81481-12-1

Basic information

• Product Name: 2α,3α-dihydroxy-24S-ethyl-5α-cholest-22E-en-6-one
• Synonyms: 2α,3α-dihydroxy-24S-ethyl-5α-cholest-22E-en-6-one
• CAS NO: 81481-12-1
• Molecular Weight: 444.698
• Mol File: 81481-12-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2α,3α-dihydroxy-24S-ethyl-5α-cholest-22E-en-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2α,3α-dihydroxy-24S-ethyl-5α-cholest-22E-en-6-one(81481-12-1)
• EPA Substance Registry System: 2α,3α-dihydroxy-24S-ethyl-5α-cholest-22E-en-6-one(81481-12-1)

Safety Data

• Hazardous Substances Data: 81481-12-1(Hazardous Substances Data)

Upstream product

• 74174-45-1 (22E)-stigmasta-2,22-dien-6-one 

Downstream Products

• 81481-19-8 6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-22ξ-acetoxy-23ξ-phenylsulfonyl-24S-methyl-5α-cholestane 
• 83510-06-9 (22S,23S)-28-homocastasterone 
• 80736-41-0 castasterone 
• 72962-43-7 (3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one 

Relevant articles and documents

Facile synthesis of (22R,23R)-homobrassinolide

-

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.

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.