80483-89-2

Basic information

• Product Name: 22(S),23(S)-Homobrassinolide
• Synonyms: (2R,3S,22S,24S)-2,3,22,23-TETRAHYDROXY-24-ETHYL-BETA-HOMO-7-OXA-5A-CHOLESTAN-6-ONE;Etpihomobrassinolide;EPIHOMOBRASSINOLIDE;Brassins;Kayanaminor;SS-HOMOCASTASTERONE;(1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-1-[(1S,2S,3S,4S)-4-Ethyl-2,3-dihydroxy-1,5-dimethylhexyl]hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-6H-benz[c]indeno[5,4-e]oxepin-6-one;Isohomobrassinolide
• CAS NO: 80483-89-2
• Molecular Formula: C₂₉H₅₀O₆
• Molecular Weight: 494.7
• EINECS: 2017-001-1
• Product Categories: Miscellaneous Plant Growth Regulators;Plant Growth Regulators;Plant Tissue Culture;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 80483-89-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 193-194°C
• Boiling Point: 642.985 °C at 760 mmHg
• Flash Point: 203.248 °C
• Appearance: Crystalline Solid
• Density: 1.103
• Vapor Pressure: 1.04E-18mmHg at 25°C
• Refractive Index: 1.526
• PKA: 14.27±0.70(Predicted)
• CAS DataBase Reference: 22(S),23(S)-Homobrassinolide(CAS DataBase Reference)
• NIST Chemistry Reference: 22(S),23(S)-Homobrassinolide(80483-89-2)
• EPA Substance Registry System: 22(S),23(S)-Homobrassinolide(80483-89-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 80483-89-2(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Uses

Different sources of media describe the Uses of 80483-89-2 differently. You can refer to the following data:
1. 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.
2. A new class of steroidal phytohormones with high growth-promoting and antistress activity.

Biochem/physiol Actions

22(S),23(S)-Homobrassinolide is a brassinosteroid. It might play a role in the control of plant embryogenesis.

InChI:InChI=1/C29H50O6/c1-7-18(14(2)3)25(32)24(31)15(4)28-23-22(20-13-17(30)10-11-19(20)16(5)35-28)27(34)26(33)21-9-8-12-29(21,23)6/h14-16,18-28,31-34H,7-13H2,1-6H3/t15?,16-,18-,19+,20?,21?,22?,23?,24-,25-,26+,27-,28-,29-/m0/s1

Synthetic route

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

Conditions	Yield
With osmium(VIII) oxide; sulfuric acid; sodium sulfite 1.) pyridine, room temp. 30h, 2.) 45 - 50 deg C, 0.5h;	95%

(2α,3α,22S,23S)-tetraacetoxy-B-homo-7-oxastigmastan-6-one (80483-88-1) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
Stage #1: (2α,3α,22S,23S)-tetraacetoxy-B-homo-7-oxastigmastan-6-one With potassium carbonate In methanol for 4h; Heating; Stage #2: With hydrogenchloride In methanol for 1h; Heating;	84%
With sodium hydroxide In methanol; water for 1h; Heating;	70%
Yield given;
With hydrogenchloride; potassium carbonate 1.) MeOH, reflux, 4 h, 2.) 90 deg C, 30 min; Yield given. Multistep reaction;

(2R,3S,22S,23S)-2,3;22,23,-di-isopropylidenedioxy-B-homo-7-oxa-5α-stigmastan 6-one (110556-61-1) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating; Yield given;

(22E)-stigmasta-2,22-dien-6-one (74174-45-1) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions

Yield

Multi-step reaction with 8 steps 1: 1.) lithium di-isopropylamide, 2.) triethylamine / 1.) THF, -78 deg C, 1 h; 2.) -78 deg C, 15 min; rt, 1 h. 2: 1.) osmium tetraoxide; 2.) hydrogen sulphide / 1.) pyridine, 70 h; 2.) MeOH-CH2Cl2, 7 h. 3: toluene-p-sulphonic acid / CH2Cl2 / 2 h / 0 °C 4: periodic acid dihydrate / diethyl ether / 1.) 0 deg C, 1 h; 2.) rt, 3 h. 5: diethyl ether / 0 °C 6: sodium borohydride / diethyl ether; methanol; propan-2-ol / 0.5 h / 0 °C 7: toluene / 0.17 h / Heating 8: HCl / methanol / 1 h / Heating View Scheme

(22E,24S)-3β-bromo-5α-stigmasta-22-en-6-one (92804-65-4) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 37 percent / Br2 / CHCl3 2: 54 percent / lithium carbonate / dimethylformamide / 1 h / Heating 3: 95 percent / 1.) osmium tetroxide, 2.)sodium sulfite, sulfuric acid / 1.) pyridine, room temp. 30h, 2.) 45 - 50 deg C, 0.5h View Scheme

3β,22R,23S-tribromo-24S-ethyl-5α-cholestan-6-one (99646-98-7) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / lithium carbonate / dimethylformamide / 1 h / Heating 2: 95 percent / 1.) osmium tetroxide, 2.)sodium sulfite, sulfuric acid / 1.) pyridine, room temp. 30h, 2.) 45 - 50 deg C, 0.5h View Scheme

6-trimethylsiloxy-5α-stigmasta-2,6,22-triene (110556-55-3) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions

