CAS 54-28-4 (+)-gamma-Tocopherol (HCID 92729)

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Basic information

CAS: 54-28-4
Standard SMILES: Cc1c(O)cc2c(c1C)O[C@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)CC2
InChIKey: QUEDXNHFTDJVIY-DQCZWYHMSA-N
Molecular formula: C28H48O2
Average molar mass: 416.7 g/mol
Monoisotopic mass: 416.36543078

Overview

Gamma-tocopherol is a tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 7 and 8. It is found particularly in maize (corn) oil and soya bean (soybean) oils. It has a role as a plant metabolite, a food antioxidant and an algal metabolite. It is a tocopherol and a vitamin E.

Names & identifiers

Preferred name: (+)-gamma-Tocopherol
IUPAC: (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
English name: D-gamma-Tocopherol
Molecular formula: C28H48O2
Molecular weight: 416.68

Names & synonyms

gamma-Tocopherol54-28-4(+)-gamma-Tocopherol7,8-Dimethyltocolo-XylotocopherolGamma tocopherolDTXSID90490318EF1Z1238FJ213.540JDTXCID0028957CHEBI:18185(2R)-3,4-dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol

Show more names

VITAMIN E(GAMMA)(+)-γ-Tocopherol(+)-γ-TocopherolD-G-TOCOPHEROLD-γ-Tocopherol(+)-g-TocopherolD-GAMMA-TOCOPHEROLVITAMIN E(GAMMA)(RG)

(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-olRRR-gamma-Tocopherol(R,R,R)-gamma-Tocopherol(2R)-3,4-DIHYDRO-2,7,8-TRIMETHYL-2-((4R,8R)-4,8,12-TRIMETHYLTRIDECYL)-2H-1-BENZOPYRAN-6-OL2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-DTXSID5044075

Database identifiers

CAS

Properties

Computed structural properties

XLogP: 10.3
Topological polar surface area: 29.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 12
Heavy atoms: 30
Formal charge: 0
Complexity: 475

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Quinones and hydroquinones [PR02] -> Vitamin E [PR0202]

FragrancesFragrance Ingredient (2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-) -> IFRA transparency List

Solubility128 mg/mL

Boiling Point226.20 °C. @ 760.00 mm Hg

Melting Point-67.50 °C. @ 760.00 mm Hg

Refractive Index[n]D/20 1,503-1,507

Physicochemical properties

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (115 of 115) of all reports.

Not Classified

Aggregated GHS information provided per 115 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-

Regulation (EC) No 1333/2008 (amended)

2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-(4R,8R)-4,8,12-trimethyltridecyl-, (2R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationEvaluation - Tocopherols and their salts and esters

EPA Safer ChemicalChemical: D-gamma-Tocopherol

Hazard Classes and CategoriesNot Classified

Safety data

F: 8-10-23
PPE: Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
ridadr: UN1230 - class 3 - PG 2 - Methanol, solution
hs_code: 29362800
risk_code: 11-23/24/25-39/23/24/25
Signal word: Danger
Symbol(GHS): GHS02,GHS06,GHS08
hazard_code: F,T

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body.

Tissue LocationsAdipose Tissue

Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 4 items

EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Food additives

Fragrance Ingredients

General Manufacturing Information2H-1-Benzopyran-6-ol, 3,4-dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-: ACTIVE

Applications · 4 items

UsesOne of the naturally occurring forms of Vitamin E. Most abundant Tocopherol in soybean and corn oils.

Uses(+)-γ-Tocopherol has been used:as reference material for the quantification of γ-tocopherol in the oil sample using high performance liquid chromatography with diode array detector (HPLC/DAD)(192}as a component of diet to feed vitamin-E-depleted rats to study its effectsas an additive in the feed to study its effects in reducing dietary induced oxidative stress in vivo and improving meat lipid stability in broilers

UsesThis Certified Spiking Solution is suitable for use as a starting material in the preparation of linearity standards, calibrators, and controls in a variety of testing applications from diagnostic testing of Vitamin E deficiency by LC-MS/MS or HPLC to quality control testing of tocopherol-based dietary supplements or pharmaceutical preparations.