6-Oxolithocholic acid is a bile acid metabolite derived from lithocholic acid. 6-Oxolithocholic acid is highly cytotoxic and can induce apoptosis, especially in hepatocytes. 6-Oxolithocholic acid can participate in the regulation of bile acid metabolism and synthesis, affecting the cholesterol metabolic pathway. 6-Oxolithocholic acid can be used to study the role of bile acids in health and disease, especially in the context of digestive system and liver diseases.

Physicochemical Properties

Molecular Formula	C24H38O4
Molecular Weight	390.56
CAS #	2393-61-5
Appearance	White to off-white solid powder
Vapour Pressure	3.42E-14mmHg at 25°C
LogP	4.686
SMILES	[C@@]12(C(C[C@]3([H])[C@@](CC[C@@]4([C@@]([H])([C@@H](CCC(O)=O)C)CC[C@]43[H])C)([H])[C@]1(CC[C@@H](O)C2)C)=O)[H]
Synonyms	6-Ketolithocholic acid; 2393-61-5; 5?-Cholanic Acid-3?-ol-6-one; 3-ALPHA-HYDROXY-6-KETOCHOLANIC ACID; 5alpha-CHOLANIC ACID-3alpha-OL-6-ONE; 4-(3-hydroxy-10,13-dimethyl-6-oxo-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)pentanoic acid; CHEBI:182882; 5-Beta-cholanic acid-3-alpha-ol-6-one;
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)

Biological Activity

Targets	Lithocholic acid metabolite
ln Vitro	The hydroxylation of lithocholic acid (3 alpha-hydroxy-5 beta-cholanoic acid) by adult male Sprague-Dawley rat liver microsomes supplemented with NADPH was studied. Metabolites were separated by a combination of thin-layer chromatography and high pressure liquid chromatography, both with and without prior methylation and acetylation of the samples. The resulting products were characterized by thin-layer, gas-liquid, and high pressure liquid chromatography by comparison with authentic bile acid standards; final structure determination was by proton nuclear magnetic resonance spectroscopy and by mass spectrometry. The following reaction products were found: 3 alpha, 6 beta-dihydroxy-5 beta-cholanoic acid (80% of total metabolites) and 3 alpha, 6 alpha-dihydroxy-5 beta-cholanoic, 3 alpha, 7 alpha-dihydroxy-5 beta-cholanoic, 3 alpha, 6 beta,7 beta-trihydroxy-5 beta-cholanoic, and 3 alpha-hydroxy-6-oxo-5 beta-cholanoic acids (less than or equal to 5% each). In addition, one unidentified trihydroxylic bile acid and several minor compounds were present. It is concluded that four different hydroxylation reactions of lithocholic acid, namely the predominant 6 beta as well as the minor 6 alpha, 7 alpha, and 7 beta hydroxylations, are catalyzed by rat hepatic microsomes; 7 beta-hydroxylation may occur only with dihydroxylated bile acids but not with lithocholate itself. The presence of the 6-oxo bile acid can be explained either by direct oxidation of a hydroxyl group by cytochrome P-450, or by the action of microsomal dehydrogenase(s) which could also catalyze the epimerization of hydroxyl groups via their oxidation. The results form the basis of a proposed scheme of the oxidative metabolism of lithocholic acid in rat liver microsomes [1].
References	[1]. Zimniak P, et al. Detoxification of lithocholic acid. Elucidation of the pathways of oxidative metabolism in rat liver microsomes[J]. Journal of lipid research, 1989, 30(6): 907-918.
Additional Infomation	4-(3-Hydroxy-10,13-dimethyl-6-oxo-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)pentanoic acid is a bile acid.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~256.04 mM; with ultrasonication)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.40 mM) (saturation unknown) in 10% DMSO +40% PEG300 +5% Tween-80 +45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution。 Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.40 mM) (saturation unknown) 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 the 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD in saline 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 3: ≥ 2.5 mg/mL (6.40 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 the 25.0 mg/mL clear DMSO stock solution to 900 μL corn oil and mix well. " (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.5604 mL	12.8021 mL	25.6043 mL
	5 mM	0.5121 mL	2.5604 mL	5.1209 mL
	10 mM	0.2560 mL	1.2802 mL	2.5604 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.