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C9282

Sigma-Aldrich

Cholate de sodium hydrate

suitable for cell culture, BioReagent

Synonyme(s) :

Acide 3α,7α,12α-trihydroxy-5β-cholan-24-oïque sodium salt, Acide cholalique sodium salt

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About This Item

Formule empirique (notation de Hill):
C24H39NaO5 · xH2O
Numéro CAS:
206986-87-0
Poids moléculaire :
430.55 (anhydrous basis)
Numéro Beilstein :
3582354
Numéro CE :
206-643-5
Numéro MDL:
MFCD00150749
Code UNSPSC :
12161902
ID de substance PubChem :
24893147
Nomenclature NACRES :
NA.75

Source biologique

bovine bile
ovine bile

Niveau de qualité

200

Description

anionic

Gamme de produits

BioReagent

Pureté

≥99.0% (HPLC)

Forme

powder

Poids mol.

micellar avg mol wt 900-1300

Nombre d'agrégation

2-3

Technique(s)

cell culture | mammalian: suitable

CMC

9-15 mM (20-25°C)

Solubilité

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

HLB

18

Chaîne SMILES 

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

Clé InChI

MUVVIYFKOVLQHL-RCVKHMDESA-M

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Description générale

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

Actions biochimiques/physiologiques

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

En option

Réf. du produit
Description
Tarif

Mentions de danger

H412

Conseils de prudence

P273 - P501

Classification des risques

Aquatic Chronic 3

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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)
Katrin Rössger et al.
Metabolic engineering, 21, 81-90 (2013-11-28)
In recent years, using trigger-inducible mammalian gene switches to design sophisticated transcription-control networks has become standard practice in synthetic biology. These switches provide unprecedented precision, complexity and reliability when programming novel mammalian cell functions. Metabolite-responsive repressors of human-pathogenic bacteria are
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