3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

• ChemBase编号: 2116
• 分子式: C15H10O8
• 平均质量: 318.2351
• 单一同位素质量: 318.03756728
• SMILES: Oc1cc(O)c2c(=O)c(O)c(oc2c1)c1cc(O)c(O)c(O)c1
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(c(c2=O)O)c1cc(O)c(c(c1)O)O
• InChI: InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H
• InChIKey: IKMDFBPHZNJCSN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
• IUPAC传统名: 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one; myricetin
• 别名: 3,3′,4′,5,5′,7-Hexahydroxyflavone; Myricetin; Cannabiscetin; 3,5,7,3',4',5'-Hexahydroxyflavone; Myricetol; Myricitin; 3,3',4,4',5',7-Hexahydro-2-phenyl-4H-chromen-4-one; 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one; 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one; MYC; Myricetin; 3,3',4',5,5',7-Hexahydroxyflavone

登记号

• CAS号: 529-44-2
• EC号: 208-463-2
• MDL号: MFCD00006827
• Beilstein号: 332331
• PubChem SID: 24886044; 24278566; 46508126; 160965570
• PubChem CID: 5281672

理论计算性质

JChem

• Acid pKa: 6.3728395
• 质子受体: 8
• 质子供体: 6
• LogD (pH = 5.5): 1.7982366
• LogD (pH = 7.4): 0.6469261
• Log P: 1.8527341
• 摩尔折射率: 78.8431 cm^3
• 极化性: 29.087542 Å^3
• 极化表面积: 147.68 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 1.66
• LOG S: -3.02
• 溶解度: 3.01e-01 g/l

分子性质

理化性质

• 溶解度: ethanol: soluble10 mg/mL, clear to very faintly turbid, yellow to very deep greenish-yellow
• 外观: crystalline; Yellow powder
• 熔点: > 300°C (decomposes at 350°C); >300 °C(lit.); ≥300 °C

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• RTECS编号: LK8646000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... CYP1A2(1544)mouse ... Hexa(15211)rat ... Il4(287287), Tnf(24835)
• 生物活性机理: Novel natural inhibitor of neoplastic cell transformation and MEK1

产品相关信息

• 纯度: ≥96.0%; ≥96.0% (HPLC); 85%
• 成盐信息: Free Base
• 生物来源: Isol. from the bark of Myrica rubra and Myrica nagi; widespread in the plant world, occurring in seeds, flowers and stems, often as glycosides
• 应用领域: Antibacterial; Antioxidant; Antiviral activity; Bioflavonoid; Shows anti-HIV activity
• Empirical Formula (Hill Notation): C15H10O8

详细说明

MP Biomedicals - 02155748

(3,3',4',5,5',7-Hexahydroxyflavone) Purity: 85% Light yellow-green crystals

DrugBank - DB02375

Drug information: experimental

Selleck Chemicals - S2326

Research Area: Metabolic Disease
Biological Activity:
Myricetin(Cannabiscetin) is a naturally occurring flavonol, a flavonoid found in many grapes, berries, fruits, vegetables, herbs, as well as other plants. Walnuts are a rich dietary source. Trace amounts can be found as glycosides. It is one of the phenolic compounds present in red wine.Myricetin has antioxidant properties. In vitro research suggests that myricetin in high concentrations can modify LDL cholesterol such that uptake by white blood cells is increased. A Finnish study correlated high myricetin consumption with lowered rates of prostate cancer.Another 8-year study found that three flavonols(kaempferol, quercetin, and myricetin) reduced the risk of pancreatic cancer by 23 percent.[2]

Sigma Aldrich - M6760

Biochem/physiol Actions
Myricetin is a naturally occurring flavonol with antioxidant properties.

Sigma Aldrich - 70050

Biochem/physiol Actions
Strongly inhibits yeast α-glucosidase,1 glyoxalase I in vitro,2 and bovine milk xanthine oxidase.3 Promotes complex formation between DNA and both topoisomerase I and II, an effect that may have implications in cancer chemotherapy.4

参考文献

• http://www.drugbank.ca/drugs/DB02375
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 97D, (ir)
• Perkin, A.G., J.C.S., 1902, 81, 203-210, (struct)
• Kalff, J. et al., J.C.S., 1925, 127, 181-184, (synth)
• Nierenstein, M., Ber., 1928, 61, 361-362, (Myricetin, synth)
• Seshadri, T.R. et al., Proc. - Indian Acad. Sci., Sect. A, 1946, 23, 296-304; CA, 40, 6447, (struct)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1575; 1576, (occur)
• Gaydou, E.M. et al., Ann. Chim. (Paris), 1977, 2, 303-308, (synth, uv, cmr)
• Zapesochnaya, G.G. et al., Khim. Prir. Soedin., 1978,
• Markham, K.R. et al., Tetrahedron, 1978, 34, 1389, (cmr)
• The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988
• Ono, K., Eur. J. Biochem., 1990, 190, 469-476, (Myricetin, anti-HIV activity)