Lithocholic acid

Alias: Lithocolic acid; Lithocholate;3α-Hydroxy-5β-cholanic acid
Cat No.:V1843 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.
Lithocholic acid Chemical Structure CAS No.: 434-13-9
Product category: FXR
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
2g
5g
10g
50g
Other Sizes

Other Forms of Lithocholic acid:

  • Allolithocholic acid
  • Isoallolithocholic acid (3β-Hydroxy-5α-cholanic acid)
  • Isolithocholic acid (3β-Hydroxy-5β-cholanic acid; 3-Epilithocholic acid; β-Lithocholic acid)
  • Lithocholic acid-d4 (3α-Hydroxy-5β-cholanic acid-d4)
  • Lithocholic acid-d5
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

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.

Biological Activity I Assay Protocols (From Reference)
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].
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].
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.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C24H40O3
Molecular Weight
376.57
CAS #
434-13-9
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]
InChi Key
SMEROWZSTRWXGI-HVATVPOCSA-N
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
Chemical Name
3alpha-Hydroxy-5beta-cholan-24-oic acid
Synonyms
Lithocolic acid; Lithocholate;3α-Hydroxy-5β-cholanic acid
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 75 mg/mL (199.2 mM)
Water:<1 mg/mL
Ethanol: 47 mg/mL (124.8 mM)
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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
+
+
+

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.

Contact Us