6,7-dihydroxy-2H-chromen-2-one

• ChemBase ID: 107226
• Molecular Formular: C9H6O4
• Molecular Mass: 178.14154
• Monoisotopic Mass: 178.02660867
• SMILES: Oc1cc2c(ccc(=O)o2)cc1O
• Canonical SMILES: O=c1ccc2c(o1)cc(c(c2)O)O
• InChI: InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
• InChIKey: ILEDWLMCKZNDJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,7-dihydroxy-2H-chromen-2-one
• IUPAC Traditional name: esculetin; 6,7-dihydroxy-2H-chromen-2-one
• Synonyms: 6,7-DIHYDROXYCOUMARIN; esculetin; cichorigenin; 6,7-dihydroxycoumarin; Aesculetin; 6,7-Dihydroxycoumarin; Aesculetin; Esculetol; Esculetin; 七叶亭; 秦皮乙素; 6,7-二羟基香豆素

Database IDs

• CAS Number: 305-01-1
• EC Number: 206-161-5
• MDL Number: MFCD00006874
• Beilstein Number: 152788
• Merck Index: 143697
• PubChem SID: 162093172; 24854815
• PubChem CID: 5281416
• CHEBI ID: 490095
• CHEMBL: 244743
• Chemspider ID: 4444764
• KEGG ID: C09263
• Wikipedia Title: Aesculetin

CALCULATED PROPERTIES

• Acid pKa: 7.914908
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.1745733
• LogD (pH = 7.4): 1.0613594
• Log P: 1.176229
• Molar Refractivity: 45.5104 cm^3
• Polarizability: 16.96244 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white or light yellow powder; Yellow powder
• Melting Point: 268-270 °C; 271-273 °C(lit.); ca 270°C dec.

Safety Information

• RTECS: GN6382500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Mechanism of Action: Leukotriene antagonist in-vitro; Prostaglandin antagonist

Product Information

• Purity: ≥98.0% (HPLC); 98%; 98+%
• Grade: purum
• Biological Source: Metab. of infected sweet potato also found in Aesculus, Atropa, Datura, Digitalis and other plants; found in some ferns
• Application(s): Antifungal
• Empirical Formula (Hill Notation): C9H6O4

DETAILS

MP Biomedicals - 05202985

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 246573

Packaging
1, 5 g in glass bottle

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 324A; 324C; 326C, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1314C; 1318A, (nmr)
• Head, F.S.H. et al., J.C.S., 1939, 1266, (synth)
• Bohlmann, F. et al., Chem. Ber., 1957, 90, 1512, (synth)
• Jain, B.D., Anal. Chim. Acta, 1967, 37, 1358, (detn, Nb, U)
• Bursey, M.M. et al., Chem. Comm., 1967, 712, (ms)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1325-1327, (occur)
• Sato, M. et al., Phytochemistry, 1972, 11, 657, (biosynth)
• Gnther, H. et al., Org. Magn. Reson., 1975, 7, 339, (cmr, deriv)
• Cussans, N.J. et al., Tetrahedron, 1975, 31, 2719, (cmr)
• Ashwood-Smith, M.J. et al., Experientia, 1982, 39, 262, (physiol, tox, deriv)
• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (occur, rev)
• Kelkar, S.L. et al., Indian J. Chem., Sect. B, 1984, 23, 458, (synth)
• Joseph-Nathan, P. et al., J. Het. Chem., 1984, 21, 1141, (pmr, deriv)
• Abu-Eittah, R.H. et al., Can. J. Chem., 1985, 63, 1173, (uv)
• Jackson, Y.A. et al., Heterocycles, 1995, 41, 1979, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DRS800
• Ultraviolet absorbent.