MilliporeSigma
All Photos(1)

30960

Sigma-Aldrich

Deoxycholic acid

≥99.0% (T)

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

Quality Level

biological source

ox bile

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)

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

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
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
Lotta K Stenman et al.
American journal of physiology. Gastrointestinal and liver physiology, 304(3), G227-G234 (2012-12-04)
Impairment of gut barrier is associated with a fat-rich diet, but mechanisms are unknown. We have earlier shown that dietary fat modifies fecal bile acids in mice, decreasing the proportion of ursodeoxycholic acid (UDCA) vs. deoxycholic acid (DCA). To clarify
Shin Yoshimoto et al.
Nature, 499(7456), 97-101 (2013-06-28)
Obesity has become more prevalent in most developed countries over the past few decades, and is increasingly recognized as a major risk factor for several common types of cancer. As the worldwide obesity epidemic has shown no signs of abating
M V St-Pierre et al.
The Journal of experimental biology, 204(Pt 10), 1673-1686 (2001-04-24)
Bile acids are steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service