4-Methylumbelliferone

4-Methylumbelliferone Basic information
Product Name:4-Methylumbelliferone
Synonyms:2H-1-Benzopyran, 7-hydroxy-4-methyl-2-oxo-;2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-;2H-1-Benzopyren-2-one, 7-hydroxy-4-methyl-;4-Methylumbelliferon;4-Metylumbelliferone;7-hydroxy-4-methyl-2h-1-benzopyran-2-on;7-Hydroxy-4-methyl-2H-1-benzopyran-2-one;lm94
CAS:90-33-5
MF:C10H8O3
MW:176.17
EINECS:201-986-7
Product Categories:CANTABILINE;intermediate;Aromatics;Fluorescent Labels & Indicators;Coumarin;Fluorescent;ketone;Aromatics Compounds;90-33-5
Mol File:90-33-5.mol
4-Methylumbelliferone Structure
4-Methylumbelliferone Chemical Properties
Melting point 188.5-190 °C(lit.)
Boiling point 267.77°C (rough estimate)
density 1.1958 (rough estimate)
refractive index 1.5036 (estimate)
storage temp. 2-8°C
solubility Practically insoluble in water; slightly soluble in ethanol, ether,chloroform; soluble inmethanol
pka7.79(at 25℃)
form Crystalline Powder
color off-white to yellow
PH RangeGreen 1 uorescent (0.0) to weak blue 1 uorescent (2.0);Weak blue 1 uorescent (6.5) blue 1 uorescent (8.0)
Water Solubility slightly soluble
λmax221nm, 251nm, 322nm
Merck 14,4854
BRN 142217
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
Major Applicationcolor filter, electroluminescent displays, document security processes, lasers, integrated circuits, liquid crystal displays, surface brightening composition, oil products, teeth whitening agent, lysosomal enzyme assay, substrate for lipase, determining protein-protein-interactions in living cells, Antitrypanosomal, antileishmanial, anticancer, antiHIV, antimalarial, antibacterial, antifungal
InChIKeyHSHNITRMYYLLCV-UHFFFAOYSA-N
LogP2.370 (est)
CAS DataBase Reference90-33-5(CAS DataBase Reference)
NIST Chemistry ReferenceCoumarin, 7-hydroxy-4-methyl-(90-33-5)
EPA Substance Registry System4-Methylumbelliferone (90-33-5)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-20/21/22
Safety Statements 26-37/39-36
WGK Germany 2
RTECS GN7000000
Hazard Note Irritant
TSCA Yes
HS Code 29329990
ToxicityLD50 oral in rat: 3850mg/kg
MSDS Information
ProviderLanguage
7-Hydroxy-4-methylcoumarin English
ACROS English
SigmaAldrich English
ALFA English
4-Methylumbelliferone Usage And Synthesis
Chemical PropertiesOff-White to Yellow Crystals
OriginatorOdeston,Merck
UsesStandard for the fluorometric determination of enzyme activity. Highly fluorescent in alkaline solution. Fluorescence: max Abs. l = 360nm, max. Em. l = 449nm; pH > 9
Usescholoretic, spasmolytic, sunscreen, Analytical reagent.
Uses4-methylumbelliferone (4-MU) is a dietary supplement that inhibits hyaluronic acid (HA) synthesis. Hyaluronan (HA) is a prominent component of the extracellular matrix at many sites of chronic inflammation, including type 1 diabetes (T1D), multiple sclerosis, and numerous malignancies. 4-MU is an already approved drug in Europe and Asia called “hymecromone” where it is used to treat biliary spasm.
4-Methylumbelliferone is useful as an indicator in the determination of nitric acid. It is also useful in the kinetic investigation of enzyme activity. 4-Methylumbelliferone is fluorescent in alkaline solution.
DefinitionChEBI: A hydroxycoumarin that is umbelliferone substituted by a methyl group at position 4.
Manufacturing ProcessResorcin reacted with 3-oxo-butyric acid ethyl ester in the presence sulfuric acid and phosphorous pentaoxide and 4-methyl-7-hydroxycoumarine (hymecromone) was obtained.
Therapeutic FunctionCholeretic, Spasmolytic, Sunscreen agent
General DescriptionColorless crystals. Insoluble in water.
Air & Water ReactionsInsoluble in water.
Fire HazardFlash point data for 4-Methylumbelliferone are not available. 4-Methylumbelliferone is probably combustible.
Pharmaceutical Applications4-Methylumbelliferone is primarily used in synthesizing medicinal compounds and as a building block for fluorescent probes. Applications include synthesis of:
coumarin triazole derivatives as potential antimicrobial agents.
coumarin salen-based fluorescence sensors for Mg2+ detection.
pyranocoumarin derivatives as anti-hyperglycemic and anti-dyslipidemic agents.
coumarin piperazine derivatives as potential multireceptor atypical antipsychotics.
4-methylumbelliferyl T-antigen as a substrate for endo-α-N-acetylgalactosaminidase.




