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Sigma-Aldrich

Deoxycholic acid

≥99.0% (T)

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Synonym(s):
3α,12α-Dihydroxy-5β-cholanic acid, 7-Deoxycholic acid, Desoxycholic acid
Empirical Formula (Hill Notation):
C24H40O4
CAS Number:
83-44-3
Molecular Weight:
392.57
Beilstein:
3219882
EC Number:
201-478-5
MDL number:
MFCD00003673
UNSPSC Code:
12352106
PubChem Substance ID:
329753610
NACRES:
NA.77

biological source

ox bile

Quality Level

100

description

anionic

Assay

≥99.0% (T)

form

powder

optical activity

[α]20/D +54±1°, c = 1% in ethanol

mol wt

392.57 g/mol

impurities

≤1% cholic acid (TLC)

mp

170-175 °C
171-174 °C (lit.)

functional group

carboxylic acid

SMILES string

C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C

InChI

1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1

InChI key

KXGVEGMKQFWNSR-LLQZFEROSA-N

Gene Information

human ... ATIC(471)

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General description

Deoxycholic acid is an amphiphilic molecule and an important constituent of bile acid. It contains hydroxyl groups substituted at the 3α and 12α positions and a carboxyl group towards the end of the branched-chain. These moieties contribute to the hydrophilic nature of the molecule and the hydrophobic cyclopentanophenanthrene forms its center.

Application

Deoxycholic acid has been used as:
  • a hyphal-inhibitory compound in an ex vivo assay to study the hyphal morphogenesis of Candida albicans in the gastrointestinal tract
  • an internal standard to estimate the toxin concentration in the cell pellet
  • a bile acid (BA) standard to quantitatively measure BA in various samples from treated mice by ultra-performance liquid chromatography triple quadrupole mass spectrometry

Biochem/physiol Actions

Deoxycholic acid, due to its amphiphilicity, significantly helps to solubilize, emulsify, and absorb fat, vitamins, and cholesterol in the body. High levels of intestinal deoxycholic acid might cause colorectal cancer by inducing oxidative stress and leading to DNA damage. It acts as an oncogene and pro-tumor factor.

Other Notes

For the solubilization of the β-adrenergic receptor

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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)

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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Preparation and characterizations of a novel deoxycholic acid-O-carboxymethylated chitosan-folic acid conjugates and self-aggregates
Wang F, et al.
Carbohydrate Polymers, 84, 1192-1200 (2011)
E Nedivi et al.
The Journal of biological chemistry, 259(9), 5803-5808 (1984-05-10)
Agonist, but not antagonist, protects the beta-adrenergic receptor from inactivation during solubilization in deoxycholate. Protection is apparently due to locking of the agonist in the receptor, a high affinity interaction induced or stabilized by this detergent. The guanyl nucleotide-binding protein
Jeffery L Smith et al.
Hepatology (Baltimore, Md.), 39(6), 1673-1682 (2004-06-09)
Focal biliary cirrhosis causes significant morbidity and mortality in cystic fibrosis (CF). Although the mechanisms of pathogenesis remain unclear, bile acids have been proposed as potential mediators of liver injury. This study examined bile acid composition in CF and assessed
J Stadler et al.
Cancer letters, 38(3), 315-320 (1988-01-01)
Rectal biopsies and fecal collections were obtained from a consecutive series of 34 outpatients prior to colonoscopy at a gastroenterology clinic. Subsequently, 14 were found to have no colonic pathology, 13 had adenomatous polyps, (3 of those had a previous
Thierry Claudel et al.
Arteriosclerosis, thrombosis, and vascular biology, 25(10), 2020-2030 (2005-07-23)
Bile acids are the end products of cholesterol metabolism. They are synthesized in the liver and secreted via bile into the intestine, where they aid in the absorption of fat-soluble vitamins and dietary fat. Subsequently, bile acids return to the
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