(3S)-3,4-bis[(3-hydroxyphenyl)methyl](2,3,5-13C3)oxolan-2-one

• ChemBase编号: 168022
• 分子式: C18H18O4
• 平均质量: 301.31108451
• 单一同位素质量: 301.13057357
• SMILES: c1c(cc(cc1)CC1[13C@@H]([13C](=O)O[13CH2]1)Cc1cccc(c1)O)O
• Canonical SMILES: Oc1cccc(c1)C[13C@@H]1[13C](=O)O[13CH2]C1Cc1cccc(c1)O
• InChI: InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14?,17-/m0/s1/i11+1,17+1,18+1
• InChIKey: HVDGDHBAMCBBLR-AQPGKPQVSA-N

名称和登记号

名称

• IUPAC标准名: (3S)-3,4-bis[(3-hydroxyphenyl)methyl](2,3,5-^1^3C₃)oxolan-2-one
• IUPAC传统名: (3S)-3,4-bis[(3-hydroxyphenyl)methyl](2,3,5-^1^3C₃)oxolan-2-one
• 别名: (3R,4R)-rel-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanone-13C3; trans-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-Furanone-13C3; HPMF-13C3; trans-2,3-Bis(3-hydroxybenzyl)-γ-butyrolactone-13C3; rac Enterolactone -13C3

登记号

• CAS号: 918502-72-4
• PubChem SID: 162262154
• PubChem CID: 71316343

理论计算性质

• Acid pKa: 9.163039
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.6070313
• LogD (pH = 7.4): 3.5997064
• Log P: 3.607125
• 摩尔折射率: 82.708 cm^3
• 极化性: 32.213398 Å^3
• 极化表面积: 66.76 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Methanol
• 外观: Off-White Solid
• 熔点: 70-73°C

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - E558952

A labelled metabolite of sesame lignans (sesamin, sesamolin). Inhibits colonic cancer cell growth by inducing cell cycle arrest and apoptosis. Possible relationship between exposure and reduced risk of breast cancer.

参考文献

• Ayella, A. et al.: Nut. Res., 30, 762 (2010)
• Pianjing, P. et al.: J. Agric. Food Chem., 59, 212 (2010)
• Buck, K. et al.: Am. J. Clinic. Nut., 92, 141 (2010)