19124-90-4

Usage

Uses

Used in Agricultural Applications:
Gibberellin A4 methyl ester is used as a growth regulator for promoting growth and development in plants. It stimulates cell elongation, seed germination, and fruit development, leading to increased crop yields and improved quality.
Used in Plant Tissue Culture:
In the field of plant tissue culture, gibberellin A4 methyl ester is used as a growth enhancer to improve the success rate of plant regeneration and the production of genetically identical plants.
Used in Dwarfism Research:
Gibberellin A4 methyl ester is utilized as a research tool in studying the effects of gibberellins on plant growth and dwarfism, helping scientists understand the underlying mechanisms and develop strategies to address growth-related issues in plants.
Used in Stress Resistance:
Gibberellin A4 methyl ester is employed as a stress resistance inducer, helping plants cope with various environmental stresses such as drought, salinity, and temperature fluctuations, thereby improving their overall resilience and survival.
Used in Plant Breeding:
In plant breeding, gibberellin A4 methyl ester is used as a tool to manipulate plant growth and development, enabling the creation of new plant varieties with desired traits such as increased height, improved fruit quality, or resistance to diseases.
Used in Pharmaceutical Applications:
Although not explicitly mentioned in the provided materials, gibberellin A4 methyl ester may also have potential applications in the pharmaceutical industry, particularly in the development of drugs targeting growth-related disorders or conditions. Further research would be required to explore these possibilities.

Upstream product

• 75884-80-9 methyl 3-didehydrogibberellin A₇ 
• 113359-70-9 ent-3α,10β-dihydroxy-16β,17-epoxy-20-norgibberellane-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 2074-29-5 3-epi-gibberellin A₄ methyl ester 
• 2348-07-4 gibberellin A₄ methyl ester nor-ketone 
• 186581-53-3 diazomethane 
• 2074-29-5 gibberellin A₄ methyl ester 
• 468-44-0 Gibberellin A₄ 
• 75884-80-9 ent-10β-hydroxy-3-oxo-20-norgibberell-1,16-diene-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 198990-73-7 ent-3α-acetoxy-10β-hydroxy-13-iodo-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 55732-63-3 ent-3α-acetoxy-13-hydroxy-gibberella-1,16-dien-7-oic acid 7-mehyl ester 19,10-lactone 
• 151670-90-5 ent-3α-acetoxy-10β-hydroxy-13-methylsulfonyloxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 53399-75-0 2β-acetoxy-4a,7-dihydroxy-1β-methyl-8-methylene-4aα,7β-gibbane-1α,10β-dicarboxylic acid-1=>4a lactone-10-methyl ester 
• 510-50-9 gibberellic acid methyl ester 

Downstream Products

• 2074-29-5 3-epi-gibberellin A₄ methyl ester 
• 2112-08-5 gibberellin A₉ 7-methyl ester 

Relevant academic research and scientific papers

GIBBERELLINS A82 and A83 IN SEED OF LUPINUS ALBUS

Extracts from seeds of Lupinus albus at 14, 22, 35 and 52 days after anthesis were seperated into free gibberellins, ester conjugates and ether conjugates.Capillary GC-MS of the methylated and trimethylsilylated free gibberellin fractions showed the presence of the known gibberellins A1, A3, A4, A17, A18, A23 and A43.In addition six new gibberellin-like compounds were detected that corresponded to the addition of the elements of water to gibberellins A3, A4, A7, A14, A18 and A34.Two of these components were identified by chemical syntheses as ent-3α,10β,17-trihydroxy-20-nor-16αHgibberellane-7,19-dioic acid 19,10-lactone and ent-3α,17-dihydroxy-16αHgibberellane-7,19-dioic acid, which are accorded the gibberellin numbers A82 and A83, respectively, ent-3α,10β,16β,17-tetrahydroxy-20-nor-16βHgibberellane-7,19-dioic acid 19,10-lactone was also identified by synthesis of the methyl ester.Similar analyses of the hydrolysed ether conjugate fractions showed the presence of the known gibberellins A1, A3, A13, A18 and A43, the new gibberellin A82 and the "hydrated" gibberellins A18 and A34; the 15-ene isomers of gibberellins A13 and A43 and the 16ξ17-epoxide of gibberellin A18 were also identified as probable artefacts.In the hydrolysed ester conjugate fractions the new gibberellin A82 and the "hydrated" gibberellin A34 were detected.Gibberellin A18 was by far the most abundant GA but quantitation of the GAs was not carried out.

