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90-33-5 molecular structure
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7-hydroxy-4-methyl-2H-chromen-2-one

ChemBase ID: 4771
Molecular Formular: C10H8O3
Molecular Mass: 176.16872
Monoisotopic Mass: 176.04734412
SMILES and InChIs

SMILES:
c1cc(cc2oc(=O)cc(C)c12)O
Canonical SMILES:
Oc1ccc2c(c1)oc(=O)cc2C
InChI:
InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
InChIKey:
HSHNITRMYYLLCV-UHFFFAOYSA-N

Cite this record

CBID:4771 http://www.chembase.cn/molecule-4771.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
7-hydroxy-4-methyl-2H-chromen-2-one
IUPAC Traditional name
4-methylumbelliferone
7-hydroxy-4-methyl-2H-chromen-2-one
Synonyms
7-hydroxy-4-methyl-2H-chromen-2-one
7-Hydroxy-4-methyl-2H-chromen-2-one
7-Hydroxy-4-methyl-2-oxo-2H-chromene
4-Methylumbelliferone
7-Hydroxy-4-methylcoumarin
Coumarin 4
7-Hydroxy-4-methylcoumarin
4-Methylumbelliferone
Hymecromone
Cantabiline
Hymechromone
Hymecromone
7-Hydroxy-4-methyl-2H-1-benzopyran-2-one
7-Hydroxy-4-methyl-coumarin
7-Hydroxy-4-methyl-2-chromenone
7-Hydroxy-4-methyl-2-oxo-3-chromene
NSC 19026
NSC 9408
Omega 127
Pilot 447
β-Methylumbelliferone
β-METHYLUMBELLIFERONE
COUMARIN 4
7-Hydroxy-4-methylcoumarin
4-Methyl-7-hydroxycoumarin
β-Methylumbelliferone
4-METHYLUMBELLIFERONE
4-MU
4-Methylumbelliferone(4-MU)
4-甲基伞形酮
香豆素 4
7-羟基-4-甲基香豆素
β-甲基伞形酮
7-羟基-4-甲基香豆素
4-甲基伞形酮
CAS Number
90-33-5
90-33-5(anhydrous)
EC Number
201-986-7
MDL Number
MFCD00006866
Beilstein Number
142217
Merck Index
144854
PubChem SID
24896640
160968203
99443589
24885952
PubChem CID
5280567

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 7.8000727  H Acceptors
H Donor LogD (pH = 5.5) 1.7770318 
LogD (pH = 7.4) 1.6347547  Log P 1.7791889 
Molar Refractivity 47.8115 cm3 Polarizability 18.149475 Å3
Polar Surface Area 46.53 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.19  LOG S -1.95 
Solubility (Water) 1.99e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Methanol expand Show data source
Soluble in alcohol. Insoluble in cold water expand Show data source
Apperance
off-white to yellow expand Show data source
Off-White to Yellow Solid expand Show data source
Melting Point
185-190 °C expand Show data source
186-191°C expand Show data source
188.5-190 °C(lit.) expand Show data source
190-192°C expand Show data source
190-192°C expand Show data source
Absorption Wavelength
λmax 221 nm expand Show data source
Fluorescence
λex 365 nm; λem 445 nm in methanol expand Show data source
λex 372 nm; λem 445 nm in ethanol expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
Irritant/Lachrymatory/Teratogenic expand Show data source
Light Sensitive - Protect from Light expand Show data source
RTECS
GN7000000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Mechanism of Action
Bile secretion regulator expand Show data source
Spasmolytic expand Show data source
Purity
≥98% expand Show data source
≥98.0% (HPLC) expand Show data source
97% expand Show data source
Grade
for fluorescence expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Biological Source
Isol. from young branches of Dalbergia volubilis and from Eupatorium pauciflorum expand Show data source
Application(s)
Choleretic expand Show data source
Spasmolytic expand Show data source
Sunscreen agent expand Show data source
Empirical Formula (Hill Notation)
C10H8O3 expand Show data source
C10H8O3 · H2O expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich Selleck Chemicals Selleck Chemicals TRC TRC
MP Biomedicals - 05206609 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02151680 external link
Free Acid
Off-white to yellow crystals
Purity: 97%
Highly fluorescent in alkaline solution.
MP Biomedicals - 02190346 external link
Laser Grade
For pulsed and CW operation.
DrugBank - DB07118 external link
Drug information: experimental
Sigma Aldrich - 69580 external link
Other Notes
Indicator for the determination of nitric acid. Used in 4-MU-O-substrates for the kinetic investigation of enzyme activity1
Sigma Aldrich - 128724 external link
Application
Standard for the fluorometric determination of enzyme activity.1
Suitable as laser dye
Sigma Aldrich - M1381 external link
Application
碱性溶液中具有高荧光性。
包装
25, 100 g in poly bottle
Selleck Chemicals - S2256 external link
Research Area: Cancer
Biological Activity:
4-Methylumbelliferone(4-MU) is a hyaluronic acid (HA) synthesis inhibitor with an IC50 of 0.4 mM. 4-MU inhibited proliferation, motility, and invasion of DU145, PC3-ML, LNCaP, C4-2B, and/or LAPC-4 cells. At IC(50) for HA synthesis (0.4 mM), 4-MU induced >3-fold apoptosis in prostate cancer cells, which could be prevented by the addition of HA. The anticancer effects of 4-MU, an orally bioavailable and relatively nontoxic agent, are primarily mediated by inhibition of HA signaling. [1][2] 
Toronto Research Chemicals - M333000 external link
Standard for the fluorometric determination of enzyme activity. Highly fluorescent in alkaline solution.Fluorescence: max Abs. l = 360nm, max. Em. l = 449nm; pH > 9

