4-Methylumbelliferyl-beta-D-glucuronide supplier

Name
4-Methylumbelliferyl-beta-D-glucuronide
EINECS 228-186-0
CAS No. 6160-80-1
Article Data13
CAS DataBase
Density 1.632 g/cm₃
Solubility slightly soluble in water
Melting Point 102 °C
Formula C₁₆H₁₆O₉
Boiling Point 683.106 °C at 760 mmHg
Molecular Weight 352.298
Flash Point 254.961 °C
Transport Information
Appearance white to off-white powder.
Safety 24/25-36/37
Risk Codes 22-40
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Glucopyranosiduronicacid, 4-methyl-2-oxo-2H-1-benzopyran-7-yl, b-D- (8CI);4-Methylumbelliferone glucuronide;4-Methylumbelliferone b-D-glucuronide;4-Methylumbelliferyl glucuronide;4-Methylumbelliferyl b-D-glucuronide;4-Methylumbelliferyl-b-D-glucuronic acid;Hymecromon-7-O-4-b-D-glucuronide;
PSA 146.66000
LogP -0.62760

Synthetic route

: 101014-65-7
methyl (4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)urinate

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
With water; potassium carbonate In methanol; dichloromethane at 0 - 5℃; for 12h;	89%
With barium hydroxide monohydrate In methanol; water for 4h; Inert atmosphere; Cooling with ice;	47%
With barium hydroxide monohydrate In methanol; water at 0℃; for 4h; Inert atmosphere;	47%
Multi-step reaction with 2 steps 1: NaOMe; MeOH / 1 h / 20 °C 2: 0.068 mmol / LiOH / tetrahydrofuran; H2O / 1 h / 20 °C View Scheme

: 937018-37-6
4-methylumbelliferyl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
With barium methoxide In methanol at 0 - 5℃; for 24h;	85%

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: 2616-64-0
UDP-glucuronic acid

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;	75%
With rat liver microsome solution; magnesium chloride In various solvent(s) at 37℃; for 0.166667h; pH=7.4;

: 18997-57-4
4-methylumbelliferyl β-D-glucopyranoside

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
With oxygen; sodium hydrogencarbonate; platinum at 90℃;
Multi-step reaction with 5 steps 1: pyridine / 5 h / 90 - 100 °C 2: 7.60 g / pyridine / 24 h / 20 °C 3: 92 percent / iodine; methanol / benzene / 24 h / 65 °C 4: 68 percent / aqueous sodium hypochlorite; TBAB; NaBr / 2,2,6,6-tetramethyl-1-piperidinyloxy; tetrabutylammonium bromide / aq. NaHCO3; CH2Cl2 / 3 h / 0 °C 5: 85 percent / barium methoxide / methanol / 24 h / 0 - 5 °C View Scheme

: 116523-82-1
methyl 4-methylcoumarin-7-yl-β-D-glucopyranuronate

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water at 20℃; for 1h;	0.068 mmol

: 937018-36-5
4-methylumbelliferyl-2,3,4-tri-O-acetyl-β-glucopyranoside

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 68 percent / aqueous sodium hypochlorite; TBAB; NaBr / 2,2,6,6-tetramethyl-1-piperidinyloxy; tetrabutylammonium bromide / aq. NaHCO3; CH2Cl2 / 3 h / 0 °C 2: 85 percent / barium methoxide / methanol / 24 h / 0 - 5 °C View Scheme

: 4-methyl-7-(3,4,5-trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-chromen-2-one

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 7.60 g / pyridine / 24 h / 20 °C 2: 92 percent / iodine; methanol / benzene / 24 h / 65 °C 3: 68 percent / aqueous sodium hypochlorite; TBAB; NaBr / 2,2,6,6-tetramethyl-1-piperidinyloxy; tetrabutylammonium bromide / aq. NaHCO3; CH2Cl2 / 3 h / 0 °C 4: 85 percent / barium methoxide / methanol / 24 h / 0 - 5 °C View Scheme

