Gibberellin A9 methyl ester

Base Information

• Chemical Name: Gibberellin A9 methyl ester
• CAS No.: 2112-08-5
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.424
• DSSTox Substance ID: DTXSID30555159
• Metabolomics Workbench ID: 66326
• Nikkaji Number: J103.625D
• Wikidata: Q27140405
• Mol file: 2112-08-5.mol

Synonyms:Gibberellin A9 methyl ester;methyl GA9;2112-08-5;MeGA9;O-methyl gibberellin A9;GA9 methyl ester;methyl gibberellin A9;methyl (1R,2R,5R,8R,9S,10R,11R)-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylate;methyl (1R,4aR,4bR,7R,9aR,10S,10aR)-1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate;methyl 1beta-methyl-8-methylidene-13-oxo-4a,1alpha-epoxymethano-4aalpha,4bbeta-gibbane-10beta-carboxylate;CHEBI:73256;DTXSID30555159;Q27140405;methyl (1R, 2R, 5R, 8R, 9S, 10R, 11R)-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15, 8.01, 10.02, 8]heptadecane-9-carboxylate;Methyl (4aR,4bR,7R,9aR,10S,10aR)-1-methyl-8-methylidene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate

Chemical Property of Gibberellin A9 methyl ester

Chemical Property:

• Refractive Index: 1.566
• PSA: 52.60000
• LogP: 3.25380
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 330.18310931
• Heavy Atom Count: 24
• Complexity: 669

Purity/Quality:

99%, ^*data from raw suppliers

Gibberellin A9 methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC3(C1C(C45C3CCC(C4)C(=C)C5)C(=O)OC)OC2=O
• Isomeric SMILES: C[C@@]12CCC[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@H](C4)C(=C)C5)C(=O)OC)OC2=O
• Uses: Gibberellin A9 Methyl Ester is a derivative of the plant hormone Gibberellin which regulates growth and various developmental processes.

Technology Process of Gibberellin A9 methyl ester

There total 18 articles about Gibberellin A9 methyl ester 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:

C23H28O8 → gibberellin A4 methyl ester (2074-29-5,19124-90-4,22553-16-8,22553-19-1) + gibberellin A9 7-methyl ester (2112-08-5) + C22H26O8

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1039/c39850001588

Reference yield:

3-epi-gibberellin A4 methyl ester (2074-29-5) → gibberellin A9 methyl ester (2112-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) hydrogen sulphide / 1.) THF, CH₂Cl₂, room temperature, 40 h, 2.) pyridine, 5 min

2: 35 mg / tri-n-butylstannane, 2,2'-azobis(2-methylpropionitrile) / toluene / 1 h / Heating

With 2,2'-azobis(isobutyronitrile); hydrogen sulfide; tri-n-butyl-tin hydride; In toluene;

Reference yield:

ent-3α-chloro-10β-hydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10β-lactone 7-methyl ester (75885-05-1) → gibberellin A9 methyl ester (2112-08-5)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 1.5h; Heating;

upstream raw materials:

diazomethane

Gibberellin-A⁽⁹⁾

C₂₁H₃₀O₇S

C₂₇H₃₀O₅S

Downstream raw materials:

15β-hydroxy-GA₉

15α-hydroxy-GA₉

gibberellin A₂₀ methyl ester

12α-hydroxy-GA₉-Me

Refernces

• 1、 Sassa, Takeshi,Suzuki, Katsuhiro,Haruki, Emi. "Isolation and Identification of Gibberellins A4 and A9 from a Fungus Phaeosphaeria sp.". . p. 303 - 304. Retrieved 2007/10/02.
• 2、 Fraga, Braulio M.,Gonzalez, Antonio G.,Hernandez, Melchor G.,Duri, Zvitendo J.,Hanson, James R.. "The Partial Synthesis of Beyergibberellin A4 and A9 Methyl Esters". . p. 1105 - 1107. Retrieved 2007/10/02.