61951-99-3

Basic information

• Product Name: Tixocortol
• Synonyms: (11β)-11,17-Dihydroxy-21-Mercaptopregn-4-ene-3,20-dione;11β,17-Dihydroxy-21-Mercaptoprogesterone;Cortisol 21-Thiol
• CAS NO: 61951-99-3
• Molecular Formula: C₂₁H₃₀O₄S
• Molecular Weight: 378.53
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Sulfur & Selenium Compounds
• Mol File: 61951-99-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 559.3°Cat760mmHg
• Flash Point: 292.1°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 7.71E-15mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: Tixocortol(CAS DataBase Reference)
• NIST Chemistry Reference: Tixocortol(61951-99-3)
• EPA Substance Registry System: Tixocortol(61951-99-3)

Safety Data

• Hazardous Substances Data: 61951-99-3(Hazardous Substances Data)

Usage

Uses

Tixocortol is an anti-inflammatory agent. Tixocortol is used in fluorescent chemoaffinity labeling.

Definition

ChEBI: A steroid sulfide in which the sulfanyl group is at C-21 of a polyoxygenated derivative of pregn-4-ene.

Therapeutic Function

Antiinflammatory

InChI:InChI=1/C21H30O4S/c1-19-7-5-13(22)9-12(19)3-4-14-15-6-8-21(25,17(24)11-26)20(15,2)10-16(23)18(14)19/h9,14-16,18,23,25-26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1

Upstream product

• 33767-06-5 11β,17α-dihydroxy-21-iodopregn-4-ene-3,20-dione 

Relevant articles and documents

Expeditious synthesis of steroids containing a 2-methylsulfanyl-acetyl side chain as potential glucocorticoid receptor imaging agents

In our effort to develop imaging agents for brain glucocorticoid receptors, we have prepared several novel glucocorticoids possessing a 2-methylsulfanyl-acetyl side chain. The synthesis was accomplished via a Mitsunobu reaction with thiobenzoic acid starting from cortisol, prednisolone, dexamethasone and triamcinolone acetonide to give the corresponding S-thiobenzoates in 75-82% yield. Subsequent saponification and reaction with methyl iodide afforded C-21 methylthioethers in 68-82% yield. All compounds were tested in an in vitro glucocorticoid receptor-binding assay. Triamcinolone acetonide-based compound 12 showed promising binding affinity of 144% relative to dexamethasone (100%). Compound 12 was selected for radiolabeling with the short-lived positron emitter carbon-11. The radiolabeling was carried out starting from S-thiobenzoate 8 and in situ formation of the corresponding sodium thiolate, which was further reacted with [11C]methyl iodide. The obtained radiochemical yield was 20-30%. The specific activity was determined to be 20-40 GBq/μmol at the end-of-synthesis, and the radiochemical purity exceeded 98%.

REDUCTIVE DEHALOGENATION OF 21-IODO DERIVATIVES OF CORTICOSTEROIDS

In the reactions of 21-iodo derivatives of corticosteroids with hydrogen sulfide and thiol-containing reagents in a medium of dipolar aprotic and amide protogenic solvents at room temperature reductive-deiodination reactions occur with the formation of 21-deoxycorticosteroids in quantitative yield.Reactions of solutions of 21-iodomethyl ketones, heated to 80 deg C, with hydrogen sulfide and thiol-containing reagents give not only reduction products, but also products of nucleophilic substitution at C21 in yields of 20-30percent.