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A8292

Sigma-Aldrich

Acetobromo-α-D-glucuronic acid methyl ester

≥93% (GC)

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Synonym(s):
(2,3,4-Tri-O-acetyl-α-D-glucopyranosyl bromide)uronic acid methyl ester, Bromo-2,3,4-tri-O-acetyl-α-D-glucopyranuronic acid methyl ester, Methyl acetobromo-α-D-glucuronate
Empirical Formula (Hill Notation):
C13H17BrO9
CAS Number:
21085-72-3
Molecular Weight:
397.17
Beilstein:
96281
EC Number:
244-203-4
MDL number:
MFCD00061613
PubChem Substance ID:
24891328
NACRES:
NA.25

Quality Level

200

Assay

≥93% (GC)

form

powder

optical activity

[α]/D 188 to 198 °, c = 1% (w/v) in ethyl acetate

color

white

mp

80-110 °C (lit.)

solubility

ethyl acetate: 50 mg/mL, clear, colorless to faintly yellow

shipped in

dry ice

storage temp.

−20°C

SMILES string

COC(=O)[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI

1S/C13H17BrO9/c1-5(15)20-8-9(21-6(2)16)11(13(18)19-4)23-12(14)10(8)22-7(3)17/h8-12H,1-4H3/t8-,9-,10+,11-,12-/m0/s1

InChI key

GWTNLHGTLIBHHZ-SVNGYHJRSA-N

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Application

Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of HMR1098-S-Glucuronide Methyl Ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

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

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John C Quindry et al.
American journal of physiology. Heart and circulatory physiology, 299(1), H175-H183 (2010-05-04)
The mechanisms responsible for anti-arrhythmic protection during ischemia-reperfusion (IR) in exercised hearts are not fully understood. The purpose of this investigation was to examine whether the ATP-sensitive potassium channels in the mitochondria (mito K(ATP)) and sarcolemma (sarc K(ATP)) provide anti-arrhythmic
Katarzyna Choma et al.
Journal of bioenergetics and biomembranes, 41(4), 323-334 (2009-10-13)
Mitochondrial potassium channels in the brain have been suggested to have an important role in neuroprotection. The single channel activity of mitochondrial potassium channels was measured after reconstitution of the purified inner membrane from rat brain mitochondria into a planar
Brian T Ethell et al.
Drug metabolism and disposition: the biological fate of chemicals, 31(8), 1027-1034 (2003-07-18)
HMR1098, a novel KATP-blocking agent, is metabolized to form an S-glucuronide in rat and dog bile. Synthesis of the S-glucuronide metabolite was studied in human liver and kidney microsomes. Recombinant UPD-glucuronosyltransferases (UGTs) were screened for activity, and kinetic analysis was

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