22(S),23(S)-Homobrassinolide

Base Information

• Chemical Name: 22(S),23(S)-Homobrassinolide
• CAS No.: 80483-89-2
• Molecular Formula: C29H50O6
• Molecular Weight: 494.712
• Mol file: 80483-89-2.mol

Synonyms:(22S,23S)-28-Homobrassinolide;(22S,23S)-Homobrassinolide;22,23-Diepi-28-homobrassinolide;6H-Benz[c]indeno[5,4-e]oxepin-6-one, 1-(4-ethyl-2,3-dihydroxy-1,5-dimethylhexyl)hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-,[1R-[1a(1S*,2S*,3S*,4S*),3ab,3ba,6ab,8b,9b,10aa,10bb,12aa]]-;BR 120;B-Homo-7-oxastigmastan-6-one,2,3,22,23-tetrahydroxy-, (2a,3a,5a,22S,23S)-;

Chemical Property of 22(S),23(S)-Homobrassinolide

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Vapor Pressure: 1.04E-18mmHg at 25°C
• Melting Point: 193-194 °C
• Refractive Index: 1.526
• Boiling Point: 642.985 °C at 760 mmHg
• PKA: 14.27±0.70(Predicted)
• Flash Point: 203.248 °C
• PSA: 107.22000
• Density: 1.131 g/cm³
• LogP: 3.78010
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 494.36073931
• Heavy Atom Count: 35
• Complexity: 770

Purity/Quality:

98%, ^*data from raw suppliers

(22S,23S)-28-HomoBrassinolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C(C)C)C(C(C(C)C1CCC2C1(CCC3C2COC(=O)C4C3(CC(C(C4)O)O)C)C)O)O
• Uses: 22(S),23(S)-Homobrassinolide has been used as a brassinosteroid supplement:to study its effects on DNA methylation, callus growth and regeneration in barley.to study its effects on cell elongation in Arabidopsis thaliana.to study its effects on cell division, root germination and anti-oxidant system enzymes in barley. A new class of steroidal phytohormones with high growth-promoting and antistress activity.

Technology Process of 22(S),23(S)-Homobrassinolide

There total 15 articles about 22(S),23(S)-Homobrassinolide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(22E,24S)-B-homo-7-oxa-5α-stigmasta-2,22-dien-6-one (99647-00-4) → (22S,23S)-28-homobrassinolide (80483-89-2)

Guidance literature:

With osmium(VIII) oxide; sulfuric acid; sodium sulfite; 1.) pyridine, room temp. 30h, 2.) 45 - 50 deg C, 0.5h;

Reference yield: 91.0%

Acetic acid (1S,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8-acetoxy-1-((1S,2R,3R,4S)-2,3-diacetoxy-4-ethyl-1,5-dimethyl-hexyl)-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-9-yl ester (74174-48-4,80483-88-1,83509-43-7,88495-70-9) → (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-24-ethyl-B-homo-7-oxa-5α-cholestan-6-one (74174-44-0,80483-89-2,80513-15-1,82373-95-3,83509-44-8,88495-64-1,88495-66-3,93860-63-0,93860-64-1,93860-65-2,94062-50-7,110415-23-1,147200-28-0,147200-29-1)

Guidance literature:

With potassium hydroxide; In methanol; for 1.5h; Heating;

Reference yield: 90.0%

Acetic acid (1S,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8-acetoxy-1-((1S,2S,3S,4S)-2,3-diacetoxy-4-ethyl-1,5-dimethyl-hexyl)-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-9-yl ester (74174-48-4,80483-88-1,83509-43-7,88495-70-9) → (22S,23S,24S)-2α,3α,22,23-tetrahydroxy-24-ethyl-B-homo-7-oxa-5α-cholestan-6-one (74174-44-0,80483-89-2,80513-15-1,82373-95-3,83509-44-8,88495-64-1,88495-66-3,93860-63-0,93860-64-1,93860-65-2,94062-50-7,110415-23-1,147200-28-0,147200-29-1)

Guidance literature:

With potassium hydroxide; In methanol; for 1.5h; Heating;

upstream raw materials:

(22E,24S)-B-homo-7-oxa-5α-stigmasta-2,22-dien-6-one

(2R,3S,22S,23S)-2,3;22,23,-di-isopropylidenedioxy-B-homo-7-oxa-5α-stigmastan 6-one

(2α,3α,22S,23S)-tetraacetoxy-B-homo-7-oxastigmastan-6-one

(22E)-stigmasta-2,22-dien-6-one

Refernces

• 1、 Massey, Archna P.,Pore, Vandana S.,Hazra, Braja G.. "New route for the synthesis of (22S,23S)-28-homobrassinolide". . p. 426 - 430. Retrieved 2007/10/03.
• 2、 Anastasia, Mario,Allevi, Pietro,Ciuffreda, Pierangela,Fiecchi, Alberto,Scala, Antonio. "Synthesis of (2R,3S,22S,23S)-2,3,22,23-Tetrahydroxy-B-homo-7-aza-5α-stigmastan-6-one, an Aza-analogue of Homobrassinolide". . p. 2117 - 2122. Retrieved 2007/10/02.