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Adrenosterone

CAS# 382-45-6

Adrenosterone

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Chemical structure

Adrenosterone

3D structure

Chemical Properties of Adrenosterone

Cas No. 382-45-6 SDF Download SDF
PubChem ID 223997 Appearance Powder
Formula C19H24O3 M.Wt 300.39
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 33.33 mg/mL (110.96 mM; Need ultrasonic)
Chemical Name (8S,9S,10R,13S,14S)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11,17-trione
SMILES CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4=O)C
Standard InChIKey RZRPTBIGEANTGU-IRIMSJTPSA-N
Standard InChI InChI=1S/C19H24O3/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/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Adrenosterone Dilution Calculator

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Adrenosterone Molarity Calculator

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Preparing Stock Solutions of Adrenosterone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.329 mL 16.645 mL 33.2901 mL 66.5801 mL 83.2251 mL
5 mM 0.6658 mL 3.329 mL 6.658 mL 13.316 mL 16.645 mL
10 mM 0.3329 mL 1.6645 mL 3.329 mL 6.658 mL 8.3225 mL
50 mM 0.0666 mL 0.3329 mL 0.6658 mL 1.3316 mL 1.6645 mL
100 mM 0.0333 mL 0.1665 mL 0.3329 mL 0.6658 mL 0.8323 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Adrenosterone

Adrenosterone is a steroid hormone with weak androgenic effect.

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References on Adrenosterone

Development of criteria for the detection of adrenosterone administration by gas chromatography-mass spectrometry and gas chromatography-combustion-isotope ratio mass spectrometry for doping control.[Pubmed:20355175]

Drug Test Anal. 2009 Nov;1(11-12):587-95.

Adrenosterone (androst-4-ene-3,11,17-trione, 11-oxoandrostenedione) is an endogenous steroid hormone that has been promoted as a dietary supplement capable of reducing body fat and increasing muscle mass. It is proposed that Adrenosterone may function as an inhibitor of the 11beta-hydroxysteroid dehydrogenase type 1 enzyme (11beta-HSD1), which is primarily responsible for reactivation of cortisol from cortisone. The urinary metabolism of Adrenosterone was investigated, after a single oral administration in two male subjects, by gas chromatography-mass spectrometry (GC-MS) and gas chromatography-combustion-isotope ratio mass spectrometry (GC-C-IRMS). Substantially increased excretion of 11beta-hydroxyandrosterone, 11beta-hydroxyetiocholanolone, 11-oxoandrosterone and 11-oxoetiocholanolone was observed. Minor metabolites such as 3alpha,17beta-dihydroxy-5beta-androstan-11-one, 3alpha-hydroxyandrost-4-ene-11,17-dione and 3alpha,11beta-dihydroxyandrost-4-en-17-one were also identified. The exogenous origin of the most abundant Adrenosterone metabolites was confirmed by GC-C-IRMS according to World Anti-Doping Agency criteria. Through analysis of a reference population data set obtained from urine samples provided by elite athlete volunteers (n = 85), GC-MS doping control screening criteria are proposed: 11beta-hydroxyandrosterone concentration greater than 10 000 ng/mL (specific gravity adjusted to 1.020) or 11beta-hydroxyandrosterone/11beta-hydroxyetiocholanolone ratio greater than 20.Urine samples fulfilling these screening criteria may be subjected to GC-C-IRMS analysis for confirmation of Adrenosterone administration.

Carbon isotope ratio analysis of endogenous glucocorticoid urinary metabolites after cortisone acetate and adrenosterone administration for doping control.[Pubmed:22987608]

Drug Test Anal. 2012 Dec;4(12):951-61.

Glucocorticoids are listed on the World Anti-Doping Agency (WADA) Prohibited List of substances. The detection of the administration of hydrocortisone and cortisone is complicated by the fact that the human body also produces these steroids naturally. Gas chromatography-combustion-isotope ratio mass spectrometry can be utilized to determine the use of endogenous glucocorticoids by measuring the carbon isotope ratio (CIR) of their resulting metabolites in human urine samples. A comprehensive sample preparation protocol for the analysis of endogenous glucocorticoid urinary metabolites was developed and validated, incorporating the use of high performance liquid chromatography (HPLC) for purification and chemical oxidation for derivatisation. Target compounds were tetrahydrocortisol and tetrahydrocortisone, and 11beta-hydroxyetiocholanolone, 11-oxoetiocholanolone and 11beta-hydroxyandrosterone, while pregnanediol functioned as the endogenous reference compound. Urine samples from a population of 50 volunteers were analyzed to determine CIR reference limits. Excretion studies of the endogenous glucocorticoid preparation cortisone acetate (25 mg oral) and the dietary supplement Adrenosterone (75 mg oral) were conducted with six male individuals. Variable changes in steroid metabolite isotopic composition were found across subjects after administration. The study also revealed that CIR analysis of the major glucocorticoid metabolites tetrahydrocortisol and tetrahydrocortisone is necessary to unambiguously distinguish administration of cortisone and Adrenosterone, the former officially restricted to out-of-competition use by athletes, the latter not being restricted at the current time. Moreover, this study reaffirms that CIR methods for the doping control of endogenous steroids should not rely upon a single ERC, as the administration of an appropriate precursor to that ERC could cause complications during analysis.

Microbial transformation of (+)-adrenosterone.[Pubmed:12434991]

Nat Prod Lett. 2002 Oct;16(5):345-9.

The microbial transformation of (+)-Adrenosterone (1) by Cephalosporium aphidicola afforded three metabolites identified as androsta-1,4-diene-3,11,17-trione (2), 17beta-hydroxyandrost-4-ene-3,11-dione (3) and 17beta-hydroxyandrosta-1,4-diene-3,11-dione (4). The fermentation of 1 with Fusarium lini also produced metabolites 2 and 4, while the fermentation with Trichothecium roseum afforded metabolite 3. The structures of transformed products were determined by spectroscopic methods.

Biotransformation of adrenosterone by filamentous fungus, Cunninghamella elegans.[Pubmed:17889091]

Steroids. 2007 Dec;72(14):923-9.

Microbial transformation of Adrenosterone (1) by suspended-cell cultures of the filamentous fungus Cunninghamella elegans resulted in the production of five metabolites 2-6, which were identified as 9alpha-hydroxyAdrenosterone (2), 11-ketotestosterone (3), 6beta-hydroxyAdrenosterone (4), 9alpha-hydroxy-11-ketotestosterone (5), and 6beta-hydroxy-11-ketotestosterone (6). Structures of new metabolites 2, 5, and 6 were established by single-crystal X-ray diffraction analysis.

Description

Adrenosterone is a steroid hormone with weak androgenic effect.

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