| Identification | More | [Name]
4-Methylumbelliferone | [CAS]
90-33-5 | [Synonyms]
4-METHYL-7-HYDROXYCOUMARIN
4-METHYLUMBELLIFERONE
4-MU
7-HYDROXY-4-METHYL-1,2-BENZOPYRONE
7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE
7-HYDROXY-4-METHYL-CHROMEN-2-ONE
7-HYDROXY-4-METHYLCOUMARIN
AKOS NCG-0056
AURORA KA-3734
BETA-METHYLUMBELLIFERONE
B-METHYLUMBELLIFERONE
COUMARIN 4
COUMARIN 456
HYMECROMONE
IFLAB-BB F1918-0038
LABOTEST-BB LT01272564
METHYLUMBELLIFERONE, 4-
TIMTEC-BB SBB009085
| [EINECS(EC#)]
201-986-7 | [Molecular Formula]
C10H8O3 | [MDL Number]
MFCD00006866 | [Molecular Weight]
176.17 | [MOL File]
90-33-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White to Yellow Crystals | [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 | [form ]
Crystalline Powder | [pka]
7.79(at 25℃) | [color ]
off-white to yellow
| [PH Range]
Green 1 uorescent (0.0) to weak blue 1 uorescent (2.0);Weak blue 1 uorescent (6.5) blue 1 uorescent (8.0) | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [Water Solubility ]
slightly soluble | [Usage]
Standard for the fluorometric determination of enzyme activity. Highly fluorescent in alkaline solution.
Fluorescence: max Abs. l = 360nm, max. Em. l = 449nm; pH > | [λmax]
221nm, 251nm, 322nm | [Detection Methods]
HPLC,MS,NMR | [Merck ]
14,4854 | [BRN ]
142217 | [Major Application]
color 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 | [InChIKey]
HSHNITRMYYLLCV-UHFFFAOYSA-N | [LogP]
2.370 (est) | [CAS DataBase Reference]
90-33-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Coumarin, 7-hydroxy-4-methyl-(90-33-5) | [EPA Substance Registry System]
90-33-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
GN7000000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29322000 | [Safety Profile]
Moderately toxic by
ingestion and intraperitoneal routes. An
experimental teratogen. Experimental
reproductive effects. When heated to
decomposition it emits acrid smoke and
irritating fumes. | [Toxicity]
LD50 oral in rat: 3850mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white to yellow crystals. Soluble in ethanol, acetic acid, alkali solutions, and ammonia. Slightly soluble in hot water, ether, and chloroform. Exhibits blue fluorescence when exposed to concentrated sulfuric acid. | [Originator]
Odeston,Merck | [Uses]
4-methylumbelliferone (4-MU) is a dietary supplement that inhibits hyaluronic acid (HA) synthesis. 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. | [Definition]
ChEBI: 4-methylumbelliferone is a hydroxycoumarin that is umbelliferone substituted by a methyl group at position 4. It has a role as an antineoplastic agent and a hyaluronic acid synthesis inhibitor. It is functionally related to an umbelliferone. | [Preparation]
4-Methylumbelliferone is obtained by the cyclization reaction between resorcinol and ethyl acetate. Concentrated sulfuric acid is cooled to below 10 ° C, and a solution prepared from resorcinol and ethyl acetate is slowly added to the stirring solution. After dropping it completely, let it stand for 12 hours. Then, the reaction mixture is added into ice-cold water. The precipitate is filtered out and purified with a dilute sodium hydroxide solution and dilute sulfuric acid to obtain the final product. | [Manufacturing Process]
Resorcin 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 Function]
Choleretic, Spasmolytic, Sunscreen agent | [General Description]
4-Methylumbelliferone[90-33-5] is a useful indicator for nitric acid determination and enzyme activity investigation. It emits fluorescence in alkaline solution and Standard for the fluorometric determination of enzyme activity. Highly fluorescent in alkaline solution. Fluorescence: max Abs. l = 360nm, max. Em. l = 449nm; pH > 9.
| [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data for 4-Methylumbelliferone are not available. 4-Methylumbelliferone is probably combustible. | [Pharmaceutical Applications]
4-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 Activity]
4-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. | [in vitro]
4-methylumbelliferone (mu, 90-33-5), 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].
| [target]
P450 (e.g. CYP17) | NADPH-oxidase | PKC | ROS | [IC 50]
0.4 mm | [Purification Methods]
Purify 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. |
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