78821-42-8

Basic information

• Product Name: 22S,23S-EPIBRASSINOLIDE
• Synonyms: 22S,23S-EPIBRASSINOLIDE;(22S,23S)-2α,3α,22,23-Tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one;22,23,24-Triepibrassinolide;22,23,24-Trisepibrassinolide;B-1072;Brassinosteroid;Epibrassinolide S;TRIS-EPIBRASSINOLIDE (TEBI)
• CAS NO: 78821-42-8
• Molecular Formula: C₂₈H₄₈O₆
• Molecular Weight: 480.68
• Product Categories: Miscellaneous Natural Products;Bio-Pesticide
• Mol File: 78821-42-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 22S,23S-EPIBRASSINOLIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 22S,23S-EPIBRASSINOLIDE(78821-42-8)
• EPA Substance Registry System: 22S,23S-EPIBRASSINOLIDE(78821-42-8)

Safety Data

• Hazardous Substances Data: 78821-42-8(Hazardous Substances Data)

Usage

Description

22S,23S-EPIBRASSINOLIDE, also known as tris-Epibrassinolide, is a plant hormone belonging to the brassinosteroid family. It plays a crucial role in plant growth and development by regulating various physiological processes, such as cell elongation, cell division, and stress responses. Its unique structure and biological activity make it a valuable compound for research and potential applications in agriculture and plant biology.
Source:
22S,23S-EPIBRASSINOLIDE is naturally found in plants, where it is synthesized and plays a vital role in their growth and development.
Production Methods:
The production of 22S,23S-EPIBRASSINOLIDE can be achieved through both chemical synthesis and extraction from plant sources. Chemical synthesis involves the stepwise assembly of the brassinosteroid core structure, while extraction from plants requires purification and isolation techniques to obtain the compound in a pure form.

Uses

Used in Plant Biology Research:
22S,23S-EPIBRASSINOLIDE is used as a research tool for studying the molecular mechanisms underlying plant growth and development. It helps researchers understand the role of brassinosteroids in various physiological processes, such as cell elongation, cell division, and stress responses.
Used in Biological Studies:
22S,23S-EPIBRASSINOLIDE is used in biological studies for epinasty, which is the downward bending of plant organs, in the context of auxin input pathways. It helps researchers investigate the role of reactive oxygen species, nitric oxide, and cytoskeleton structure in the development of nastic phenotypes in Arabidopsis thaliana, a model plant species.
Used in Agriculture:
22S,23S-EPIBRASSINOLIDE has potential applications in agriculture as a growth promoter and stress protectant. It can be used to enhance crop yield, improve plant growth, and increase resistance to various environmental stresses, such as drought, salinity, and extreme temperatures.
Used in Plant Breeding:
22S,23S-EPIBRASSINOLIDE can be employed in plant breeding programs to develop new plant varieties with improved growth characteristics, stress tolerance, and higher yields. By understanding the role of brassinosteroids in plant development, researchers can potentially manipulate these pathways to create plants with desired traits.

Upstream product

• 125627-05-6 (1S,2S)-1-Furan-2-yl-2-((1aR,3aR,5aS,6R,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-propan-1-ol 
• 125627-05-6 (1R,2S)-1-Furan-2-yl-2-((1aR,3aR,5aS,6R,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-propan-1-ol 
• 72050-70-5 Acetic acid (2R,3S,5S,8S,9S,10R,13S,14S,17R)-3-acetoxy-17-((S)-2,3-diacetoxy-1,4,5-trimethyl-hexyl)-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-2-yl ester 
• 72050-70-5 Acetic acid (2R,3S,5S,8S,9S,10R,13S,14S,17R)-3-acetoxy-17-((S)-2,3-diacetoxy-1,4,5-trimethyl-hexyl)-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-2-yl ester 
• 124696-45-3 (22E,24R)-B-Homo-7-oxa-5α-ergost-2,22-dien-6-one 
• 125627-08-9 (2R,6R)-6-(2-Ethoxy-ethoxy)-2-[(S)-1-((1aR,3aR,5aS,6R,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-6H-pyran-3-one 
• 125627-08-9 (R)-6-(2-Ethoxy-ethoxy)-2-[(S)-1-((1aR,3aR,5aS,6R,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-6H-pyran-3-one 
• 125627-10-3 (2R,4S,5S)-6-(2-Ethoxy-ethoxy)-2-[(S)-1-((1aR,3aR,5aS,6R,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-4,5-dimethyl-dihydro-pyran-3-one 
• 125627-13-6 Acetic acid (3S,10R,13S,17R)-17-{(S)-1-[(4R,5R)-5-((1S,2S)-3-hydroxy-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 125664-69-9 (2R,5S)-6-(2-Ethoxy-ethoxy)-2-[(S)-1-((1aR,3aR,5aS,6R,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-5-methyl-dihydro-pyran-3-one 
• 125627-11-4 (2R,3R,4S,5S)-6-(2-Ethoxy-ethoxy)-2-[(S)-1-((1aR,3aR,5aS,6R,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-4,5-dimethyl-tetrahydro-pyran-3-ol 
• 125627-07-8 (R)-6-Hydroxy-2-[(S)-1-((1aR,3aR,5aS,6R,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-6H-pyran-3-one 
• 90866-87-8 (2S,3S,4R,5R,6S)-6-((1aR,3aR,5aS,6R,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2,3-dimethyl-heptane-1,4,5-triol 
• 25819-77-6 (20S)-6β-Methoxy-3α,5-cyclo-5α-pregnane-20-carboxaldehyde 

Relevant articles and documents

The development and use of a general route to brassinolide, its biosynthetic precursors, metabolites and analogues

A new method for the construction of steroid side chains through the addition of lithium salts of dithianes to a C-22 aldehyde was developed. An efficient one-pot procedure for the preparation of a suitable C-22 aldehyde from commercial epibrassinolide in three steps in 86% isolated yield was described. Enantioselective hydroxymethylation of isovaleraldehyde and Kulinkovich cyclopropanation of silylated Roche esters were used as key steps for the dithiane syntheses. The method was applied for the preparation of brassinolide, its biosynthetic precursors and metabolites. In addition, a number of brassinosteroids with a double bond in the side chain were prepared as precursors for tritiated derivatives for biosynthetic studies.

The shortest route from ergosterol to 24-epibrassinolide and its 22S,23S-isomer

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STEREOCONTROLLED SYNTHESIS OF THE BRASSINOLIDE SIDE CHAIN VIA A PYRANONE DERIVATIVE

A new method for assembling the brassinolide side chain from 20-carboxaldehyde 2 was developed via the stereoselective construction of the pyranone moiety as key steps.