4-Methylumbelliferyl-beta-D-glucoside

Base Information

• Chemical Name: 4-Methylumbelliferyl-beta-D-glucoside
• CAS No.: 18997-57-4
• Molecular Formula: C16H18 O8
• Molecular Weight: 338.314
• Hs Code.: 29389090
• Mol file: 18997-57-4.mol

Synonyms:4-Methylumbelliferyl-beta-D-glucoside;EINECS 242-736-7;SCHEMBL755988

Chemical Property of 4-Methylumbelliferyl-beta-D-glucoside

Chemical Property:

• Appearance/Colour: White Powder
• Melting Point: 258-263 °C (dec.)
• Refractive Index: 1.4430 (estimate)
• Boiling Point: 626.9 °C at 760 mmHg
• PKA: 12.73±0.70(Predicted)
• Flash Point: 233.9 °C
• PSA: 129.59000
• Density: 1.522 g/cm³
• LogP: -0.71990
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in DMF or water
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 338.10016753
• Heavy Atom Count: 24
• Complexity: 506

Purity/Quality:

98%, ^*data from raw suppliers

4-Methylumbelliferyl b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• Description: 4-Methylumbelliferyl-β-D-Glucopyranoside (4-MUG) is a fluorogenic substrate of β-glucosidase and β-glucocerebrosidase (also known as glucosylceramidase). In addition to its use in characterizing novel β-glucosidases, 4-MUG is used in assays to evaluate deficiency in β- glucocerebrosidase activity related to Gaucher disease. Hydrolysis of 4-MUG releases the fluorescent product 4-MU, which has an emission maximum at 445-454 nm. The excitation maximum for 4-MU is pH-dependent: 330, 370, and 385 nm at pH 4.6, 7.4, and 10.4, respectively.
• Uses: A fluorogenic substrate in the assay of ?-glucosidase. Fluorescence: max. Abs. 316nm; max. Em. 372nm; e x 10-3: 15 A fluorogenic substrate in the assay of ?-glucosidase.Fluorescence: max. Abs. 316nm; max. Em. 372nm; e x 10-3: 15 4-Methylumbelliferyl β-D-glucopyranoside has been used as substrate:in glucosylceramidase β enzyme activity assay in lysosome-enriched fractions from primary hippocampal neuronsin β-glucosidase assay during yeast fermentationto assay glucocerebrosidase 1 (GBA1)-related glucosidase activity in macrophage cell line (RAW)

Technology Process of 4-Methylumbelliferyl-beta-D-glucoside

There total 20 articles about 4-Methylumbelliferyl-beta-D-glucoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (67909-25-5) → 4-methylumbelliferyl β-D-glucopyranoside (18997-57-4,39940-54-0)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 1h;

DOI:10.3390/molecules201219789

Reference yield: 82.0%

alpha-D-glucopyranose (492-62-6) + 7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 4-methylumbelliferyl β-D-glucopyranoside (18997-57-4,39940-54-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 55 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01549

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 4-methylumbelliferyl β-D-glucopyranoside (18997-57-4,39940-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / aq. NaOH / acetone / 7 h / Ambient temperature

2: 6mM methanolic MeONa / 5 h / Ambient temperature

With sodium hydroxide; sodium methylate; In acetone;

DOI:10.1016/0008-6215(95)00102-Y

upstream raw materials:

4′-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

4-methylumbelliferyl β-laminaratetraoside

4-methylumbelliferyl β-laminarapentaoside

7-hydroxy-4-methyl-chromen-2-one

Downstream raw materials:

4-methylumbelliferyl 4,6-O-benzylidene-β-D-glucopyranoside

D-Glucose

7-hydroxy-4-methyl-chromen-2-one

4-methylumbelliferyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Refernces

• 1、 Huang, Yin-Peng,Cao, Yun-Feng,Fang, Zhong-Ze,Zhang, Yan-Yan,Hu, Cui-Min,Sun, Xiao-Yu,Yu, Zhen-Wen,Zhu, Xu,Hong, Mo,Yang, Lu,Sun, Hong-Zhi. "Glycyrrhetinic acid exhibits strong inhibitory effects towards UDP-glucuronosyltransferase (UGT) 1A3 and 2B7". . p. 1358 - 1361. Retrieved 2013.
• 2、 Xu, Xiping,Yan, Yaru,Huang, Wenqian,Mo, Ting,Wang, Xiaohui,Wang, Juan,Li, Jun,Shi, Shepo,Liu, Xiao,Tu, Pengfei. "Molecular cloning and biochemical characterization of a new coumarin glycosyltransferase CtUGT1 from Cistanche tubulosa". . . Retrieved 2021.
• 3、 -. "Based on 4 - methyl [...] synthesis method of a plurality of glycoside". Paragraph 0080; 0081. . Retrieved 2018/10/11.