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MedKoo Cat#: 599015 | Name: Glycolithocholic acid
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Description:

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

Glycolithocholic acid is a glycine conjugate of lithocholic acid, a bile acid. It is increased in livers of mice that are fed diets supplemented with ursadeoxycholic acid. Glycolithocholic acid levels are decreased in lean mice treated with obestatin. Serum glycolithocholic acid levels increase with age in children.

Chemical Structure

Glycolithocholic acid
Glycolithocholic acid
CAS#474-74-8

Theoretical Analysis

MedKoo Cat#: 599015

Name: Glycolithocholic acid

CAS#: 474-74-8

Chemical Formula: C26H43NO4

Exact Mass: 433.3192

Molecular Weight: 433.63

Elemental Analysis: C, 72.02; H, 10.00; N, 3.23; O, 14.76

Price and Availability

Size Price Availability Quantity
50mg USD 250.00 2 Weeks
100mg USD 450.00 2 Weeks
500mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Glycolithocholic acid; Lithocholylglycine; Lithocholic acid glycine conjugate; GLCA​;
IUPAC/Chemical Name
((R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyl)glycine
InChi Key
XBSQTYHEGZTYJE-OETIFKLTSA-N
InChi Code
InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1
SMILES Code
O=C(O)CNC(CC[C@@H](C)[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)=O
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Glycolithocholic acid, an endogenous metabolite, is a glycine-conjugated secondary bile acid. Glycolithocholic acid can be used to diagnose ulcerative colitis (UC), non-alcoholic steatohepatitis (NASH) and primary sclerosing cholangitis (PSC).
In vitro activity:
TBD
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMF 30.0 69.18
DMF:PBS (pH 7.2) (1:1) 0.5 1.15
DMSO 110.0 253.67
Ethanol 20.0 46.12
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 433.63 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:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Kuipers F, Derksen JP, Gerding A, Scherphof GL, Vonk RJ. Biliary lipid secretion in the rat. The uncoupling of biliary cholesterol and phospholipid secretion from bile acid secretion by sulfated glycolithocholic acid. Biochim Biophys Acta. 1987 Nov 21;922(2):136-44. PubMed PMID: 3676338. 2: Kuipers F, Hardonk MJ, Vonk RJ, van der Meer R. Bile secretion of sulfated glycolithocholic acid is required for its cholestatic action in rats. Am J Physiol. 1992 Feb;262(2 Pt 1):G267-73. PubMed PMID: 1539660. 3: 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. 4: Kobayashi N, Katsumata H, Uto Y, Goto J, Niwa T, Kobayashi K, Mizuuchi Y. A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. Steroids. 2002 Sep;67(10):827-33. PubMed PMID: 12231118. 5: Kuipers F, Havinga R, Vonk RJ. Cholestasis induced by sulphated glycolithocholic acid in the rat: protection by endogenous bile acids. Clin Sci (Lond). 1985 Feb;68(2):127-34. PubMed PMID: 3967462. 6: Wildgrube HJ, Stang H, Schiller D, Winkler M, Weber J, Campana H, Mauritz G. [Conjugated bile acids and sulphated glycolithocholic acid in the serum of healthy probands (author's transl)]. J Clin Chem Clin Biochem. 1982 May;20(5):319-23. German. PubMed PMID: 7108452. 7: Kuipers F, Heslinga H, Havinga R, Vonk RJ. Intestinal absorption of lithocholic acid sulfates in the rat: inhibitory effects of calcium. Am J Physiol. 1986 Aug;251(2 Pt 1):G189-94. PubMed PMID: 3740261. 8: Bremmelgaard A, Ranek L, Bahnsen M, Andreasen PB, Christensen E. Cholic acid conjugation test and quantitative liver function in acute liver failure. Scand J Gastroenterol. 1983 Sep;18(6):797-802. PubMed PMID: 6669944. 9: Washizu T, Ishida T, Washizu M, Tomoda I, Kaneko JJ. Changes in bile acid composition of serum and gallbladder bile in bile duct ligated dogs. J Vet Med Sci. 1994 Apr;56(2):299-303. PubMed PMID: 8075218. 10: Baba M, Schols D, Nakashima H, Pauwels R, Parmentier G, Meijer DK, De Clercq E. Selective activity of several cholic acid derivatives against human immunodeficiency virus replication in vitro. J Acquir Immune Defic Syndr. 1989;2(3):264-71. PubMed PMID: 2470892. 11: Barnes S, Buchina ES, King RJ, McBurnett T, Taylor KB. Bile acid sulfotransferase I from rat liver sulfates bile acids and 3-hydroxy steroids: purification, N-terminal amino acid sequence, and kinetic properties. J Lipid Res. 1989 Apr;30(4):529-40. PubMed PMID: 2754334. 12: Batta AK, Shefer S, Salen G. Thin-layer chromatographic separation of conjugates of ursodeoxycholic acid from those of litho-, chenodeoxy-, deoxy-, and cholic acids. J Lipid Res. 1981 May;22(4):712-4. PubMed PMID: 7276746. 13: Cowan E, Kumar P, Burch KJ, Grieve DJ, Green BD, Graham SF. Treatment of lean and diet-induced obesity (DIO) mice with a novel stable obestatin analogue alters plasma metabolite levels as detected by untargeted LC-MS metabolomics. Metabolomics. 2016;12:124. doi: 10.1007/s11306-016-1063-0. Epub 2016 Jul 5. PubMed PMID: 27471436; PubMed Central PMCID: PMC4932145. 14: Scates DK, Spigelman AD, Venitt S. Appearance of artefacts when using 32P-postlabelling to investigate DNA adduct formation by bile acids in vitro: lack of evidence for covalent binding. Carcinogenesis. 1995 Jul;16(7):1489-91. PubMed PMID: 7614681. 15: Barnes S, Burhol PG, Zander R, Haggstrom G, Settine RL, Hirschowitz BI. Enzymatic sulfation of glycochenodeoxycholic acid by tissue fractions from adult hamsters. J Lipid Res. 1979 Nov;20(8):952-9. PubMed PMID: 533830. 16: Kuipers F, Enserink M, Havinga R, van der Steen AB, Hardonk MJ, Fevery J, Vonk RJ. Separate transport systems for biliary secretion of sulfated and unsulfated bile acids in the rat. J Clin Invest. 1988 May;81(5):1593-9. PubMed PMID: 3366909; PubMed Central PMCID: PMC442594. 17: Mamianetti A, Konopka HF, Lago N, Vescina C, Scarlato E, Carducci CN. Morphologic changes in livers of hamsters treated with high doses of ursodeoxycholic acid: correlation with bile acids in bile. Pharmacol Res. 1994 Feb-Mar;29(2):187-95. PubMed PMID: 8058592. 18: Singer SS, Dravis D, Henkels K, Trulzsch DV. Fatty acid binding protein inhibits glycolithocholate sulfation. Biochem Int. 1992 Jul;27(3):373-83. PubMed PMID: 1417875. 19: Kirkpatrick RB, Green MD, Hagey LR, Hofmann AF, Tephly TR. Effect of side chain length on bile acid conjugation: glucuronidation, sulfation and coenzyme A formation of nor-bile acids and their natural C24 homologs by human and rat liver fractions. Hepatology. 1988 Mar-Apr;8(2):353-7. PubMed PMID: 3356416. 20: Kato T, Yoneda M, Nakamura K, Makino I. Enzymatic determination of serum 3 alpha-sulfated bile acids concentration with bile acid 3 alpha-sulfate sulfohydrolase. Dig Dis Sci. 1996 Aug;41(8):1564-70. PubMed PMID: 8769280.

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