Taurolithocholic acid

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MedKoo CAT#: 599016

CAS#: 516-90-5

Description: Taurolithocholic acid is a bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. It is a cholagogue and choleretic.

Chemical Structure

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Taurolithocholic acid
CAS# 516-90-5
Instruction

Theoretical Analysis

MedKoo Cat#: 599016
Name: Taurolithocholic acid
CAS#: 516-90-5
Chemical Formula: C26H45NO5S
Exact Mass: 483.30
Molecular Weight: 483.700
Elemental Analysis: C, 64.56; H, 9.38; N, 2.90; O, 16.54; S, 6.63

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Taurolithocholic acid; Lithocholyltaurine; Lithocholic acid taurine conjugate;

IUPAC/Chemical Name: 2-((R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)ethane-1-sulfonic acid

InChi Key: QBYUNVOYXHFVKC-GBURMNQMSA-N

InChi Code: InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18-,19-,20+,21-,22+,23+,25+,26-/m1/s1

SMILES Code: C[C@H](CCC(NCCS(=O)(O)=O)=O)[C@H]1CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 483.70 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Amonyingcharoen S, Suriyo T, Thiantanawat A, Watcharasit P, Satayavivad J. Taurolithocholic acid promotes intrahepatic cholangiocarcinoma cell growth via muscarinic acetylcholine receptor and EGFR/ERK1/2 signaling pathway. Int J Oncol. 2015;46(6):2317-26. doi: 10.3892/ijo.2015.2939. Epub 2015 Mar 27. PubMed PMID: 25815516; PubMed Central PMCID: PMC4441291.

2: Li Z, Lu M, Chu J, Qiao X, Meng X, Sun B, Zhang W, Xue D. Early proteome analysis of rat pancreatic acinar AR42J cells treated with taurolithocholic acid 3-sulfate. Pancreatology. 2012 May-Jun;12(3):248-56. doi: 10.1016/j.pan.2012.02.006. Epub 2012 Feb 16. PubMed PMID: 22687381.

3: Ma B, Wu L, Lu M, Gao B, Qiao X, Sun B, Xue D, Zhang W. Differentially expressed kinase genes associated with trypsinogen activation in rat pancreatic acinar cells treated with taurolithocholic acid 3-sulfate. Mol Med Rep. 2013 May;7(5):1591-6. doi: 10.3892/mmr.2013.1355. Epub 2013 Mar 4. PubMed PMID: 23467886.

4: Denk GU, Maitz S, Wimmer R, Rust C, Invernizzi P, Ferdinandusse S, Kulik W, Fuchsbichler A, Fickert P, Trauner M, Hofmann AF, Beuers U. Conjugation is essential for the anticholestatic effect of NorUrsodeoxycholic acid in taurolithocholic acid-induced cholestasis in rat liver. Hepatology. 2010 Nov;52(5):1758-68. doi: 10.1002/hep.23911. PubMed PMID: 21038414.

5: Fuentes-Broto L, Miana-Mena FJ, Piedrafita E, Berzosa C, Martínez-Ballarín E, García-Gil FA, Reiter RJ, García JJ. Melatonin protects against taurolithocholic-induced oxidative stress in rat liver. J Cell Biochem. 2010 Aug 1;110(5):1219-25. doi: 10.1002/jcb.22636. PubMed PMID: 20564217.

6: Tserng KY, Klein PD. Synthesis of sulfate esters of lithocholic acid, glycolithocholic acid, and taurolithocholic acid with sulfur trioxide-triethylamine. J Lipid Res. 1977 Jul;18(4):491-5. PubMed PMID: 894140.

7: Brighton CA, Rievaj J, Kuhre RE, Glass LL, Schoonjans K, Holst JJ, Gribble FM, Reimann F. Bile Acids Trigger GLP-1 Release Predominantly by Accessing Basolaterally Located G Protein-Coupled Bile Acid Receptors. Endocrinology. 2015 Nov;156(11):3961-70. doi: 10.1210/en.2015-1321. Epub 2015 Aug 17. PubMed PMID: 26280129; PubMed Central PMCID: PMC4606749.

8: Beuers U, Denk GU, Soroka CJ, Wimmer R, Rust C, Paumgartner G, Boyer JL. Taurolithocholic acid exerts cholestatic effects via phosphatidylinositol 3-kinase-dependent mechanisms in perfused rat livers and rat hepatocyte couplets. J Biol Chem. 2003 May 16;278(20):17810-8. Epub 2003 Mar 7. PubMed PMID: 12626520.

