14773-00-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Oxo-7α-hydroxy-5β-cholan-24-oic acid methyl ester is used as a bile acid transporter for the regulation of cholesterol and lipid metabolism. Its steroidal structure allows it to interact with specific transport proteins, making it a valuable compound for the development of drugs targeting cholesterol-related disorders.
Used in Chemical Research:
As a steroidal compound, 3-Oxo-7α-hydroxy-5β-cholan-24-oic acid methyl ester is used as a starting material or intermediate in the synthesis of various steroidal drugs and hormones. Its unique functional groups and structural features make it a versatile building block for the development of new pharmaceuticals with potential therapeutic applications.
Used in Drug Delivery Systems:
3-Oxo-7α-hydroxy-5β-cholan-24-oic acid methyl ester can be utilized in the development of targeted drug delivery systems, particularly for compounds that require transport across biological membranes. Its steroidal structure and bile acid transporter properties can be exploited to enhance the bioavailability and efficacy of various drugs, particularly those with poor membrane permeability.

Upstream product

• 186581-53-3 diazomethane 
• 106351-12-6 3-keto-7α-formyloxy-5β-cholan-24-oic acid 
• 3057-04-3 chenodeoxycholic acid methyl ester 
• 125626-78-0 (R)-4-((7R,8S,9S,10R,13R,14S,17R)-7-Hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 474-25-9 chenodeoxycholic acid 
• 944409-57-8 6,7-epoxycholan-4-en-3-one-24-oic acid methyl ester 
• 1434-27-1 7α-acetoxy-3,3-ethanediyldioxy-12-oxo-5β-cholan-24-oic acid methyl ester 
• 60354-42-9 methyl 7α-acetoxy-3,12-dioxo-5β-cholanoate 

Downstream Products

• 96475-65-9 C₃₂H₄₈N₂O₅S 
• 610313-09-2 (R)-4-((7R,8S,9S,10R,13R,14S,17R)-4,7-Dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 99220-84-5 24-methyl-3-oxo-5β-chol-1,4,7-trienoate 
• 80097-58-1 25,26,27-trisnorcholesta-1,4,6-trien-3-on-24-oic acid methyl ester 
• 148456-90-0 24-methyl-3-oxo-5β-chol-1,7-dienoate 
• 148456-89-7 24-methyl-2β-bromo-3-oxo-5β-chol-7-enoate 
• 28050-19-3 methyl 7α-hydroxy-5β-cholan-24-oate 
• 1377666-88-0 Δ^1,7-dafachronic acid 
• 949004-11-9 (25R)-3-keto-5α-cholest-7-en-26-oic acid 
• 1579829-35-8 (25R)-Δ^1,7-dafachronic acid 
• 1579830-33-3 C₂₇H₄₁ClO₂ 
• 1579830-48-0 C₃₅H₅₀N₂O₅ 
• 16265-22-8 3-oxo-5α-7α-hydroxy-cholan-24-al 
• 1579830-92-4 (25R)-2-bromo-Δ⁷-dafachronic acid 

Relevant academic research and scientific papers

Efficient and selective microwave Oppenauer oxidation of sterol derivatives

An improved, fast, and accurate procedure for regioselective microwave Oppenauer oxidation of sterol derivatives is reported leading to the expected corresponding ketosterols in moderate to excellent isolated yields ranging from 58 to 81%. The influence of different parameters dealing with the nature of the solvent and of the Lewis acid/ketone couple used, the reaction temperature as well as the hydrolysis conditions were also investigated on the outcome of the reaction.

METHOD AND COMPOSITIONS FOR FORMING A COPPER-CONTAINING COMPLEX AND USES THEREOF

Provided is a method of forming a copper-containing complex, including contacting a sample containing copper with a compound of Formula (I): wherein R is -OH or -O-CH3. Also provided is a method of inhibiting enzymatic activity of a kinase in a sample, including contacting the sample with a compound of Formula (I). Further provided is a method of administering to a subject a pharmaceutical composition including a compound of Formula (I) optionally complexed with copper. Also provided is a pharmaceutical composition including copper complexed with a compound of Formula (I).

