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486-35-1 molecular structure
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7,8-dihydroxy-2H-chromen-2-one

ChemBase ID: 63564
Molecular Formular: C9H6O4
Molecular Mass: 178.14154
Monoisotopic Mass: 178.02660867
SMILES and InChIs

SMILES:
c12oc(=O)ccc1ccc(O)c2O
Canonical SMILES:
O=c1ccc2c(o1)c(O)c(cc2)O
InChI:
InChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H
InChIKey:
ATEFPOUAMCWAQS-UHFFFAOYSA-N

Cite this record

CBID:63564 http://www.chembase.cn/molecule-63564.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
7,8-dihydroxy-2H-chromen-2-one
IUPAC Traditional name
7,8-dihydroxy-2H-chromen-2-one
daphnetin
Synonyms
Daphnetol
Daphnetin
7,8-Dihydroxychromen-2-one
Daphnetin
Daphnetin
7,8-Dihydroxycoumarin
CAS Number
486-35-1
EC Number
207-632-8
MDL Number
MFCD00016977
PubChem SID
162029303
24882342
24278375
PubChem CID
5280569

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 8.045391  H Acceptors
H Donor LogD (pH = 5.5) 1.8250022 
LogD (pH = 7.4) 1.7383214  Log P 1.826229 
Molar Refractivity 45.5104 cm3 Polarizability 16.96474 Å3
Polar Surface Area 66.76 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Apperance
solid expand Show data source
Storage Condition
-20°C expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
GN6382600 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
TSCA Listed
false expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Mechanism of Action
Antioxydant expand Show data source
Inhibitor of various protein kinases expand Show data source
Purity
>95% expand Show data source
≥97% expand Show data source
90% expand Show data source
Salt Data
Free Base expand Show data source
Biological Source
Isol. from Daphne odora and from other plants expand Show data source
Application(s)
Analgesic expand Show data source
Anticoagulant expand Show data source
Antioxydant expand Show data source
Empirical Formula (Hill Notation)
C9H6O4 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
Selleck Chemicals - S2554 external link
Research Area: Cancer
Biological Activity:
It is also a chelator and an antioxidant. In vitro, daphnetin causes a 50% inhibition (IC50) of 3H-hypoxanthine incorporation by Plasmodium falciparum at concentrations between 25 and 40 µM.
Sigma Aldrich - D5564 external link
Biochem/physiol Actions
Inhibitor of protein kinases.
Packaging
5, 25 mg in glass bottle
Sigma Aldrich - 630764 external link
Packaging
5 g in glass bottle

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Bohm, B.A. et al., Can. J. Biochem., 1961, 39, 1389, (struct)
  • • Barnes, C.S. et al., Aust. J. Chem., 1964, 17, 975, (ms)
  • • Brown, S.A. et al., Phytochemistry, 1964, 469, (biosynth)
  • • Jain, B.D., Anal. Chim. Acta, 1967, 37, 1358, (use)
  • • Mendz, J. et al., Microchem. J., 1969, 14, 567, (uv)
  • • Wildenhaim, W. et al., J. Prakt. Chem., 1970, 312, 690, (isol)
  • • Herz, W. et al., Phytochemistry, 1970, 9, 891, (isol)
  • • Sato, M. et al., Phytochemistry, 1972, 11, 657; 2367, (biosynth)
  • • Jurd, L. et al., Aust. J. Chem., 1974, 27, 2697, (synth)
  • • Abyshev, A.Z., Khim. Prir. Soedin., 1974, 10, 568; Chem. Nat. Compd. (Engl. Transl.), 1974, 10, 581, (isol)
  • • Gnther, H. et al., Org. Magn. Reson., 1975, 7, 339, (cmr, deriv)
  • • Cussans, N.J. et al., Tetrahedron, 1975, 31, 2719, (cmr)
  • • Ueno, K. et al., Acta Cryst. B, 1976, 31, 946, (cryst struct)
  • • Rybalko, K.S. et al., Khim. Prir. Soedin., 1976, 12, 294; Chem. Nat. Compd. (Engl. Transl.), 1976, 12, 262, (isol)
  • • MacLeod, J.K. et al., Aust. J. Chem., 1978, 31, 1545, (synth)
  • • Shimomura, H. et al., Chem. Pharm. Bull., 1980, 347, (deriv)
  • • Barua, N.C. et al., Phytochemistry, 1980, 19, 2217, (deriv)
  • • Gray, A.I. et al., Phytochemistry, 1981, 26, 1171; 1987, 257, (derivs)
  • • Joseph-Nathan, P. et al., J. Het. Chem., 1984, 21, 1141, (pmr, deriv)
  • • Borges del Castillo, J. et al., Phytochemistry, 1984, 23, 859, (derivs)
  • • Brown, S.A., Z. Naturforsch., C, 1986, 41, 247, (biosynth)
  • • Pastor, R.E. et al., Can. J. Chem., 1987, 65, 1356, (cmr)
  • • Reisch, J. et al., Monatsh. Chem., 1988, 119, 1333, (synth)
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PATENTS

PATENTS

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INTERNET

INTERNET

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