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dextro-gamma-tocopherol
Dextro-gamma-tocopherol is a tocopherol derivative characterized by antioxidant and skin-conditioning properties used primarily in cosmetic formulations.
General Material Description
Dextro-gamma-tocopherol is a stereoisomer of gamma-tocopherol, part of the tocopherol family known for vitamin E activity. It appears as a lipophilic compound with the molecular formula C28H48O2, featuring a chromanol ring and a long aliphatic side chain. Its chemical structure relates to a 2H-1-benzopyran-6-ol backbone with trimethyl substitutions and distinct chiral centers. Sensory-wise, tocopherols typically present minimal odor; the compound’s primary uses lie beyond aroma contribution. The compound is synonymous with (+)-gamma-tocopherol, d-gamma-tocopherol, and similar stereochemical descriptors. Sourced mainly from natural oils rich in tocopherols or synthesized for cosmetic formulations, it is referenced by controlled vocabularies such as ChEBI.
Occurrence, Applicability & Potential Uses
Dextro-gamma-tocopherol occurs naturally in various vegetable oils and plant-derived materials as part of the vitamin E complex. It functions primarily as an antioxidant, protecting lipids and cellular components from oxidative damage. Its biological relevance includes potential roles in maintaining membrane stability. In applied contexts, it is utilized in cosmetic products for its antioxidant capacity and skin-conditioning benefits. Regulatory standards such as REACH (EU) guide its safety evaluation, with recommendations against its use as a fragrance or flavor additive. This compound's lipophilicity supports its formulation in oil-based cosmetic agents, contributing to product stability and skin protection.
Physico-Chemical Properties Summary
Dextro-gamma-tocopherol exhibits significant lipophilicity, indicated by a high estimated log P value around 11.4, confirming its solubility predominance in nonpolar, oily media. Its molecular weight is approximately 416.7 Da, consistent with a large aliphatic structure coupled with a chromanol ring. The compound has extremely low water solubility, estimated near 1 µg/L at 25 °C, reinforcing its preference for lipid phases. Its flash point is approximately 403 °F (206 °C), suggesting stability under typical cosmetic processing temperatures. These properties influence its formulation compatibility, favoring inclusion in oil-phase cosmetic and pharmaceutical products where antioxidant stability is required.
FAQ
What is dextro-gamma-tocopherol and what are its primary characteristics?
Dextro-gamma-tocopherol is a chemically distinct stereoisomer of gamma-tocopherol, classified within the vitamin E family of compounds. It possesses a chromanol ring structure with a long aliphatic side chain and multiple chiral centers. This compound is known for its lipophilic nature and antioxidant properties. It primarily contributes to product stability in cosmetic formulations and serves skin-conditioning roles due to its chemical structure.
Where is dextro-gamma-tocopherol found and how is it typically used?
This tocopherol is naturally present in plant oils and certain biological materials rich in vitamin E. It is widely incorporated into cosmetic products as an antioxidant and skin-conditioning agent, where it helps to inhibit oxidative degradation of ingredients and supports skin health. Its high lipid solubility makes it especially suited for oil-based formulations. Regulatory guidance limits its use to cosmetic applications and excludes it from flavor or fragrance use.
What are the regulatory considerations and sourcing for dextro-gamma-tocopherol?
Dextro-gamma-tocopherol is regulated by frameworks such as REACH in the European Union, which governs its manufacturing, import, and safety evaluation in cosmetic products. Official classification records indicate no identified hazards under OSHA standards (US). It is generally sourced either via extraction from natural oils rich in tocopherols or through controlled synthetic processes. Safety data sheets indicate no specific precautionary statements, and usage recommendations restrict its application to non-flavor and non-fragrance contexts.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 54-28-4 |
| Pubchem (cid): | 92729 |
| Pubchem (sid): | 135051177 |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| CHEMBL: | View |
| KEGG (GenomeNet): | C02483 |
| HMDB (The Human Metabolome Database): | Search |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | dextro-gamma-tocopherol |
| Trivial Name | (+)-γ-Tocopherol |
| Short Description | 2H-1-benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)- |
| Formula | C28 H48 O2 |
| CAS Number | 54-28-4 |
| ECHA Number | 200-201-5 |
| FDA UNII | 8EF1Z1238F |
| Nikkaji Number | J213.540J |
| Beilstein Number | 93072 |
| MDL | MFCD00066529 |
| xLogP3-AA | 10.30 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 416.68896484375 |
| Flash Point TCC Value | 206 °C TCC |
| logP (o/w) | 11.44 est |
| Solubility | |
| water, 1.069e-006 mg/L @ 25 °C (est) | Yes |
Safety Information
Safety information
| Preferred SDS: View | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| cosmetic agents | |||
| Recommendation for dextro-gamma-tocopherol usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for dextro-gamma-tocopherol flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| European Food Safety Authority (EFSA) reference(s): |
| Scientific Opinion on the re-evaluation of tocopherol-rich extract (E 306), a-tocopherol (E 307), ?-tocopherol (E 308) and d-tocopherol (E 309) as food additives View page or View pdf |
| EPI System: View |
| ClinicalTrials.gov:search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):54-28-4 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :92729 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol |
| Chemidplus:0000054284 |