Gibberellin A72

Base Information

• Chemical Name: Gibberellin A72
• CAS No.: 105593-21-3
• Molecular Formula: C₁₉H₂₄O₇
• Molecular Weight: 364.395
• DSSTox Substance ID: DTXSID501106880
• Nikkaji Number: J302.609D
• Wikidata: Q105253998
• Mol file: 105593-21-3.mol

Synonyms:Gibberellin A72;(1S,2S,4aR,4bR,7S,9S,9aR,10S,10aR)-2,7,9-trihydroxy-1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;(1R,2R,5S,7S,8R,9S,10R,11S,12S)-5,7,12-Trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid;GA72;CHEBI:142023;DTXSID501106880;(1S,2S,4aR,4bR,7S,9S,9aR,10S,10aR)-2,7,9-trihydroxy-1-methyl-8-methylidene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;2beta,7alpha,9beta-trihydroxy-1beta-methyl-8-methylidene-13-oxo-4a,1alpha-epoxymethano-4aalpha,4bbeta-gibbane-10beta-carboxylic acid;ent-3alpha,10beta,13,15alpha-tetrahydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone;Gibbane-1,10-dicarboxylic acid, 2,4a,7,9-tetrahydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,9beta,10beta)-

Chemical Property of Gibberellin A72

Chemical Property:

• Melting Point: >250°C (dec.)
• PSA: 124.29000
• LogP: 0.22190
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 364.15220310
• Heavy Atom Count: 26
• Complexity: 763

Purity/Quality:

Gibberellin A72 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C(CCC3(C1C(C45C3CCC(C4)(C(=C)C5O)O)C(=O)O)OC2=O)O
• Isomeric SMILES: C[C@@]12[C@H](CC[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)[C@H]5O)O)C(=O)O)OC2=O)O
• Uses: Gibberellin A72 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 A72

There total 4 articles about Gibberellin A72 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:

ent-3α,13-diacetoxy-10β-hydroxy-15-oxo-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone (105593-12-2) → ent-3α,10β,13,15α-tetrahydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone (105593-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 mg / Zn / acetic acid / 2 h / Ambient temperature

2: 1.) K₂CO₃; 2.) NaH, PrSH / 1.) CH₃OH, r.t.; 2.) HMPA

With 1-thiopropane; sodium hydride; potassium carbonate; zinc; In acetic acid;

Reference yield:

ent-3α,13-diacetoxy-10β,15β-dihydroxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone (105593-07-5) → ent-3α,10β,13,15α-tetrahydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone (105593-21-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 103 mg / (COCl)2, DMSO, i-Pr₂NEt / CH₂Cl₂ / 0.75 h / -72 - -60 °C

2: 50 mg / Zn / acetic acid / 2 h / Ambient temperature

3: 1.) K₂CO₃; 2.) NaH, PrSH / 1.) CH₃OH, r.t.; 2.) HMPA

With oxalyl dichloride; 1-thiopropane; sodium hydride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; zinc; In dichloromethane; acetic acid;

Reference yield:

2β,7-diacetoxy-4a-hydroxy-1β-methyl-8-methylene-4aα,7β-gibbane-1α,10β-dicarboxylic acid-1-lactone-10-methyl ester (57784-14-2) → ent-3α,10β,13,15α-tetrahydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone (105593-21-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 380 mg / SeO₂, t-BuOOH / CH₂Cl₂ / 14 h / Ambient temperature

2: 103 mg / (COCl)2, DMSO, i-Pr₂NEt / CH₂Cl₂ / 0.75 h / -72 - -60 °C

3: 50 mg / Zn / acetic acid / 2 h / Ambient temperature

4: 1.) K₂CO₃; 2.) NaH, PrSH / 1.) CH₃OH, r.t.; 2.) HMPA

With tert.-butylhydroperoxide; selenium(IV) oxide; oxalyl dichloride; 1-thiopropane; sodium hydride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; zinc; In dichloromethane; acetic acid;

upstream raw materials:

15α-Hydroxygibberellin A₁ methyl ester diacetate

ent-3α,13-diacetoxy-10β-hydroxy-15-oxo-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone

ent-3α,13-diacetoxy-10β,15β-dihydroxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone

2β,7-diacetoxy-4a-hydroxy-1β-methyl-8-methylene-4aα,7β-gibbane-1α,10β-dicarboxylic acid-1-lactone-10-methyl ester

Refernces