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529-44-2 molecular structure
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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 and InChIs

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

Cite this record

CBID:2116 http://www.chembase.cn/molecule-2116.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
529-44-2
EC Number
208-463-2
MDL Number
MFCD00006827
Beilstein Number
332331
PubChem SID
24886044
24278566
46508126
160965570
PubChem CID
5281672

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 6.3728395  H Acceptors
H Donor LogD (pH = 5.5) 1.7982366 
LogD (pH = 7.4) 0.6469261  Log P 1.8527341 
Molar Refractivity 78.8431 cm3 Polarizability 29.087542 Å3
Polar Surface Area 147.68 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 1.66  LOG S -3.02 
Solubility (Water) 3.01e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
ethanol: soluble10 mg/mL, clear to very faintly turbid, yellow to very deep greenish-yellow expand Show data source
Apperance
crystalline expand Show data source
Yellow powder expand Show data source
Melting Point
> 300°C (decomposes at 350°C) expand Show data source
>300 °C(lit.) expand Show data source
≥300 °C expand Show data source
Storage Condition
-20°C expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
LK8646000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Gene Information
human ... CYP1A2(1544)mouse ... Hexa(15211)rat ... Il4(287287), Tnf(24835) expand Show data source
Mechanism of Action
Novel natural inhibitor of neoplastic cell transformation and MEK1 expand Show data source
Purity
≥96.0% expand Show data source
≥96.0% (HPLC) expand Show data source
85% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
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 expand Show data source
Application(s)
Antibacterial expand Show data source
Antioxidant expand Show data source
Antiviral activity expand Show data source
Bioflavonoid expand Show data source
Shows anti-HIV activity expand Show data source
Empirical Formula (Hill Notation)
C15H10O8 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02155748 external link
(3,3',4',5,5',7-Hexahydroxyflavone) Purity: 85% Light yellow-green crystals
DrugBank - DB02375 external link
Drug information: experimental
Selleck Chemicals - S2326 external link
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 external link
Biochem/physiol Actions
Myricetin is a naturally occurring flavonol with antioxidant properties.
Sigma Aldrich - 70050 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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