Gibberellin A9

Base Information

• Chemical Name: Gibberellin A9
• CAS No.: 427-77-0
• Molecular Formula: C₁₉H₂₄O₄
• Molecular Weight: 316.397
• UNII: SWC5WIK98K
• Nikkaji Number: J4.735J
• Wikidata: Q27110172
• Mol file: 427-77-0.mol

Synonyms:Gibberellin A9;427-77-0;SWC5WIK98K;UNII-SWC5WIK98K;Gibbane-1,10-dicarboxylic acid, 4a-hydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,4aalpha,4bbeta,10beta)-;(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-carboxylic acid;(1R,4aR,4bR,7R,9aR,10S,10aR)-1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;Gibbane-1,10-dicarboxylic acid, 4a-hydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1.alpha.,4a.alpha.,4b.beta.,10.beta.)-;GA9;SCHEMBL3370009;CHEBI:29605;Q27110172;(1R,2R,5R,8R,9S,10R,11R)-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1(5,8).0(1,10).0(2,8)]heptadecane-9-carboxylic acid;1beta-methyl-8-methylidene-13-oxo-4a,1alpha-epoxymethano-4aalpha,4bbeta-gibbane-10beta-carboxylic acid;1H-7,9A-METHANOBENZ(A)AZULENE-1,10-DICARBOXYLIC ACID, DODECAHYDRO-4A-HYDROXY-1-METHYL-8-METHYLENE-, 1,4A-LACTONE;4A.ALPHA.,4B.BETA.-GIBBANE-1.ALPHA.,10.BETA.-DICARBOXYLIC ACID, 4A-HYDROXY-1-METHYL-8-METHYLENE-, 1,4A-LACTONE

Chemical Property of Gibberellin A9

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >181°C (dec.)
• Boiling Point: 525.9°Cat760mmHg
• PKA: 4.34±0.40(Predicted)
• Flash Point: 192.3°C
• PSA: 63.60000
• Density: 1.29g/cm³
• LogP: 3.16540
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 316.16745924
• Heavy Atom Count: 23
• Complexity: 654

Purity/Quality:

99% ^*data from raw suppliers

GibberellinA9 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCCC3(C1C(C45C3CCC(C4)C(=C)C5)C(=O)O)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)O)OC2=O
• Uses: Gibberellin A9 is a derivative of Gibberellic Acid (G377450), a hormone that is found in plants which promotes the growth and elongation of cells. Gibberellic acid acts as a plant growth regulator on account of its physiological and morphological effects in extremely low concentrations.

Technology Process of Gibberellin A9

There total 6 articles about Gibberellin A9 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:

3-epi-gibberellin A4 methyl ester (2074-29-5) → Gibberellin-A(9) (427-77-0,19885-97-3)

Guidance literature:

Multi-step reaction with 3 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

3: 61 mg / 2M NaOH / dioxane; H₂O / 1.) reflux, 15 h, 2.) stream-bath, 0.5 h

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); hydrogen sulfide; tri-n-butyl-tin hydride; In 1,4-dioxane; water; toluene;

Reference yield:

C27H30O5S (75885-06-2) → Gibberellin-A(9) (427-77-0,19885-97-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 61 mg / 2M NaOH / dioxane; H₂O / 1.) reflux, 15 h, 2.) stream-bath, 0.5 h

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In 1,4-dioxane; water; toluene;

Reference yield:

gibberellin A9 methyl ester (2112-08-5) → Gibberellin-A(9) (427-77-0,19885-97-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; 1.) reflux, 15 h, 2.) stream-bath, 0.5 h;

upstream raw materials:

gibberellin A₉ methyl ester

3-epi-gibberellin A₄ methyl ester

C₂₇H₃₀O₅S

ent-3α-chloro-10β-hydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10β-lactone 7-methyl ester

Downstream raw materials:

gibberellin A₉ methyl ester

C₂₇H₃₀O₅

ent-10-hydroxy-20-nor-15-oxogibberell-16-ene-7.19-dioic acid 19,10-lactone-7-phenacyl ester

15α-hydroxyGA₉ 7-phenacyl ester

Refernces