Yield

Multi-step reaction with 7 steps 1: 1.) osmium tetraoxide; 2.) hydrogen sulphide / 1.) pyridine, 70 h; 2.) MeOH-CH2Cl2, 7 h. 2: toluene-p-sulphonic acid / CH2Cl2 / 2 h / 0 °C 3: periodic acid dihydrate / diethyl ether / 1.) 0 deg C, 1 h; 2.) rt, 3 h. 4: diethyl ether / 0 °C 5: sodium borohydride / diethyl ether; methanol; propan-2-ol / 0.5 h / 0 °C 6: toluene / 0.17 h / Heating 7: HCl / methanol / 1 h / Heating View Scheme

(2R,3S,7S,22S,23S)-2,3,7,22,23-pentahydroxy-5α-stigmastan-6-one (110556-56-4) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: toluene-p-sulphonic acid / CH2Cl2 / 2 h / 0 °C 2: periodic acid dihydrate / diethyl ether / 1.) 0 deg C, 1 h; 2.) rt, 3 h. 3: diethyl ether / 0 °C 4: sodium borohydride / diethyl ether; methanol; propan-2-ol / 0.5 h / 0 °C 5: toluene / 0.17 h / Heating 6: HCl / methanol / 1 h / Heating View Scheme

(2R,3S,7S,22S,23S)-7-hydroxy-2,3;22,23-di-isopropylidenedioxy-5α-stigmastan-6-one (110556-57-5) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: periodic acid dihydrate / diethyl ether / 1.) 0 deg C, 1 h; 2.) rt, 3 h. 2: diethyl ether / 0 °C 3: sodium borohydride / diethyl ether; methanol; propan-2-ol / 0.5 h / 0 °C 4: toluene / 0.17 h / Heating 5: HCl / methanol / 1 h / Heating View Scheme

methyl (2R,3S,22S,23S)-7-hydroxy-2,3;22,23-di-isopropylidene-dioxy-6,7-seco-5α-stigmastan-6-oate (110556-60-0) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 0.17 h / Heating 2: HCl / methanol / 1 h / Heating View Scheme

(2R,3S,22S,23S)-2,3;22,23-di-isopropylidenedioxy-7-oxo-6,7-seco-5α-stigmastan-6-oic acid (110556-58-6) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: diethyl ether / 0 °C 2: sodium borohydride / diethyl ether; methanol; propan-2-ol / 0.5 h / 0 °C 3: toluene / 0.17 h / Heating 4: HCl / methanol / 1 h / Heating View Scheme

methyl (2R,3S,22S,23S)-2,3;22,23-di-isopropylidenedioxy-7-oxo-6,7-seco-5α-stigmastan-6-oate (110556-59-7) → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium borohydride / diethyl ether; methanol; propan-2-ol / 0.5 h / 0 °C 2: toluene / 0.17 h / Heating 3: HCl / methanol / 1 h / Heating View Scheme

C29H48O4 → (22S,23S)-28-homobrassinolide (80483-89-2)

Conditions	Yield
With osmium(VIII) oxide

Upstream product

• 74174-48-4 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 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 
• 110556-59-7 methyl (2R,3S,22S,23S)-2,3;22,23-di-isopropylidenedioxy-7-oxo-6,7-seco-5α-stigmastan-6-oate 
• 110556-58-6 (2R,3S,22S,23S)-2,3;22,23-di-isopropylidenedioxy-7-oxo-6,7-seco-5α-stigmastan-6-oic acid 
• 110556-60-0 methyl (2R,3S,22S,23S)-7-hydroxy-2,3;22,23-di-isopropylidene-dioxy-6,7-seco-5α-stigmastan-6-oate 
• 110556-57-5 (2R,3S,7S,22S,23S)-7-hydroxy-2,3;22,23-di-isopropylidenedioxy-5α-stigmastan-6-one 
• 110556-56-4 (2R,3S,7S,22S,23S)-2,3,7,22,23-pentahydroxy-5α-stigmastan-6-one 
• 110556-55-3 6-trimethylsiloxy-5α-stigmasta-2,6,22-triene 
• 80483-88-1 (2α,3α,22S,23S)-tetraacetoxy-B-homo-7-oxastigmastan-6-one 
• 110556-61-1 (2R,3S,22S,23S)-2,3;22,23,-di-isopropylidenedioxy-B-homo-7-oxa-5α-stigmastan 6-one 
• 99647-00-4 (22E,24S)-B-homo-7-oxa-5α-stigmasta-2,22-dien-6-one 
• 99646-98-7 3β,22R,23S-tribromo-24S-ethyl-5α-cholestan-6-one 
• 92804-65-4 (22E,24S)-3β-bromo-5α-stigmasta-22-en-6-one 
• 74174-45-1 (22E)-stigmasta-2,22-dien-6-one 

Relevant articles and documents

Toxicity of (22R,23R)-22,23-dihydroxystigmastane derivatives to cultured cancer cells

Toxicity of eight 22,23-dihydroxystigmastane derivatives (four pairs of (22R,23R)- and (22S,23S)-isomers differing in steroid backbone structure) to human breast carcinoma MCF-7 cells was compared. For every pair of structurally related compounds, (22R,23

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 (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