lithocholic acid
lithocholic acid
CAS: 434-13-9
Molecular Formula: C24H40O3
lithocholic acid - Names and Identifiers
| 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 |
lithocholic acid - Physico-chemical Properties
| 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. |
lithocholic acid - Risk and Safety
| 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 |
lithocholic acid - Reference
| 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 |
lithocholic acid - Introduction
One of the bile acids. Not by direct biosynthesis of cholesterol in the liver, but by a substance produced by goose deoxycholic acid through bacterial metabolism in the intestine. Most of this substance produced in the intestine is excreted together with feces, and a very small part is absorbed. A binding reaction occurs in the liver and appears in the bile in the form of taurocholic acid (taurolithocholic aCld) or glycinic acid (glyclithocholic aCld). It is more toxic than other bile acids, and feeding a large number of experimental animals can cause various obstacles to the hepatobiliary system.
Last Update：2022-10-16 17:25:13
lithocholic acid - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | Lithocholic acid is a secondary bile acid, also known as cholic acid, 3 A- hydroxycholanic acid, lithocholic acid, 3 A- alkanic acid, lithic acid, 3-hydroxycholenic acid, lithic acid, exist in the bile of higher vertebrates. Its molecular structure contains both hydrophilic groups and hydrophobic groups, so the three-dimensional configuration of bile acids has two properties: hydrophilic and hydrophobic, so bile acids have strong interfacial activity. After consulting the literature, it is found that lithocholic acid has more pharmacological activities, such as: inhibiting tumor growth, selectively killing breast cancer cells, and selectively inhibiting the activity of mammalian DNA polymerase. |
| Classification | Bile acids are structurally divided into two categories: one is free bile acids, including cholic acid, Deoxycholic acid (deoxycholic acid), chenodeoxycholic acid, and lithocholic acid; the other is conjugated bile acid, it is formed by the combination of the above free bile acids with glycine or taurine, mainly including glycocholic acid, glycochenodeoxycholate acid, taurocholic acid and taurochenodeoxycholate acid. |
| pharmacological action | lithocholic acid can kill glioma cells and is harmless to normal nerve cells. the specific principle of action: low concentration of lithocholic acid (LCA) can make BE(2)-m17 and SK-n-MCIXC cells sensitive to hydrogen peroxide-induced cell decline, A certain concentration of LCA makes the original culture of human neuron cells have a certain ability to resist this type of cell death. LCA can kill BE(2)-m17 and SK-n-MCIXC cells not only through the path of internal decay cell death driven by triggering the permeabilization of the outer mitochondrial membrane and the activation of the initiator CASPASE-9, but also through the external path of cell decay involving the CASPASE-8 activation of the initiator. These intrinsic and extrinsic pathways of tumor cell decay can be interpreted by the apoptotic cascade. |
| biological activity | Lithocholic acid is a bile acid that can dissolve fat for absorption. |
| Target | Value |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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