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Chemical Structure| 90-33-5 Chemical Structure| 90-33-5
Chemical Structure| 90-33-5

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4-Methylumbelliferone, a natural product isolated and purified from the herbs of Ruta graveolens L., is a hyaluronic acid (HA) synthesis inhibitor with an IC50 of 0.4 mM.

Synonyms: Hymecromone; 4-MU; Imecromone

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Product Details of 4-Methylumbelliferone

CAS No. :90-33-5
Formula : C10H8O3
M.W : 176.17
SMILES Code : O=C1C=C(C)C2=C(O1)C=C(O)C=C2
Synonyms :
Hymecromone; 4-MU; Imecromone
MDL No. :MFCD00006866
InChI Key :HSHNITRMYYLLCV-UHFFFAOYSA-N
Pubchem ID :5280567

Safety of 4-Methylumbelliferone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-Methylumbelliferone

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 90-33-5 ]

[ 90-33-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 90-33-5 ]
  • [ 6174-86-3 ]
YieldReaction ConditionsOperation in experiment
83.5% With N-chloro-succinimide; copper(II) chloride monohydrate; zinc(II) chloride; In acetonitrile; at 82℃; for 0.05h; General procedure: To a 50 mL flask, the coumarin (1 mmol), appropriate amount of NXS, the Lewisacid catalyst and 20 mL anhydrous solvent were added in. The mixture was heated toreflux with a condenser under the protection of a drying tube. The reaction progresswas monitored by TLC. When the reaction was completed, the mixture was cooled toroom temperature. The solvent was removed by vacuum rotary evaporation, and theresidue was dispensed in 25 mL 5% sodium hydrogen sulfite (NaHSO3) aqueoussolution and then extracted with 25 mL ethyl acetate (EtOAc) for three times. Theorganic layer was combined, washed with 10 mL water and dried over anhydroussodium sulphate (Na2SO4). After the solvent was removed, the crude product waspurified by silica gel (300-400 mesh) column chromatograph.
  • 2
  • [ 50-00-0 ]
  • [ 90-33-5 ]
  • [ 828-81-9 ]
  • 8-[5-(2-Chloro-phenyl)-[1,3,4]thiadiazol-2-ylamino]-methyl}-7-hydroxy-4-methyl-chromen-2-one [ No CAS ]
  • 3
  • [ 90-33-5 ]
  • [ 6642-30-4 ]
  • 4-methyl-7-coumarinyl N-methylcarbamate [ No CAS ]
  • 4
  • [ 56-23-5 ]
  • [ 90-33-5 ]
  • [ 7782-50-5 ]
  • [ 64-19-7 ]
  • [ 6174-86-3 ]
  • 5
  • [ 66033-92-9 ]
  • [ 90-33-5 ]
  • 1,5-dihalo-pentane [ No CAS ]
  • [ 66042-60-2 ]
  • 7
  • [ 90-33-5 ]
  • H3PO4 [ No CAS ]
  • [ 137215-27-1 ]
  • 8
  • [ 90-33-5 ]
  • [ 4876-10-2 ]
  • [ 1299366-41-8 ]
  • 9
  • [ 90-33-5 ]
  • [ 520-26-3 ]
  • [ 1356391-89-3 ]
  • [ 520-33-2 ]
YieldReaction ConditionsOperation in experiment
28% With water; In dimethyl sulfoxide; at 30℃; for 1h;pH 5;aq. buffer; Enzymatic reaction; alpha-Rhamnosyl-beta-glucosidase was incubated with the aromatic alcohol 1.8 mM 4-methylumbelliferone (4-MU) as acceptor and 1.8 mM <strong>[520-26-3]hesperidin</strong> as rutinose donor. Thin layer chromatography (TLC) of the enzymatic reaction mixture gave a weak fluorescent spot (Rf = 0.72), similar to that of 4-MU-glucoside (4-MU-Glc, Rf = 0.80). The spot was found to be a glycoconjugate that, taking into account the enzyme mechanism,10 strongly suggested the synthesis of 4-MU-rutinoside (Fig. 2). The yield of transglycosylation was 28% after the first hour of reaction at 30 C (Fig. 3). Subsequently, the amount of transglycosylation product remained constant for at least 3 h, while the hydrolysis was shown to proceed up to completion. This behavior is in agreement with that observed for other glycosidase-catalyzed synthesis. Transglycosylation rate is usually higher than free sugar formation rate during the first stage of the reaction and, later on, transglycosylation product concentration reaches a plateau or diminishes because it acts as a substrate of the enzyme. [24] and [25] The increment of the reaction temperature up to the near-optimal for hydrolysis (60 C) was shown to diminish the yield of 4-MU-rutinoside, probably by favoring the hydrolysis of the transglycosylation product. The highest yield was obtained for the acceptor donor ratio in the range 0.8-1:1 (data not shown).
  • 10
  • [ 90-33-5 ]
  • [ 32608-29-0 ]
  • [ 1415232-55-1 ]
  • 11
  • [ 90-33-5 ]
  • [ 97-08-5 ]
  • 4-methyl-2-oxo-2H-chromen-7-yl 4-chloro-3-nitro benzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; In tetrahydrofuran; at 20℃; for 4h; General procedure: Coumarin sulfonates 1-38 were synthesized by reactingdifferent hydroxylated coumarin derivatives (1 mmol) withcommercially available sulfonyl chlorides derivatives (1.2 mmol) inTHF (15 mL) and triethyl amine (1 mmol) was used as base. Reactionmixture was stirred for 4 h at room temperature to afford avariety of coumarin sulfonate esters 1e38. TLC monitoring wasused to determine the progress of the reaction. After the completionof reaction, THF was evaporated under reduced pressure andthe solid product obtained was washed with distilled water anddried under vacuum. The products were recrystallized in methanoland gave good yields. All the synthetic compounds 1-38 werecharacterized by different spectroscopic techniques such as EI-MS,HREI-MS, 1H-NMR, and 13C-NMR.
 

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