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Merck
CN

L0720800

Lithocholic acid

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

3α-Hydroxy-5β-cholan-24-oic acid, 3α-Hydroxy-5β-cholanic acid, 5β-Cholan-24-oic acid-3α-ol

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About This Item

Empirical Formula (Hill Notation):
C24H40O3
CAS Number:
434-13-9
Molecular Weight:
376.57
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329817372
MDL number:
MFCD00003682
Beilstein/REAXYS Number:
3217757

Key Documents

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Product Name

Lithocholic acid, European Pharmacopoeia (EP) Reference Standard

InChI key

SMEROWZSTRWXGI-HVATVPOCSA-N

SMILES string

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

InChI

1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1

grade

pharmaceutical primary standard

API family

lithocholic acid

manufacturer/tradename

EDQM

mp

183-188 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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Application

Lithocholic acid EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Benjamin L Woolbright et al.
Toxicology letters, 228(1), 56-66 (2014-04-20)
Lithocholic acid (LCA) supplementation in the diet results in intrahepatic cholestasis and bile infarcts. Previously we showed that an innate immune response is critical for cholestatic liver injury in the bile duct ligated mice. Thus, the purpose of this study
Alan F Hofmann
Drug metabolism reviews, 36(3-4), 703-722 (2004-11-24)
Lithocholic acid, a monohydroxy, secondary bile acid, is formed by bacterial 7-dehydroxylation of the primary bile acid chenodeoxycholic acid (CDCA) and of the secondary bile acid ursodeoxycholic acid (UDCA). Lithocholic acid and its precursor CDCA are toxic when fed to
Simon M Vogel et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(42), 16906-16910 (2012-10-05)
The proteins MDM2 and MDM4 are key negative regulators of the tumor suppressor protein p53, which are frequently upregulated in cancer cells. They inhibit the transactivation activity of p53 by binding separately or in concert to its transactivation domain. MDM2
Yu-Guang Wang et al.
Chemico-biological interactions, 200(1), 11-20 (2012-09-18)
Licorice (LE) has been commonly used in traditional Chinese medicine (TCM) for over 4000 years to reconcile various drugs and for hepatic disorders. Glycyrrhizin is the main bioactive component isolated from LE herbs. In the present study we examined the
Tanmay Bera et al.
Langmuir : the ACS journal of surfaces and colloids, 29(1), 387-392 (2012-12-21)
The concentration level of bile acids is a clinical biomarker for the diagnosis of intestinal diseases because individuals suffering from intestinal diseases have a sharply increased concentration of bile acids at micromolar levels. Here, we report the detection of lithocholic
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