T3634

(+)-α-Tocopherol

from vegetable oil, Type V, ~1000 IU/g

• Synonym(s): 2,5,7,8-Tetramethyl-2-(4′,8′,12′-trimethyltridecyl)-6-chromanol, 5,7,8-Trimethyltocol, D-α-Tocopherol, Vitamin E
• Empirical Formula (Hill Notation): C₂₉H₅₀O₂
• CAS Number: 59-02-9
• Molecular Weight: 430.71
• Beilstein: 4712525
• EC Number: 200-412-2
• MDL number: MFCD00072045
• UNSPSC Code: 12352205
• eCl@ss: 34058016
• PubChem Substance ID: 24900154
• NACRES: NA.79

Properties

• biological source: vegetable oil
• Quality Level: 200
• type: Type V
• form: viscous liquid
• specific activity: ~1000 IU/g
• color: clear yellow to red
• refractive index: n20/D 1.505 (lit.)
• bp: 200-220 °C/0.1 mmHg (lit.)
• density: 0.95 g/mL at 25 °C (lit.)
• storage temp.: −20°C
• SMILES string: CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2c(C)c(O)c(C)c(C)c2O1
• InChI: 1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1
• InChI key: GVJHHUAWPYXKBD-IEOSBIPESA-N

Description

General description

α-Tocopherol is synthesized from γ-tocopherol by the action of enzyme γ-tocopherol methyltransferase.[1] It is the major form of Vitamin E in human plasma. It is present in sunflower seed oil.[2]

This product is miscible with chloroform or ethanol. It is practically insoluble in water but it is miscible with ether, acetone, and vegetable oils. It is unstable to alkaline conditions.

Application

(+)-α-Tocopherol has been used:

• as a food supplement for juvenile cobia fish[3]
• to evaluate its protective effect on bisphenol A induced oxidative stress in rats[4]
• to test its chemopreventive efficacy in estrogen-mediated mammary cancer rats[5]

Biochem/physiol Actions

α-Tocopherol is essential for the photosynthesis in Synechocystis sp. strain PCC 6803.[1] Supplementation with α-Tocopherol decreases lipid peroxidation and platelet aggregation. It inhibits protein kinase C and may play key role in gene regulation.[6]

Tocopherols (TCP) (vitamin E) are a series (α, β, γ and δ) of chiral organic molecules that vary in their degree of methylation of the phenol moiety of the chromanol ring. Tocopherols are lipid soluble anti-oxidants that protect cell membranes from oxidative damage. α-Tocopherol is the form of tocopherol preferentially absorbed by homo sapiens. Various isofroms and analogues of tocopherol have opposing and differentiated regulatory activities in vivo.

Packaging

Packaged under argon in a sealed ampule.

Analysis Note

Approx. 670 mg D-α-tocopherol per gram. The non-α content is typically between 5-35 mg/g

Other Notes

Mixed constitutional (α, β, γ, δ) isomers.

Disclaimer

Subject to air oxidation.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 1
• Flash Point(F): 230.0 °F - closed cup
• Flash Point(C): 110 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves