Dehydrocholic Acid | CAS#81-23-2 | Semisynthetic Bile Acid

MedKoo Cat#: 531015 | Name: Dehydrocholic Acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dehydrocholic acid is a semisynthetic bile acid synthesized from cholic acid. Dehydrocholic acid caused a dramatic decrease of phospholipid, cholesterol and bilirubin concentration but had little effect on bile acids concentration. Bile flow, expressed as the ratio of bile flow to bile acid excretion, was increased after dehydrocholic acid administration. It was speculated that the hydroxy keto metabolites are hydrocholeretics. The proportion of cholesterol to lecithin and bile acids did not change significantly after dehydrocholic acid administration.

Chemical Structure

Dehydrocholic Acid

CAS#81-23-2 (acid)

Theoretical Analysis

MedKoo Cat#: 531015

Name: Dehydrocholic Acid

CAS#: 81-23-2 (acid)

Chemical Formula: C24H34O5

Exact Mass: 402.2406

Molecular Weight: 402.53

Elemental Analysis: C, 71.61; H, 8.51; O, 19.87

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Related CAS #

81-23-2 (acid) 145-41-5 (sodium)

Synonym

Dehydrocholic acid, Dehydrocholate sodium, Dehychol, Oxycholin, Cholic acid, Procholon

IUPAC/Chemical Name

(R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

InChi Key

OHXPGWPVLFPUSM-KLRNGDHRSA-N

InChi Code

InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-18,22H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,22+,23+,24-/m1/s1

SMILES Code

C[C@H](CCC(O)=O)[C@H]([C@]12C)CC[C@@]1([H])[C@]3([H])C(C[C@]4([H])CC(CC[C@]4(C)[C@@]3([H])CC2=O)=O)=O

Appearance

White to off-white crystalline 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

>2 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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 402.53 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.

