468-44-0

Basic information

• Product Name: Gibberellin A4
• Synonyms: Einecs 207-406-9;Gibbane-1,10-dicarboxylicacid, 2,4a-dihydroxy-1-Methyl-8-Methylene-, 1,4a-lactone, (1a,2b,4aa,4bb,10b)-;gibberellina4plantcellculture*tested;GIBBERELLIC ACID A4;GIBBERELLIN A4;(1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a-dihydroxy-1-methyl-8-methylene-gibbane-1,10-dicarboxylic acid 1,4a-lactone;Gibbane-1,10-dicarboxylic acid, 2,4a-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,10beta)-;Giclazide
• CAS NO: 468-44-0
• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.39
• EINECS: 207-406-9
• Product Categories: FINE Chemical & INTERMEDIATES;Antibiotic Explorer;Miscellaneous Plant Growth Regulators;Plant Growth Regulators;Plant Tissue Culture
• Mol File: 468-44-0.mol

Chemical Properties

• Boiling Point: 574℃
• Flash Point: >110°(230°F)
• Appearance: /
• Density: 1.376 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: −20°C
• Solubility: Soluble in methanol or ethanol. Also soluble in aqueous sodium b
• PKA: 4.24±0.60(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: Gibberellin A4(CAS DataBase Reference)
• NIST Chemistry Reference: Gibberellin A4(468-44-0)
• EPA Substance Registry System: Gibberellin A4(468-44-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 468-44-0(Hazardous Substances Data)

Usage

Uses

Used in Plant Growth Regulation:
Gibberellin A4 is used as a growth regulator for promoting elongation, germination, and enzyme induction in plants, thereby enhancing their overall growth and development.
Used in Plant Tissue Culture:
Gibberellin A4 is used as a supplement in Murashige and Skoog (MS) media for enhancing plant growth during tissue culture processes, improving the success rate of plant regeneration and propagation.

Biochem/physiol Actions

Gibberillic acids (GA) are important plant growth hormones that promote plant cell growth and elongation. Gebberillins promote rapid stem and root growth, induce mitotic division and initiate (break dormancy) and increase seed germination rates. The gibberellins are also involved in processes such as gravitropism, tensioning and floral display.

InChI:InChI=1/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)/t10-,11-,12+,13-,14-,17-,18+,19-/m1/s1

Upstream product

• 2074-31-9 3-didehydroGA₇ 
• 2619-66-1 3-didehydroGA₄ 
• 2074-32-0 gibberellin A₄ norketone 
• 77-06-5 (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 
• 77584-35-1 +/-gibberellin A₄ 3-benzoate 
• 2348-07-4 C₁₉H₂₄O₆ 
• 77584-34-0 C₂₆H₂₈O₇ 

Downstream Products

• 113973-97-0 C₁₈H₂₂O₃ 
• 113888-88-3 C₁₉H₂₄O₃ 
• 561-68-2 gibberellin A2 
• 79368-09-5 GA₄ phenacyl ester 
• 63351-80-4 ent-3α,10,15α-trihydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone 
• 97344-09-7 C₂₉H₃₂O₇ 
• 97344-11-1 15α-hydroxyGA₄ 3-acetate-7-phenacyl ester 
• 97344-15-5 ent-3α-acetoxy-10-hydroxy-20-nor-15-oxogibberell-16-ene-7.19-dioic acid 19,10-lactone-7-phenacyl ester 
• 79679-63-3 C₂₆H₃₄N₂O₄ 
• 79684-48-3 C₂₆H₃₅N₂O₄⁽¹⁺⁾*Br^(1-) 
• 2074-29-5 gibberellin A₄ methyl ester 
• 79368-10-8 3-epiGA₄ phenacyl ester 
• 79368-21-1 2,3-didehydroGA₉ norketone phenacyl ester 
• 79368-19-7 GA₄ norketone phenacyl ester 

Relevant articles and documents

Probing the mechanism of loss of carbon-20 in gibberellin biosynthesis. Synthesis of gibberellin 3α,20-hemiacetal and 19,20-lactol analogues and their metabolism by a recombinant GA 20-oxidase

A gibberellin 3α,20-hemiacetal,1 (equivalent to 3-epi-gibberellin A36), has been synthesised from gibberellin A13. Turnover of this hemiacetal by recombinant gibberellin 20-oxidase occurred with loss of the 20-carbon atom to give the 20-nor-19,10-lactone (3-epi-gibberellin A4). In addition, two other enzyme products were detected and identified by synthesis as 3-epi-20-norgibberellin A13 and 3-epi-1,10-didehydro-20-norgibberellin A13. These by-products indicate that the enzymatic reaction proceeds via a C-10 radical intermediate. Carbon radicals at C-10 and acyl radicals at C-20 were generated chemically and their decomposition products were studied with reference to the biological mechanism. The corresponding 19-nor-3α,20-hemiacetal 3 and 19-methylene analogue 4 were synthesised but were not oxidised at C-20 by the enzyme. These results indicate that the 19-carboxylic acid is an essential component of the enzyme reaction.

METHYLENATION OF CARBONYL COMPOUNDS WITH Zn-CH2Br2-TiCl4.APPLICATIONS TO GIBBERELLINS

A highly active species prepared from Zn-CH2Br2-TiCl4 reacted instantaneously with aldehydes and ketones to give methylenated products with exceptional selectivity.

PREPARATION OF 2- AND 3-SUBSTITUTED GIBBERELLINS A9 AND A4 FOR BIOASSAY

Key Word Index - Partial synthesis; 2α,2β- and 3β-derivatives; gibberellin A4; gibberellin A9. To test the effects of preventing enzymatic 2β- and 3β-hydroxylation on the biological activities of gibberellins, the preparation of the following compounds is described: 2β-methyl- and 2,2-dimethyl-gibberellins A4 and A9; 2α-fluoro-, 2β-fluoro- and 2β-methoxy-gibberellin A9; and 3β-fluoro, 3β-methoxy-and 3-methylene A9.

STEREOSELECTIVE REDUCTION OF 3-KETO GIBBERELLIN ACIDS TO 3β-OLS USING K-SELECTRIDE WITH KH2PO4 BUFFER

KH2PO4 buffered K-Selectride gives with 3-keto gibberellin acids, borates which are reduced stereoselectively to 3β-ols.

TOTAL SYNTHESIS OF GIBBERELLIN A4

A general approach to the preparation of 13-deoxy C19 gibberellins has been established with the total synthesis of (+/-)gibberellin A4 (3).