Gibberellin A5

Base Information

• Chemical Name: Gibberellin A5
• CAS No.: 561-56-8
• Molecular Formula: C19H22O5
• Molecular Weight: 330.381
• Mol file: 561-56-8.mol

Synonyms:Gibberellin A5;

Chemical Property of Gibberellin A5

Chemical Property:

• Vapor Pressure: 1.48E-15mmHg at 25°C
• Melting Point: 255 - 257°C
• Boiling Point: 573.8°Cat760mmHg
• Flash Point: 211.3°C
• PSA: 83.83000
• Density: 1.41g/cm³
• LogP: 2.05630
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Gibberellin A5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Gibberellin A5 is a plant hormone which promotes floral development but have little effect on stem elongation.

Technology Process of Gibberellin A5

There total 16 articles about Gibberellin A5 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: 85.0%

ent-13-hydroxy-20-norgibberell-1,16-diene-7,19-dioic acid 19,10-lactone (78259-50-4) → gibberellin A5 (561-56-8)

Guidance literature:

With Wilkinson's catalyst; In ethanol; at 95 - 100 ℃; for 4h;

DOI:10.1248/cpb.38.276

Reference yield: 70.0%

ent-13-acetoxy-10-hydroxy-20-norgobberella-2,16-diene-7,19-dioic acid 19,10-lactone 7-methyl ester (75885-02-8) → gibberellin A5 (561-56-8)

Guidance literature:

With water; alkaline hydrolysis;

DOI:10.1039/P19810000672

Reference yield:

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid (77-06-5) → gibberellin A5 (561-56-8)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol; diethyl ether

2: pyridine / 25 h

3: 1.) tri-n-butylstannane, 2,2'-azobis-(2-methylpropiononitrile), 2.) toluene-p-sulphonic acid / 1.) benzene, reflux, 1 h, 2.) room temperature, 18 h

4: 70 percent / H₂O / alkaline hydrolysis

With 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In pyridine; methanol; diethyl ether;

DOI:10.1039/P19810000672

upstream raw materials:

ent-13-acetoxy-10-hydroxy-20-norgobberella-2,16-diene-7,19-dioic acid 19,10-lactone 7-methyl ester

ent-13-hydroxy-20-norgibberell-1,16-diene-7,19-dioic acid 19,10-lactone

1β-chlorogibberellin A₅

ent-3β-chloro-10,13-dihydroxy-20-norgibberella-1,16-diene-7,19-dioic acid 19,10-lactone

Downstream raw materials:

gibberellin A₅ methyl ester

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Gibberellin A₆

Refernces

• 1、 Shimano,Nagaoka,Yamada. "Synthesis of gibberellin A1, A55 and A60. Metal-ammonia reduction of gibberellic acid and its derivative". . p. 276 - 278. Retrieved 2007/10/02.
• 2、 Bearder, John R.,Kirkwood, Paul S.,MacMillan, Jake. "Allylic Chlorination of Gibberellins A3 and A7 Methyl Esters and of Gibberellin A3: Preparation of Gibberellin A5". . p. 672 - 678. Retrieved 2007/10/02.