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M5890

Sigma-Aldrich

Methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate

≥98% (GC)

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About This Item

Empirical Formula (Hill Notation):
C15H20O11
CAS Number:
Molecular Weight:
376.31
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

biological source

synthetic (organic)

Assay

≥98% (GC)

form

powder

optical activity

[α]20/D 8.1 to 9.5 °, c = 1% (w/v) in chloroform

technique(s)

gas chromatography (GC): suitable

storage temp.

2-8°C

SMILES string

COC(=O)C1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

InChI

1S/C15H20O11/c1-6(16)22-10-11(23-7(2)17)13(24-8(3)18)15(25-9(4)19)26-12(10)14(20)21-5/h10-13,15H,1-5H3

InChI key

DPOQCELSZBSZGX-UHFFFAOYSA-N

Application

Methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate has been used in a study to assess design and synthesis of a water-soluble glucuronide derivatives of camptothecin for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy. It has also been used in a study to investigate the synthesis and role of glycosylthio heterocycles in carbohydrate chemistry.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Y L Leu et al.
Journal of medicinal chemistry, 42(18), 3623-3628 (1999-09-10)
Glucuronide prodrugs of 9-aminocamptothecin were synthesized. Prodrug 4, in which 9-aminocamptothecin was connected to glucuronic acid by an aromatic spacer via a carbamate linkage, was stable in both aqueous solution and human plasma. Prodrug 4 and its potassium salt 12
Synthesis and role of glycosylthio heterocycles in carbohydrate chemistry
Ashry, E., et al.
Tetrahedron, 62, 2943-2998 (2006)

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