Gibbane-1,10-dicarboxylic acid, 2,4a-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-

Base Information

• Chemical Name: Gibbane-1,10-dicarboxylic acid, 2,4a-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-
• CAS No.: 468-44-0
• Molecular Formula: C19H24O5
• Molecular Weight: 332.397
• European Community (EC) Number: 207-406-9
• Wikidata: Q75063263
• Metabolomics Workbench ID: 28577
• Mol file: 468-44-0.mol

Synonyms:gibberellin A4

Chemical Property of Gibbane-1,10-dicarboxylic acid, 2,4a-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 201 - 205oC
• Refractive Index: 1.615
• Boiling Point: 574.191 °C at 760 mmHg
• PKA: 4.24±0.60(Predicted)
• Flash Point: 210.438 °C
• PSA: 83.83000
• Density: 1.376 g/cm³
• LogP: 2.13620
• Storage Temp.: −20°C
• Solubility.: Soluble in methanol or ethanol. Also soluble in aqueous sodium b
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 332.16237386
• Heavy Atom Count: 24
• Complexity: 685

Purity/Quality:

99% ^*data from raw suppliers

Gibberellin A4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12C(CCC3(C1C(C45C3CCC(C4)C(=C)C5)C(=O)O)OC2=O)O
• Isomeric SMILES: CC12[C@H](CC[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@H](C4)C(=C)C5)C(=O)O)OC2=O)O
• Uses: Gibberellin A4 is a plant growth hormone that regulates growth and differentiation of plant cells for elongation, germination and enzyme induction. Gibberellin A4 has been used as a supplement in Murashige and Skoog (MS) media for enhancing plant growth.

Technology Process of Gibbane-1,10-dicarboxylic acid, 2,4a-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-

There total 17 articles about Gibbane-1,10-dicarboxylic acid, 2,4a-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)- 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: 95.0%

3-didehydroGA7 (2074-31-9) → gibberellin A4 (468-44-0)

Guidance literature:

With potassium dihydrogenphosphate; potassium tri-sec-butyl-borohydride; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1016/S0040-4039(01)92368-8

Reference yield: 80.0%

gibberellin A4 norketone (2074-32-0) → gibberellin A4 (468-44-0)

Guidance literature:

In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)88728-6

Reference yield: 17.0%

3-didehydroGA4 (2619-66-1) → gibberellin A4 (468-44-0) + 3-epi-gibberellin A4 (468-44-0,2934-94-3,19885-96-2,22553-18-0)

Guidance literature:

With potassium dihydrogenphosphate; potassium tri-sec-butyl-borohydride; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1016/S0040-4039(01)92368-8

upstream raw materials:

3-didehydroGA₇

3-didehydroGA₄

gibberellin A₄ norketone

(3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid

Downstream raw materials:

gibberellin A₄ methyl ester

C₂₆H₃₅N₂O₄⁽¹⁺⁾*Br^(1-)

C₂₆H₃₄N₂O₄

ent-3α-acetoxy-10-hydroxy-20-nor-15-oxogibberell-16-ene-7.19-dioic acid 19,10-lactone-7-phenacyl ester

Refernces

• 1、 Voigt, B.,Adam, G.. "Eine neue Partialsynthese von Gibberellin A4 und A7". . p. 263. Retrieved 2007/10/02.
• 2、 Bell, Russell A.,Turner, John V.. "STEREOSELECTIVE REDUCTION OF 3-KETO GIBBERELLIN ACIDS TO 3β-OLS USING K-SELECTRIDE WITH KH2PO4 BUFFER". . p. 4871 - 4872. Retrieved 2007/10/02.