15355-45-0

Usage

Uses

Used in Agricultural Industry:
Gibberellin A5 Methyl Ester is used as a growth regulator for enhancing plant growth and development. It is particularly effective in promoting floral development, which can lead to increased fruit and seed production. This application is beneficial for improving crop yields and quality in various agricultural settings.
Used in Plant Research:
In the field of plant biology and research, Gibberellin A5 Methyl Ester is used as a tool to study the effects of plant hormones on growth and development. By manipulating the levels of GIBBERELLIN A5 METHYL ESTER, researchers can gain insights into the underlying mechanisms of plant growth regulation and identify potential targets for crop improvement.
Used in Plant Tissue Culture:
Gibberellin A5 Methyl Ester is also used in plant tissue culture as a growth-promoting agent. It can help in the successful propagation of plants by influencing cell division and elongation, which are essential for the development of new plantlets from tissue culture explants.
Used in Ornamental Plant Industry:
In the ornamental plant industry, Gibberellin A5 Methyl Ester is used to control plant growth and enhance the aesthetic appeal of plants. By regulating the balance between vegetative and reproductive growth, GIBBERELLIN A5 METHYL ESTER can help in producing plants with desired characteristics, such as increased flower production or improved branching patterns.

Upstream product

• 75885-02-8 ent-13-acetoxy-10-hydroxy-20-norgobberella-2,16-diene-7,19-dioic acid 19,10-lactone 7-methyl ester 
• 4747-53-9 gibberellin A₁ methyl ester 
• 5034-25-3 ent-10β,13-dihydroxy-3-oxo-20-norgibberella-1,6-diene-7,19-dioic acid 19,10β-lactone 7-methyl ester 
• 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 
• 109950-80-3 ent-13-acetoxy-3α,10β-dihydroxy-1α-iodo-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 35584-82-8 ent-13-acetoxy-3α,10β-dihydroxy-20-norgibberell-1,16-diene-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 65003-46-5 Gibberellin A₁ methyl ester 13-acetate 
• 561-56-8 gibberellin A₅ 
• 510-50-9 gibberellic acid methyl ester 
• 63693-24-3 gibberellin A₅ β-D-(2,3,4,6-tetra-O-acetyl)glucopyranosyl ester 
• 76236-19-6 4β-chloro-7-hydroxy-10β-methoxycarbonyl-1β-methyl-8-methylenegibb-2-ene-1α,4aα-carbolactone 
• 78259-43-5 ent-3β-chloro-10β,13-dihydroxy-7-methoxycarbonyl-20-norgibberella-1,16-dien-19-oic acd 19,10-lactone 

Downstream Products

• 561-56-8 gibberellin A₅ 
• 19147-78-5 Gibberellin A₆ 

Relevant academic research and scientific papers

Preparation and Occurrence of Gibberellins A75 and A76 and 3-Epi-A72

Three water-soluble compounds were detected in extracts from mature seeds of Helianthus annuus by g.l.c.-mass spectrometry.The structures of these putative gibberellins were confirmed by comparison with authentic samples of the 15β-hydroxygibberellins GA75, GA76, and 3-epi-GA72 prepared from GA3.

An efficient method for the reductive transposition of allylic alcohols

The Mitsunobu reaction of allylic alcohols with o- nitrobenzenesulfonylhydrazine (NBSH) as nucleophile proceeds at -30 °C with invertive displacement; warming the resultant N-allylic sulfonylhydrazine derivative to 23 °C then leads to allylic diazene formation followed by sigmatropic elimination of dinitrogen. This one-step method for reductive 1,3-transposition is shown to be efficient and highly regio- and stereocontrolled within a wide range of allylic alcohol substrates.

Synthesis of 13-O-β-D-Glucopyranosylgibberellin A5 β-D-Glucopyranosyl Ester

13-O-β-D-Glucopyranosylgibberellin A5 β-D-glucopyranosyl ester (2a) was synthesized by base-catalyzed (triethylamine) reaction of gibberellin A5 13-O-β-D-glucopyranoside (4a) with α-acetobromoglucose followed by mild sodium methanolate deacetylation.Structures of the gibberellin A5 glucosyl conjugates were established by LSI-MS, ESI-MS, and 1H-NMR spectroscopy. - Key Words: Gibberellins / Plant hormones / Glucosyl conjugates / Hormones / Koenigs-Knorr reactions

Allylic Chlorination of Gibberellins A3 and A7 Methyl Esters and of Gibberellin A3: Preparation of Gibberellin A5

A high-yield conversion of gibberellin A3 to gibberellin A5 is described.With thionyl chloride, gibberellin A3 methyl ester gives mainly 1β-chlorogibberellin A5 methyl ester; the isomeric 3α-chloro-1-ene was the main product from the reaction with toluene-p-sulphonyl chloride and lithium chloride.Each product is reduced by tri-n-butylstannane and acetylated to give the same mixture of the 13-acetates of gibberellin A5 methyl ester and of the isomeric 1(10)-ene-19,2-lactone.Hydrolysis of gibberellin A5 methyl ester 13-acetate gives gibberellin A5 in 20percent overall yield from gibberellin A3. 2H1>Gibberellin A5 is obtained in the same way by using tri-n-butyl2H1>stannane in the reduction step.Analogous chlorination products of gibberellin A7 methyl ester and of gibberellin A3 are described.

Preparation of Gibberellins A9 and A20 from Gibberellic Acid

Methyl gibberellate has been converted via the methyl ester of 3-epigibberellin A1 into the 3β-chloro- and 3β,13-dichloro-derivatives using triphenylphosphine and carbon tetrachloride.Hydrogenolysis of the chlorides with tributyltin hydride afforded gibberellins A20 and A9 as their methyl esters.Gibberellin A9 methyl ester was also prepared from the gibberellin A4/A7 mixture.The stereochemistry of the conjugate reduction of the ring-A-unsaturated ketone is defined.