Gibberellin A60

Base Information

• Chemical Name: Gibberellin A60
• CAS No.: 81826-97-3
• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.396
• DSSTox Substance ID: DTXSID701317019
• Nikkaji Number: J4.789I
• Mol file: 81826-97-3.mol

Synonyms:Gibberellin A60;GA60;1beta-GA20;81826-97-3;CHEBI:141990;DTXSID701317019;(1R,2R,5S,8S,9S,10R,11R,14R)-5,14-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid;(1R,4R,4aR,4bR,7S,9aS,10S,10aR)-4,7-dihydroxy-1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;(1R,4R,4aR,4bR,7S,9aS,10S,10aR)-4,7-dihydroxy-1-methyl-8-methylidene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;4beta,7alpha-dihydroxy-1beta-methyl-8-methylidene-13-oxo-4a,1alpha-epoxymethano-4aalpha,4bbeta-gibbane-10beta-carboxylic acid

Chemical Property of Gibberellin A60

Chemical Property:

• PSA: 104.06000
• LogP: 1.25110
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 348.15728848
• Heavy Atom Count: 25
• Complexity: 731

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(C3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)O
• Isomeric SMILES: C[C@@]12CC[C@H]([C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)C5)O)C(=O)O)OC2=O)O

Technology Process of Gibberellin A60

There total 14 articles about Gibberellin A60 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: 24.0%

1-oxo-GA20 (83455-33-8) → gibberellin A60 (81826-97-3) + 1α-hydroxy-GA20 (83455-35-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 1h;

DOI:10.1016/S0040-4020(01)88545-8

Reference yield:

gibberellin A3-ketone (5087-25-2,58917-17-2) → gibberellin A60 (81826-97-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) hydrazoic acid; 2.) NaBH₄ / 1.) THF, ether, RT, 2 days; 2.) MeOH, RT, 0.5 h

2: 56 percent / tetrahydrofuran; H₂O / 2 h / 25 - 30 °C / Irradiation

3: 68 percent / pyridine / 1.5 h / Ambient temperature

4: 63 percent / H₂ / 10 percent Pd(OH)2CaCO₃ / tetrahydrofuran; pyridine

5: 14 percent / NaBH₄ / methanol / 1 h

With sodium tetrahydroborate; hydrogen azide; hydrogen; palladium dihydroxide; calcium carbonate; In tetrahydrofuran; pyridine; methanol; water;

DOI:10.1016/S0040-4020(01)88545-8

Reference yield:

1-oxo-GA5 (83455-32-7) → gibberellin A60 (81826-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / H₂ / 10 percent Pd(OH)2CaCO₃ / tetrahydrofuran; pyridine

2: 14 percent / NaBH₄ / methanol / 1 h

With sodium tetrahydroborate; hydrogen; palladium dihydroxide; calcium carbonate; In tetrahydrofuran; pyridine; methanol;

DOI:10.1016/S0040-4020(01)88545-8

upstream raw materials:

C₂₅H₃₆O₉

1-oxo-GA₂₀

gibberellin A₆₀ methyl ester

ent-1α,13-dihydroxy-3-oxo-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone