83510-06-9

Basic information

• Product Name: 22S,23S-HOMOCASTASTERONE
• Synonyms: (22S,23S)-Homocastasterone;(22S,23S,24S)-24-Ethylbrassinone; (2a,3a,22S,23S)-Tetrahydroxy-5a-stigmastan-6-one
• CAS NO: 83510-06-9
• Molecular Formula: C29H50O5
• Molecular Weight: 478.7043
• Product Categories: Miscellaneous Natural Products
• Mol File: 83510-06-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 22S,23S-HOMOCASTASTERONE(CAS DataBase Reference)
• NIST Chemistry Reference: 22S,23S-HOMOCASTASTERONE(83510-06-9)
• EPA Substance Registry System: 22S,23S-HOMOCASTASTERONE(83510-06-9)

Safety Data

• Hazardous Substances Data: 83510-06-9(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
22S,23S-HOMOCASTASTERONE is used as a plant growth regulator for enhancing plant growth and development. It promotes cell elongation and division, leading to increased plant size and improved crop yields.
Used in Plant Biotechnology:
22S,23S-HOMOCASTASTERONE is used as a research tool in plant biotechnology for studying the mechanisms of plant growth and development. It helps researchers understand the role of brassinosteroids in plant physiology and identify potential targets for improving crop performance.
Used in Plant Breeding:
22S,23S-HOMOCASTASTERONE is used as a selective agent in plant breeding programs to develop new plant varieties with enhanced growth characteristics. By understanding the effects of this hormone on plant growth, breeders can create plants that are more productive and resilient to environmental stressors.

Upstream product

• 74174-45-1 (22E)-stigmasta-2,22-dien-6-one 
• 80459-67-2 Toluene-4-sulfonic acid (3S,5S,8S,9S,10R,13R,14S,17S)-17-((E)-(1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 122008-70-2 Acetic acid (2R,3S,5S,8S,9S,10R,13S,14S,17S)-3-acetoxy-17-((1S,4S)-4-ethyl-2,3-dihydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-2-yl ester 
• 85197-32-6 Acetic acid (2R,3S,5S,8S,9S,10R,13S,14S,17S)-3-acetoxy-17-{(S)-1-[3-((S)-1-ethyl-2-methyl-propyl)-oxiranyl]-ethyl}-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-2-yl ester 
• 85197-31-5 (24S)-2α,3α-diacetoxy-24-ethyl-5α-cholest-22-en-6-one 
• 80459-66-1 (3S,5S,8S,9S,10R,13R,14S,17S)-17-((E)-(1R,4S)-4-Ethyl-1,5-dimethyl-hex-2-enyl)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one 
• 74174-45-1 (5S,8S,9S,10R,13R,14S,17S)-17-((E)-(1R,4S)-4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-1,4,5,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-6-one 
• 74174-47-3 (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-24-ethyl-5α-cholestan-6-one 
• 74174-47-3 (22S,23S,24S)-2α,3α,22,23-tetrahydroxy-24-ethyl-5α-cholestan-6-one 
• 58274-46-7 (22E)-3α,5-cyclo-6β-hydroxy-5α-stigmast-22-ene 
• 80459-67-2 3β-hydroxy-24S-ethyl-5α-cholest-22-en-6-one tosylate 
• 103881-47-6 (22E,24S)-24-ethyl-3α,5-cyclo-5α-cholest-22-en-6-ol 
• 74174-49-5 (22E,24S)-3β,5-cyclo-24-ethylcholest-22-en-6-one 
• 113159-84-5 22S,23S-epoxy-3β-bromo-24S-ethyl-5α-cholestan-6-one 

Relevant articles and documents

Synthesis and preliminary evaluation of dimeric-28-homobrassinosteroids for plant growth regulators

Preparation of synthetic analogues of 28-homobrassinosteroids is reported. Also, the addition of the 28-homocastasterone at the C6 carbonyl group via allyl Gringard reagent followed by olefin cross metathesis resulted in dimeric analogues. Rice lamina inclination assay showed that the replacement of the C6 carbonyl group by 6α-allyl and 6β hydroxyl groups led to a decrease in bioactivity, whereas the dimeric analogues showed a reduced but significant bioactivity when compared to the 28-homocastasterone.

