CAS 92-61-5|7-Hydroxy-6-methoxycoumarin|Scopoletin|7-hydroxy-6-methoxy-2H-chromen-2-one|7-Hydroxy-6-methoxy-2H-chromen-2-one|6-Methoxyumbelliferone|scopoletin|钩吻酸|6-甲氧基伞形酮|7-羟基-6-甲氧基-2...

General Information

Structure

Molecular Formula

C₁₀H₈O₄

Molecular Mass

192.16812

Exact Mass

192.04225874

Charge

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

Canonic Smiles

COc1cc2ccc(=O)oc2cc1O

Isomeric Smiles

o1c2cc(c(cc2ccc1=O)OC)O

Calculated Properties

JChem

Acid pKa

8.263752

H Acceptors

H Donor

LogD (pH = 5.5)

1.3213807

LogD (pH = 7.4)

1.26684

Log P

1.322123

Molar Refractivity

49.9927

Polarizability

18.85889

Polar Surface Area

55.76

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

Scopoletin7-Hydroxy-6-methoxycoumarin7-Hydroxy-6-methoxy-2H-chromen-2-one6-Methoxyumbelliferone6-甲氧基伞形酮钩吻酸七叶亭-6-甲醚东莨菪内酯柯阿托酸Scopoletin7-羟基-6-甲氧基-2H-1-苯并吡喃-2-酮7-羟基-5-甲氧基香豆素6-Methylesculetin6-O-Methylesculetin7-Hydroxy-6-methoxy-2H-1-benzopyran-2-oneMurrayetinEscopoletinScopoletol7-Hydroxy-5-methoxycoumarinEsculetin-6-methyl etherSCOPOLETINChrysatropic acidScopoletineGelseminic acidMethylesculetinCHRYSATROPIC ACIDNSC 4056476-Methoxy-umbelliferoneβ-Methylesculetin7-Hydroxy-6-methoxy-coumarin7-Hydroxy-6-methoxycoumarinAesculetin 6-methyl etherBaogongteng BGelseminic acid; beta-Methylaesculetin; Buxuletin

IUPAC name

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

IUPAC Traditional name

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

Names and Identifiers

Registration numbers

Beilstein Number

EC Number

CAS Number

MDL Number

PubChem SID

2489952416204461924888268

PubChem CID

5280460

Wikipedia Title

Scopoletin

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... ACHE(43)

Mechanism of Action

C (PKC) protein kinase inhibitor

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02156590

Crystalline

05210164

MP Biomedicals Rare Chemical collection

Wikipedia

Scopoletin

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

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

84792

38332

TRC

S200500

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

Molecule Details

References

PubChem Literature

From Data Sources

• Gonzlez, A.G. et al., An. Quim., 1973, 69, 1013, (pmr)

• Head, F.G.H. et al., J.C.S., 1931, 1241, (synth)

• Abu-Eittah, R.H. et al., Can. J. Chem., 1985, 63, 1173, (uv)

• Wollenweber, E. et al., Fitoterapia, 1989, 60, 460, (isol, derivs)

• Seka, R. et al., Ber., 1931, 64, 909

• Herath, W.H.M. et al., Phytochemistry, 1978, 17, 1007, (isol)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 324B, (ir)

• Tanaka, S. et al., Arzneim.-Forsch., 1977, 27, 2039, (isol)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1314B, (nmr)

• Udovin, A.D. et al., Khim. Prir. Soedin., 1987, 23, 796; Chem. Nat. Compd. (Engl. Transl.), 1987, 23, 660, (cmr)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1328; 1329, (occur)

• Hauer, H. et al., Arch. Pharm. (Weinheim, Ger.), 1995, 328, 737, (synth)

• Ishibura, N. et al., Z. Naturforsch., C, 1979, 34, 628

• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (occur, rev)

• Koul, S.K. et al., Indian J. Chem., Sect. B, 1987, 26, 574, (synth)

• Mizuno, M. et al., Phytochemistry, 1992, 31, 717, (deriv)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

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

IUPAC Traditional name

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

Registration numbers

Beilstein Number

EC Number

CAS Number

MDL Number

PubChem SID

2489952416204461924888268

PubChem CID

Wikipedia Title

Molecule Details

Crystalline

MP Biomedicals Rare Chemical collection

Wikipedia

Scopoletin

Sigma Aldrich

S2500

246581

84792

38332

TRC

S200500

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

References

PubChem Literature

From Data Sources

• Gonzlez, A.G. et al., An. Quim., 1973, 69, 1013, (pmr)

• Head, F.G.H. et al., J.C.S., 1931, 1241, (synth)

• Abu-Eittah, R.H. et al., Can. J. Chem., 1985, 63, 1173, (uv)

• Wollenweber, E. et al., Fitoterapia, 1989, 60, 460, (isol, derivs)

• Seka, R. et al., Ber., 1931, 64, 909

• Herath, W.H.M. et al., Phytochemistry, 1978, 17, 1007, (isol)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 324B, (ir)

• Tanaka, S. et al., Arzneim.-Forsch., 1977, 27, 2039, (isol)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1314B, (nmr)

• Udovin, A.D. et al., Khim. Prir. Soedin., 1987, 23, 796; Chem. Nat. Compd. (Engl. Transl.), 1987, 23, 660, (cmr)

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1328; 1329, (occur)

• Hauer, H. et al., Arch. Pharm. (Weinheim, Ger.), 1995, 328, 737, (synth)

• Ishibura, N. et al., Z. Naturforsch., C, 1979, 34, 628

• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (occur, rev)

• Koul, S.K. et al., Indian J. Chem., Sect. B, 1987, 26, 574, (synth)

• Mizuno, M. et al., Phytochemistry, 1992, 31, 717, (deriv)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Gene Information

human ... ACHE(43)

Mechanism of Action

C (PKC) protein kinase inhibitor

Molecule

ID:79856