9: Graf D, Kurz AK, Fischer R, Reinehr R, Häussinger D. Taurolithocholic acid-3 sulfate induces CD95 trafficking and apoptosis in a c-Jun N-terminal kinase-dependent manner. Gastroenterology. 2002 May;122(5):1411-27. PubMed PMID: 11984527.

10: Muili KA, Jin S, Orabi AI, Eisses JF, Javed TA, Le T, Bottino R, Jayaraman T, Husain SZ. Pancreatic acinar cell nuclear factor κB activation because of bile acid exposure is dependent on calcineurin. J Biol Chem. 2013 Jul 19;288(29):21065-73. doi: 10.1074/jbc.M113.471425. Epub 2013 Jun 6. PubMed PMID: 23744075; PubMed Central PMCID: PMC3774373.

11: Ding L, Yang L, Wang Z, Huang W. Bile acid nuclear receptor FXR and digestive system diseases. Acta Pharm Sin B. 2015 Mar;5(2):135-44. doi: 10.1016/j.apsb.2015.01.004. Epub 2015 Feb 25. Review. PubMed PMID: 26579439; PubMed Central PMCID: PMC4629217.

12: Mannack G, Graf D, Donner MM, Richter L, Gorg B, Vom Dahl S, Haussinger D, Schliess F. Taurolithocholic acid-3 sulfate impairs insulin signaling in cultured rat hepatocytes and perfused rat liver. Cell Physiol Biochem. 2008;21(1-3):137-50. doi: 10.1159/000113756. Epub 2008 Jan 16. PubMed PMID: 18209481.

13: Beuers U, Probst I, Soroka C, Boyer JL, Kullak-Ublick GA, Paumgartner G. Modulation of protein kinase C by taurolithocholic acid in isolated rat hepatocytes. Hepatology. 1999 Feb;29(2):477-82. PubMed PMID: 9918925.

14: Kida T, Tsubosaka Y, Hori M, Ozaki H, Murata T. Bile acid receptor TGR5 agonism induces NO production and reduces monocyte adhesion in vascular endothelial cells. Arterioscler Thromb Vasc Biol. 2013 Jul;33(7):1663-9. doi: 10.1161/ATVBAHA.113.301565. Epub 2013 Apr 25. PubMed PMID: 23619297.

15: Dahlström-King L, Couture J, Plaa GL. Influence of agents affecting monooxygenase activity on taurolithocholic acid-induced cholestasis. Toxicol Lett. 1992 Dec;63(3):243-52. PubMed PMID: 1283232.

16: Husain SZ, Orabi AI, Muili KA, Luo Y, Sarwar S, Mahmood SM, Wang D, Choo-Wing R, Singh VP, Parness J, Ananthanaravanan M, Bhandari V, Perides G. Ryanodine receptors contribute to bile acid-induced pathological calcium signaling and pancreatitis in mice. Am J Physiol Gastrointest Liver Physiol. 2012 Jun 15;302(12):G1423-33. doi: 10.1152/ajpgi.00546.2011. Epub 2012 Apr 19. PubMed PMID: 22517774; PubMed Central PMCID: PMC3774209.

17: Strasberg SM, Kay RM, Ilson RG, Petrunka CN, Paloheimo JE. Taurolithocholic acid and chlorpromazine cholestasis in the rhesus monkey. Can J Physiol Pharmacol. 1979 Oct;57(10):1138-47. PubMed PMID: 116762.

18: Woudenberg-Vrenken TE, Buist-Homan M, Conde de la Rosa L, Faber KN, Moshage H. Anti-oxidants do not prevent bile acid-induced cell death in rat hepatocytes. Liver Int. 2010 Nov;30(10):1511-21. doi: 10.1111/j.1478-3231.2010.02325.x. Epub 2010 Sep 2. PubMed PMID: 20825559.

19: Adinolfi LE, Gaeta GB, Utili R. [Effect of pretreatment with bacterial endotoxin on sodium taurolithocholic acid-induced cholestasis]. Boll Soc Ital Biol Sper. 1982 Apr 30;58(8):509-12. Italian. PubMed PMID: 7093061.

20: Muili KA, Wang D, Orabi AI, Sarwar S, Luo Y, Javed TA, Eisses JF, Mahmood SM, Jin S, Singh VP, Ananthanaravanan M, Perides G, Williams JA, Molkentin JD, Husain SZ. Bile acids induce pancreatic acinar cell injury and pancreatitis by activating calcineurin. J Biol Chem. 2013 Jan 4;288(1):570-80. doi: 10.1074/jbc.M112.428896. Epub 2012 Nov 12. PubMed PMID: 23148215; PubMed Central PMCID: PMC3537054.