53-02-1

Usage

Uses

Used in Medical Diagnostics:
Tetrahydrocortisol is used as a biomarker for early breast cancer in premenopausal patients. The increased concentration of Tetrahydrocortisol in these patients serves as an indicator of the presence of cancer, aiding in early detection and timely treatment.
Used in Immunology Research:
Tetrahydrocortisol is used as a research tool to study the role of lymphocytes in cancer development. The fact that it is produced by lymphocytes in both normal and cancer-bearing patients suggests that it may play a role in the immune response to cancer, providing valuable insights for immunological research and potential therapeutic applications.
Used in Cancer Treatment Monitoring:
Tetrahydrocortisol can be used as a monitoring agent to track the progress of cancer treatment in patients. Changes in the concentration of Tetrahydrocortisol may reflect the effectiveness of the treatment and help healthcare professionals make informed decisions regarding the patient's care plan.

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

• 50-23-7 HYDROCORTISONE 
• 4004-80-2 21-acetoxy-3α,11β,17α-trihydroxy-5β-pregnan-20-one 
• 1482-50-4 5β-pregnane-11β,17α,21-triol-3,20-dione 
• 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 academic research and scientific papers

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.

Potential corticoid metabolites: Chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5 α- and 5 β-series

Here, we describe the chemical synthesis of the complete sets of 18 novel 3- and 21-monosulfates and their double-conjugated form of tetrahydrocortisol (THF), tetrahydro-11-deoxycortisol (THS), and tetrahydrocortisone (THE) in the 5 α- and 5 β-series. The principal reactions involved are: (1) selective protection of a specific hydroxy group in substrates; (2) catalytic hydrogenation at C-5 of Δ4-3-ketosteroids with 10% Pd(OH) 2/C to yield 3-oxo-5 β-steroids and reductive allomerization with 10% Pd/C to yield 3-oxo-5 α-isomers; (3) reduction of the resulting 3-oxo-5 β- and 3-oxo-5 α-steroids to the corresponding 3 α-hydroxy-compounds with Zn(BH4)2 and K-Selectride, respectively; and (4) sulfation of hydroxy groups at C-3 and/or C-21 in the tetrahydrocorticosteroid derivatives with sulfur trioxide-triethylamine complex.

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.