7801-32-3

Basic information

• Product Name: 1,2,4,5-tetrahydrotestolactone
• Synonyms: 1,2,4,5-tetrahydrotestolactone
• CAS NO: 7801-32-3
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.42382
• Mol File: 7801-32-3.mol

Chemical Properties

• Boiling Point: 456.2°C at 760 mmHg
• Flash Point: 200.5°C
• Appearance: /
• Density: 1.103g/cm³
• Vapor Pressure: 1.65E-08mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1,2,4,5-tetrahydrotestolactone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4,5-tetrahydrotestolactone(7801-32-3)
• EPA Substance Registry System: 1,2,4,5-tetrahydrotestolactone(7801-32-3)

Safety Data

• Hazardous Substances Data: 7801-32-3(Hazardous Substances Data)

Usage

Uses

1,2,4,5-Tetrahydrotestolactone is a steroid with estrogenic properties. A steroid lactone.

InChI:InChI=1/C19H28O3/c1-18-9-7-13(20)11-12(18)3-4-14-15(18)8-10-19(2)16(14)5-6-17(21)22-19/h12,14-16H,3-11H2,1-2H3/t12-,14+,15-,16-,18-,19-/m0/s1

Upstream product

• 481-29-8 Epiandrosterone 
• 53-41-8 cis-androsterone 

Relevant articles and documents

Microbial Modifications of Androstane and Androstene Steroids by Penicillium vinaceum

The biotransformation of steroid compounds is a promising, environmentally friendly route to new pharmaceuticals and hormones. One of the reaction types common in the metabolic fate of steroids is Baeyer-Villiger oxidation, which in the case of cyclic ketones, such as steroids, leads to lactones. Fungal enzymes catalyzing this reaction, Baeyer-Villiger monooxygenases (BVMOs), have been shown to possess broad substrate scope, selectivity, and catalytic performance competitive to chemical oxidation, being far more environmentally green. This study covers the biotransformation of a series of androstane steroids (epiandrosterone and androsterone) and androstene steroids (progesterone, pregnenolone, dehydroepiandrosterone, androstenedione, 19-OH-androstenedione, testosterone, and 19-nortestosterone) by the cultures of filamentous fungus Penicillium vinaceum AM110. The transformation was monitored by GC and the resulting products were identified on the basis of chromatographic and spectral data. The investigated fungus carries out effective Baeyer-Villiger oxidation of the substrates. Interestingly, introduction of the 19-OH group into androstenedione skeleton has significant inhibitory effect on the BVMO activity, as the 10-day transformation leaves half of the 19-OH-androstenedione unreacted. The metabolic fate of epiandrosterone and androsterone, the only 5α-saturated substrates among the investigated compounds, is more complicated. The transformation of these two substrates combined with time course monitoring revealed that each substrate is converted into three products, corresponding to oxidation at C-3 and C-17, with different time profiles and yields.

Investigation on the regioselectivities of intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in Situ

We found that dioxiranes generated in situ from ketones 1-6 and Oxone underwent intramolecular oxidation of unactivated C-H bonds at δ sites of ketones to yield tetrahydropyrans. From the trans/cis ratio of oxidation products 1a and 2a as well as the retention of the configuration at the δ site of ketone 5, we proposed that the oxidation reaction proceeds through a concerted pathway under a spiro transition state. The intramolecular oxidation of ketone 6 showed the preference for a tertiary δ C-H bond over a secondary one. This intramolecular oxidation method can be extended to the oxidation of the tertiary γ′ C-H bond of ketones 9 and 10. For ketone 11 with two δ C-H bonds and one γ′ C-H bond linked respectively by a sp3 hydrocarbon tether and a sp2 ester tether, the oxidation took place exclusively at the δ C-H bonds. Finally, by introducing proper tethers, regioselective hydroxylation of steroid ketones 12-14 have been achieved at the C-17, C-16, C-3, and C-5 positions.