3-EPI-GA63, ANTHERIDIOGEN IN ANEMIA PHYLLITIDIS

3-Epi-Gibberellin A63 (3-epi-GA63) was identified by full-scan GC-mass spectrometry of a purified extract from culture media of prothallia of the fern, Anemia phyllitidis.This is the third antheriodiogen, following antheridic acid and 3α-hydroxy-9,15-cyclo-GA9, in this species. 3-Epi-GA63 showed slightly less activity than antheridic acid in antheridial formation and dark spore germination assays. - Key words: Anemia phyllitidis; Schizaeaceae; fern; prothallia; antheridiogen; antheridic acid; 3-epi-gibberellin A63.

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.

Displacement of bridgehead sulfonate esters with organometallic reagents: Synthesis of 13-alkylated gibberellins

Gibberellin A3 is converted to 13-methyl GA4 in nine steps and 58% overall yield. A key step in the synthesis is the substitution of a bridgehead sulfonate ester by an alkyl group. A series of organometallic reagents have been investigated to effect this transformation; optimal yields are obtained from reaction of a methanesulfonate with a Gilman-type organocuprate in diethyl ether, in the presence of boron trifluoride-diethyl ether, thus enabling a variety of bridgehead substituents to be introduced in good to excellent yield.

Isolation and stereocontrolled synthesis of a 17-hydroxy-16β, 17-dihydrogibberellin, GA82

A 17-hydroxy-16β, 17-dihydrogibberellin, GA829, was first isolated from a fungus, Phaeosphaeria sp. L487, and was synthesized from naturally abundant GA41 in a highly stereocontrolled manner whose essential step was inversion of C(16) configuration of readily accessible 16β-formyl intermediate 5 to more stable 16α-epimer 6 by base treatment.

A New Method for the Deoxygenation of Tertiary and Secondary Alcohols

The derivatisation of alcohols as their methyl oxalyl esters is shown to be a convenient and selective method for deoxygenation by stannyl radicals.

N.m.r. Assignements of Ring A Hydrogens in Gibberellin A4 Methyl Esters and some Derivatives

Full assignements of the 1H n.m.r. chemical shifts of the ring A protons in gibberellin A4, 3-epi-gibberellin A4 and 3-oxogibberellin A4 methyl esters have been made on the basis of 1H and 2H n.m.r. data of -, -, and -labelled derivatives.These assignements have been used to determine the stereochemistry of the deuterium atoms in gibberellin A4 methyl ester, prepared via catalytic deuteriogenation of gibberellin A7 16,17-epoxide methyl ester.

Mechanism and Stereochemistry of Conjugate Reduction of Enones from Gibberellins A3 and A7

Conjugate reduction of the methyl esters of 3-didehydrogibberellin A3 13-acetate and of 3-didehydrogibberellin A7, in aprotic solvents by borohydride (or borodeuteride), is shown to introduce hydrogen (or deuterium) at the 1β- and 3β-positions in the products, 3-epi-gibberellin A1 13-acetate and 3-epi-gibberellin A4 methyl esters.The third hydrogen (or deuterium) comes from the proton (or deuteron) source used in the work-up.A mechanism for conjugate reduction of enones is proposed.The products from the borodeuteride reduction of 3-didehydrogibberellin A7 methyl ester with proton and deuteron work-up were chemically converted into -, -, and -gibberellin A4 and the stereochemistries of the deuterium atoms were determined from the deuterium content of the metabolites, formed from these labelled gibberellins in cultures of Gibberella fujikuroi, mutant B1-41a.