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C9282

Sigma-Aldrich

Sodium cholate hydrate

suitable for cell culture, BioReagent

Synonym(s):

3α,7α,12α-Trihydroxy-5β-cholan-24-oic acid sodium salt, Cholalic acid sodium salt

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About This Item

Empirical Formula (Hill Notation):
C24H39NaO5 · xH2O
CAS Number:
206986-87-0
Molecular Weight:
430.55 (anhydrous basis)
Beilstein:
3582354
EC Number:
206-643-5
MDL number:
MFCD00150749
UNSPSC Code:
12161902
PubChem Substance ID:
24893147
NACRES:
NA.75

biological source

bovine bile
ovine bile

Quality Level

200

description

anionic

product line

BioReagent

Assay

≥99.0% (HPLC)

form

powder

mol wt

micellar avg mol wt 900-1300

aggregation number

2-3

technique(s)

cell culture | mammalian: suitable

CMC

9-15 mM (20-25°C)

solubility

water: 100 mg/mL, clear, colorless to light yellow

HLB

18

SMILES string

O.[Na+].C[C@H](CCC([O-])=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@]12C

InChI

1S/C24H40O5.Na.H2O/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);;1H2/q;+1;/p-1/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-;;/m1../s1

InChI key

MUVVIYFKOVLQHL-RCVKHMDESA-M

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General description

Cholate is a primary bile acid produced from cholesterol in the liver. It is an anionic detergent synthesized from cholesterol in the presence of sterol 12α-hydroxylase (CYP8B1).

Application

Cholate is a bile acid produced in liver during cholesterol breakdown. Cholate downregulates cholesterol-7-α-hydroxylase (rate-limiting step in bile acid synthesis). Cholate, an anionic detergent, is used alone and in combination with urea to extract and reconstitute membrane proteins and protein complexes.
Sodium cholate hydrate has been used:
  • as a bile acid to induce bile acid-responsive (BEAR) transcription system,
  • as a component of Campylobacter defined broth (CDB) to test its effect on stress response in Campylobacter jejuni{52
  • to test its sensitivity towards the bile acid sensor

Biochem/physiol Actions

Reduction in 12-α hydroxylase activity leads to low levels of cholic acid in liver disease.

recommended

Product No.
Description
Pricing

Hazard Statements

H412

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 3

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)

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P Fafournoux et al.
The Journal of biological chemistry, 264(9), 4805-4811 (1989-03-25)
In the liver, System A-mediated uptake of neutral amino acids may play a key role in metabolic control. Knowing the properties of the solubilized and reconstituted System A activity is important for future studies on the purification of the carrier
A Ambesi et al.
Analytical biochemistry, 198(2), 312-317 (1991-11-01)
Solubilization and reconstitution of the cardiac sarcolemmal Na+/Ca2+ exchanger by use of the anionic detergent cholate and its application for reconstitution of the exchanger following solubilization with zwitterionic or nonionic detergents is described. Solubilization and reconstitution with cholate provided a
Proteome Profiling by Label-Free Mass Spectrometry Reveals Differentiated Response of Campylobacter jejuni 81-176 to Sublethal Concentrations of Bile Acids
Masanta WO, et al.
Proteomics. Clinical Applications, 13(3), 1800083-1800083 (2019)
John Y L Chiang
Journal of lipid research, 50(10), 1955-1966 (2009-04-07)
Bile acids are physiological detergents that generate bile flow and facilitate intestinal absorption and transport of lipids, nutrients, and vitamins. Bile acids also are signaling molecules and inflammatory agents that rapidly activate nuclear receptors and cell signaling pathways that regulate
Mahendra Singh et al.
Cell biochemistry and biophysics, 48(1), 54-72 (2007-08-19)
Upregulation of the scaffolding protein HEF1, also known as NEDD9 and Cas-L, has recently been identified as a pro-metastatic stimulus in a number of different solid tumors, and has also been strongly associated with pathogenesis of BCR-Abl-dependent tumors. As the
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