3-Oxocholic acid is an oxo-bile acid (secondary bile acid) and a metabolite of cholic acid isolated from C. perfringens, which is a bacteria found in the intestines of mammals and in the environment. 3-Oxocholic acid serum levels increase following ileal transposition surgery in rats.

Physicochemical Properties

Molecular Formula	C₂₄H₃₈O₅
Molecular Weight	406.56
Exact Mass	406.272
CAS #	2304-89-4
PubChem CID	5283956
Appearance	White to off-white solid powder
Density	1.180±0.06g/ml(Predicted)
Boiling Point	583.0±50.0℃(Predicted)
Melting Point	185℃
Vapour Pressure	5.08E-16mmHg at 25°C
LogP	3.656
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Heavy Atom Count	29
Complexity	676
Defined Atom Stereocenter Count	10
SMILES	C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CCC(=O)C4)C)O)O)C
InChi Key	OEKUSRBIIZNLHZ-DJDNIQJZSA-N
InChi Code	InChI=1S/C24H38O5/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/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
Chemical Name	(4R)-4-[(5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
Synonyms	3Oxocholic acid 3 Oxocholic acid
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

ln Vivo	Ileal transposition (IT) surgery is performed on male Goto-Kakizaki (GK) rats. The metabolomics research shows that the IT rats have higher 3-Oxocholic acid than the Sham-IT animals[2].
References	[1]. Identification of 7alpha-, 12alpha-dihydroxy-3-oxo cholanoic acid as the major degradation product from cholic by C. perfringens. J Steroid Biochem. 1978 Apr;9(4):353-8. [2]. The Changes of Serum Metabolites in Diabetic GK Rats after Ileal Transposition Surgery. Obes Surg. 2019 Mar;29(3):882-890. [3]. Intestinal Crosstalk between Bile Acids and Microbiota and Its Impact on Host Metabolism. Cell Metab. 2016 Jul 12;24(1):41-50.
Additional Infomation	7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid is a 3-oxo steroid that is cholic acid in which the hydroxy group at position 3 has undergone formal oxidation to the corresponding ketone. It has a role as a human metabolite. It is a bile acid, a 12alpha-hydroxy steroid, a dihydroxy-5beta-cholanic acid, a 7alpha-hydroxy steroid and a 3-oxo-5beta-steroid. It is a conjugate acid of a 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oate.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~245.97 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.15 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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 2: ≥ 2.5 mg/mL (6.15 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.4597 mL	12.2983 mL	24.5966 mL
	5 mM	0.4919 mL	2.4597 mL	4.9193 mL
	10 mM	0.2460 mL	1.2298 mL	2.4597 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.