Gibberellin A24

Base Information

• Chemical Name: Gibberellin A24
• CAS No.: 19427-32-8
• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.423
• DSSTox Substance ID: DTXSID90941155
• Nikkaji Number: J4.752J
• Wikidata: Q27104245
• Metabolomics Workbench ID: 28574
• Mol file: 19427-32-8.mol

Synonyms:GA24 cpd;gibberellin A(24);gibberellin A24

Chemical Property of Gibberellin A24

Chemical Property:

• Vapor Pressure: 6.62E-12mmHg at 25°C
• Boiling Point: 503.3°Cat760mmHg
• Flash Point: 272.3°C
• PSA: 91.67000
• Density: 1.37g/cm³
• LogP: 3.13970
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 346.17802393
• Heavy Atom Count: 25
• Complexity: 684

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1C(C34C2CCC(C3)C(=C)C4)C(=O)O)C=O)C(=O)O
• Isomeric SMILES: C[C@]1(CCC[C@@]2([C@@H]1[C@@H]([C@]34[C@H]2CC[C@H](C3)C(=C)C4)C(=O)O)C=O)C(=O)O
• Uses: Gibberellin A24 is a derivative of the plant hormone Gibberellin which regulates growth and various developmental processes.

Technology Process of Gibberellin A24

There total 8 articles about Gibberellin A24 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: 87.0%

(1R,4aR,4bR,7R,9aR,10S,10aS)-4a-formyl-10-(methoxycarbonyl)-1-methyl-8-methylenedodecahydro-1H-7,9a-methanobenzo[a]-azulene-1-carboxylic acid → gibberellin A24 (19427-32-8)

Guidance literature:

With sodium hydroxide; In methanol; water; at 100 ℃; for 20h;

DOI:10.1021/acs.joc.8b00876

Reference yield:

gibberellin A12 (1164-45-0) → gibberellin A15 (13744-18-8) + gibberellin A24 (19427-32-8)

Guidance literature:

With Fusarium fujikuroi Δcpr mutant; In methanol; at 28 ℃; for 72h;

DOI:10.1016/j.phytochem.2007.08.026

Reference yield:

C20H25ClO3 → gibberellin A24 (19427-32-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diethyl ether / 16 h / 0 - 18 °C

2.1: bis(N-tert-butylsalicylaldiminato)copper(II) / tetrahydrofuran; cyclohexane / 2 h / 90 °C

3.1: lithium; ammonia / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C

3.2: 5 h / 0 °C

4.1: potassium hexamethylsilazane; oxygen / tetrahydrofuran; N,N-dimethyl-formamide; toluene / 3 h / 0 °C

5.1: sodium hydroxide / methanol; water / 20 h / 100 °C

With bis(N-tert-butylsalicylaldiminato)copper(II); ammonia; oxygen; lithium; potassium hexamethylsilazane; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; cyclohexane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/acs.joc.8b00876

upstream raw materials:

gibberellin A₁₂

methyl (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-1-methyl-8-methylene-2,7-bis((methylsulfonyl)oxy)-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate

(1R,4bR,7R,9aR,10S,10aS)-10-(methoxycarbonyl)-1-methyl-8-methylene-2,3,4b,5,6,7,8,9,10,10a-decahydro-1H-7,9a-methanobenzo[a]azulene-1-carboxylic acid

Downstream raw materials:

gibberellin A₂₅

Refernces

• 1、 Troncoso, Claudia,Carcamo, Jose,Hedden, Peter,Tudzynski, Bettina,Cecilia Rojas. "Influence of electron transport proteins on the reactions catalyzed by Fusarium fujikuroi gibberellin monooxygenases". . p. 672 - 683. Retrieved 2008/09/19.