| Size | Price | Stock | Qty |
|---|---|---|---|
| 1g |
|
||
| 2g |
|
||
| 5g |
|
||
| 10g |
|
||
| 50g |
|
||
| Other Sizes |
|
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].
|
|---|---|
| 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. |
| ADME/Pharmacokinetics |
Metabolism / Metabolites
LITHOCHOLIC ACID (24)C(14) IS CONVERTED BY RAT LIVER HOMOGENATE INTO 3ALPHA-6BETA-DIHYDROXY-5BETA-CHOLANIC ACID, 7SIGMA-HYDROXYLATION OCCURS, HYDROXYLATION CONJUGATION WITH TAURINE & FORMATION OF 3-SULFATE ESTER CAN BE DEMONSTRATED. LABELED LITHOCHOLATE WAS INJECTED INTO GALLSTONE PATIENTS & HEALTHY VOLUNTEERS, MAJORITY OF RADIOACTIVITY IN BILE (50-60%) WAS PRESENT AS SULFATED CONJUGATES. DEGREE OF SULFATION WAS GREATER FOR GLYCINE THAN TAURINE CONJUGATES, WHICH SUGGESTED PREFERENTIAL SULFATION OF GLYCINE CONJUGATES. Lithocholic Acid has known human metabolites that include 6alpha-Hydroxylithocholic acid. |
| Toxicity/Toxicokinetics |
Interactions
SKIN TUMOR INHIBITION DECR IN FOLLOWING ORDER OF ACIDS: CHENODEOXYCHOLIC, LITHOCHOLIC, DEOXYCHOLIC, & CHOLIC. 16ALPHA-CYANOPREGNENOLONE (5 MG IP TWICE DAILY FOR 2 DAYS) INCR IN VITRO RAT LIVER MICROSOMAL 6BETA- & 7ALPHA-HYDROXYLATION OF LITHOCHOLIC ACID BY FACTORS OF 2 & 3-4 RESPECTIVELY. THIS MAY ACCOUNT FOR PREVENTION OF LITHOCHOLIC ACID-INDUCED CHOLELITHIASIS. LITHOCHOLIC ACID (24)C(14) IS CONVERTED BY RAT LIVER HOMOGENATE INTO 3ALPHA-6BETA-DIHYDROXY-5BETA-CHOLANIC ACID. ADDN OF ETHANOL TO ENZYMATIC SYSTEM RESULTS IN INHIBITION OF FORMATION OF 3ALPHA, 6BETA-DIHYDROXY-5BETA-CHOLANIC ACID. SODIUM LITHOCHOLATE INCR MNNG (N-METHYL-N'-NITRO-N-NITROSOGUANIDINE) INDUCED COLON TUMOR INCIDENCE IN BOTH GERM-FREE & CONVENTIONAL RATS (F344). /SODIUM LITHOCHOLATE/ LCA was also tested as a promoter of N-Nitrobis(2-hydroxypropyl)amine (BHP) induced carcinogenesis. Two groups of 5 to 6-wk-old hamsters (number not stated) were given 500 mg/kg BHP subcutaneously once per week for 5 weeks, and group 3 was given no further treatment; group 4 was given 0.5% LCA in feed for 30 weeks, all animals were autopsied at 35 weeks. There was no difference in food consumption or body weight between these 2 groups. There were no differences in number on liver lesions (group 3: 15/15 hyperplastic nodules, 2/15 hepatocellular carcinoma, 1/15 cholangiocarcinoma; group 4: 22/22 hyperplastic nodules, 3/22 hepatocellular carcinoma, 3/22 cholangiocarcinoma). However, there was a significant difference in the pancreatic tumors: group 3 had 4/15 gross tumors, 5/15 carcinomas, 4/15 adenomas while group 4 had 13/22 gross tumors, 15/22 carcinomas (P<.04) and 2/22 adenomas. Under the conditions of this experiment, LCA was not carcinogenic when administered alone, but was an effective promoter of BHP pancreatic carcinogenesis. |
| References |
|
| Additional Infomation |
Hexagonal leaflets (from alcohols) or prisms (from acetic acid) or white powder. (NTP, 1992)
Lithocholic acid is a monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action. It has a role as a human metabolite, a mouse metabolite and a geroprotector. It is a bile acid, a monohydroxy-5beta-cholanic acid and a C24-steroid. It is a conjugate acid of a lithocholate. Lithocholic acid has been reported in Homo sapiens with data available. A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic. |
| Molecular Formula |
C24H40O3
|
|
|---|---|---|
| Molecular Weight |
376.57
|
|
| Exact Mass |
376.297
|
|
| CAS # |
434-13-9
|
|
| 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
|
|
| PubChem CID |
9903
|
|
| Appearance |
White to off-white solid powder
|
|
| Density |
1.1±0.1 g/cm3
|
|
| Boiling Point |
511.0±23.0 °C at 760 mmHg
|
|
| Melting Point |
183-188 °C(lit.)
|
|
| Flash Point |
276.9±19.1 °C
|
|
| Vapour Pressure |
0.0±3.0 mmHg at 25°C
|
|
| Index of Refraction |
1.528
|
|
| LogP |
6.7
|
|
| Hydrogen Bond Donor Count |
2
|
|
| Hydrogen Bond Acceptor Count |
3
|
|
| Rotatable Bond Count |
4
|
|
| Heavy Atom Count |
27
|
|
| Complexity |
574
|
|
| Defined Atom Stereocenter Count |
9
|
|
| SMILES |
C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
|
|
| 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 |
|
|
| HS Tariff Code |
2934.99.9001
|
|
| 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 (In Vitro) |
|
|||
|---|---|---|---|---|
| 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
COA