A photocleavable masked nuclear-receptor ligand enables temporal control of C.elegans development

The development and lifespan of C.elegans are controlled by the nuclear hormone receptor DAF-12, an important model for the vertebrate vitaminD and liverX receptors. As with its mammalian homologues, DAF-12 function is regulated by bile acid-like steroidal ligands; however, tools for investigating their biosynthesis and function invivo are lacking. A flexible synthesis for DAF-12 ligands and masked ligand derivatives that enable precise temporal control of DAF-12 function was developed. For ligand masking, photocleavable amides of 5-methoxy-N-methyl-2-nitroaniline (MMNA) were introduced. MMNA-masked ligands are bioavailable and after incorporation into the worm, brief UV irradiation can be used to trigger the expression of DAF-12 target genes and initiate development from dauer larvae into adults. The invivo release of DAF-12 ligands and other small-molecule signals by using photocleavable MMNA-masked ligands will enable functional studies with precise spatial and temporal resolution. Copyright

A stereoselective synthesis of the allo-bile acids from the 5β-isomers

The allo-bile acids are a subset of the family of steroidal detergents found in most vertebrates. Because there are no major biological feedstocks for isolation of the allo-bile acids, they must be synthesized from the abundant 5β-reduced isomers. Here we report a general set of methods for the synthesis of allo-bile acids from the corresponding 5-β isomers demarcated by a selective C-3 oxidation, IBX unsaturation, and stereoselective saturation.

PROCESS FOR PRODUCTION OF STEROIDS

It is an object of the present invention to provide a novel method for producing a steroid compound. The present invention provides a method for producing 5β-3,7-dioxocholanic acid or an ester derivative thereof, using, as a raw material, a sterol having double bonds at position 5 and at position 24, such as cholesta-5,7,24-trien-3β-ol, ergosta-5,7,24(28)-trien-3β-ol, desmosterol, fucosterol, or ergosta-5,24(28)-dien-3β-ol, via the following 4 steps: (I) a step involving oxidation of a hydroxyl group at position 3 and isomerization of a double bond at position 5 to position 4; (II) a step involving the oxidative cleavage of a side chain to convert position 24 to a carboxyl group or an ester derivative thereof; (III) a step of introducing an oxygen functional group into position 7; and (IV) a step of constructing a 5β configuration by reductive saturation of a double bond at position 4.

Two-way enantioselective control in the epoxidation of alkenes with the keto bile acid-Oxone system

A number of 3-keto bile acid derivatives has been prepared and evaluated in the asymmetric epoxidation of unfunctionalized olefins with Oxone. The control of the enantioselectivity with the production of both enantiomers is strictly regulated by the bile acid inductor, as a function of substitution at carbons C(7) or C(12). Up to 98% ee has been achieved. The stereochemical outcome of the reaction may be rationalized in terms of spiro transition state model.

A concise and stereoselective synthesis of squalamine

(Matrix presented) A short and highly stereoselective synthesis of the novel steroid squalamine (1) was accomplished in nine steps from easily available methyl chenodeoxylcholanate 2. Our synthesis featured improved dehydrogenation of 4 followed by conjugate reduction to construct the trans AB-ring system and efficient asymmetric isopropylation of aldehyde 6 to introduce the C-24R-hydroxyl group.

Selective dimethyldioxirane oxidation of bile acid methyl esters

DMDO oxidation of the hydroxy groups of bile acid methyl esters establishes the positional order of reactivity as 3-7 > 6 > 12 and supports a mechanism involving C-H oxygen insertion through a planar intramolecularly hydrogen bonded transition state.

Synthesis of a tritiated 3-dehydroecdysteroid putative precursor of ecdysteroid biosynthesis

We have synthesized a tritiated form of 5β-cholest-7-ene-3,6-dione (5β-diketone) of high specific activity (9.2 TBq/mmol) in ten steps from deoxychenocholic acid, which possessed the desired A/B cis ring junction (5β-H configuration). We have conceived a synthetic pathway which permits labelling by tritiation at the final step and allowing for the introduction of the tritium label into the side chain and the nucleus. We have examined the ability of insect endocrine glands (prothoracic glands) of Pieris Brassicae to use this molecule as a precursor of 3-dehydroecdysone and of ecdysone biosynthesis. No conversion can be detected. In the myriapod Lithobius forficatus only reduction of the 3-ketone can be observed. It seems that the 5β-diketone is not an intermediate in the ecdysone biosynthetic pathway.

An efficient synthesis of 4β and 6α-hydroxylated bile acids

An efficient method for the preparation of 4β- and 6α-hydroxylated bile acids has been developed.It involved a highly stereoselective acetoxylation at the 4β and 6α positions of 3- and 7-oxo bile acids, respectively, with lead tetraacetate in the presence of boron trifluoride etherate in acetic acid.Reduction of the resulting α-acetoxy ketones with sodium borohydride or tert-butylamine borane complex, and alkaline hydrolysis, provided the desired bile acids in good yields. Keywords: sterols; bile acid; 4β-hydroxylated bile acid;6α-hydroxylated bile acid; acetoxylation; lead tetraacetate oxidation