1816-85-9

Basic information

• Product Name: 11BETA-HYDROXYTESTOSTERONE
• Synonyms: 11-hydroxytestosterone;4-ANDROSTEN-11-BETA, 17-BETA-DIOL-3-ONE;4-ANDROSTENE-11BETA,17BETA-DIOL-3-ONE;11BETA-HYDROXYTESTOSTERONE;11B-hydroxytestosterone--dea*schedule iii;11β,17β-dihydroxyandrost-4-en-3-one;4-Androstene-11B,17B-diol-3-one;11β,17β-Dihydroxyandrost-4-en-3-one, 4-Androstene-11β,17β-diol-3-one
• CAS NO: 1816-85-9
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.42
• Mol File: 1816-85-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 476.2°Cat760mmHg
• Flash Point: 255.9°C
• Appearance: light yellow/crystalline
• Density: 1.19g/cm³
• Vapor Pressure: 4.56E-11mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 11BETA-HYDROXYTESTOSTERONE(CAS DataBase Reference)
• NIST Chemistry Reference: 11BETA-HYDROXYTESTOSTERONE(1816-85-9)
• EPA Substance Registry System: 11BETA-HYDROXYTESTOSTERONE(1816-85-9)

Safety Data

• Hazard Codes: Xn,T
• Statements: 61-40
• Safety Statements: 53-22-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 1816-85-9(Hazardous Substances Data)

Usage

General Description

11β-Hydroxytestosterone, also known as 11β-OHT, is a steroid hormone and an intermediate in the biosynthesis of the androgen, testosterone. It is produced in the adrenal glands and is then converted into testosterone via the enzyme 11β-hydroxysteroid dehydrogenase. 11β-OHT has been found to have anti-inflammatory properties and has been studied for its potential therapeutic effects in conditions such as chronic obstructive pulmonary disease (COPD) and inflammatory bowel disease (IBD). Additionally, it has been shown to have anabolic effects, promoting muscle growth and bone density. However, further research is needed to fully understand the potential benefits and risks of 11β-hydroxytestosterone.

InChI:InChI=1/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14-,15-,16-,17+,18-,19-/m0/s1

Upstream product

• 382-44-5 (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 382-45-6 adrenosterone 
• 17519-94-7 3-pyrrolidino-androsta-3,5-diene-11,17-dione 
• 50-23-7 HYDROCORTISONE 
• 599-11-1 11β-hydroxyandrostenedione 

Downstream Products

• 2398-99-4 hydroxy-17β androstadiene-4,9(11) one-3,7 
• 96771-18-5 17β-benzoyloxy-11β-hydroxy-androst-4-en-3-one 
• 7801-30-1 11β,17β-dihydroxy-5α-androstan-3-one 
• 15375-19-6 (5α)-androst-9(11)-ene-3,17-dione 
• 1035-69-4 androst-4,9⁽¹¹⁾-dien-3,17-dione 
• 36025-78-2 17β-benzoyloxy-androsta-4,9(11)-dien-3-one 
• 3924-22-9 (3S,10R,11S,13S,14S,17R)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,11,17-triol 

Relevant articles and documents

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Biotransformation of hydrocortisone by a natural isolate of Nostoc muscorum

Hydrocortisone was converted in the culture of an isolated strain of the cyanobacterium Nostoc muscorum PTCC 1636 into some androstane and pregnane derivatives. The microorganism was isolated during a screening program from soil samples collected from paddy fields of north of Iran. The bioproducts obtained were purified using chromatographic methods and identified as 11β-hydroxytestosterone, 11β-hydroxyandrost-4-en-3,17-dione and 11β,17α,20β,21-tetrahydroxypregn-4-en-3-one on the basis of their spectroscopic features.

