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

• ChemBase ID: 127528
• Molecular Formular: C28H48O2
• Molecular Mass: 416.67952
• Monoisotopic Mass: 416.36543078
• SMILES: C[C@H](CCC[C@H](C)CCCC(C)C)CCC[C@@]1(C)Oc2c(C)c(C)c(O)cc2CC1
• Canonical SMILES: C[C@H](CCC[C@@H](CCCC(C)C)C)CCC[C@]1(C)CCc2c(O1)c(C)c(c(c2)O)C
• InChI: InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1
• InChIKey: QUEDXNHFTDJVIY-DQCZWYHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
• IUPAC Traditional name: gamma-tocopherol
• Synonyms: (2R)-3,4-Dihydro-2,7,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol; (+)- 2,7,8-Trimethyl-(7-methyl-d3)-2-(4,8,12-trimethyltridecyl)-6-chromanol; (+)-γ-Tocopherol; (2R,4'R,8'R)-γ-Tocopherol; D-γ-Tocopherol; all-(R)-γ-Tocopherol; γ-Tocopherol; (R,R,R)-γ-Tocopherol; 7,8-Dimethyltocol; (+)-γ-Tocopherol; Gamma-Tocopherol; (R,R,R)-γ-生育酚; 7,8-二甲基母育酚; (+)-γ-生育酚

Database IDs

• CAS Number: 54-28-4
• EC Number: 200-201-5
• MDL Number: MFCD00066529
• Beilstein Number: 93072
• PubChem SID: 162221847; 24871422; 24899992
• PubChem CID: 92729
• Unique Ingredient Identifier: 8EF1Z1238F
• Wikipedia Title: Gamma-Tocopherol
• E Number: E308

CALCULATED PROPERTIES

• Acid pKa: 10.470461
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 9.994291
• LogD (pH = 7.4): 9.993929
• Log P: 9.994296
• Molar Refractivity: 130.3329 cm^3
• Polarizability: 51.216278 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Pale Yellow Oil
• Refractive Index: n20/D 1.505

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... HMGCR(3156)

Product Information

• Purity: ≥96% (HPLC); ≥97.0% (UV)
• Grade: analytical standard
• Packaging: ampule of 25 mg
• Empirical Formula (Hill Notation): C28H48O2

DETAILS

Sigma Aldrich - T1782

Biochem/physiol Actions
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 antioxidants 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.

Sigma Aldrich - 89560

Other Notes
Review: Vitamin E: Application of the principles of physical organic chemistry to the exploration of its structure and function1.

Toronto Research Chemicals - T526140

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

REFERENCES

• Emerson, et al.: Science, 83, 421 (1936)
• Bieri, J.G., et al.: J. Nutr., 104, 850 (1936)
• Jiang, Q., et al.: Am. J. Clin. Nutr., 74, 714 (1936)