521-18-6Relevant articles and documents
A kinetic analysis of the 5α-reductases from human prostate and liver
Houston,Chisholm,Habib
, p. 355 - 369 (1987)
A kinetic analysis of the 5α-reductases from human liver and prostate is presented. Human prostatic 5α-reductase follows an ordered sequential mechanism in which NADPh binds first followed by testosterone. The order of release of products is DHT followed by NADP+. The apparent K(m) of prostatic 5α-reductase for testosterone is 0.0339 ± 0.006μM, while the apparent K(m) for NADPh is 2.52 ± 0.65μM. Human liver 5α-reductase also follows a sequential mechanism. The apparent K(m) of the liver enzyme is 0.110 ± 0.08μM; the apparent K(m) for NADPH is 6.2 ± 0.6μM. The fact that both the liver and prostatic 5α-reductases have a sequential kinetic mechanism rules out the possibility that the reduction of testosterone to dihydrotestosterone involves an electron transport system as previously proposed.
Jones,Price
, p. 999,1003 (1966)
Significance of the delta 5 and delta 4 steroidogenic pathways in the hamster preovulatory follicle.
Makris,Olsen,Ryan
, p. 641 - 651 (1983)
Isolated hamster granulosa cells and theca from preovulatory follicles were incubated in vitro for 2 and 6 h in the absence/or presence of LH and steroid substrates. The purpose of the experiments was to determine, in theca, the relative activities of the delta 5 and delta 4 pathways under controlled conditions, and to compare the ability of granulosa cells and theca to form progesterone from exogenous pregnenolone. The results of the experiments show that the delta 5 pathway in theca predominates before and up to 2 h after LH stimulation. The delayed effect of LH after 2 h is a switch from delta 5 to delta 4 as the major metabolic pathway. Progesterone formation from exogenous pregnenolone is 7 to 10 times greater in unstimulated granulosa cells than in theca. Acute effects of LH lead to increased conversion of exogenous pregnenolone to progesterone in granulosa cells but not theca. LH does, however, acutely stimulate the thecal conversion of DHEA to androstenedione. The longer term effect of LH in both cell types is to increase pregnenolone conversion to progesterone.
On the photochemical conversion of an alpha, beta-unsaturated gamma, delta-epoxy ketone: 3-oxo-6-alpha, 7-alpha-oxide-17-beta-acetoxy-Delta-androstane
Saboz,Iizuka,Wehrli,Schaffner,Jeger
, p. 1362 - 1371 (1968)
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Synthetic method of androstenone
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Paragraph 0087-0089; 0097-0099; 0102-0104; 0107-0109, (2021/05/12)
The invention relates to the field of medicine preparation, in particular to a synthetic method of androstenone. The preparation method comprises the following steps: S100, catalyzing testosterone by a catalyst, and carrying out hydrogenation addition reaction to obtain a compound I; S200, converting a 17-site hydroxyl group of the compound I into a halogen group or a sulfonate group which is easy to leave, so as to obtain a compound II; and S300, subjecting the compound II and alkali to an elimination reaction under the heating condition, namely, a dehalogenation reaction or a desulphonate reaction, so as to obtain androstenone. The synthesis method of androsteneone has the following beneficial effects: the raw materials are cheap and easy to obtain; the process is simple, the route is short, and the requirement on equipment is low; dangerous reagents and operation are avoided, and large-scale industrial production is easy to realize; and isomer impurities are not generated in the synthesis process, and the yield of the target product androsteneone is high.
The A-ring reduction of 11-ketotestosterone is efficiently catalysed by AKR1D1 and SRD5A2 but not SRD5A1
Barnard, Lise,Nikolaou, Nikolaos,Louw, Carla,Schiffer, Lina,Gibson, Hylton,Gilligan, Lorna C.,Gangitano, Elena,Snoep, Jacky,Arlt, Wiebke,Tomlinson, Jeremy W.,Storbeck, Karl-Heinz
, (2020/07/21)
Testosterone and its 5α-reduced form, 5α-dihydrotestosterone, were previously thought to represent the only active androgens in humans. However, recent studies have shown that the potent androgen, 11-ketotestosterone, derived from the adrenal androgen precursor, 11β-hydroxyandrostenedione, may in fact serve as the primary androgen in healthy women. Yet, despite recent renewed interest in these steroids, their downstream metabolism has remained undetermined. We therefore set out to investigate the metabolism of 11-ketotestosterone by characterising the 5α- or 5β-reduction commitment step. We show that inactivation of 11-ketotestosterone is predominantly driven by AKR1D1, which efficiently catalyses the 5β-reduction of 11-ketotestosterone, committing it to a metabolic pathway that terminates in 11-ketoetiocholanolone. We demonstrate that 5α-reduction of 11-ketotestosterone is catalysed by SRD5A2, but not SRD5A1, and terminates in 11-ketoandrosterone, but is only responsible for a minority of 11-ketotestosterone inactivation. However, as 11-ketoetiocholanolone is also generated by the metabolism of the glucocorticoid cortisone, 11-ketoandrosterone should be considered a more specific urinary marker of 11-ketotestosterone production.
Purified mCPBA, a Useful Reagent for the Oxidation of Aldehydes
Horn, Alexander,Kazmaier, Uli
, p. 2531 - 2536 (2018/03/21)
Purified mCPBA is a useful reagent for the oxidation of several classes of aldehyde. Although linear unbranched aliphatic aldehydes are oxidized to the corresponding carboxylic acids, α-branched ones undergo Baeyer–Villiger oxidation to formates. α-Branched α,β-unsaturated aldehydes provide enolformates and/or epoxides, which can be saponified to α-hydroxy ketones with shortening of the carbon chain by 1 carbon. Unbranched α,β-unsaturated aldehydes undergo an interesting Baeyer–Villiger oxidation/epoxidation/formate migration/BV oxidation cascade, which results in formyl-protected hydrates with an overall loss of two carbon atoms.