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

• ChemBase编号: 127528
• 分子式: C28H48O2
• 平均质量: 416.67952
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
• IUPAC传统名: gamma-tocopherol
• 别名: (R,R,R)-γ-生育酚; 7,8-二甲基母育酚; (+)-γ-生育酚; (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

登记号

• CAS号: 54-28-4
• EC号: 200-201-5
• MDL号: MFCD00066529
• Beilstein号: 93072
• PubChem SID: 162221847; 24871422; 24899992
• PubChem CID: 92729
• 美国药典/FDA物质标识码: 8EF1Z1238F
• 维基百科标题: Gamma-Tocopherol
• E编码: E308

理论计算性质

• Acid pKa: 10.470461
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 9.994291
• LogD (pH = 7.4): 9.993929
• Log P: 9.994296
• 摩尔折射率: 130.3329 cm^3
• 极化性: 51.216278 Å^3
• 极化表面积: 29.46 Å^2
• 可自由旋转的化学键: 12
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform
• 外观: Pale Pale Yellow Oil
• 折射率: n20/D 1.505

安全信息

• 保存条件: -20°C Freezer
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves
• 保存温度: -20°C; 2-8°C

药理学性质

• 相关基因信息: human ... HMGCR(3156)

产品相关信息

• 纯度: ≥96% (HPLC); ≥97.0% (UV)
• 级别: analytical standard
• 包装: ampule of 25 mg
• Empirical Formula (Hill Notation): C28H48O2

详细说明

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.

参考文献

• 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)