: 937018-35-4
4-methylumbelliferyl-2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / iodine; methanol / benzene / 24 h / 65 °C 2: 68 percent / aqueous sodium hypochlorite; TBAB; NaBr / 2,2,6,6-tetramethyl-1-piperidinyloxy; tetrabutylammonium bromide / aq. NaHCO3; CH2Cl2 / 3 h / 0 °C 3: 85 percent / barium methoxide / methanol / 24 h / 0 - 5 °C View Scheme

: 5980-33-6
sodium 4-methylumbelliferonate

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 45 percent / benzyltriethylammonium chloride; aq. NaOH / CHCl3 / 5 h / Heating 2: NaOMe; MeOH / 1 h / 20 °C 3: 0.068 mmol / LiOH / tetrahydrofuran; H2O / 1 h / 20 °C View Scheme

: 21085-72-3
1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 45 percent / benzyltriethylammonium chloride; aq. NaOH / CHCl3 / 5 h / Heating 2: NaOMe; MeOH / 1 h / 20 °C 3: 0.068 mmol / LiOH / tetrahydrofuran; H2O / 1 h / 20 °C View Scheme

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: 63700-19-6
uridine-5'-diphospho-α-D-glucuronic acid trisodium salt

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
With magnesium chloride In phosphate buffer at 37℃; for 1.25h; pH=7.4; Enzyme kinetics; Further Variations:; Solvents;
With recombinant human UDP-glucuronosyltransferase isoform 1A7; magnesium chloride In dimethyl sulfoxide pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction;

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: uridine diphosphate glucuronic acidammonium salt

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
With magnesium(II) chloride hexahydrate; recombinant human uridine 5′-diphosphate-glucuronosyltransferase 1A9; bovine serum albumin In aq. phosphate buffer at 37℃; for 1h; pH=7.4; Kinetics; Time; Concentration; Reagent/catalyst; Darkness; Enzymatic reaction;

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: 777038-38-7
α-D-glucuronyl fluoride

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
With Escherichia coli β-glucuronidase E504G mutant In aq. phosphate buffer; tert-butyl alcohol at 37℃; for 48h; pH=7.5; Enzymatic reaction;

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

: 7355-18-2
(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate; dmap / 1,2-dichloro-ethane / 5 h / 60 °C / Inert atmosphere 2: barium hydroxide monohydrate / water; methanol / 4 h / Inert atmosphere; Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate; dmap / 1,2-dichloro-ethane / 5 h / 60 °C / Inert atmosphere 2: barium hydroxide monohydrate / water; methanol / 4 h / Inert atmosphere; Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: triethylamine; boron trifluoride diethyl etherate / dichloromethane / 72 h / 20 °C / Inert atmosphere 2: barium hydroxide monohydrate / water; methanol / 4 h / 0 °C / Inert atmosphere View Scheme

: 186581-53-3, 908094-01-9
diazomethane

: 108-24-7
acetic anhydride

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

: 101014-65-7
methyl (4′-methylumbelliferyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)urinate

Conditions

Conditions	Yield
With pyridine; diethyl ether Reaktion ueber zwei Stufen;

...Expand

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

Conditions

Conditions	Yield
With ethylenediaminetetraacetic acid; sodium acetate; Triton X-100; β-glucuronidase in human liver homogenate at 37℃; for 0.5h; pH=5; Enzyme kinetics; Further Variations:; Catalysts;

: UDP disodium

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

: 90-33-5, 79566-13-5
7-hydroxy-4-methyl-chromen-2-one

Conditions

Conditions	Yield
With magnesium(II) chloride hexahydrate; recombinant human uridine 5′-diphosphate-glucuronosyltransferase 1A9; bovine serum albumin In aq. phosphate buffer at 37℃; for 1h; pH=7.4; Kinetics; Time; Reagent/catalyst; Darkness; Enzymatic reaction;

: 67-56-1
methanol

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

: 116523-82-1
methyl 4-methylcoumarin-7-yl-β-D-glucopyranuronate

Conditions

Conditions	Yield
With sulfuric acid at 65℃; for 1h;

