11-ALPHA-HYDROCORTISONE

Base Information

• Chemical Name: 11-ALPHA-HYDROCORTISONE
• CAS No.: 566-35-8
• Molecular Formula: C21H30 O5
• Molecular Weight: 362.466
• Mol file: 566-35-8.mol

Synonyms:Pregn-4-ene-3,20-dione,11a,17,21-trihydroxy- (8CI);11-Epicortisol; 11-Epihydrocortisone; 11-Isocortisol; 11a,17,21-Trihydroxypregn-4-ene-3,20-dione;11a,17,21-Trihydroxypregnen-4-en-3,20-dione;11a,17a,21-Trihydroxy-4-pregnene-3,20-dione; 11a,17a,21-Trihydroxyprogesterone; 11a-Cortisol; 11a-Epicortisol; 11a-Hydroxycortisol; Epi-F;Epicortisol; Epihydrocortisone; NSC 23903; NSC 27390; Pregn-4-ene-11a,17a,21-triol-3,20-dione; U 1676; epi-F

Chemical Property of 11-ALPHA-HYDROCORTISONE

Chemical Property:

• Melting Point: 217-219 °C
• Boiling Point: 566.4°Cat760mmHg
• PKA: 12.47±0.70(Predicted)
• Flash Point: 310.4°C
• PSA: 94.83000
• Density: 1.28g/cm³
• LogP: 1.78160
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

11-Epihydrocortisone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 11-Epihydrocortisone is an isomer of Hydrocortisone (H714615), a glucocorticord which functions primarily to increase blood sugar through gluconeogenesis, suppression of immune system and aid in fat, protein and carbohydrate metabolism. 11-Epihydrocortisone (Hydrocortisone EP Impurity M) is an isomer of Hydrocortisone (H714615), a glucocorticord which functions primarily to increase blood sugar through gluconeogenesis, suppression of immune system and aid in fat, protein and carbohydrate metabolism.

Technology Process of 11-ALPHA-HYDROCORTISONE

There total 16 articles about 11-ALPHA-HYDROCORTISONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.3%

9-Bromo-11,17-dihydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one → Hydrocortison (50-23-7,566-35-8,4068-92-2,4480-78-8,15437-76-0,15437-77-1,15888-35-4,60103-17-5,116907-82-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); sodium carbonate; HSiPh₃; In isopropyl alcohol; at 80 ℃; Green chemistry;

Reference yield:

Cortexolone (152-58-9) → HYDROCORTISONE (50-23-7) + Cortisone (53-06-5) + Epicortisol (566-35-8) + 14,17,21-trihydroxy-pregn-4-ene-3,20-dione (595-18-6) + (8S,9S,10R,11S,13S,14S,17R)-17-((R)-1,2-dihydroxyethyl)-11,17-dihydroxy-10,13-dimethyl-6,7,8, 9,10,11,12,13,14,15,16, 17-dodecahydro-1H-cyclopenta[a] phenanthrene-3 (2H)-one (2899-95-8)

Guidance literature:

In ethanol; Product distribution; culture of Cunningamella urvilaria lunata; also other cultures: C_. blakesleeana, Th_. hyalospora or Th_. hiegemella orchidis were used; different times and temperatures of their preparation before reaction;

DOI:10.1007/BF00765389

Reference yield:

→ Cortisol (50-23-7,566-35-8,4068-92-2,4480-78-8,15437-76-0,15437-77-1,15888-35-4,60103-17-5,116907-82-5)

Guidance literature:

s.a. Bsp. 2c, 3b, 4, 5b, 6b, 7b, 10b;

upstream raw materials:

C₂₁H₃₀O₄

HYDROCORTISONE

Cortexolone

Downstream raw materials:

21-acetoxy-17-hydroxy-11α-(toluene-4-sulfonyloxy)-pregn-4-ene-3,20-dione

3,20-bis(ethylenedioxy)-11α,17α,21-trihydroxypregn-5-ene

HYDROCORTISONE

Cortisone

Refernces

• 1、 Ryzhkova, V. M.,Bykova, T. M.,Klubnichkina, G. A.,Zvereva, M. L.,Gusarova, T. I.,et al.. "INVESTIGATION OF THE DEPENDENCE OF THE DIRECTION OF MICROBIOLOGICAL HYDROXYLATION ON THE STRUCTURE OF SUBSTITUTED PREGNANES". . p. 511 - 517. Retrieved 2007/10/02.
• 2、 Sallam,el-Refai,el-Kady. "Transformation of progesterone by Aspergillus niger 100 and Rhizopus nigricans REF, 129.". . p. 1239 - 1242. Retrieved 2007/10/06.