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Androstenedione

$64

  • Brand : BIOFRON

  • Catalogue Number : BN-O1269

  • Specification : 98%(HPLC)

  • CAS number : 63-05-8

  • Formula : C19H26O2

  • Molecular Weight : 286.4

  • PUBCHEM ID : 6128

  • Volume : 20mg

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Catalogue Number

BN-O1269

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

286.4

Appearance

Botanical Source

Structure Type

Category

SMILES

CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4=O)C

Synonyms

Delta-4-Androstene-3,17-Dione/Androst-4-ene-3,17-dione/D4-Androstenedione/Androstendione/Androstenedione (JAN)/17-Ketotestosterone/4-Androsten-3,17-dione/δ4-androstenedione/Androstenedione/ANDERSTERODIONE

IUPAC Name

(8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione

Density

1.1±0.1 g/cm3

Solubility

Flash Point

161.1±25.7 °C

Boiling Point

431.4±45.0 °C at 760 mmHg

Melting Point

170-173ºC

InChl

InChl Key

AEMFNILZOJDQLW-QAGGRKNESA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:63-05-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

28710630

Abstract

Phytosterols, generated as a by-product of vegetable oils or wood pulp, contain the cyclopentane-perhydro-phenanthrene nucleus, and can be converted into steroid intermediates by removing the C17 side chain. This chapter shows the scale-up, from flask to fermentor, of the phytosterols bioconversion into 4-androstene-3,17-dione (androstenedione; AD) with Mycobacterium neoaurum B-3805. Due to the fact that phytosterols and AD are nearly insoluble in water, two-phase systems and the use of chemically modified cyclodextrins have been described as methods to solve it. Here we use a water-oil two-phase system that allows for the bioconversion of up to 20 g/L of phytosterols into AD in 20 L fermentor.

KEYWORDS

4-Androstene-3,17-dione; AD; Androstenedione; Bioconversion; Fermentation; Mycobacterium neoaurum; Phytosterols

Title

Scale-Up of Phytosterols Bioconversion into Androstenedione.

Author

Martinez-Camara S1, Bahillo E1, Barredo JL1, Rodriguez-Saiz M2.

Publish date

2017

PMID

28710629

Abstract

The chapter describes the bioconversion of phytosterols to androstenedione (AD) with Mycobacterium spp. in shake flasks and fermenters, as well as LC-MS based methods for analysis of phytosterols and steroid products.Phytosterols are derived as a by-product of vegetable oil refining and of manufacture of wood pulp. Phytosterols contain the same four-ring nucleus as steroids, and may be converted to high-value steroids by removing the side chain at C17 and minor changes at other sites in the ring structure.Many bacteria, including Mycobacterium spp., are able to degrade phytosterols. Mutants of Mycobacterium spp. unable of ring cleavage can, when growing on phytosterols, accumulate the steroid intermediates androstenedione (AD) and/or androstadienedione (ADD).The practical challenge with microbial conversion of phytosterols to steroids is that both the substrate and the product are virtually insoluble in water. In addition, some steroids, notably ADD, may be toxic to cells.Two main strategies have been employed to overcome this challenge: the use of two-phase systems, and the addition of chemically modified cyclodextrins. The latter method is used here.Defined cultivation and bioconversion media for both shake flask and fermenter are given, as well as suggestions to minimize the practical problems caused by the water-insoluble phytosterol. Sampling, sample extraction, and quantification of substrates and products using LC-MS analysis are described.

KEYWORDS

Analysis; Fermentation; LC-MS; Mycobacterium; Phytosterols; Steroids; Transformation

Title

Bioconversion of Phytosterols into Androstenedione by Mycobacterium.

Author

Josefsen KD1, Nordborg A2, Sletta H2.

Publish date

2017

PMID

29425789

Abstract

Androstenedione is an androgen and intermediate in the biosynthesis of most adrenocortical, anabolic, sex and synthetic steroids, such as canrenone, eplerenone, norethindrone and spironolactone. Bisnorcholenaldehyde is an important intermediate in the synthesis of progesterone. This study established an androstenedione and bisnorcholenaldehyde separation method that used a macroporous adsorption resin and an ethanol-water mixture as eluent. The adsorption properties of 12 non-polar or weakly polar macroporous adsorption resins were compared, and three resins exhibited a high adsorption capacity and high desorption rate for both androstenedione and bisnorcholenaldehyde. The three resins were then compared using column chromatography, and one resin was selected and parameters (flow rate, resin size, ethanol concentration and volume) of chromatography were optimized to obtain high purity and recovery. Chromatography eluate was concentrated, dissolved in suitable solvent and crystallized at an optimal temperature to obtain a high purity of both androstenedione and bisnorcholenaldehyde from the same starting material. The levels of androstenedione and bisnorcholenaldehyde in the raw material were 39.78% and 19.15%, respectively. After preparative separation and enrichment by resin column chromatography and crystallization, the purity of androstenedione and bisnorcholenaldehyde was 94.3% and 98.6%, respectively, with their recovery yields of 66.8% and 57.9%, respectively. In addition, the resin maintained over 90% separation efficiency for 5 cycles of adsorption. These results indicated that the combination of macroporous resin chromatography followed by crystallization provide a simple, effective, environmentally friendly and low-cost method for the simultaneous purification of androstenedione and bisnorcholenaldehyde.

Copyright © 2017 Elsevier B.V. All rights reserved.

KEYWORDS

Androstenedione; Bisnorcholenaldehyde; Chromatography; Crystallization; Macroporous resin

Title

Refining androstenedione and bisnorcholenaldehyde from mother liquor of phytosterol fermentation using macroporous resin column chromatography followed by crystallization.

Author

Xu SD1, Ning FH1, Jiang BH1, Xu HX2, Liu ZZ1.

Publish date

2018 Mar 15


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