize free radicals, which are unstable molecules that can cause oxidative stress and premature aging. By protecting the skin from oxidative damage, 3-O-Ethylascorbic acid aids in maintaining a youthful and radiant complexion.

Moreover, 3-O-Ethylascorbic acid is also effective in promoting collagen synthesis. Collagen is a structural protein that provides the skin with elasticity and firmness. As we age, collagen production decreases, leading to the formation of wrinkles and sagging skin. By stimulating collagen production, 3-O-Ethylascorbic acid helps to reduce the appearance of fine lines and wrinkles, making it a popular ingredient in anti-aging formulations.

The application of 3-O-Ethylascorbic acid extends beyond cosmetic uses. In the pharmaceutical field, it is explored for its potential in wound healing and tissue repair. Its ability to promote collagen synthesis and its antioxidant properties make it a valuable component in treatments aimed at accelerating the healing process and improving skin regeneration.

References

2023. Biomolecular and cellular effects in skin wound healing: the association between ascorbic acid and hypoxia-induced factor. Journal of Biological Engineering, 17.
DOI: 10.1186/s13036-023-00380-6

2019. Suppression of riboflavin-sensitized singlet oxygen generation by l-ascorbic acid, 3-O-ethyl-l-ascorbic acid and Trolox. Journal of Photochemistry and Photobiology B: Biology, 192.
DOI: 10.1016/j.jphotobiol.2018.12.012

2014. A simple efficient synthesis and biological evaluation of 3-O-ethylascorbic acid. Bioscience, Biotechnology, and Biochemistry, 78(12).
DOI: 10.1080/09168451.2014.946396