New route for the synthesis of (22S,23S)-28-homobrassinolide

A new and highly efficient synthesis of (22S,23S)-28-homobrassinolide (3) has been achieved. (2α,3α,22S,23S)-Tetrahydroxy-5α-stigmastan-6-one (4), a key intermediate for the synthesis of 3, and (2α,3α)-dihydroxy-5α-stigmast-22-en-6-one (6), a versatile intermediate for the synthesis of 3, and several naturally occurring brassinosteroids have been obtained in excellent yield from stigmasta-2,(22E)-dien-6-one (5) by catalytic RuO4 hydroxylation. Sodium perborate, a cheap and large-scale industrial chemical is used for Baeyer-Villiger oxidation of B-ring ketone 9 to its lactone 10.

Improved synthesis of brassinolide

Brassinolide has been synthesized from stigmasterol in an overall yield of 7%. The key step in the synthesis is aldol condensation of 2α,3α-isopropylidenedioxy-6-oxo-23,24-dinor-5α-cholan-22-al with 3-isopropylbut-2-enolide carried out at -78°C, which gives a product with 22R,23R stereochemistry in high yield. Catalytic hydrogenation of this product is highly stereoselective leading to the desired 245 stereochemistry in an intermediate which is readily transformed into brassinolide. Copyright 1996 by the Royal Society of Chemistry.

SYNTHESIS AND BIOLOGICAL ACTIVITY OF 28-HOMOBRASSINOLIDE AND ANALOGUES

28-Homobrassinolide has been synthesized from stigmasterol in an overall yield of 21percent.The biological activity of 28-homobrassinolide, brassinolide, 24-epibrassinolide, 22S,23S,24-epibrassinolide, and 22S,23S,28-homobrassinolide have been compared in the soybean epicotyl elongation assay.All the steroids except 22S,23S,28-homobrassinolide exhibited a similar biological activity, but the latter compound was substantially less active.There appears to be a correlation between biological activity and overall dimensions of the steroidal side chain.

Studies on Steroidal Plant-growth Regulators. Part 29. Osmium Tetroxide-catalysed Asymmetric Dihydroxylation of the (22E,24R)- and the (22E,24S)-24-Alkyl Steroidal Unsaturated Side Chain

The osmium tetroxide-catalysed asymmetric dihydroxylation of the (22E,24R)- and (22E,24S)-24-methyl steroidal unsaturated side chain with dihydroquinidine p-chlorobenzoate (DHQD) as chiral ligand gave an 8:1 ratio of (22R,23R)- and (22S,23S)-22,23-dihydroxylated products; with a 24-ethyl substituent only a 1.5:1 ratio of (22R,23R)- and (22S,23S)-products was obtained.With the chiral ligand 9-O-(9'-phenanthryl) dihydroquinidine (DHQD-PHN), a 8:1 ratio of (22R,23R)- and (22S,23S)-products was obtained from the (22E,24S)-24-ethyl substituted side chain.

Studies on Steroidal Plant Growth Regulators 22. Osmium Tetroxide Catalyzed Asymmetric Dihydroxylation of the (22E, 24R)- and the (22E, 24 S)-24-Alkyl Steroidal Unsaturated Side Chain

The osmium tetroxide catalyzed asymmetric hydroxylation of the (22E,24R)- and (22E,24S)-24-alkyl steroidal unsaturated side chain are described.High stereoselectivity was obtained on dihydroxylation of these unsaturated side chains, when the 24-alkyl is methyl, while in the case of a 24-ethyl substituent the chiral ligand would be the dihydroquinine p-chlorobenzoate (DHQ).

SYNTHESIS OF 22S,23S-BRASSINOSTEROIDS BASED ON STIGMASTEROL

The analogs of 29C-brassinosteroids based on stigmasterol , i.e., 22S,23S-homocastasterone and 22S,23S-homobrassinolide, were synthesized.Electrophilic additions at the Δ22-bond, hydroxylation with osmium tetroxide, and epoxidation followed by conversion of the epoxide into the diol were used for the construction of the 22S,23S-diol grouping.

Synthesis of Analogues of Brassinolide and Castasterone

Syntheses of 2α,3α,22R,23R-tetrahydroxy-24S-ethyl-B-homo-7-oxa-5α-cholestan-6-one (5) and 2α,3α-dihydroxy-24S-ethyl-B-homo-7-oxa-5α-cholestan-6-one (7) are described starting from stigmasterol and β-sitosterol respectively.

Synthesis of (22R,23R)-28-Homobrassinolide

(22R,23R)-28-Homobrassinolide (18), an analog of brassinolide (1), was synthesized from stigmasterol (3).Keywords - brassinolide; plant growth-promoting substance; active analogs of brassinolide; structure-activity relationship; stigmasterol; plant hormones; Baeyer-Villiger oxidation