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4-Methylumbelliferone

4-Methylumbelliferone Structure
CAS No.
90-33-5
Chemical Name:
4-Methylumbelliferone
Synonyms
HYMECROMONE;7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE;7-HYDROXY-4-METHYLCOUMARIN;4-MU;4-Methylumbelliferon;4-METHYL-7-HYDROXYCOUMARIN;7-HYDROXY-4-METHYL-CHROMEN-2-ONE;Medilla;Bilcolic;Hymecromon
CBNumber:
CB5745737
Molecular Formula:
C10H8O3
Molecular Weight:
176.17
MOL File:
90-33-5.mol
Modify Date:
2024/7/10 9:20:07
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4-Methylumbelliferone 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
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)
Water Solubility slightly soluble
λmax 221nm, 251nm, 322nm
Merck 14,4854
BRN 142217
Stability Stable. Combustible. Incompatible with strong oxidizing agents.
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 4-Methylumbelliferone (90-33-5)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H303-H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a
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
Toxicity LD50 oral in rat: 3850mg/kg
NFPA 704
1
2 0

4-Methylumbelliferone price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) M1381 4-Methylumbelliferone ≥98% 90-33-5 25G ₹4449.08 2022-06-14 Buy
Sigma-Aldrich(India) M1381 4-Methylumbelliferone ≥98% 90-33-5 100G ₹5726.43 2022-06-14 Buy
ALFA India ALF-A10337-30 4-Methylumbelliferone, 97% 90-33-5 250g ₹5923 2022-05-26 Buy
TCI Chemicals (India) M0453 4-Methylumbelliferone 90-33-5 25G ₹2600 2022-05-26 Buy
ALFA India ALF-A10337-18 4-Methylumbelliferone, 97% 90-33-5 50g ₹2833 2022-05-26 Buy
Product number Packaging Price Buy
M1381 25G ₹4449.08 Buy
M1381 100G ₹5726.43 Buy
ALF-A10337-30 250g ₹5923 Buy
M0453 25G ₹2600 Buy
ALF-A10337-18 50g ₹2833 Buy

4-Methylumbelliferone Chemical Properties,Uses,Production

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.

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.

General Description

4-Methylumbelliferone 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.

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.

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.]

4-Methylumbelliferone Preparation Products And Raw materials

Raw materials

Ethyl acetoacetate dilute sulphuric acid Benzene Sulfuric acid PhosPhorous Pentaoxide
Resorcinol
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Preparation Products

8-ACETYL-7-HYDROXY-4-METHYLCOUMARIN

4-Methylumbelliferone Suppliers

Global( 658)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
BTC pharm India +918790379245 AndhraPradesh, India 1269 58 Inquiry
GLR Innovations +91 9891111994 New Delhi, India 4542 58 Inquiry
chromsynth pvt ltd +919704220374 Hyderabad, India 244 58 Inquiry
Hyderabad +91-9676447615 +91-9676447615 Telangana, India 192 58 Inquiry
GOALSY PHARMA +91-8247562464 +91-9885583385 Hyderabad, India 479 58 Inquiry
SVH BIOSCIENCES +91-6303499280 +91-6303499280 Hyderabad, India 478 58 Inquiry
SYNOVA CHEMICALS +91-9920741772 +91-9920741772 Mumbai, India 428 58 Inquiry
CNS CHEMICALS +91-9381957258 +91-9381957258 Telangana, India 354 58 Inquiry
CHEMAZON LABORATORIES +91 9848551964 Hyderabad, India 1320 58 Inquiry
Ortin Laboratories Limited +91-9241566560 +91-9241566560 Hyderabad, India 31 58 Inquiry
Supplier Advantage
BTC pharm India 58
GLR Innovations 58
chromsynth pvt ltd 58
Hyderabad 58
GOALSY PHARMA 58
SVH BIOSCIENCES 58
SYNOVA CHEMICALS 58
CNS CHEMICALS 58
CHEMAZON LABORATORIES 58
Ortin Laboratories Limited 58

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