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

1: Liu L, Braun M, Gebhardt G, Weuster-Botz D, Gross R, Schmid RD. One-step synthesis of 12-ketoursodeoxycholic acid from dehydrocholic acid using a multienzymatic system. Appl Microbiol Biotechnol. 2013 Jan;97(2):633-9. doi: 10.1007/s00253-012-4340-5. Epub 2012 Aug 17. PubMed PMID: 22899496. 2: Sun B, Kantzow C, Bresch S, Castiglione K, Weuster-Botz D. Multi-enzymatic one-pot reduction of dehydrocholic acid to 12-keto-ursodeoxycholic acid with whole-cell biocatalysts. Biotechnol Bioeng. 2013 Jan;110(1):68-77. doi: 10.1002/bit.24606. Epub 2012 Sep 18. PubMed PMID: 22806613. 3: Sun B, Hartl F, Castiglione K, Weuster-Botz D. Dynamic mechanistic modeling of the multienzymatic one-pot reduction of dehydrocholic acid to 12-keto ursodeoxycholic acid with competing substrates and cofactors. Biotechnol Prog. 2015 Mar-Apr;31(2):375-86. doi: 10.1002/btpr.2036. Epub 2015 Feb 2. PubMed PMID: 25641915. 4: Braun M, Sun B, Anselment B, Weuster-Botz D. Novel whole-cell biocatalysts with recombinant hydroxysteroid dehydrogenases for the asymmetric reduction of dehydrocholic acid. Appl Microbiol Biotechnol. 2012 Sep;95(6):1457-68. doi: 10.1007/s00253-012-4072-6. Epub 2012 May 15. PubMed PMID: 22581067. 5: Mohamed AA, Matijević E. Preparation and characterization of uniform drug particles: dehydrocholic acid. J Colloid Interface Sci. 2012 Feb 15;368(1):625-8. doi: 10.1016/j.jcis.2011.11.005. Epub 2011 Nov 11. PubMed PMID: 22153852. 6: Yanaura S, Ishikawa S. [Effect of ursodeoxycholic acid on bile secretion and bile components. Comparison with chenodeoxycholic acid and dehydrocholic acid]. Nihon Yakurigaku Zasshi. 1976 Sep;72(6):689-700. Japanese. PubMed PMID: 1034593. 7: Messina PV, Prieto G, Ruso JM, Fernández-Leyes MD, Schulz PC, Sarmiento F. Thermodynamic and elastic fluctuation analysis of Langmuir mixed monolayers composed by dehydrocholic acid (HDHC) and didodecyldimethylammonium bromide (DDAB). Colloids Surf B Biointerfaces. 2010 Jan 1;75(1):34-41. doi: 10.1016/j.colsurfb.2009.08.008. Epub 2009 Aug 13. PubMed PMID: 19734023. 8: Tamasawa N. [Detection of the reduced dehydrocholic acid in serum following administration of dehydrocholic acid and its metabolism in normal subjects]. Nihon Shokakibyo Gakkai Zasshi. 1987 Apr;84(4):948. Japanese. PubMed PMID: 3613238. 9: Úriz M, Sáez E, Prieto J, Medina JF, Banales JM. Ursodeoxycholic acid is conjugated with taurine to promote secretin-stimulated biliary hydrocholeresis in the normal rat. PLoS One. 2011;6(12):e28717. doi: 10.1371/journal.pone.0028717. Epub 2011 Dec 14. PubMed PMID: 22194894; PubMed Central PMCID: PMC3237485. 10: Cravotto G, Binello A, Boffa L, Rosati O, Boccalini M, Chimichi S. Regio- and stereoselective reductions of dehydrocholic acid. Steroids. 2006 Jun;71(6):469-75. Epub 2006 Feb 28. PubMed PMID: 16504228. 11: Soloway RD, Hofmann AF, Thomas PJ, Schoenfield LJ, Klein PD. Triketocholanoic (dehydrocholic) acid. Hepatic metabolism and effect on bile flow and biliary lipid secretion in man. J Clin Invest. 1973 Mar;52(3):715-24. PubMed PMID: 4685091; PubMed Central PMCID: PMC302310. 12: Chanussot F, Lafont H, Hauton J, Tuchweber B, Yousef I. Studies on the origin of biliary phospholipid. Effect of dehydrocholic acid and cholic acid infusions on hepatic and biliary phospholipids. Biochem J. 1990 Sep 15;270(3):691-5. PubMed PMID: 2241901; PubMed Central PMCID: PMC1131787. 13: Akao T, Akao T, Hattori M, Namba T, Kobashi K. Enzymes involved in the formation of 3 beta, 7 beta-dihydroxy-12-oxo-5 beta-cholanic acid from dehydrocholic acid by Ruminococcus sp. obtained from human intestine. Biochim Biophys Acta. 1987 Sep 25;921(2):275-80. PubMed PMID: 3477291. 14: Tani M, Goto J, Makino I. Identification and characterization of dehydrocholic acid reductase system in the cytosol of human red blood cells. J Gastroenterol. 1994 Oct;29(5):621-30. PubMed PMID: 8000511. 15: Yoneda M, Makino I, Tamasawa N, Takebe K, Sakuraba K, Goto J, Nambara T. The biotransformed metabolite profiles in blood after intravenous administration of dehydrocholic acid. Am J Gastroenterol. 1989 Mar;84(3):290-5. PubMed PMID: 2919585. 16: Yousef IM, Mignault D, Weber AM, Tuchweber B. Influence of dehydrocholic acid on the secretion of bile acids and biliary lipids in rats. Digestion. 1990;45(1):40-51. PubMed PMID: 2340963. 17: Fürll M. [Effects of dehydrocholic acid (Biliton) on metabolism and liver function in cows]. Dtsch Tierarztl Wochenschr. 1993 Sep;100(9):375-8. German. PubMed PMID: 8223242. 18: YAMASAKI K. [Dehydrocholic acid loading as a liver function test. Route of the injected dehydrocholate]. Nisshin Igaku Jpn J Med Prog. 1962 Sep;49:595-606. Japanese. PubMed PMID: 14002389. 19: Macioci F, Fiotek C. [Quantitative determination of dehydrocholic acid by means of reaction with concentrated sulfuric acid]. Boll Chim Farm. 1976 Jun;115(6):457-66. Italian. PubMed PMID: 1008951. 20: Uchida K, Nomura Y, Kadowaki M, Arisue K, Takeuchi N, Ishikawa Y. Effects of sodium ursodeoxycholate, hyodeoxycholate and dehydrocholate on cholesterol and bile acid metabolism in rats. J Pharmacobiodyn. 1983 May;6(5):346-57. PubMed PMID: 6620121.