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Opt. Commun., 7: 248 (1973).
  • • Kultti A et al. Exp Cell Res. 2009 Jul 1;315(11):1914-23
  • • Clin. Chim. Acta., 39, 49 (1972)
  • • Anal. Biochem., 54, 40 (1972)
  • • J. Biochem. Biophys. Methods 19, 207 (1989).
  • • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 323B; 325C, (ir)
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1313A; 1316A; 1320B, (nmr)
  • • v. Pechmann, H. et al., Ber., 1883, 16, 2122, (synth)
  • • Org. Synth., Coll. Vol., 3, 1955, 282, (synth)
  • • Fernley, H.N. et al., Biochem. J., 1965, 97, 95; 1966, 99, 39; 1967, 102, 48, (synth, phosphate)
  • • Aguila, J.F., Talanta, 1967, 14, 1195, (synth, detn, Al)
  • • Kappe, T. et al., Org. Prep. Proced., 1969, 1, 61, (synth)
  • • Bishop, E., Indicators, Pergamon, Oxford, 1972, 695, (use, indicator)
  • • Shimizu, S. et al., Acta Cryst. B, 1975, 31, 1287, (cryst struct)
  • • Sojka, S.A., J.O.C., 1975, 40, 1175, (cmr)
  • • Bhardwaj, D.K. et al., Indian J. Chem., Sect. B, 1977, 15, 94, (isol, Ac)
  • • Chawla, H.M. et al., Indian J. Chem., Sect. B, 1977, 15, 492, (isol)
  • • Krejcoves, J. et al., Coll. Czech. Chem. Comm., 1979, 44, 2211, (synth)
  • • Kauffman, J.M., Appl. Opt., 1980, 19, 3431, (use)
  • • Sankar, S.S. et al., Org. Magn. Reson., 1982, 19, 222, (cmr)
  • • Taylor, R.T. et al., Synthesis, 1982, 672, (synth)
  • • Chaudhari, D.D., Chem. Ind. (London), 1983, 24, 568, (synth)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1420
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1378
  • • Jasinski, J.P. et al., Acta Cryst. C, 1994, 50, 1952, (cryst struct)
  • • Sigma-Aldrich Library of Stains, Dyes and Indicators, 399
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HMB000; MKP500
  • • Standard for fluorimetric determination of enzyme activity: Anal. Biochem., 54, 40; 55, 85 (1973).
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PATENTS

PATENTS

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