1178-00-3

Usage

Uses

Used in Metabolic Disorder Research:
2,3-secocholestan-2,3-dioic acid is used as a biomarker for identifying and studying certain metabolic disorders due to its involvement in cholesterol metabolism and bile acid degradation.
Used in Cardiovascular System Research:
2,3-secocholestan-2,3-dioic acid is used as a research compound to investigate its potential effects on the cardiovascular system, given its connection to cholesterol metabolism.
Used in Pharmaceutical Development:
2,3-secocholestan-2,3-dioic acid is utilized as a starting material or intermediate in the development of pharmaceuticals targeting cholesterol-related conditions and metabolic disorders.
Used in Disease Biomarker Identification:
2,3-secocholestan-2,3-dioic acid is employed as a potential biomarker for certain diseases, aiding in disease diagnosis, prognosis, and treatment monitoring.

InChI:InChI=1/C27H46O4/c1-17(2)7-6-8-18(3)23-11-12-24-21-10-9-19(15-25(28)29)22(16-26(30)31-5)20(21)13-14-27(23,24)4/h17-24H,6-16H2,1-5H3,(H,28,29)/t18?,19-,20-,21+,22-,23?,24-,27+/m0/s1

Upstream product

• 80-97-7 Cholestanol 
• 74332-46-0 3-oxo-5α-cholestane-sulfonic acid-(2ξ) 
• 13901-19-4 cholest-2-ene 
• 13163-67-2 2-benzylidene-5α-cholestan-3-one 
• 2696-52-8 4a-homo-3-oxa-5α-cholestane-2,4-dione 
• 566-88-1 dihydrocholesterone 
• 14161-45-6 2α-acetoxy-5α-cholestan-3-one 
• 1255-89-6 5α-cholest-2-en-3-ol 3-acetate 
• 16126-32-2 (2β-3α-5α)-cholestane-2,3-diol 
• 20780-35-2 5α-cholest-14-en-3β-ol 
• 63866-20-6 3β-bromo-5α-cholestan-6-one 
• 1056-93-5 3β-chloro-5α-cholestan-6-one 
• 21072-86-6 3α-chloro-5α-cholestan-6-one 
• 20281-69-0 5α-cholest-2-en-6-one 

Downstream Products

• 1180-24-1 Dimethyl 2,3-seco-5α-cholestane-2,3-dioate 
• 2310-36-3 A-nor-5α-cholestan-2-one 
• 14124-56-2 2,3-seco-5α-cholestane-2,3-diol 
• 114670-18-7 2,3-Bis-(p-toluolsulfonyloxy)-2,3-secocholestan 

Relevant academic research and scientific papers

Silver(I)-Catalyzed Widely Applicable Aerobic 1,2-Diol Oxidative Cleavage

The oxidative cleavage of 1,2-diols is a fundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage, such as H5IO6, Pb(OAc)4, and KMnO4, generate stoichiometric hazardous waste. Herein, we describe a widely applicable and highly selective silver(I)-catalyzed oxidative cleavage of 1,2-diols that consumes atmospheric oxygen as the sole oxidant, thus serving as a potentially greener alternative to the classical transformations.

The oxidation of Δ2, Δ2,4 and Δ4,6 steroids with RuO4

In order to find new ways for the functionalization of the A and B rings of the steroid nucleus, the reaction of 5α-androst-2-en-17β-ol 17-acetate (1), cholesta-2,4-diene (4) and cholesta-4,6-dien-3β-ol 3-acetate (7) was examined using stoichiometric amounts of ruthenium tetraoxide to yield 1,2-cis diols and/or α-hydroxy ketones. The reaction of 5α-cholest-2-en-3-ol 3-acetate (9) with ruthenium tetraoxide was also carried out and afforded, apart from an α-hydroxy ketone, also a diketone and a seco-dicarboxylic acid. The structures of all new steroids, including stereochemical details, were deduced by analysis of spectral data.

Autoxidation vs hydrolysis in 16α-acyloxy steroids

Some enolizable α-hydroxy ketones are extremely susceptible to oxidation with traces of air in a reaction vessel. Autoxidation can be used in synthesis of oxo acids or diacids and their derivatives. Yet alkaline hydrolysis of the substrate is possible though under strictly air-free conditions.

A New α-Iodination of Ketones Using Iodine-Ammonium Cerium(IV) Nitrate in Alcohol or Acetic Acid

The direct α-iodination of various ketones using iodine-ammonium cerium(IV) nitrate in acetic acid or alcohol gave the corresponding α-iodo ketones in high yields. The effect of cerium salt on the iodination of ketones, and the iodination of 5α-cholestan-3-one using several methods are also discussed. In the reaction of 3,3,5-trimethylcyclohexanone and unsymmetrical ketones, such as 2-hexanone and 2-heptanone, using methanol, ethanol, 1-propanol, and 2-propanol, the regioselective iodination product was obtained. In the case of bromination, the reaction of ketones with bromine and ammonium cerium(IV) nitrate also yielded the corresponding α-bromo ketones.

Photoinduced Molecular Transformations. Part 106. The Formation of Cyclic Anhydrides via Regioselective β-Scission of Alkoxyl Radicals generated from 5- and 6-Membered α-Hydroxy Cyclic Ketones.

The irradiation of the hypoiodites of 5- or 6-membered cyclic α-ketols in benzene containing mercury(II) oxide and iodine (each 3 equiv.) resulted in the formation of the corresponding cyclic anhydrides arising from the insertion of an oxygen.A novel formation of a methylenedioxy group arising from an intramolecular hydrogen abstraction, on the other hand, was found when a steroidal α,α-dimethoxy alcohol hypoiodite was irradiated in benzene.An 18O labelling study of the formation of the cyclic anhydride on photolysis of 17β-hydroxy-4β-methoxy-5α-androstan-16-one hypoiodite generated in situ by an excess of mercury(II) oxide and iodine in benzene indicated that the heavy oxygen of Hg18O is incorporated as the ring oxygen of the anhydride.On the basis of this result, a pathway involving a regioselective β-scission of the alkoxyl radical is proposed as leading to formation of the cyclic anhydride.

Oxidation of Azasteroid Lactams and Alcohols with Benzeneseleninic Anhydride

Reaction of 4-azasteroid δ-lactams 6, 9, 10 and 12 with benzeneseleninic anhydride (2) in diglyme at 120 deg C smoothly effects dehydrogenation to the corresponding Δ1 derivatives 13-16.Oxidation of 3-aza-A-homo-4a-cholesten-4-one (17) or its s