: 6160-80-1
4-methylumbelliferyl-β-D-glucuronide

A: 489-91-8, 528-16-5, 552-12-5, 577-46-8, 643-33-4, 2240-07-5, 6294-16-2, 10133-02-5, 18402-78-3, 18968-14-4, 21179-08-8, 23018-83-9, 33599-45-0, 33599-46-1, 46171-67-9, 46171-69-1, 46172-26-3, 70021-34-0, 71031-08-8, 104195-06-4, 106499-29-0, 124817-72-7
D-glucuronic acid

B: 2373-31-1
6-hydroxy-4-methyl-chromen-2-one

Conditions

Conditions	Yield
With β-glucuronidase In aq. phosphate buffer pH=7.4; Concentration; Enzymatic reaction;

4-Methylumbelliferyl-beta-D-glucuronide Chemical Properties

Product Name: beta-D-Glucopyranosiduronic acid,4-methyl-2-oxo-2H-1-benzopyran-7-yl (CAS NO.6160-80-1)

Molecular Formula: C1₆H₁₆O₉
Molecular Weight: 352.30g/mol
Mol File: 6160-80-1.mol
EINECS: 228-186-0
Index of Refraction: 1.663
Molar Refractivity: 80.05 cm³
Molar Volume: 215.8 cm³
Surface Tension: 84.7 dyne/cm
Density: 1.632 g/cm³
Flash Point: 255 °C
Enthalpy of Vaporization: 105.25 kJ/mol
Boiling Point: 683.1 °C at 760 mmHg
Vapour Pressure: 1.35E-19 mmHg at 25°C
XLogP3-AA: -0.5
H-Bond Donor: 4
H-Bond Acceptor: 9
Structure Descriptors of beta-D-Glucopyranosiduronic acid,4-methyl-2-oxo-2H-1-benzopyran-7-yl (CAS NO.6160-80-1):
IUPAC Name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methyl-2-oxochromen-7-yl)oxyoxane-2-carboxylic acid
Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)C(=O)O)O)O)O
Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O
InChI: InChI=1S/C16H16O9/c1-6-4-10(17)24-9-5-7(2-3-8(6)9)23-16-13(20)11(18)12(19)14(25-16)15(21)22/h2-5,11-14,16,18-20H,1H3,(H,21,22)/t11-,12-,13+,14-,16+/m0/s1
InChIKey: ARQXEQLMMNGFDU-JHZZJYKESA-N
Product Categories: Substrates; Fluorescent Labels & Indicators; Glucuronides

4-Methylumbelliferyl-beta-D-glucuronide Safety Profile

Safety Information of beta-D-Glucopyranosiduronic acid,4-methyl-2-oxo-2H-1-benzopyran-7-yl (CAS NO.6160-80-1):
Hazard Codes: Xi Irritant ,Xn Harmful
Risk Statements: 22-40
R22:Harmful if swallowed.
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 24/25-36/37
S24/25:Avoid contact with skin and eyes.
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 3

4-Methylumbelliferyl-beta-D-glucuronide Specification

beta-D-Glucopyranosiduronic acid,4-methyl-2-oxo-2H-1-benzopyran-7-yl , its CAS NO. is 6160-80-1, the synonyms are 4-Methylumbelliferyl glucuronide ; 4-Methylumbelliferyl beta-glucuronide ; 4-Methyl-2-oxo-2H-1-benzopyran-7-yl beta-D-
glucopyranosiduronic acid ; beta-D-Glucopyranosiduronic acid, 4-methyl-2-oxo-2H-1-benzopyran-7-yl .

Product Name

4-Methylumbelliferyl-beta-D-glucuronide

Synthetic route

4-Methylumbelliferyl-beta-D-glucuronide Chemical Properties

4-Methylumbelliferyl-beta-D-glucuronide Safety Profile

4-Methylumbelliferyl-beta-D-glucuronide Specification

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