53-02-1

Basic information

• Product Name: TETRAHYDROCORTISOL
• Synonyms: SOLVENT A, TETRAHYDROFURAN;UROCORTISOL;TETRAMETHYLENE OXIDE;3-ALPHA,11-BETA,17-ALPHA,21-TETRAHYDROXY-5-BETA-PREGNAN-20-ONE;5BETA-PREGNAN-3BETA,11BETA,17ALPHA,21-TETROL-20-ONE;5BETA-PREGNAN-3ALPHA,11BETA,17ALPHA,21-TETROL-20-ONE;5-BETA-PREGNAN-3-ALPHA, 11-BETA, 17,21-TETROL-20-ONE;AKOS BBS-00004225
• CAS NO: 53-02-1
• Molecular Formula: C21H34O5
• Molecular Weight: 366.49
• EINECS: 203-726-8
• Mol File: 53-02-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: −108 °C(lit.)
• Boiling Point: 65-67 °C(lit.)
• Flash Point: 1 °F
• Appearance: <10(APHA)/Solid
• Density: 0.889 g/mL at 25 °C(lit.)
• Vapor Density: 2.5 (vs air)
• Vapor Pressure: 114 mm Hg ( 15 °C)
• Refractive Index: n20/D 1.407(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Very Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Sligh
• PKA: 12.48±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: TETRAHYDROCORTISOL(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAHYDROCORTISOL(53-02-1)
• EPA Substance Registry System: TETRAHYDROCORTISOL(53-02-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37-40
• Safety Statements: 26-36-36/37
• RIDADR: UN 2056 3/PG 2
• WGK Germany: 1
• RTECS: LU5950000
• F: 3-10-23
• Hazardous Substances Data: 53-02-1(Hazardous Substances Data)

Usage

Uses

Tetrahydrocortisol is excreted in large amounts in premenopausal patients with early breast cancer. Tetrahydrocortisol has been found to be produced by lymphocytes in both normal and cancer bearing patients however, the concentration of Tetrahydrocortisol has increased in patients with cancer.

InChI:InChI=1/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1

Upstream product

• 1482-50-4 5β-pregnane-11β,17α,21-triol-3,20-dione 
• 4004-80-2 21-acetoxy-3α,11β,17α-trihydroxy-5β-pregnan-20-one 
• 50-23-7 HYDROCORTISONE 
• 26312-90-3 11β,17,21-trihydroxy-20-oxo-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid 

Downstream Products

• 739-26-4 11β-hydroxyetiocholanolone 

Relevant articles and documents

METHODS FOR THE PURIFICATION OF DEOXYCHOLIC ACID

Synthetic methods for preparing deoxycholic acid and intermediates thereof, high purity synthetic deoxycholic acid, compositions and methods of use are provided. Also, provided are processes for the synthesis of 12-keto or 12-α-hydroxy-steroids from Δ-9,11-ene, 11-keto or 11-hydroxy-β-steroids. This invention is also directed to novel compounds prepared during the synthesis. This invention is also directed to the synthesis of deoxycholic acid starting from hydrocortisone.

C-3 GLUCOSIDURONATES OF METABOLITES OF ADRENAL STEROIDS

On treatment with methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-α-D-glucuronate and silver carbonate, tetrahydrocortisone 21-acetate gave the corresponding 3-glucosiduronate triacetyl methyl ester.This product was converted into the 20-semicarbazone which, by treatment with alkali to hydrolyze the ester functions and acid to hydrolyze the semicarbazone moiety, gave tetrahydrocortisone 3-glucosiduronic acid.The acid was converted into the crystalline barium salt and into the methyl ester.An analogous series of reactions was carried out on tetrahydrocortexolone 21-acetate.Treatment of the 20-semicarbazone of tetrahydrocortisone 3-glucosiduronic acid with potassium borohydride reduced the 11-oxo function to an 11β hydroxyl group; acid-catalyzed removal of the semicarbazone group produced tetrahydrocortisol 3-glucosiduronic acid which also was obtained as the barium salt and the methyl ester.