7-hydroxy-6-methoxy-2H-chromen-2-one

• ChemBase ID: 79856
• Molecular Formular: C10H8O4
• Molecular Mass: 192.16812
• Monoisotopic Mass: 192.04225874
• SMILES: o1c2cc(c(cc2ccc1=O)OC)O
• Canonical SMILES: COc1cc2ccc(=O)oc2cc1O
• InChI: InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3
• InChIKey: RODXRVNMMDRFIK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-6-methoxy-2H-chromen-2-one
• IUPAC Traditional name: scopoletin; 7-hydroxy-6-methoxy-2H-chromen-2-one
• Synonyms: 7-Hydroxy-6-methoxy-2H-chromen-2-one; 6-Methoxyumbelliferone; Scopoletin; 7-Hydroxy-6-methoxycoumarin; CHRYSATROPIC ACID; Gelseminic acid; Chrysatropic acid; Scopoletine; 6-Methylesculetin; Murrayetin; Scopoletol; Escopoletin; Methylesculetin; 6-O-Methylesculetin; Esculetin-6-methyl ether; 7-Hydroxy-5-methoxycoumarin; Scopoletin; 7-Hydroxy-6-methoxycoumarin; Aesculetin 6-methyl ether; Gelseminic acid; beta-Methylaesculetin; Buxuletin; Baogongteng B; 7-Hydroxy-6-methoxy-coumarin; 6-Methoxy-umbelliferone; β-Methylesculetin; NSC 405647; 7-Hydroxy-6-methoxy-2H-1-benzopyran-2-one; SCOPOLETIN; 6-甲氧基伞形酮; 7-羟基-6-甲氧基-2H-1-苯并吡喃-2-酮; 7-羟基-5-甲氧基香豆素; 七叶亭-6-甲醚; 柯阿托酸; 钩吻酸; 东莨菪内酯

Database IDs

• CAS Number: 92-61-5
• EC Number: 202-171-9
• MDL Number: MFCD00006872
• Beilstein Number: 156296
• PubChem SID: 162044619; 24899524; 24888268
• PubChem CID: 5280460
• Wikipedia Title: Scopoletin

CALCULATED PROPERTIES

• Acid pKa: 8.263752
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3213807
• LogD (pH = 7.4): 1.26684
• Log P: 1.322123
• Molar Refractivity: 49.9927 cm^3
• Polarizability: 18.85889 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Sparingly Soluble in Chloroform and Methanol
• Apperance: Off-Whhite Solid; Powder
• Melting Point: 202-205°C; 203-205 °C(lit.); 203-205°C; 204-207 °C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: Irritant
• RTECS: GN6930000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26-36; S:20-25-26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ACHE(43)
• Mechanism of Action: C (PKC) protein kinase inhibitor

Product Information

• Purity: ≥98.0% (HPLC); ≥98.5% (HPLC); ≥99%; 95%; 98.5
• Grade: analytical standard; purum
• Biological Source: Occurs widely in the plant world, for example, the root of Gelsemium sempervirens, Atropa belladonna, Convolvulus scammonia, Ipomoea orizabensis, Prunus serotina, Fabiana imbricata and also Diospyros spp., Peucedanum spp., Heracleum spp., Skimmia spp. Also occurs in the Chinese crude drug Toki (from Angelica acutiloba )
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antispasmodic; Antitumour agent
• Empirical Formula (Hill Notation): C10H8O4

DETAILS

MP Biomedicals - 02156590

Crystalline

MP Biomedicals - 05210164

MP Biomedicals Rare Chemical collection

Sigma Aldrich - S2500

Biochem/physiol Actions
Dye that can be used to detect the release of reactive oxygen species during the oxidative burst; peroxynitrite scavenger; acetylcholinesterase inhibitor.
Scopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.
包装
1 g in glass bottle
100, 500 mg in glass bottle
50 mg in poly bottle

Sigma Aldrich - 246581

Biochem/physiol Actions
Scopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.1

Sigma Aldrich - 38332

Biochem/physiol Actions
Scopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.1

Sigma Aldrich - 84792

Biochem/physiol Actions
Scopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.1

Toronto Research Chemicals - S200500

The aglucone of Scopolin. Used for cosmetics, topical formulations, and foods.

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 324B, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1314B, (nmr)
• Seka, R. et al., Ber., 1931, 64, 909
• Head, F.G.H. et al., J.C.S., 1931, 1241, (synth)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1328; 1329, (occur)
• Gonzlez, A.G. et al., An. Quim., 1973, 69, 1013, (pmr)
• Tanaka, S. et al., Arzneim.-Forsch., 1977, 27, 2039, (isol)
• Herath, W.H.M. et al., Phytochemistry, 1978, 17, 1007, (isol)
• Ishibura, N. et al., Z. Naturforsch., C, 1979, 34, 628
• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (occur, rev)
• Abu-Eittah, R.H. et al., Can. J. Chem., 1985, 63, 1173, (uv)
• Koul, S.K. et al., Indian J. Chem., Sect. B, 1987, 26, 574, (synth)
• Udovin, A.D. et al., Khim. Prir. Soedin., 1987, 23, 796; Chem. Nat. Compd. (Engl. Transl.), 1987, 23, 660, (cmr)
• Wollenweber, E. et al., Fitoterapia, 1989, 60, 460, (isol, derivs)
• Mizuno, M. et al., Phytochemistry, 1992, 31, 717, (deriv)
• Hauer, H. et al., Arch. Pharm. (Weinheim, Ger.), 1995, 328, 737, (synth)