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Sigma-Aldrich

Dehydrocholic acid

≥99.0% (T)

Synonym(s):

(5β)-3,7,12-Trioxocholan-24-oic acid, 3,7,12-Trioxo-5β-cholanic acid, 5β-Cholanic acid-3,5,12-trione

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About This Item

Empirical Formula (Hill Notation):
C24H34O5
CAS Number:
81-23-2
Molecular Weight:
402.52
Beilstein/REAXYS Number:
3226734
EC Number:
201-335-7
MDL number:
MFCD00066410
UNSPSC Code:
41141802
PubChem Substance ID:
57648489
NACRES:
NA.77

biological source

bovine bile
synthetic

description

anionic

assay

≥99.0% (T)

form

powder

optical activity

[α]20/D +26±1°, c = 1% in ethanol

mp

238-240 °C

solubility

ethanol: 10 mg/mL, clear (hot)

functional group

carboxylic acid

SMILES string

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

InChI

1S/C24H34O5/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/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1

InChI key

OHXPGWPVLFPUSM-KLRNGDHRSA-N

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Application

Dehydrocholic acid was used to study the interaction of bile salts with copper ions in unbuffered systems.

Biochem/physiol Actions

Dehydrocholic acid is an oxidation product of cholic acid by chromic acid that is not present in physiological conditions. When used in animal experiments, it stimulates bile secretion.

Preparation Note

Dehydrocholic acid yields clear solution in hot ethanol at 10 mg/ml.

Other Notes

In the production of chenodeoxycholic acid by bioconversion

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)

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H. Sawada et al.
Adv. Biotechnol., [Proc. Int. Ferment. Symp.], 6th (1980) (C.Vezina,K.Singh eds., 3, 495-495 (1981)
R D Soloway et al.
The Journal of clinical investigation, 52(3), 715-724 (1973-03-01)
[24-(14)C]Dehydrocholic acid (triketo-5-beta-cholanoic acid) was synthesized from [24-(14)C]cholic acid, mixed with 200 mg of carrier, and administered intravenously to two patients with indwelling T tubes designed to permit bile sampling without interruption of the enterohepatic circulation. More than 80% of
G Feroci et al.
Journal of pharmaceutical sciences, 84(1), 119-125 (1995-01-01)
Interaction of bile salts with Cu2+ ions in unbuffered systems containing 0.15 M NaNO3 was followed by measuring polarographic limiting currents and half-wave potentials. Whereas taurocholate forms neither soluble complexes nor compounds of limited solubility, cholate, glycocholate, and dehydrocholate from
F Chanussot et al.
The Biochemical journal, 270(3), 691-695 (1990-09-15)
The correlation between the secretion of biliary phospholipid (PL) and bile acid suggests a regulatory effect of bile acid on PL secretion. Bile acids may influence PL synthesis and/or the mobilization of a preformed PL pool. The objective of this
Paula V Messina et al.
Colloids and surfaces. B, Biointerfaces, 75(1), 34-41 (2009-09-08)
The physicochemical and elastic properties of Langmuir mixed monolayers composed by dehydrocholic acid (HDHC) and didodecyldimethylammonium bromide (DDAB) were evaluated. The experiments were performed with a constant surface pressure penetration Langmuir balance based on Axisymmetric Drop Shape Analysis (ADSA). The
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