17520-02-4

Usage

Steroid hormone

11-KETODEHYDROEPIANDROSTERONE is a steroid hormone that is derived from the adrenal gland.

Metabolite of Dehydroepiandrosterone (DHEA)

It is a metabolite of DHEA, which is a hormone produced by the adrenal glands.

Regulation of androgen and estrogen levels

11-KETODEHYDROEPIANDROSTERONE is involved in the regulation of androgen and estrogen levels in the body.

Anti-inflammatory properties

It has been studied for its potential anti-inflammatory properties.

Antioxidant properties

It has been studied for its potential antioxidant properties.

Neuroprotective properties

It has been studied for its potential neuroprotective properties.

Regulation of metabolism and energy balance

It plays a role in the regulation of metabolism and energy balance.

Growth and development of reproductive tissues

It plays a role in the growth and development of reproductive tissues.

Therapeutic applications

It may have potential therapeutic applications in the treatment of various conditions, such as obesity, diabetes, and neurodegenerative diseases.

More research needed

More research is needed to fully understand the effects and potential applications of 11-KETODEHYDROEPIANDROSTERONE.

Upstream product

• 118319-81-6 3β-(t-butyldimethylsilyloxy)androst-5-en-11,17-dione 
• 54296-19-4 3,17,21-triacetoxy-pregna-3,5-diene-11,20-dione 
• 50-04-4 Cortisone acetate 
• 50-03-3 hydrocortisone acetate 
• 17520-04-6 3-acetoxyandrosta-3,5-diene-11,17-dione 
• 118319-88-3 3β-(t-butyldimethylsilyloxy)-11β,17β-dihydroxyandrost-5-ene 
• 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 
• 382-45-6 adrenosterone 

Downstream Products

• 82251-59-0 dehydro-oogoniol 
• 82251-59-0 dehydro-oogoniol 

Relevant academic research and scientific papers

Synthesis of Oogoniol

Oogoniol , a female-activating hormone of Achlya, has been synthesized from 4-androstene-3,11,17-trione.A novel step involved 1,4-addition of the magnesium cyanocuprate derivative of (S)-3-(1-methylethyl)-5-pentyl bromide to 3β-hydroxy-15β,16β-epoxy-11-oxo-(17(20)E)-pregna-5,17(20)-diene 3-tert-butyldimethylsilyl ether.Selective hydrogenation of the resulting Δ16 double bond gave only the stigmastene product with the correct stereochemistry at C15, C17, and C20.

OXYSTEROLS AND METHODS OF USE THEREOF

Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, and R6, R11a, and R11b are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Synthesis of dehydro-oogoniol and oogoniol: The adrenosterone route

Dehydro-oogoniol(3β, 11α, 15β,29-tetrahydroxystigmasta-5,24(28)(E)-dien-7-one), a female-activating hormone of the water mold Achlya, has been synthesized from 4-androstene-3,11,17-trione by a series of highly stereoselective reactions. One of these involved 1,4-addition of the magnesium cyanocuprate derivative of 3-(1,3-dioxolan-2-yl)-4-methylpentyl bromide to 3β-hydroxy-15β,16β-epoxy-11-oxo-(17E)-pregna -5, 17(20)-diene 3-tert -butyidimethylsilyl ether. The structure of an intermediate, 3β,11 β,15β-triacetoxy-5-cholesten-24-one, was confirmed by X-ray crystallographic analysis. Oogoniol [(24R)-3β,11α,15β,29-tetrahydroxy-stigmast-5-en-7-one] was synthesized in a similar manner by reaction of the magnesium cyanocuprate of (S)-3-(1-methylethyl)-5-[(tert-butyldimethylsilyl)oxy]pentyl bromide with the above epoxy pregnadiene.