[CAS NO. 434-13-9] Lithocholic acid

Name: Lithocholic acid
Brand: Arctom Scientific
SKU: SLK-S4003

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PRODUCTS SPECIFICATIONS [434-13-9]

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Catalog

SLK-S4003

Brand

Selleck

CAS

434-13-9

DESCRIPTION [434-13-9]

Overview

MDL	-
Molecular Weight	376.57
Molecular Formula	C24H40O3
SMILES	C[C@@]12[C@]([C@]3([C@@]([C@]4(C)[C@](CC3)(C[C@H](O)CC4)[H])(CC1)[H])[H])(CC[C@@]2([C@@H](CCC(O)=O)C)[H])[H]

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Concentration Volume Mass	1 mg	5 mg	10 mg
1 mM	2.6555 mL	13.2777 mL	26.5555 mL
5 mM	0.5311 mL	2.6555 mL	5.3111 mL
10 mM	0.2656 mL	1.3278 mL	2.6555 mL
50 mM	0.0531 mL	0.2656 mL	0.5311 mL

Description

Lithocholic acid is a toxic secondary bile acid, causes intrahepatic cholestasis, has tumor-promoting activity, its toxic effect can be protected after it activates the , and .

Targets

FXR ^[1]

PXR ^[1]

vitamin D receptor ^[1]

In vitro

Lithocholic acid (LCA) is a hydrophobic secondary bile acid that is primarily formed in the intestine by the bacterial 7α-dehydroxylation of chenodeoxycholic acid. LCA causes intrahepatic cholestasis (cessation or impairment of bile flow). LCA activates PXR (pregnane X receptor), and the LCA-induced severe liver damage can be protected by the activation of PXR. LCA is a ligand for farnesoid X receptor (FXR) with EC50 of 3.8 μM. LCA directly binds VDR (vitamin D receptor) with K of 29μM, activates VDR (vitamin D receptor) 30 μM, with much more sensitivity than the other nuclear receptors (eg. PXR, FXR), and its toxic effect is thus protected. LCA has tumor-promoting activity, inhibits mammalian DNA Polymerase β with IC50 of 15 μM.

In vivo

Administration of LCA and its conjugates to rodents causes intrahepatic cholestasis,a pathogenic state characterized by decreased bile flow and the accumulation of bile constituents in the liver and blood. In DMH (dimethyldydrazine)-induced murine carcinogenesis model, LCA suppresses apoptosis almost completely in premalignant colon. LCA activates VDR, induces expression in vivo of CYP3A, a cytochrome P450 enzyme that detoxifies LCA in the liver and intestine.

References

[1] Staudinger JL, et al. PNAS, 2001, 98(6), 3369-3374.
[2] Parks DJ, et al. Science, 1999, 284(5418), 1365-1368.
[3] Makishima M, et al. Science, 2002, 296(5571), 1313-1316.
[4] Ogawa A, et al. Jpn J Cancer Res, 1998, 89(11), 1154-1159.
[5] Kozoni V, et al. Carcinogenesis, 2000, 21(5), 999-1005.

Synonyms

Cholan-24-oic acid, 3-hydroxy-, (3α,5β)-

5β-Cholan-24-oic acid, 3α-hydroxy-

5β-Cholanic acid, 3α-hydroxy-

(3α,5β)-3-Hydroxycholan-24-oic acid

3α-Hydroxycholanic acid

3α-Hydroxy-5β-cholanic acid

Lithocholic acid

3α-Hydroxy-5β-cholanoic acid

3α-Hydroxy-5β-cholan-24-oate

3-Hydroxycholan-24-oic acid

17β-(1-Methyl-3-carboxypropyl)etiocholan-3α-ol

3α-Hydroxy-5β-cholan-24-oic acid

NSC 683770