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CAS 475-31-0 Glycine-Conjugated Bile Acid Glycine-Conjugated Bile Acid

Glycocholic Acid

IUPAC: N-(3a,7a,12a-Trihydroxy-5ß-cholan-24-oyl)glycine View on PubChem
CAS NUMBER
475-31-0
MOL. FORMULA
C26H43NO6
MOL. WEIGHT
465.62 g/mol
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Scientific Overview

Conjugation with glycine increases cholic acid's water solubility and lowers its pKa relative to the unconjugated acid, keeping it ionized (and thus more surface-active) across the physiological pH range of the intestine. Glycocholic acid plays a central role in dietary fat emulsification and is increasingly studied as a serum/bile biomarker for cholestatic and malignant hepatobiliary conditions.

Glycocholic Acid is the glycine-conjugated form of cholic acid and one of the most abundant bile acids in human bile, used as a research reagent for studying lipid absorption, bile acid transport, and as a biomarker in hepatobiliary disease diagnostics.

Full Technical Data
Chemical Name Glycocholic Acid (Cholylglycine)
CAS Number 475-31-0
IUPAC Name N-(3a,7a,12a-Trihydroxy-5ß-cholan-24-oyl)glycine
Molecular Formula C26H43NO6
Molecular Weight 465.62 g/mol g/mol
Reaction Scheme
Cholic Acid
Glycine
NA
Glycocholic Acid
NA
Commercial Applications

Bile Acid Metabolism Research

Used as a reference bile acid conjugate for studying enterohepatic circulation and fat digestion.

Hepatobiliary Disease Biomarker Research

Studied as a candidate serum biomarker for cholangiocarcinoma and other hepatobiliary conditions.

Drug Absorption & Transporter Studies

Used to investigate bile-acid transporter-mediated drug absorption and interactions.

Analytical Reference Standard

Serves as a chromatographic reference standard for bile acid profiling assays.

Market Therapeutic Focus
GLYCINE-CONJUGATED BILE ACID PHARMACEUTICAL MANUFACTURING HEPATOBILIARY DISEASE RESEARCH DRUG TRANSPORTER STUDIES ANALYTICAL REFERENCE STANDARDS CRO/CDMO
Scientific Literature

Discovery of Glycocholic Acid and Taurochenodeoxycholic Acid as Phenotypic Biomarkers in Cholangiocarcinoma

Authors: Song, W.S. et al.

Sci. Rep.

DOI: 10.1038/s41598-018-29095-2

Quantification of Glycocholic Acid in Human Serum by Stable Isotope Dilution UPLC-ESI-MS/MS

Authors: Guo, C. et al.

J. Chromatogr. B

DOI: 10.1016/j.jchromb.2017.11.026

Role of Bile Acids and Bile Acid Receptors in Metabolic Regulation

Authors: Lefebvre, P. et al.

Physiol. Rev.

DOI: 10.1152/physrev.00010.2008
Peer Queries & FAQs
What does 'glycine-conjugated' mean for a bile acid?
It means cholic acid has been enzymatically linked via an amide bond to the amino acid glycine, a natural modification that increases water solubility and detergent efficiency in the gut.
Why is Glycocholic Acid studied as a cancer biomarker?
Elevated serum and bile levels of glycocholic acid (and related conjugated bile acids) have been observed in patients with cholangiocarcinoma and other hepatobiliary diseases, making it a candidate diagnostic marker.
How does Glycocholic Acid differ from Cholic Acid itself?
It is the glycine-amide conjugate of cholic acid, giving it a lower pKa and higher water solubility, which makes it the predominant physiological form of cholic acid found in human bile.
What is the recommended storage condition?
Store in a tightly sealed container at 2-8°C, protected from moisture and light; the material is noted to be hygroscopic.

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