Name | lithocholic acid |
Synonyms | lithocholic acid HYDROYCHOLANIC ACID 3-HYDROXYCHOLANIC ACID 3ALPHA-HYDROXYCHOLANIC ACID BETA-CHOLANIC ACID-3-ALPHA-OL 3ALPHA-HYDROXY-5BETA-CHOLANIC ACID 3ALPHA-HYDROXY-5BETA-CHOLAN-24-OIC ACID 17beta-(1-methyl-3-carboxypropyl)etiocholan-3alpha-ol 17-beta-(1-Methyl-3-carboxypropyl)ethiocholan-3-alpha-ol |
CAS | 434-13-9 |
EINECS | 207-099-1 |
InChI | InChI=1/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)/p-1/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1 |
InChIKey | SMEROWZSTRWXGI-HVATVPOCSA-N |
Molecular Formula | C24H40O3 |
Molar Mass | 376.57 |
Density | 1.0454 (rough estimate) |
Melting Point | 183-188 °C (lit.) |
Boling Point | 445.09°C (rough estimate) |
Specific Rotation(α) | D20 +33.7° (c = 1.5 in abs ethanol); D19 +23.3° (Wieland); D20 +32.1° (Fischer) |
Flash Point | 9℃ |
Water Solubility | 18.83ug/L(25 ºC) |
Solubility | Easily soluble in hot alcohol, slightly soluble in glacial acetic acid, insoluble in petroleum ether, gasoline, water |
Vapor Presure | 1.4E-12mmHg at 25°C |
Appearance | prismatic crystallization |
Color | White to off-white |
Merck | 5545 |
BRN | 3217757 |
pKa | 4.76±0.10(Predicted) |
Storage Condition | room temp |
Refractive Index | 35.5 ° (C=1, EtOH) |
MDL | MFCD00003682 |
In vitro study | Lithocholic acid (LCA) is a hydrophobic secondary bile acid formed by the 7α-dehydroxylation of the bacterium chenocholic acid in the intestine. LCA causes intrahepatic cholestasis (termination or obstruction of bile flow). LCA activates PXR (pregnane X receptor), and LCA-induced severe liver injury can be protected by PXR activation. LCA is a ligand for the farnesol X receptor (FXR) with an EC50 of 3.8 μm. LCA binds directly to VDR (vitamin D receptor),K I is 29 μm, and activates VDR (vitamin D receptor),K I is 30 μm, compared with other nuclear receptors (e. G. PXR,FXR) it has a higher sensitivity, and its toxic effects are therefore suppressed. LCA has tumor-promoting activity and inhibits mammalian DNA polymerase β with an IC50 of 15 μm. |
In vivo study | Binding with rodents after administration of LCA causes intrahepatic cholestasis, a pathological condition characterized by a decrease in bile flow and accumulation of bile components in the liver and blood. In a DMH (dimethylhydrazine)-induced mouse model of carcinogenesis, LCA almost completely inhibited apoptosis in the precancerous colon. LCA activates VDR, inducing in vivo expression of CYP3A, a cytochrome P450 enzyme that detoxizes LCA in the liver and intestine. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
UN IDs | UN1230 - class 3 - PG 2 - Methanol, solution |
WGK Germany | 2 |
RTECS | FZ2275000 |
HS Code | 29181998 |
Reference Show more | 1. Li Yaqi, Wang Zixuan, Xiao Zhijun, etc. Qualitative and Quantitative Analysis of main bile acids in swine bile powder [J]. Chinese Journal of Traditional Chinese Medicine, 2019, 29 (9). 2. Cao Yan, Song Qingqing, Li Jun, etc. Analysis of chemical constituents of bile acids in yak bile [J]. Chinese Journal of Traditional Chinese Medicine, 44 Vol. 12,, pp. 2538-2543, MEDLINE ISTIC PKU CSCD CA BP, 2019. 3. Cao Yan, Li Ting, Chang Anqi, Jiang Zhenzhen, Yu Juan, Tu Peng-fei, Song Yue-Lin. Analysis of chemical constituents of bile acids in snake bile [J]. Chinese Journal of Traditional Chinese Medicine, 2021,46(01):130-138. 4. [IF = 5.396] Shiming Huang et al.. "Food Funct. 2019 Jun;10(6):3224-3236 5. [IF = 3.935] Song Lin et al."A systemic combined nontargeted and targeted LC-MS based metabolomic strategy of plasma and liver on pathology exploration of alpha-naphthylisothiocyanate induced cholestatic liver injury in mice."J Pharmaceut Biomed. 2019 Jul;171:180 6. [IF=5.396] Juan Wu et al."Sargassum fusiforme polysaccharide is a potential auxiliary substance for metformin in the management of diabetes."Food Funct. 2022 Feb;: 7. [IF=6.558] Yan Cao et al."Widely quasi-quantitative analysis enables temporal bile acids-targeted metabolomics in rat after oral administration of ursodeoxycholic acid."ANALYTICA CHIMICA ACTA. 2022 Jun;1212:339885 8. [IF=6.558] Yan Cao et al."Widely quasi-quantitative analysis enables temporal bile acids-targeted metabolomics in rat after oral administration of ursodeoxycholic acid."ANALYTICA CHIMICA ACTA. 2022 Jun;1212:339885 9. [IF=4.412] Hongfa Lv et al."Synergistic Effect of Lithocholic Acid with Gentamicin against Gram-Positive Bacteria but Not against Gram-Negative Bacteria."Molecules. 2022 Jan;27(7):2318 |