Gibberellin A6

Base Information

• Chemical Name: Gibberellin A6
• CAS No.: 19147-78-5
• Molecular Formula: C19H22O6
• Molecular Weight: 346.3744
• Metabolomics Workbench ID: 28569
• Wikidata: Q27110170
• Mol file: 19147-78-5.mol

Synonyms:19147-78-5;Gibberellin A6;(1R,2R,5S,8S,9S,10R,11S,12R,14S)-5-Hydroxy-11-methyl-6-methylidene-17-oxo-13,16-dioxahexacyclo[9.4.2.15,8.01,10.02,8.012,14]octadecane-9-carboxylic acid;2beta,3beta-Epoxy-4aalpha,7-dihydroxy-1beta-methyl-8-methylenegibbane-1alpha,10beta-dicarboxylic acid 1,4a-lactone;SCHEMBL22582345;CHEBI:29602;GA6;Q27110170;ent-2alpha,3alpha-epoxy-13-hydroxy-20-norgibberell-16-en-19-oic acid 19,10-lactone;(1R,2R,5S,8S,9S,10R,11S,12R,14S)-5-hydroxy-11-methyl-6-methylidene-17-oxo-13,16-dioxahexacyclo[9.4.2.1(5,8).0(1,10).0(2,8).0(12,14)]octadecane-9-carboxylic acid;2beta,3beta-epoxy-7alpha-hydroxy-1beta-methyl-8-methylidene-13-oxo-4a,1alpha-epoxymethano-4aalpha,4bbeta-gibbane-10beta-carboxylic acid

Chemical Property of Gibberellin A6

Chemical Property:

• Vapor Pressure: 2E-17mmHg at 25°C
• Melting Point: >206°C (dec.)
• Boiling Point: 609.9°Cat760mmHg
• Flash Point: 225.7°C
• PSA: 96.36000
• Density: 1.51g/cm³
• LogP: 1.26750
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 346.14163842
• Heavy Atom Count: 25
• Complexity: 776

Purity/Quality:

98.5% ^*data from raw suppliers

GibberellinA6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12C3C(C45CC(=C)C(C4)(CCC5C3(CC6C1O6)OC2=O)O)C(=O)O
• Isomeric SMILES: C[C@]12[C@H]3[C@@H]([C@@]45CC(=C)[C@@](C4)(CC[C@H]5[C@@]3(C[C@H]6[C@@H]1O6)OC2=O)O)C(=O)O
• Uses: Gibberellin A6 is a derivative of the plant hormone Gibberellin which regulates growth and various developmental processes.

Technology Process of Gibberellin A6

There total 6 articles about Gibberellin A6 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: 81.0%

ent-3α-acetoxy-2α-chloro-13-hydroxy-20-norgibberell-16-en-19-oic acid 19,10-lactone (522654-08-6) → Gibberellin A6 (19147-78-5)

Guidance literature:

With potassium hydroxide; potassium carbonate; In methanol; at 20 ℃;

DOI:10.1016/S0031-9422(02)00447-8

Reference yield:

gibberellin A5 (561-56-8) → Gibberellin A6 (19147-78-5)

Guidance literature:

With air; alpha-ketoglute dipotassium; potassium ascorbate; iron(II) sulfate; In various solvent(s); at 30 ℃; for 1h; Yield given; partially purified gibberellin 3β-hydroxylase from immature seeds of Phaseolus vulgaris, pH 8.0;

Reference yield:

gibberellin A5 methyl ester (15355-45-0) → Gibberellin A6 (19147-78-5)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. NaOH / methanol / Heating

2: iPr₂NEt / CH₂Cl₂ / 2 h / 0 °C

3: 49 mg / N-methylmorpholine N-oxide; OsO₄; aq. p-toluenesulfonic acid / 2-methyl-propan-2-ol; acetone / 0.67 h / 0 °C

4: 33 percent / acetonitrile / 0.08 h / 40 °C

5: 81 percent / K₂CO₃; aq. KOH / methanol / 20 °C

With potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetone; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0031-9422(02)00447-8

upstream raw materials:

gibberellin A₅

ent-3α-acetoxy-2α-chloro-13-hydroxy-20-norgibberell-16-en-19-oic acid 19,10-lactone

gibberellin A₅ methyl ester

ent-2α,3α,13-trihydroxy-20-norgibberell-16-en-19-oic acid 19,10-lactone 7-methoxymethyl ester