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

• ChemBase ID: 2116
• Molecular Formular: C15H10O8
• Molecular Mass: 318.2351
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one; myricetin
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.3728395
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 1.7982366
• LogD (pH = 7.4): 0.6469261
• Log P: 1.8527341
• Molar Refractivity: 78.8431 cm^3
• Polarizability: 29.087542 Å^3
• Polar Surface Area: 147.68 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.66
• LOG S: -3.02
• Solubility (Water): 3.01e-01 g/l

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: LK8646000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)mouse ... Hexa(15211)rat ... Il4(287287), Tnf(24835)
• Mechanism of Action: Novel natural inhibitor of neoplastic cell transformation and MEK1

Product Information

• Purity: ≥96.0%; ≥96.0% (HPLC); 85%
• Salt Data: Free Base
• Biological Source: Isol. from the bark of Myrica rubra and Myrica nagi; widespread in the plant world, occurring in seeds, flowers and stems, often as glycosides
• Application(s): Antibacterial; Antioxidant; Antiviral activity; Bioflavonoid; Shows anti-HIV activity
• Empirical Formula (Hill Notation): C15H10O8

DETAILS

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

REFERENCES

• 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)