Microbial Baeyer-Villiger oxidation of 5α-steroids using Beauveria bassiana. A stereochemical requirement for the 11α-hydroxylation and the lactonization pathway

Beauveria bassiana KCH 1065, as was recently demonstrated, is unusual amongst fungal biocatalysts in that it converts C19 3-oxo-4-ene and 3β-hydroxy-5-ene as well as 3β-hydroxy-5α-saturated steroids to 11α-hydroxy ring-D lactones. The Baeyer-Villiger monooxygenase (BVMO) of this strain is distinguished from other enzymes catalyzing BVO of steroidal ketones by the fact that it oxidizes solely substrates with 11α-hydroxyl group. The current study using a series of 5α-saturated steroids (androsterone, 3α-androstanediol and androstanedione) has highlighted that a small change of the steroid structure can result in significant differences of the metabolic fate. It was found that the 3α-stereochemistry of hydroxyl group restricted "normal" binding orientation of the substrate within 11α-hydroxylase and, as a result, androsterone and 3α-androstanediol were converted into a mixture of 7β-, 11α- and 7α-hydroxy derivatives. Hydroxylation of androstanedione occurred only at the 11α-position, indicating that the 3-oxo group limits the alternative binding orientation of the substrate within the hydroxylase. Only androstanedione and 3α-androstanediol were metabolized to hydroxylactones. The study uniquely demonstrated preference for oxidation of equatorial (11α-, 7β-) hydroxyketones by BVMO from B. bassiana. The time course experiments suggested that the activity of 17β-HSD is a factor determining the amount of produced ring-D lactones. The obtained 11α-hydroxylactones underwent further transformations (oxy-red reactions) at C-3. During conversion of androstanedione, a minor dehydrogenation pathway was observed with generation of 11α,17β-dihydroxy-5α-androst-1-en-3-one. The introduction of C1C2 double bond has been recorded in B. bassiana for the first time.

Synthesis of 11β-Fluoro-5α-dihydrotestosterone and 11β-Fluoro-19-nor-5α-dihydrotestosterone: Preparation via Halofluorination-Reduction, Receptor Binding, and Tissue Distribution

We have prepared 11β-fluoro-5α-dihydrotestosterone (11β-F-DHT, 1) and 11β-fluoro-19-nor-5α-dihydrotestosterone (11β-F-19-nor-DHT, 2) in order to investigate the properties of these new androgens labeled with fluorine-18 as potential androgen receptor (AR)-based imaging agents for prostate cancer.These compounds were synthesized in 6 steps from hydrocortisone and in 13 steps from 1,4-androstadiene-3,11,17-trione, respectively.Relative binding affinities (RBA) of 11β-F-DHT and 11β-F-19-nor-DHT to AR are 53.1 and 75.3 (R1881 = 100), respectively, the latter being the highest reported among fluorine-substituted androgens.The fluorination step, which involves addition of halogen fluoride across the 9(11)-double bond, followed by reductive dehalogenation at the 9α-position has been adapted to introduce a fluorine-18-label at the 11β-position of DHT and 19-nor-DHT.The two high-affinity F-18-labeled ligands -1 and -2 were evaluated in vivo, in tissue distribution studies using diethylstilbestrol-pretreated mature male rats. 11β-F-DHT shows high prostate uptake and selective prostate to blood and prostate to muscle uptake ratios, the latter two ratios increasing from 5 and 8 at 1 h to 12 and 19 at 4 h postinjection.Moreover, this compound has low uptake in bone, displaying the lowest in vivo defluorination among all androgens labeled with fluorine-18 tested so far.The in vivo properties of 11β-F-DHT in rats are thus favorable for imaging of prostate cancer.On the other hand, 11β-F-19-nor-DHT shows low prostate uptake with low selectivity and high uptake in liver, kidney, and bladder.Even though this ligand has the highest RBA and undergoes little metabolic defluorination, it appears to suffer from rapid metabolism in vivo.Therefore, it is apparent that the biodistribution properties of androgens are affected by their structure and metabolism as well as by their RBA.