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516-41-6

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516-41-6 Usage

Chemical Properties

White Powder

Uses

Metabolite of Cortisol.

Check Digit Verification of cas no

The CAS Registry Mumber 516-41-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 6 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 516-41:
(5*5)+(4*1)+(3*6)+(2*4)+(1*1)=56
56 % 10 = 6
So 516-41-6 is a valid CAS Registry Number.
InChI:InChI=1/C21H32O5/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/h12,14-16,18,22,24,26H,3-11H2,1-2H3/t12-,14-,15-,16-,18+,19-,20-,21-/m0/s1

516-41-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name (5α,11β)-11,17,21-Trihydroxypregnane-3,20-dione

1.2 Other means of identification

Product number -
Other names 5Alpha-Dihydrocortisol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:516-41-6 SDS

516-41-6Synthetic route

RU 18748
4004-68-6

RU 18748

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 1h;89%
With sodium hydroxide In methanol
With potassium hydroxide In tetrahydrofuran at 27℃; for 1.5h;
HYDROCORTISONE
50-23-7

HYDROCORTISONE

A

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

B

5β-pregnane-11β,17α,21-triol-3,20-dione
1482-50-4

5β-pregnane-11β,17α,21-triol-3,20-dione

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 5%-palladium/activated carbon In ethanol at 80℃; for 6h;A n/a
B 86%
With 3-Methylpyridine; 5%-palladium/activated carbon; hydrogen at 25℃; for 24h; Reagent/catalyst; Overall yield = 97 %; stereoselective reaction;A n/a
B n/a
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

21-tert-butyldimethylsilyloxy-11β,17α-dihydroxy-5α-pregnane-3,20-dione
1242075-38-2

21-tert-butyldimethylsilyloxy-11β,17α-dihydroxy-5α-pregnane-3,20-dione

Conditions
ConditionsYield
With pyridine; 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 5h;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

5α-dihydrocortisol 21-tetrahydropyranyl ether
131061-49-9

5α-dihydrocortisol 21-tetrahydropyranyl ether

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane for 2h; Ambient temperature;76%
formaldehyd
50-00-0

formaldehyd

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

A

17,20,20,21-bismethylenedioxy-11β-hydroxy-5α-pregnan-3-one
1056-08-2

17,20,20,21-bismethylenedioxy-11β-hydroxy-5α-pregnan-3-one

B

11-methoxymethoxy-17,20;20,21-bis-methylenedioxy-pregnan-3-one
117899-44-2

11-methoxymethoxy-17,20;20,21-bis-methylenedioxy-pregnan-3-one

Conditions
ConditionsYield
With hydrogenchloride; chloroform (20Ξ)-11β-methoxymethoxy-17,20;20,21-bis-methylenedioxy-5α-pregnan-3-one;
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

RU 18748
4004-68-6

RU 18748

Conditions
ConditionsYield
Acetylierung;
formaldehyd
50-00-0

formaldehyd

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

A

17,20,20,21-bismethylenedioxy-11β-hydroxy-5α-pregnan-3-one
1056-08-2

17,20,20,21-bismethylenedioxy-11β-hydroxy-5α-pregnan-3-one

B

(20Ξ)-11β-methoxymethoxy-17,20;20,21-bis-methylenedioxy-5α-pregnan-3-one

(20Ξ)-11β-methoxymethoxy-17,20;20,21-bis-methylenedioxy-5α-pregnan-3-one

Conditions
ConditionsYield
With hydrogenchloride; chloroform
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

3α-acetoxy-11β,17α,21-trihydroxy-5α-pregnan-20-one
20649-24-5

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 76 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature
2: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C
3: 85 percent / pyridine / Ambient temperature
4: 70 percent / 60percent AcOH / 48 h / 37 °C
View Scheme
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

2-oxa-2-((3R,5S,8S,9S,10S,11S,13S,14S,17R)-3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate
4004-75-5

