16031-66-6

Basic information

• Product Name: 14-Hydroxyprogesterone
• Synonyms: 14-Hydroxyprogesterone;14-Hydroxypregn-4-ene-3,20-dione;14α-Hydroxypregna-4-ene-3,20-dione
• CAS NO: 16031-66-6
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.46
• Mol File: 16031-66-6.mol

Chemical Properties

• Boiling Point: 481.3°Cat760mmHg
• Flash Point: 259°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 2.78E-11mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: 14-Hydroxyprogesterone(CAS DataBase Reference)
• NIST Chemistry Reference: 14-Hydroxyprogesterone(16031-66-6)
• EPA Substance Registry System: 14-Hydroxyprogesterone(16031-66-6)

Safety Data

• Hazardous Substances Data: 16031-66-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H30O3/c1-13(22)16-8-11-21(24)18-5-4-14-12-15(23)6-9-19(14,2)17(18)7-10-20(16,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18-,19+,20-,21-/m1/s1

Upstream product

• 57-83-0 progesterone 
• 57-83-0 Progesterone 

Downstream Products

• 564-63-6 14-hydroxy-4-androstene-3,17-dione 
• 24377-08-0 Pregna-4,14-diene-3,20-dione 

Relevant articles and documents

Aspects of the progesterone response in Hortaea werneckii: Steroid detoxification, protein induction and remodelling of the cell wall

Progesterone in sublethal concentrations temporarily inhibits growth of Hortaea werneckii. This study investigates some of the compensatory mechanisms which are activated in the presence of progesterone and are most probably contributing to escape from growth inhibition. These mechanisms lead on the one hand to progesterone biotransformation/detoxification but, on the other, are suggested to increase the resistance of H. werneckii to the steroid. Biotransformation can detoxify progesterone efficiently in the early logarithmic phase, with mostly inducible steroid transforming enzymes, while progesterone biotransformation/detoxification in the late logarithmic and stationary phases of growth is not very efficient. The relative contribution of constitutive steroid transforming enzymes to progesterone biotransformation is increased in these latter phases of growth. In the presence of progesterone, activation of the cell wall integrity pathway is suggested by the overexpression of Pck2 which was detected in the stationary as well as the logarithmic phase of growth of the yeast. Progesterone treated H. werneckii cells were found to be more resistant to cell lysis than mock treated cells, indicating for the first time changes in the yeast cell wall as a result of treatment with progesterone.

Biotransformations of progesterone by Chlorella spp.

Thirty-eight strains of Chlorella spp. were used as bioreactors on progesterone. Fourteen strains were ineffective whilst the others biotransformed the substrate. The observed bioreactions for progesterone were the hydroxylation, the reduction and the side-chain degradation. The kinds of biotransformation seem to fit the actual classification of the strains.

Biotransformation of progesterone by the green alga Chlorella emersonii C211-8H

2β-Hydroxyprogesterone, 6β-hydroxyprogesterone, 9α-hydroxyprogesterone, 14α-hydroxyprogesterone, 16α-hydroxyprogesterone and 21-hydroxyprogesterone are the main bioproducts in the progesterone bioconversion by axenic cultures of Chlorella emersonii C211-8

Microbial transformation of steroids: Contribution to 14α-hydroxylations

The regioselective and stereoselective hydroxylation of steroids by fungal strains previously known for their hydroxylation capabilities, such as Thamnostylum (= Helicostylum) piriforme ATCC 8992, Mucor griseocyanus ATCC 1207a, Actinomucor elegans (= Mucor parasiticus) MMP 3122 (Mucorales), and Zygodesmus sp. ATCC 14716, was investigated with special interest for the 14α-hydroxylation reaction. A preliminary screening had shown that some of these microorganisms were adequate for the production of 14α-hydroxylated derivatives of the following steroids: progesterone, 5β-pregnane-3,20- dione, 3β-hydroxy-5β-pregnane-20-one, 3β-hydroxy-5β-17(αH)-etianic acid methyl ester, androst-4-ene-3,17-dione, and testosterone. About 20 metabolites have been isolated and purified by silicagel chromatography and semi-preparative reverse-phase HPLC. These metabolites have been fully characterized by 1H, 13C NMR and mass spectrometry. All the identified metabolites were hydroxylated at some distinct positions, such as 6β-, 7α- , 9α-, 14α-, 15β-, or dihydroxylated at 6β, 14α-, 7α, 14α-, 9α, 14α- , 14α, 15α-, 14α, 15β-positions; nine of these metabolites have not been reported previously. The relationship between the structural features of the investigated steroids and the site-specific hydroxylation has been delineated, and progesterone was found to be the best substrate for the production of 14α-hydroxylated derivative, using T. piriforme.

METABOLISM OF PROGESTERONE AND TESTOSTERONE BY A BACILLUS SP.

Microbial transformations by a Bacillus sp. were employed as a means of preparing potentially important derivatives of progesterone and testosterone.Each microbial metabolite was subjected to structure elucidation employing 1H and 13C nmr, mass spectral and cd analysis.HPLC was used for the determination of the percentages of the metabolites formed.The progesterone metabolites were characterised as 14-hydroxy-4-pregnene-3,20-dione (II), 14-hydroxy-5α-pregnane-3,6,20-trione (III), 11α-hydroxy-5α-pregnane-3,6,20-trione (IV) and 11α,14-dihydroxy-4-pregnene-3,20-dione (V).The testosterone analogs were identified as 4-androstene-3,17-dione (VII), 17β-hydroxy-5α-androstane-3,6-dione (VIII), 14-hydroxy-4-androstene-3,17-dione (IX) and 14,17β-dihydroxy-4-androsten-3-one (X).The availability of the metabolites enabled complete elucidation of their 13C nmr spectra.