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80-91-1

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80-91-1 Usage

Purification Methods

Crystallise pregnane-diol (which is abundant in the urine of pregnant women) from EtOH or Me2CO and dry it in vacuo. It can be oxidised to progesterone (see below) and it is not precipitated by digitonin. Its diacetate [6100-28-3] has m 112-113o and [] D 26 +60o (c 1, CHCl3). It is a progesterone metabolite in urine during pregnancy. [Marian Biochem J 23 1090 1929, Johnson et al. J Chem Soc1302 1954, Mattox et al. J Org Chem 32 708 1967, Beillstein 6 III 4778, 6 IV 6111.]

Check Digit Verification of cas no

The CAS Registry Mumber 80-91-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 80-91:
(4*8)+(3*0)+(2*9)+(1*1)=51
51 % 10 = 1
So 80-91-1 is a valid CAS Registry Number.
InChI:InChI=1/C21H36O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h13-19,22-23H,4-12H2,1-3H3/t13-,14-,15-,16+,17-,18+,19+,20+,21-/m1/s1

80-91-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (3α,5β,20R)-Pregnane-3,20-diol

1.2 Other means of identification

Product number -
Other names 5|A-Pregnane-3|A,20|A-diol

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:80-91-1 SDS

80-91-1Relevant articles and documents

Substrate specificity and inhibitor sensitivity of rabbit 20α-hydroxysteroid dehydrogenase

Endo, Satoshi,Arai, Yuki,Hara, Akira,Kitade, Yukio,Bunai, Yasuo,El-Kabbani, Ossama,Matsunaga, Toshiyuki

, p. 1514 - 1518 (2013/10/08)

In this study, we examined the substrate specificity and inhibitor sensitivity of rabbit 20α-hydroxysteroid dehydrogenase (AKR1C5), which plays a role in the termination of pregnancy by progesterone inactivation. AKR1C5 moderately reduced the 3-keto group of only 5α-dihydrosteroids with 17β- or 20α/β-hydroxy group among 3-ketosteroids. In contrast, the enzyme reversibly and efficiently catalyzed the reduction of various 17- and 20-ketosteroids, including estrogen precursors (dehydroepiandrosterone, estrone and 5α-androstan-3β- ol-17-one) and tocolytic 5β-pregnane-3,20- dione. In addition to the progesterone inactivation, the formation of estrogens and metabolism of the tocolytic steroid by AKR1C5 may be related to its role in rabbit parturition. AKR1C5 also reduced various non-steroidal carbonyl compounds, including isatin, an antagonist of the C-type natriuretic peptide receptor, and 4-oxo-2-nonenal, suggesting its roles in controlling the bioactive isatin and detoxification of cytotoxic aldehydes. AKR1C5 was potently and competitively inhibited by flavonoids such as kaempferol and quercetin, suggesting that its activity is affected by ingested flavonoids.

A New Chiral Director for the Highly Diastereoselective Borane Reduction of Steroid-20-ones

Goendoes, Gyoergy,Dombi, Gyoergy,Orr, James C.

, p. 1055 - 1060 (2007/10/03)

The synthesis of a new chiral boroxazolidine was achieved which was used to control the stereochemistry of the borane reduction of the 20-keto group of steroids. The otherwise hardly accessible 20α-(20S)-alcohol can thus be prepared in a yield of 91 percent.

Mechanism of the D-Homoannulation of Pregnanediol Disulfate in Refluxing 3 N Hydrochloric acid

Yoshizawa, Itsuo,Itoh, Shinji,Nagata, Kyoko,Kawahara, Norio

, p. 3819 - 3828 (2007/10/02)

In order to elucidate the mechanism of D-homoannulation of pregnanediol 20-sulfate, solvolysis of -5β-pregnane-3α,20α-diol disulfate (3) in refluxing 3 N hydrochloric acid was investigated.The resulting D-homosteroids, 17percenta-methyl-D-homo-5β-androstane-3α,17aβ-diol (8) and 17α-methyl-17aβ-chloro-D-homo-5β-androstan-3α-ol (10), contained a quantitative amount of (13)C only at C-17, indicating that the ring-enlargement reaction of the 20α-ol sulfate proceeded with stereospecific migration of the C16-C17 bond.The same result was obtained from isomeric -5β-pregnane-3α,20β-diol disulfate (6).Based on these results,the D-homoannulation of pregnanediol 20-sulfate was concluded to proceed by a stepwise mechanism through the C-20 carbocation.The stereochemistry of this Wagner-Meerwein type rearrangement reaction is also discussed. Keywords --- 5β-pregnane-3α,20α-diol (pregnanediol); pregnanediol disulfate; 5β-pregnane-3α,20β-diol; D-homoannulation; stereochemistry; steroidal sulfate; acid hydrolysis; (13)C-NMR

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