2-oxa-2-((3R,5S,8S,9S,10S,11S,13S,14S,17R)-3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 76 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature
2: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C
3: imidazole / dimethylformamide; pyridine / 4 h / Ambient temperature
4: 66 percent / 90percent AcOH / 4 h / Ambient temperature
5: 81 percent / pyridine / Ambient temperature
6: 99 percent / 47percent HF / acetonitrile / 0.33 h / Ambient temperature
View Scheme
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

allotetrahydrocortisol 21-tetrahydropyranyl ether
131061-50-2

allotetrahydrocortisol 21-tetrahydropyranyl ether

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature
2: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C
View Scheme
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

3α-acetoxy-17α,21-dihydroxy-5α-pregnane-11,20-dione
115074-01-6

3α-acetoxy-17α,21-dihydroxy-5α-pregnane-11,20-dione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 76 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature
2: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C
3: 85 percent / pyridine / Ambient temperature
4: pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature
5: 60percent AcOH / 48 h / 37 °C
View Scheme
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
516-41-6

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

allotetrahydrocortisol 3-tert-butyldimethylsilyl ether
131061-54-6

allotetrahydrocortisol 3-tert-butyldimethylsilyl ether

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 76 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature
2: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C
3: imidazole / dimethylformamide; pyridine / 4 h / Ambient temperature
4: 66 percent / 90percent AcOH / 4 h / Ambient temperature
View Scheme

516-41-6Relevant articles and documents

Spectroscopic evaluation of synthesized 5β-dihydrocortisol and 5β-dihydrocortisol acetate binding mechanism with human serum albumin and their role in anticancer activity

Kallubai, Monika,Reddy, Srinivasa P.,Dubey, Shreya,Ramachary, Dhevalapally B.,Subramanyam, Rajagopal

, p. 1 - 18 (2018/02/22)

Our study focus on the biological importance of synthesized 5β-dihydrocortisol (Dhc) and 5β-dihydrocortisol acetate (DhcA) molecules, the cytotoxic study was performed on breast cancer cell line (MCF-7) normal human embryonic kidney cell line (HEK293), th

Direct organocatalytic stereoselective transfer hydrogenation of conjugated olefins of steroids

Ramachary, Dhevalapally B.,Sakthidevi, Rajasekar,Reddy, P. Srinivasa

, p. 13497 - 13506 (2013/09/02)

Kinetically controlled and organocatalytic syn-selective transfer hydrogenation has been successfully demonstrated for the reduction of the enone functional group of various steroids. Herein, diastereoselective synthesis of many 5β-steroids have been reported through organocatalysis, which have broad medicinal and pharmaceutical applications. The mechanistic studies and the selectivity of the products clearly indicated that the catalyst 1b·d-CSA is mild enough to activate the various chiral cyclic enones through iminium ion formation during the organocatalytic transfer hydrogenations with Hantzsch ester 2a as a hydrogen source. Further, clear evidence for the selective formation of intermediate iminium species [I]+ have been characterized through on-line monitoring of controlled experiments by NMR and ESI-HRMS analyses.

Biotransformation of corticosteroids by Penicillium decumbens ATCC 10436

Holland, Herbert L.

, p. 646 - 649 (2007/10/02)

The biotransformation of a series of corticosteroids by the fungus Penicillium decumbens ATCC 10436 has been investigated. Conversion to the corresponding 5α-dihydroxteroid was observed for all the Δ4-3-ketosteroids studied with the exception of deoxycorticosterone, which was converted to a Δ14-diene. Deoxycorticosterone acetate was, however, converted to a 5α- dihydro product concomitant with ester hydrolysis. Other substrates carrying a C-21 acetoxy group were also hydrolyzed to the alcohol. In two cases (resulting from deoxycorticosterone acetate and 11-deoxycortisone) the 5α- 3-keto-product was further reduced to the 3β-alcohol. No reduction of δ14-dienes was observed.

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