3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase编号: 1876
• 分子式: C21H20O9
• 平均质量: 416.3781
• 单一同位素质量: 416.11073222
• SMILES: OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)Oc1ccc2c(c1)occ(c2=O)c1ccc(O)cc1
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2)occ(c3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1
• InChIKey: KYQZWONCHDNPDP-QNDFHXLGSA-N

名称和登记号

名称

• IUPAC标准名: 3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC传统名: daidzin; 3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one; daidzein 7-O-β-D-glucoside
• 别名: Daidzein-7-O-β-D-glucopyranoside; Daidzin; Daidzoside; Daidzein 7-glucoside; Daidzein-7-glucoside; Daidzein 7-O-glucoside; 4',7-Dihydroxyisoflavone; 7-O-B-D-GLUCOPYRANOSIDE; 7-(beta-D-Glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 7-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one; Daidzin

登记号

• CAS号: 552-66-9
• EC号: 207-635-4
• MDL号: MFCD00017466
• Beilstein号: 59741
• PubChem SID: 24858323; 160965331; 46505206
• PubChem CID: 107971

理论计算性质

JChem

• Acid pKa: 8.962957
• 质子受体: 9
• 质子供体: 5
• LogD (pH = 5.5): 0.46222103
• LogD (pH = 7.4): 0.45072386
• Log P: 0.46236962
• 摩尔折射率: 101.8464 cm^3
• 极化性: 40.17439 Å^3
• 极化表面积: 145.91 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.71
• LOG S: -2.8
• 溶解度: 6.61e-01 g/l

分子性质

理化性质

• 外观: Powder

安全信息

• RTECS编号: DJ3094000; DJ3100040
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/38
• 安全公开号: 24-26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319
• GHS警示性声明: P305 + P351 + P338
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: mouse ... Aldh1a2(19378), Maoa(17161)rat ... Aldh1a2(116676)
• 生物活性机理: Antidipsotropic

产品相关信息

• 纯度: ≥95.0% (HPLC); ≥98.0% (HPLC)
• 级别: analytical standard
• 生物来源: Isol. from soya bean meal, roots of Pueraria lobata and shoots of Piptanthus nepalensis. Also from Baptisia spp., Glycine max, Medicago sativa, Thermopsis spp. and others in Leguminosae
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Cancer preventive and an alcohol dependency treatment
• Empirical Formula (Hill Notation): C21H20O9

详细说明

DrugBank - DB02115

Drug information: experimental

Sigma Aldrich - 30408

Biochem/physiol Actions
Daidzin is an isoflavone reported to have anti-oxidant, anti-carcinogenic, and anti-artherosclerotic activities. Daidzin is the major active component of the traditional Chinese medicine (TCM) derived from radix puerariae (Kudzu) that is commonly used to treat alcohol abuse. Daidzin is a potent and selective inhibitor of mitochondrial aldehyde dehydrogenase 2 (ALDH-2).
Daidzin was the most potent isoflavone glycoside tested in modulating differentiation of bone marrow stromal cells toward osteoblasts and away from adipocytes.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 30408.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 42926

Biochem/physiol Actions
Daidzin was the most potent isoflavone glycoside tested in modulating differentiation of bone marrow stromal cells toward osteoblasts and away from adipocytes.1

参考文献

• Inone, T. et al., Chem. Pharm. Bull., 1974, 22, 1422
• Ayabe, S. et al., J.C.S. Perkin 1, 1982, 2725