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Purity: ≥98%
Lithocholic acid (3α-Hydroxy-5β-cholanic acid), a secondary bile acid formed from chenodeoxycholate by bacterial action, acts as a detergent to solubilize fats for absorption and is itself absorbed. It is also a toxic secondary bile acid, causes intrahepatic cholestasis, has tumor-promoting activity, its toxic effect can be protected after it activates the vitamin D receptor, PXR and FXR. Among 17 kinds of bile acids with respect to inhibition of mammalian DNA polymerases, only LCA and its derivatives inhibited DNA polymerases, while other bile acids did not show inhibitory effect. Administration of LCA and its conjugates to rodents causes intrahepatic cholestasis, which is a pathogenic state characterized by decreased bile flow and the accumulation of bile constituents in the liver and blood.
ln Vitro |
Lithocholic Acid has an IC50 of 0.7 μM and 1.4 μM, respectively, to block FXR activation produced by GW4064 and CDCA [5]. In HepG2 cells, 100 nM GW4064-induced BSEP expression is inhibited by 10-30 μM lithocholic acid over a 24-hour period [5]. Lithocholic Acid (0-500 μM) suppresses neuroblastoma cell growth (BE(2)-m17, SK-n-SH, SK-n-MCIXC, and Lan-1) in a dose-dependent manner[3].
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ln Vivo |
When added to the food at a rate of 0.6% for seven days, lithocholic acid raises the levels of TGFB1, TGFBR1, and TGFBR2 mRNA in the liver of male C57BL/6 mice, activates SMAD3, and causes biliary injury [4]. Male C57BL/6 mice given intraperitoneal injections of lithocholic acid (125 mg/kg, twice daily for four days) develop liver damage and have elevated levels of AST, ALT, and ALP [2].
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Animal Protocol |
Animal/Disease Models: Male mice (C57BL/6)[4].
Doses: 0.6% LCA-supplement diet, with the AIN93G diet as a control Route of Administration: in diet, for 6 days Experimental Results: Induced liver injury. Activated TGFβ-SMAD3 signaling. Increased serum ALP activities. Animal/Disease Models: Male mice (C57BL/6)[2]. Doses: 125 mg/kg, dissolved in corn oil Route of Administration: ip, twice a day for four days Experimental Results: Induced liver injury, generated necrosis and neutrophilic -granulocytic infiltrate (H&E staining). Increased AST, ALT and ALP level. |
References |
[1]. Jenkins, D.J., et al., Effect on blood lipids of very high intakes of fiber in diets low in saturated fat and cholesterol. N Engl J Med, 1993. 329(1): p. 21-6.
[2]. Yang R, et al. Metabolomic analysis of cholestatic liver damage in mice. Food Chem Toxicol. 2018 Jul 14;120:253-260. [3]. Goldberg, A.A., et al., Lithocholic bile acid selectively kills neuroblastoma cells, while sparing normal neuronal cells. Oncotarget, 2011. 2(10): p. 761-82. [4]. Matsubara, T., et al., TGF-beta-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury. J Lipid Res, 2012. 53(12): p. 2698-707. [5]. Yu J, et al. Lithocholic acid decreases expression of bile salt export pump through farnesoid X receptor antagonist activity. J Biol Chem. 2002 Aug 30;277(35):31441-7. |
Molecular Formula |
C24H40O3
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Molecular Weight |
376.57
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CAS # |
434-13-9
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Related CAS # |
Allolithocholic acid;2276-94-0;Isoallolithocholic acid;2276-93-9;Isolithocholic acid;1534-35-6;Lithocholic acid-d4;83701-16-0;Lithocholic acid-d5;52840-06-9
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Appearance |
Typically exists as solids (or liquids in special cases) at room temperature
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SMILES |
O([H])[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]([H])(C1([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@]2([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C(=O)O[H])C([H])([H])C([H])([H])[C@]21[H]
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InChi Key |
SMEROWZSTRWXGI-HVATVPOCSA-N
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InChi Code |
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
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Chemical Name |
3alpha-Hydroxy-5beta-cholan-24-oic acid
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Synonyms |
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.52 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.52 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: ≥ 1 mg/mL (2.66 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: ≥ 1 mg/mL (2.66 mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix well. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 5: ≥ 1 mg/mL (2.66 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one),clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix well. |
Preparing Stock Solutions | 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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.