Biological Activity4-methylumbelliferone is a hyaluronic acid (ha) synthesis inhibitor. the activation of has2 and the over-production of ha are existed in many metastatic tumor cell lines. increased synthesis of ha is often associated with increased metastatic potential and invasivity in tumor cells.
Safety ProfileModerately toxic by ingestion and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
in vitro4-methylumbelliferone (mu), an inhibitor of ha synthesis, has been studied as a potential anti-tumor drug on account of inhibiting the growth of primary tumors and distant metastasis of tumor cells. the mechanism still needs to be clarified, although several studies revealed that the anticancer effects of mu are mediated by inhibition of ha signal pathway. in a previous study the regulation of ha synthesis was demonstrated by ceramide, and now show how mu activated nsmase2 generates ceramides and mediates mu modulated inhibition of ha synthesis (cell migration and invasion, and apoptosis of tumor cells). using a ha enriched mouse oligodendroglioma cell line g26-24, it was found that mu elevated the activity of nsmase2 and enhanced ceramide levels, which in turn potentiated phosphatase pp2a activity. further, the activated pp2a decreased phosphorylation of akt, reduced activities of ha synthase2 (has2) and calpains, and blocked both the synthesis of ha, and the migration and invasion of g26-24 tumor cells. in addition, mu mediated ceramide induced activation of p53 and caspase-3, decreased sirt1 expression and deduced g26-24 viability. the mechanism of the mu anticancer therefore initially involves nsmase2/ceramide/pp2a/akt/has2/caspase-3/p53/sirt1 and the calpain signaling pathway, indicating that ceramides play a important role in the ability of a tumor to become aggressively metastatic and grow [1].
targetP450 (e.g. CYP17) | NADPH-oxidase | PKC | ROS
IC 500.4 mm
Purification MethodsPurify it by recrystallisation from EtOH. It is very slightly soluble in cold H2O (solubility at 37o is 0.22%), slightly soluble in Et2O and CHCl3, but soluble in MeOH and AcOH. It has a blue fluorescence in aqueous EtOH and has UV: 221, max 251 and 322.5nm (MeOH). The IR has 3077 br, 1667, 1592, 1385, 1267, 1156, 1130 and 1066 cm-1.max The acetate has m 153-154o. [Woods & Sapp J Org Chem 27 3703 1962, Beilstein 18 III/IV 332, 18/1 V 439.]
references[1] qin j, kilkus j, dawson g. the hyaluronic acid inhibitor 4-methylumbelliferone is an nsmase2 activator-role of ceramide in mu anti-tumor activity. biochim biophys acta. 2016 feb;1861(2):78-90.
4-Methylumbelliferone Preparation Products And Raw materials
Raw materialsEthyl acetoacetate-->Sulfuric acid-->PhosPhorous Pentaoxide-->Resorcinol
Preparation Products8-ACETYL-7-HYDROXY-4-METHYLCOUMARIN
Methylparaben Premarin Methyl N-Methyl-2-pyrrolidone Mesotrione 2-Butanone 6-Hydroxycoumarin 4-HYDROXY MEPHENYTOIN 4-Methylumbelliferone Kresoxim-methyl 3,4-DIMETHYLUMBELLIFERONE Acetone oxime Medroxyprogesterone Acetate Methyl acrylate 6-Methylcoumarin 4-Methyl-2-pentanone Methyl bromide CHLOROPHOSPHONAZO III

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