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

• ChemBase ID: 150666
• Molecular Formular: C11H10O4
• Molecular Mass: 206.1947
• Monoisotopic Mass: 206.0579088
• SMILES: COc1cc2ccc(=O)oc2cc1OC
• Canonical SMILES: COc1cc2oc(=O)ccc2cc1OC
• InChI: InChI=1S/C11H10O4/c1-13-9-5-7-3-4-11(12)15-8(7)6-10(9)14-2/h3-6H,1-2H3
• InChIKey: GUAFOGOEJLSQBT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,7-dimethoxy-2H-chromen-2-one
• IUPAC Traditional name: scoparone; 6,7-dimethoxy-2H-chromen-2-one
• Synonyms: Scoparone; 6,7-Dimethoxycoumarin; 6,7-Dimethoxycoumarin; Escoparone; Scoparin; Scoparone; 蒿属香豆素; 6,7-二甲氧基香豆素

Database IDs

• CAS Number: 120-08-1
• EC Number: 204-369-0
• MDL Number: MFCD00006871
• PubChem SID: 162244827; 24855271
• PubChem CID: 8417

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.4680171
• LogD (pH = 7.4): 1.4680171
• Log P: 1.4680171
• Molar Refractivity: 54.475 cm^3
• Polarizability: 20.759401 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 143-145 °C(lit.)

Safety Information

• RTECS: GN6550000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H319
• GHS Precautionary statements: P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: mouse ... Maoa(17161)rat ... Aldh1a2(116676)
• Mechanism of Action: Cytochrome P450 inductor

Product Information

• Purity: 98%; 99.0
• Biological Source: Found in several citrus oils, in Artemisia scoparia, Zanthoxylum setosum and other plants
• Application(s): Antifungal activity
• Empirical Formula (Hill Notation): C11H10O4

DETAILS

Sigma Aldrich - 254886

Packaging
1 g in glass bottle
250 mg 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)
• McCabe, P.H. et al., J.C.S.(C), 1967, 145, (Prenyletin)
• Dean, F.M. et al., Tet. Lett., 1967, 2147, (Prenyletin)
• Khan, M.A.S. et al., Anal. Chim. Acta, 1968, 43, 153, (pmr)
• 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)
• 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)
• Dubery, I.A. et al., Phytochemistry, 1999, 50, 983-989, (Scoparone, activity)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DRS800