510-50-9

Usage

Uses

Used in Agriculture:
Gibberellic acid methyl ester is used as a growth stimulant for promoting germination, seedling growth, and fruit development in various crops. It helps in overcoming dormancy, improving fruit set, and enhancing overall crop yield.
Used in Horticulture:
In horticulture, gibberelic acid methyl ester is used as a growth regulator to encourage sprouting, flower induction, and to improve the quality and appearance of ornamental plants. It can also be used to break dormancy and synchronize flowering in certain species.
Used in Plant Tissue Culture:
Gibberellic acid methyl ester is used as a growth factor in plant tissue culture applications, where it aids in the development of plantlets from callus tissue and promotes root and shoot formation.
Used in Post-harvest Treatment:
Gibberellic acid methyl ester is used as a post-harvest treatment to enhance fruit ripening, improve fruit quality, and extend the shelf life of certain fruits and vegetables.
Used in Research:
In scientific research, gibberelic acid methyl ester is used as a tool to study the effects of Gibberellin on plant growth and development, as well as to investigate the underlying mechanisms of action and signaling pathways related to Gibberellin-responsive processes.

Upstream product

• 77-06-5 Gibberellic acid 
• 123972-87-2 O-Methyl (S)-prop-2-ynyl dithiocarbonate 
• 67-56-1 methanol 
• 77-06-5 gibberellic acid 
• 85622-93-1 temozolomide 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 81010-90-4 C₂₉H₃₅BrO₈Si 
• 80994-37-2 C₂₉H₃₄O₈Si 
• 80994-36-1 C₂₅H₃₈O₇Si₂ 
• 22969-10-4 C₂₆H₄₀O₆Si₂ 
• 186581-53-3 diazomethane 
• 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 
• 5034-25-3 ent-10β,13-dihydroxy-3-oxo-20-norgibberella-1,6-diene-7,19-dioic acid 19,10β-lactone 7-methyl ester 

Downstream Products

• 4747-53-9 gibberellin A₁ methyl ester 
• 62486-69-5 methyl 4α-carboxy-3β,13α-dihydroxy-4β-methyl-16-methylenegibb-1-ene-6β-carboxylate 
• 99475-54-4 C₄₂H₅₁NO₁₀Si 
• 546-09-8 gibberellenic acid 
• 107800-19-1 ent-3α,13-dihydroxy-20-norgibberella-1,9,16-triene-7,19-dioic acid 7-methyl ester 
• 78259-44-6 C₂₇H₂₉ClO₇S 
• 78259-43-5 ent-3β-chloro-10β,13-dihydroxy-7-methoxycarbonyl-20-norgibberella-1,16-dien-19-oic acd 19,10-lactone 
• 76236-19-6 4β-chloro-7-hydroxy-10β-methoxycarbonyl-1β-methyl-8-methylenegibb-2-ene-1α,4aα-carbolactone 
• 35413-59-3 ent-10β,13-dihydroxy-3α-p-tolylsulphonyloxy-20-norgibberella-1,16-diene-7,19-dioic acid 19,10β-lactone 7-methyl ester 
• 510-50-9 methyl 3-epi-gibberellin A₃ 
• 15355-45-0 gibberellin A₅ methyl ester 
• 330671-07-3 C₂₀H₂₄O₇ 
• 92470-69-4 methyl (16S)-16,17-epoxygibberellate 
• 2074-29-5 gibberellin A₄ methyl ester 

Relevant academic research and scientific papers

Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations

Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.

Syntheses of Gibberellins A15 and A24, the Key Metabolites in Gibberellin Biosynthesis

Gibberellins (GAs) are essential phytohormones involved in numerous aspects of plant growth and development. Notably, the biochemistry and genetics of GA biosynthesis, which is associated with their endogenous regulation, have been largely resolved; however, a crucial unsolved question remains: the precise mechanism of the stepwise oxidation and subsequent removal of C-20 from C20 precursors, leading to bioactive C19 gibberellins, is still unresolved. To satisfy numerous requests from biologists, practical preparations of certain GAs that were isolated in miniscule quantities are highly demanded. Herein, we report the first practical syntheses of GA15 and GA24, the key C20 metabolites in gibberellin biosynthesis, from commercially available GA3. The protocols are robust and offer the capacity to produce GA24 and GA15 under gram scales in high overall yields and thus aid in further biological and related studies.

