7-hydroxy-4-methyl-2H-chromen-2-one

• ChemBase ID: 4771
• Molecular Formular: C10H8O3
• Molecular Mass: 176.16872
• Monoisotopic Mass: 176.04734412
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• 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: 160968203; 24885952; 24896640; 99443589
• PubChem CID: 5280567

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.8000727
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.7770318
• LogD (pH = 7.4): 1.6347547
• Log P: 1.7791889
• Molar Refractivity: 47.8115 cm^3
• Polarizability: 18.149475 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.19
• LOG S: -1.95
• Solubility (Water): 1.99e+00 g/l

PROPERTIES

Physical Property

• Solubility: Methanol; Soluble in alcohol. Insoluble in cold water
• Apperance: off-white to yellow; Off-White to Yellow Solid
• Melting Point: 185-190 °C; 186-191°C; 188.5-190 °C(lit.); 190-192°C; 190-192°C
• Absorption Wavelength: λmax 221 nm
• Fluorescence: λex 365 nm; λem 445 nm in methanol; λex 372 nm; λem 445 nm in ethanol

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: Irritant/Lachrymatory/Teratogenic; Light Sensitive - Protect from Light
• RTECS: GN7000000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 是
• 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: Bile secretion regulator; Spasmolytic

Product Information

• Purity: ≥98%; ≥98.0% (HPLC); 97%
• Grade: for fluorescence
• Salt Data: Free Base
• Biological Source: Isol. from young branches of Dalbergia volubilis and from Eupatorium pauciflorum
• Application(s): Choleretic; Spasmolytic; Sunscreen agent
• Empirical Formula (Hill Notation): C10H8O3; C10H8O3 · H2O

DETAILS

MP Biomedicals - 05206609

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02151680

Free Acid
Off-white to yellow crystals
Purity: 97%
Highly fluorescent in alkaline solution.

MP Biomedicals - 02190346

Laser Grade
For pulsed and CW operation.

DrugBank - DB07118

Drug information: experimental

Sigma Aldrich - 69580

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

Application
Standard for the fluorometric determination of enzyme activity.1
Suitable as laser dye

Sigma Aldrich - M1381

Application
碱性溶液中具有高荧光性。
包装
25, 100 g in poly bottle

Selleck Chemicals - S2256

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

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

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• 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).