4-Methylumbelliferyl alpha-D-glucopyranoside
Basic information
- CAS
17833-43-1- Standard SMILES
Cc1cc(=O)oc2cc(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc12- InChIKey
YUDPTGPSBJVHCN-JZYAIQKZSA-N- Molecular formula
- C16H18O8
- Average molar mass
- 338.31 g/mol
- Monoisotopic mass
- 338.10016753
Overview
4-Methylumbelliferyl-alpha-D-glucopyranoside is a member of coumarins and a glycoside.
Names & identifiers
- Preferred name
- 4-Methylumbelliferyl alpha-D-glucopyranoside
- IUPAC
- 4-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
- English name
- 4-METHYLUMBELLIFERYL-ALPHA-D-GLUCOPYRANOSIDE HYDRATE
- Molecular formula
- C16H18O8
- Molecular weight
- 338.31
Names & synonyms
4-Methylumbelliferyl alpha-D-glucopyranosideDTXSID20863699RefChem:525744DTXCID70147844317833-43-14-Methylumbelliferyl a-D-glucopyranoside7-(alpha-D-Glucopyranosyloxy)-4-methyl-2H-1-benzopyran-2-one4-Methyl-7-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2H-chromen-2-one4-methyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-oneMFCD000676614-Methylumbelliferyl-|A-D-Glucopyranoside4-METHYLUMBELLIFERYL-ALPHA-D-GLUCOSE
Show more names
4MU-α-Glc4-MU-ALPHA-D-GLC-L-Iduronide (free acid)4-Methylumbelliferyl α4-MethyluMbelliferyl α-D-Glucose4-Methylumbeliferon α-D-glucoside4-MethyluMbellifery -α-D-glucoside4-METHYLUMBELLIFERYL-A-D-GLUCOSIDE4-Methylumbelliferyl alpha-D-glucose4-METHYLUMBELLIFERYL-ALPHA-D-GLUCOSIDE
C16H18O82H-1-Benzopyran-2-one, 7-(alpha-D-glucopyranosyloxy)-4-methyl-M04131EM068204-Methylumbelliferyl ?-D-glucopyranoside4-methylumbelliferyl alpha-glucosideEINECS 241-794-04-Methylumbelliferyl alpha-D-glucoside
Properties
Computed structural properties
- XLogP
- -0.8
- Topological polar surface area
- 126 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 506
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 171 · 171-173 °C
- Boiling point
- 626.9 · 626.9±55.0 °C(Predicted)
- Density
- 1.522 · 1.522±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 50 mg/mL, · DMSO: 50 mg/mL, clear, colorless to faintly yellow
- pka
- 12.73 · 12.73±0.70(Predicted)
- form
- White solid
- color
- White to Off-White
- BRN
- 1690776 · 1690776
- InChI
- InChI=1/C16H18O8/c1-7-4-12(18)23-10-5-8(2-3-9(7)10)22-16-15(21)14(20)13(19)11(6-17)24-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16+/s3
- InChIKey
- YUDPTGPSBJVHCN-JZYAIQKZSA-N
- SMILES
- C12OC(C=C(C)C=1C=CC(O[C@@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)=C2)=O |&1:11,12,14,15,17,r|
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- F
- 3-10-21
- wgk
- 3
- hs_code
- 2932209090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
Chemistry & industry
Applications
Description4-Methylumbelliferyl-α-D-glucopyranoside is a fluorogenic substrate for α-glucosidase. 4-Methylumbelliferyl-α-D-glucopyranoside is cleaved by α-glucosidase to release the fluorescent moiety 4-methylumbelliferyl (4-MU). 4-MU fluorescence is pH-dependent with excitation maxima of 320 and 360 nm at low (1.97-6.72) and high pH (7.12-10.3), respectively, and an emission maximum ranging from 445 to 455 nm, increasing as pH decreases. 4-Methylumbelliferyl-α-D-glucopyranoside has been used to quantify α-glucosidase activity in infant blood spot samples as a biomarker of Fabry and Pompe diseases, lysosomal storage disorders characterized by a deficiency in the enzyme.
Uses4-Methylumbelliferyl-α-D-glucopyranoside is a fluorogenic substrate in the assay of a-glucosidase,it has been used in the study of Pompe disease.
Uses4-Methylumbelliferyl α-D-glucopyranoside is used as a flurogenic substrate for the identification, characterization and kinetic analysis of α-D-glucosidase(s).
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: 4-Methylumbelliferyl-alpha-D-glucopyranoside is a member of coumarins and a glycoside.
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Compound notes
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