Synthesis and anti-proliferative activity of allogibberic acid derivatives containing 1,2,3-triazole pharmacophore

Sixty novel allogibberic acid derivatives containing 1,2,3-triazole pharmacophore were designed and synthesized. The key chemical processes include aromatization of the A ring in gibberellins, formation of allogibberic azides and its copper mediated Huisgen 1,3-dipolar cycloaddition with alkynes. A number of hybrids containing α,β-unsaturated ketone moiety exhibited excellent in vitro cytotoxic activities. Some of the hybrids were more selective to MCF-7 and SW480 cell lines with IC50 values at least 8-fold more cytotoxic than cisplatin (DDP). The most potent compounds C43 and C45 are more cytotoxic than cisplatin (DDP) against all tested five tumor cell lines, with IC50 values of 0.25–1.72 μM. Mechanism of action studies indicated that allogibberic-triazole derivative C45 could induce the S phase cell cycle arrest and apoptosis in SMMC-7721 cell lines.

Synthesis and biological evaluation of pharbinilic acid and derivatives as NF-κB pathway inhibitors

A 7-step synthesis of pharbinilic acid, a member of the gibberellin family of natural products and the first naturally occurring allogibberic acid, is reported. An efficient decarboxylative aromatization reaction enables the synthesis of pharbinilic acid and related analogs for evaluation as modulators of NF-κB activity. Remarkably, one analog displays a 2 μM IC50 in an NF-κB activity assay and inhibits an endogenous NF-κB-regulated pathway.

Synthesis of sesquiterpene-inspired derivatives designed for covalent binding and their inhibition of the NF-κB pathway

A significant portion of bioactive secondary metabolites are endowed with reactive functionalities that can engage in covalent interactions with their target. Sesquiterpene lactones in particular are rich in Michael acceptors that react with cysteines. Several polycyclic scaffolds derived from total synthesis or readily available polycyclic terpenes were used as the starting point in the synthesis of a library aiming to project mildly reactive functionalities (Michael acceptors or chloroacetates) with diverse geometries. Screening of the library for inhibition of the NF-κB pathway revealed several potent inhibitors that are chemically readily accessible.

EXPEDITIOUS SYNTHESIS OF GIBBERLLIN A5 AND ESTERS THEREOF

An expeditious synthesis of gibberellin A5 (GA5) esters is presented, from which GA5 may be prepared. The synthesis offers an inexpensive route of few steps to these compounds, starting from gibberellin A3 (GA3) esters in the presence of a metal hydride.

Synthesis of gibberellin derivatives with anti-tumor bioactivities

A series of gibberellin based molecules were designed and synthesized. Gibberellin derivatives bearing two α,β-unsaturated ketone units showed strong anticancer activities in MTT assay towards a number of human cancer cell lines including HT29, A549, HepG

Confirmation of structure and synthesis of three new 11β-OH C20 gibberellins from loquat fruit

Three new 11β-hydroxy C20 gibberellins have been isolated from immature loquat fruit and their structures were established as 11β-hydroxy-GA12, 11β-hydroxy-GA15 and 11β-hydroxy-GA53, respectively, by direct GC-M

Some Rearrangements of Gibberellins Catalysed by Tetracyanoethylene

Tetracyanoethylene in methanol has been shown to catalyse the rearrangement of ring A of gibberellic acid to give the 3β-methyl ether of gibberellenic acid and 19-2α-isolactone whilst 13-hydroxygibberellin 16,17-epoxides are converted to 8:13-isogibberellins.

Unexpected C-arylation of a gibberellin: A cautionary note on the radical deoxygenation of homoallylic secondary alcohols

Aryl 3-O-thionocarbonates (7a-c), upon treatment with tributyltin hydride and a catalytic amount of AIBN in benzene at reflux, do not undergo deoxygenation as expected, but instead afford the 10-arylated bis-γ-lactones (8a-c) in high yields.