gamma-Tocopherol

Title: g-Tocopherol
CAS Registry Number: 54-28-4; 7616-22-0 (dl-form)
CAS Name: (2R)-3,4-Dihydro-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol
Additional Names: (+)-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol; (R,R,R)-g-tocopherol; 7,8-dimethyltocol; o-xylotocopherol
Molecular Formula: C28H48O2
Molecular Weight: 416.68
Percent Composition: C 80.71%, H 11.61%, O 7.68%
Literature References: One of the naturally occurring forms of vitamin E, q.v. Most abundant tocopherol in soybean and corn oils. Isoln by fractional crystn: Emerson et al., Science 83, 421 (1936); J. Biol. Chem. 113, 319 (1936); J. G. Baxter et al., J. Am. Chem. Soc. 65, 918 (1943). Prepn of crystalline natural form: C. D. Robeson, J. Am. Chem. Soc. 65, 1660 (1943). Comparison of bioactivity with a-tocopherol, q.v.: J. G. Bieri, R. P. Evarts, J. Nutr. 104, 850 (1974). Protective effects vs reactive nitrogen oxide species: R. V. Cooney et al., Proc. Natl. Acad. Sci. USA 90, 1771 (1993); S. Christen et al., ibid. 94, 3217 (1997). HPLC determn in serum: A. Sobczak et al., J. Chromatogr. B 730, 265 (1999). Review of bioavailability, metabolism, and activity: Q. Jiang et al., Am. J. Clin. Nutr. 74, 714-722 (2001).
Properties: Pale yellow, viscous oil. Has been crystallized as transparent needles, mp -3 to -2°. bp0.1 200-210°. [a]546.125 -2.4° (c = 8.59 in benzene); [a]546.125 +2.2° (c = 9.32 in ethanol). uv max: 298 nm (E1%1cm 92.8). Insol in water. Freely sol in oils, fats, acetone, alcohol, chloroform, ether, other fat solvents. Very stable to heat and alkalies. Slowly oxidized by atmospheric oxygen, rapidly by ferric and silver salts. Gradually darkens on exposure to light.
Melting point: mp -3 to -2°
Boiling point: bp0.1 200-210°
Optical Rotation: [a]546.125 -2.4° (c = 8.59 in benzene); [a]546.125 +2.2° (c = 9.32 in ethanol)
Absorption maximum: uv max: 298 nm (E1%1cm 92.8)
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γ-Tocopherol[1]
Gamma-tocopherol.png
Identifiers
CAS number 54-28-4 YesY
PubChem 92729
UNII 8EF1Z1238F YesY
Jmol-3D images Image 1
Properties
Molecular formula C28H48O2
Molar mass 416.68 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

γ-Tocopherol is one of the chemical compounds that is considered vitamin E. As a food additive, it has E number E308.

See the main article tocopherol for more information.