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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
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grade

pharmaceutical primary standard

API family

lithocholic acid

manufacturer/tradename

EDQM

mp

183-188 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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

InChI key

SMEROWZSTRWXGI-HVATVPOCSA-N

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.

Application

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

Packaging

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

Other Notes

Sales restrictions may apply.

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Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
Matteo Incerti et al.
Journal of medicinal chemistry, 56(7), 2936-2947 (2013-03-16)
The Eph receptor-ephrin system is an emerging target for the development of novel antiangiogenetic agents. We recently identified lithocholic acid (LCA) as a small molecule able to block EphA2-dependent signals in cancer cells, suggesting that its (5β)-cholan-24-oic acid scaffold can
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
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Global Trade Item Number

SKUGTIN
L072080004061833812280