TETRAHYDROCORTISONE 3-(B-D-*GLUCURONIDE)

Base Information

• Chemical Name: TETRAHYDROCORTISONE 3-(B-D-*GLUCURONIDE)
• CAS No.: 26312-91-4
• Molecular Formula: C₂₇H₄₀O₁₁
• Molecular Weight: 540.608
• Mol file: 26312-91-4.mol

Synonyms:17,21-dihydroxy-11,20-dioxo-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid

Chemical Property of TETRAHYDROCORTISONE 3-(B-D-*GLUCURONIDE)

Chemical Property:

• Boiling Point: 768.8±60.0 °C(Predicted)
• PKA: 2.82±0.70(Predicted)
• Density: 1.45±0.1 g/cm3(Predicted)

Purity/Quality:

95%-98% ^*data from raw suppliers

Tetrahydrocortisone3-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Tetrahydrocortisone 3-Glucuronide is a derivative of Tetrahydro Cortisone (T293375) which is a normal mammalian metabolite of Cortisone (C696500).

Technology Process of TETRAHYDROCORTISONE 3-(B-D-*GLUCURONIDE)

There total 10 articles about TETRAHYDROCORTISONE 3-(B-D-*GLUCURONIDE) 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:

methyl (21-acetoxy-17-hydroxy-11-oxo-20-semicarbazono-5β-pregnan-3α-yl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate → 17,21-dihydroxy-11,20-dioxo-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid (26312-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 0.04 N NaOH / methanol; CHCl₃ / 0.75 h

2: 1) 1 N NaOH, 2) aq. H₂SO₄ / 1) CHCl₃, MeOH, r.t., 30 min, 2) r.t., 1 h

With sodium hydroxide; sulfuric acid; In methanol; chloroform;

DOI:10.1016/0039-128X(82)90110-6

Reference yield:

hydrocortisone acetate (50-03-3) → 17,21-dihydroxy-11,20-dioxo-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid (26312-91-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 7.4 g / H₂ / palladium on calcium carbonate / pyridine / 12 h

2: 1.7 g / H₂ / Raney nickel (W-2) / dioxane / 10 h

3: 390 mg / imidazole / pyridine; dimethylformamide / 1 h / Ambient temperature

4: 400 mg / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

5: 380 mg / 30 percent H₂SO₄ / acetone / 0.5 h / Ambient temperature

6: 400 mg / Ag₂CO₃ / toluene / 12 h / Ambient temperature

7: 110 mg / 2 percent KOH / Ambient temperature; 1.) KOH/MeOH; 2h 2.) 80percent pyruvic acid, AcOH, CHCl₃; 12h

With 1H-imidazole; potassium hydroxide; sulfuric acid; hydrogen; silver carbonate; pyridinium chlorochromate; palladium on activated charcoal; Raney nickel (W-2); In 1,4-dioxane; pyridine; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1248/cpb.30.2110

Reference yield:

RU 18760 (64313-94-6) → 17,21-dihydroxy-11,20-dioxo-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid (26312-91-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.7 g / H₂ / Raney nickel (W-2) / dioxane / 10 h

2: 390 mg / imidazole / pyridine; dimethylformamide / 1 h / Ambient temperature

3: 400 mg / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

4: 380 mg / 30 percent H₂SO₄ / acetone / 0.5 h / Ambient temperature

5: 400 mg / Ag₂CO₃ / toluene / 12 h / Ambient temperature

6: 110 mg / 2 percent KOH / Ambient temperature; 1.) KOH/MeOH; 2h 2.) 80percent pyruvic acid, AcOH, CHCl₃; 12h

With 1H-imidazole; potassium hydroxide; sulfuric acid; hydrogen; silver carbonate; pyridinium chlorochromate; Raney nickel (W-2); In 1,4-dioxane; pyridine; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1248/cpb.30.2110

upstream raw materials:

methyl (21-acetoxy-17α-hydroxy-11,20-dioxo-5β-pregnan-3α-yl-2',3',4'-tri-O-acetyl-β-D-glucopyranosid)-uronate

hydrocortisone acetate

21-acetoxy-3α,11β,17α-trihydroxy-5β-pregnan-20-one

RU 18760

Downstream raw materials:

tetrahydrocortisone

Refernces

• 1、 Mattox, Vernon R.,Goodrich, June E.,Nelson, Albert N.. "C-3 GLUCOSIDURONATES OF METABOLITES OF ADRENAL STEROIDS". . p. 23 - 34. Retrieved 2007/10/02.