434-13-9 Usage
Description
Lithocholic acid, a cholic acid derivative, is a bile acid found in ox bile, human bile, rabbit bile, and in ox and pig gallstones. It functions as a TGR5 modulator and has various applications in the medical and pharmaceutical fields.
Uses
Used in Pharmaceutical Industry:
Lithocholic acid is used as a chelagogue, which helps to stimulate the flow of bile from the liver to the small intestine. This aids in the digestion and absorption of fats and fat-soluble vitamins.
Used in Cholelithogenic Research:
Lithocholic acid is used as an anticholelithogenic agent, which helps to prevent the formation of gallstones. It is used in studies to investigate the underlying mechanisms and factors contributing to gallstone formation.
Used in Cholestasis Research:
Lithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. This helps in understanding the effects of cholestasis on the body and potential treatments.
Used in Hepatic Phospholipid and Bile Acid Homeostasis Research:
Lithocholic acid has been used in a study to investigate the regulation of hepatic phospholipid and bile acid homeostasis through SMAD3 activation by TGFβ. This research contributes to the understanding of the complex interactions between bile acids, phospholipids, and signaling pathways in the liver.
Toxicity:
The LD50 (mouse) value for lithocholic acid is 3900 mg/kg when administered orally, indicating its relative safety when used in appropriate doses.
Air & Water Reactions
Insoluble in water.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition LITHOCHOLIC ACID emits acrid smoke and fumes.
Fire Hazard
Flash point data for LITHOCHOLIC ACID are not available. LITHOCHOLIC ACID is probably combustible.
Biological Activity
lithocholic acid (lca) is a toxic secondary bile acid, causing intrahepatic cholestasis, which has tumor-promoting activity.
in vitro
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 [1].
in vivo
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 [2].
Purification Methods
Lithocholic acid can be purified by conversion to the rather insoluble Na or K salt by addition of the equivalent amount of aqueous NaOH or KOH, filtering off the alkali salt, washing it with ice cold H2O, dissolving it in the least volume of boiling H2O, acidifying with the dilute HCl (slight excess), filtering off the acid, washing with cold H2O and drying it thoroughly in a vacuum. Recrystallise it from Me2CO, EtOH or acetic acid. The methyl ester crystallises from MeOH, with 0.5 mol of MeOH, and has m 92-93o, [] D 25 +34o (MeOH). It has also been purified by recrystallisation from pet ether (b 40-60o) and, after chromatography on Al2O3 in pet ether, gave a labile form m 92-93o which is transformed to the stable form m 125-126o after standing for 2days in a vacuum desiccator. [Hoelm & Mason J Am Chem Soc 62 569 1940, Sarel & Yanuka J Org Chem 24 2018 1959, Beilstein 10 IV 785.]
references
[1] ogawa a, murate t, suzuki m, nimura y, yoshida s. lithocholic acid, a putative tumor promoter, inhibits mammalian dna polymerase beta. jpn j cancer res. 1998 nov;89(11):1154-9.[2] staudinger jl, goodwin b, jones sa, hawkins-brown d, mackenzie ki, latour a, liu y, klaassen cd, brown kk, reinhard j, willson tm, koller bh, kliewer sa. the nuclear receptor pxr is a lithocholic acid sensor that protects against liver toxicity. proc natl acad sci u s a. 2001 mar 13;98(6):3369-74.
Check Digit Verification of cas no
The CAS Registry Mumber 434-13-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,3 and 4 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 434-13:
(5*4)+(4*3)+(3*4)+(2*1)+(1*3)=49
49 % 10 = 9
So 434-13-9 is a valid CAS Registry Number.
InChI:InChI=1/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)/p-1/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
434-13-9Relevant articles and documents
Not available
HEUSSER,WUTHIER
, p. 2165 - 2167 (1947)
-
METHOD FOR HOMOGENIZING BILE ACID DERIVATIVES
-
Paragraph 0073-0075, (2021/05/28)
The present invention relates to a process for producing bile acid derivatives having a protected hydroxyl group in the 3 position comprising contacting a bile acid derivative having an unprotected 3-alpha-hydroxyl group with a specific lipase. The present invention further relates to a bile acid derivative obtained or obtainable by the process, to the use of the bile acid derivative obtained or obtainable by the process for producing lithocholic acid and also to a process for producing lithocholic acid and to lithocholic obtained by the process. The invention further relates to the use of lithocholic acid obtained or obtainable by the process for producing ursodeoxycholic acid or ursodeoxycholic acid derivatives.
Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
supporting information, p. 6648 - 6653 (2021/09/08)
The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
Optimization of EphA2 antagonists based on a lithocholic acid core led to the identification of UniPR505, a new 3α-carbamoyloxy derivative with antiangiogenetic properties
Incerti, Matteo,Russo, Simonetta,Corrado, Miriam,Giorgio, Carmine,Ballabeni, Vigilio,Chiodelli, Paola,Rusnati, Marco,Scalvini, Laura,Callegari, Donatella,Castelli, Riccardo,Vacondio, Federica,Ferlenghi, Francesca,Tognolini, Massimiliano,Lodola, Alessio
supporting information, (2020/01/29)
The EphA2 receptor has been validated in animal models as new target for treating tumors depending on angiogenesis and vasculogenic mimicry. In the present work, we extended our current knowledge on structure-activity relationship (SAR) data of two related classes of antagonists of the EphA2 receptor, namely 5β-cholan-24-oic acids and 5β-cholan-24-oyl L-β-homotryptophan conjugates, with the aim to develop new antiangiogenic compounds able to efficiently prevent the formation of blood vessels. As a result of our exploration, we identified UniPR505, N-[3α-(Ethylcarbamoyl)oxy-5β-cholan-24-oyl]-L-β-homo-tryptophan (compound 14), as a submicromolar antagonist of the EphA2 receptor capable to block EphA2 phosphorylation and to inhibit neovascularization in a chorioallantoic membrane (CAM) assay.
