2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one trihydrate

• ChemBase编号: 155100
• 分子式: C27H36O19
• 平均质量: 664.56334
• 单一同位素质量: 664.18507893
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O)O)O)O)O)O)O.O.O.O
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O.O.O.O
• InChI: InChI=1S/C27H30O16.3H2O/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9;;;/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3;3*1H2/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-;;;/m0.../s1
• InChIKey: NLLBWFFSGHKUSY-JPRRWYCFSA-N

名称和登记号

名称

• IUPAC标准名: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one trihydrate
• IUPAC传统名: troxerutin trihydrate
• 别名: Quercetin-3-rutinoside 水合物; Vitamin P 水合物; 芦丁 水合物; 维生素 P 三水合物; 芸香甙 三水合物; 芦丁 三水合物; Quercetin-3-rutinoside hydrate; Vitamin P hydrate; Rutin hydrate; Quercetin-3-rutinoside trihydrate; Vitamin P trihydrate; Rutin trihydrate

登记号

• CAS号: 250249-75-3; 207671-50-9
• EC号: 205-814-1
• MDL号: MFCD00149490
• Beilstein号: 75455
• PubChem SID: 24888176; 162249238; 24887256; 24899379
• PubChem CID: 16218542

理论计算性质

• Acid pKa: 6.4339614
• 质子受体: 16
• 质子供体: 10
• LogD (pH = 5.5): -0.91626626
• LogD (pH = 7.4): -1.8846226
• Log P: -0.868761
• 摩尔折射率: 140.1451 cm^3
• 极化性: 55.293434 Å^3
• 极化表面积: 265.52 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: aqueous base: soluble; DMSO: soluble; pyridine: soluble50 mg/mL
• 外观: yellow to green powder
• 熔点: 195 °C (dec.)(lit.)
• 比旋光度: [α]20/D +9±2°, c = 0.5% in absolute ethanol; [α]24/D +10.4°, c = 2 in ethanol

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥90% (HPLC); ≥94% (HPLC); ≥95.0% (HPLC); 95%
• 级别: analytical standard; primary reference standard
• 成盐信息: 3 H2O
• Empirical Formula (Hill Notation): C27H30O16 · 3H2O; C27H30O16 · xH2O
• 分类: Genuine Natural Compounds

详细说明

Sigma Aldrich - 84082

Other Notes
Review2
Biochem/physiol Actions
Rutin is the major mutagenic component of red wine; it is not itself mutagenic, but is activated to a mutagen by treatment both liver microsomal enzymes and fecal enzymes.1

Sigma Aldrich - R5143

Biochem/physiol Actions
A polyphenolic flavonoid that acts as an antioxidant and NO scavenger. It can attenuate peroxide production in glial cells by acting as a free radical scavenger and protect renal cells from oxidative injury. Inclusion of rutin in the diet of rats significantly reduced the appearance of single-strand breaks in nuclear DNA caused by hepatocarcinogens aflatoxin B1 and N-nitrosodimethylamine. This protection from DNA damage was found to be due to a reduction in the induction of repair enzymes polymerase, DNA polymerase β and DNA ligase. Since DNA damage and inefficient repair are thought to initiate the process of carcinogenesis, effects of rutin on these functions suggests a protective role of this flavonoid against carcinogenesis induced by chemical carcinogens.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - 00300590

Application
草药产品分析的标准品。
General description
由 HWI Analytik 生产和检验 证书上注明了由定量 NMR 确定的准确含量

Sigma Aldrich - R2303

包装
5, 500 g in glass bottle