6734-33-4

Basic information

• Product Name: 4-METHYLUMBELLIFERYL-BETA-D-XYLOPYRANOSIDE
• Synonyms: 4-METHYLUMBELLIFERYL-BETA-D-XYLOPYRANOSIDE;4-METHYLUMBELLIFERYL BETA-D-XYLOSIDE;4-METHYLUMBELLIFERYL-B-D-XYLOSIDE;METHYLUMBELLIFERYL-B-D-XYLOPYRANOSIDE, 4-;methylumbelliferyl-beta-d-xyloside;4-methyl-7-(beta-D-xylopyranosyloxy)-2H-1-benzopyran-2-one;4-METHYLUMBELLIFERYL-BETA-D-XYLOPYRA- &;4-Methylumbelliferyl-Beta-D-Xylo-
• CAS NO: 6734-33-4
• Molecular Formula: C₁₅H₁₆O₇
• Molecular Weight: 308.28
• EINECS: 229-784-4
• Product Categories: Substrates;substrate
• Mol File: 6734-33-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 223 °C
• Boiling Point: 572.1 °C at 760 mmHg
• Flash Point: 217.3 °C
• Appearance: White to almost white/Powder
• Density: 1.514 g/cm³
• Vapor Pressure: 6.29E-14mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 12.85±0.70(Predicted)
• Stability: Light Sensitive
• BRN: 39934
• CAS DataBase Reference: 4-METHYLUMBELLIFERYL-BETA-D-XYLOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLUMBELLIFERYL-BETA-D-XYLOPYRANOSIDE(6734-33-4)
• EPA Substance Registry System: 4-METHYLUMBELLIFERYL-BETA-D-XYLOPYRANOSIDE(6734-33-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 6734-33-4(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white powder

InChI:InChI=1/C15H16O7/c1-7-4-12(17)22-11-5-8(2-3-9(7)11)21-15-14(19)13(18)10(16)6-20-15/h2-5,10,13-16,18-19H,6H2,1H3/t10-,13+,14-,15+/m1/s1

Upstream product

• 6734-34-5 4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 2001-96-9 p-nitrophenyl β-D-xylopyranoside 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 3616-06-6 UDP-xylose 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 106820-14-8 2,3,4-Tri-O-acetyl-D-xylopyranose 
• 197144-02-8 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 

Downstream Products

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 2460-44-8 β-D-xylopyranoside 
• 158962-91-5 4-methylumbelliferyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside 

Relevant articles and documents

Based on 4 - methyl [...] synthesis method of a plurality of glycoside

The invention discloses a method for synthesizing various glucosides on a basis of 4-methylumbelliferone. According to the invention, a glycosyl donor peracetyl saccharide and a glycosyl acceptor 4-methylumbelliferone are subjected to a glycosylation reaction under room temperature or under heating with dichloromethane or 1,2-dichloroethane as a solvent and with the combined effect of Lewis acid boron trifluoride ethyl ether and organic alkali triethylamine or pyridine; and protecting groups are removed, such that various glucosides based on 4-methylumbelliferone can be obtained. The glucosides include 4-methylumbelliferone-beta-D-glucopyranosiduronide, 4-methylumbelliferone-beta-D-glucopyranoside, 4-methylumbelliferone-beta-D-xylopyranoside, 4-methylumbelliferone-beta-D-ribofuranoside, 4-methylumbelliferone-alpha-D-galactopyranoside, and 4-methylumbelliferone-alpha-D-mannopyranoside. The method is simple, and can produce a beta or alpha single-configuration target. A glycosylation reaction yield can reach 17-93%.

CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY

Compositions for the treatment of cancer comprising coumarin and thiocoumarin derivatives of Formulas I- XII are disclosed. Said derivatives preferentially inhibit carbonic anhydrase IX and XII (which are associated with hypoxic and metastatic tumours) over inhibiting carbonic anhydrase I and II activity. The compositions therefore are suited for treatment of hypoxic or metastatic cancers due to this selective mechanism of action.

The Novel UDP Glycosyltransferase 3A2: Cloning, catalytic properties, and tissue distribution

The human UDP glycosyltransferase (UGT) 3A family is one of three families involved in the metabolism of small lipophilic compounds. Members of these families catalyze the addition of sugar residues to chemicals, which enhances their excretion from the body. The UGT1 and UGT2 family members primarily use UDP glucuronic acid to glucuronidate numerous compounds, such as steroids, bile acids, and therapeutic drugs. We showed recently that UGT3A1, the first member of the UGT3 family to be characterized, is unusual in using UDP N-acetylglucosamine as sugar donor, rather than UDP glucuronic acid or other UDP sugar nucleotides (J Biol Chem 283:36205-36210, 2008). Here, we report the cloning, expression, and characterization of UGT3A2, the second member of the UGT3 family. Like UGT3A1, UGT3A2 is inactive with UDP glucuronic acid as sugar donor. However, in contrast to UGT3A1, UGT3A2 uses both UDP glucose and UDP xylose but not UDP N-acetylglucosamine to glycosidate a broad range of substrates including 4-methylumbelliferone, 1-hydroxypyrene, bioflavones, and estrogens. It has low activity toward bile acids and androgens. UGT3A2 transcripts are found in the thymus, testis, and kidney but are barely detectable in the liver and gastrointestinal tract. The low expression of UGT3A2 in the latter, which are the main organs of drug metabolism, suggests that UGT3A2 has a more selective role in protecting the organs in which it is expressed against toxic insult rather than a more generalized role in drug metabolism. The broad substrate and novel UDP sugar specificity of UGT3A2 would be advantageous for such a function. Copyright