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C1129

Sigma-Aldrich

Cholic acid

from bovine and/or ovine, ≥98%

Synonym(s):

3α,7α,12α-Trihydroxy-5β-cholanic acid, Cholanic acid

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About This Item

Empirical Formula (Hill Notation):
C24H40O5
CAS Number:
81-25-4
Molecular Weight:
408.57
Beilstein/REAXYS Number:
2822009
EC Number:
201-337-8
MDL number:
MFCD00003672
UNSPSC Code:
12161900
PubChem Substance ID:
24892356
NACRES:
NA.25

biological source

bovine and/or ovine

description

anionic

assay

≥98%

form

powder

mol wt

408.57 g/mol

mp

200-201 °C (lit.)

functional group

carboxylic acid

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]12C[C@H](O)CC[C@]1(C)[C@@]3([H])C[C@H](O)[C@]4(C)[C@]([H])(CC[C@@]4([H])[C@]3([H])[C@H](O)C2)[C@H](C)CCC(O)=O

InChI

1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChI key

BHQCQFFYRZLCQQ-OELDTZBJSA-N

Gene Information

human ... CYP1A2(1544)

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General description

Cholic acid is a major primary bile acid produced in the liver which facilitates fat absorption and cholesterol excretion. It is a non-denaturing ionic detergent.

Application

Dietary cholic acid has been used in a study to assess its effect on colonic epithelial cell proliferation. It has also been used in a study to investigate extractions and comparisons of human erythrocyte ghosts.
Non-denaturing ionic detergent used for extraction of membrane proteins.

Biochem/physiol Actions

Bile Acid

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Deoxycholic acid ≥99.0% (T)

Sigma-Aldrich

30960

Deoxycholic acid

Chenodeoxycholic acid European Pharmacopoeia (EP) Reference Standard

C1050000

Chenodeoxycholic acid

Bile acids, conjugated

Sigma-Aldrich

CBA

Bile acids, conjugated

R Coleman et al.
Biochimica et biophysica acta, 436(1), 38-44 (1976-06-04)
1. Human erythrocyte ghosts were extracted with individual free and conjugated bile salts and, for comparison, with Triton X-100 under conditions approximating to physiological temperature, pH and tonicity. 2. Treatment with cholate, glycocholate, taurocholate, or with Triton X-100 gave lipid-depleted
Hui Zhou et al.
JCI insight, 5(20) (2020-10-16)
High-fat feeding (HFF) leads to gut dysbiosis through unclear mechanisms. We hypothesize that bile acids secreted in response to high-fat diets (HFDs) may act on intestinal Paneth cells, leading to gut dysbiosis. We found that HFF resulted in widespread taxonomic
E E Deschner et al.
Digestion, 21(6), 290-296 (1981-01-01)
Administration of cholic acid (1.0% of the diet) to male Fisher rats for 3 days resulted in increased numbers of DNA synthesizing epithelial cells per colonic crypt column as compared to those found in either control or 0.2% cholic acid-fed
Michael Lazarou et al.
The FEBS journal, 276(22), 6701-6713 (2009-10-22)
Complex IV is the terminal enzyme of the mitochondrial respiratory chain. In humans, biogenesis of complex IV involves the coordinated assembly of 13 subunits encoded by both mitochondrial and nuclear genomes. The early stages of complex IV assembly involving mitochondrial
Roberto Pellicciari et al.
Journal of medicinal chemistry, 52(24), 7958-7961 (2009-12-18)
In the framework of the design and development of TGR5 agonists, we reported that the introduction of a C(23)(S)-methyl group in the side chain of bile acids such as chenodeoxycholic acid (CDCA) and 6-ethylchenodeoxycholic acid (6-ECDCA, INT-747) affords selectivity for
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