561-56-8

Basic information

• Product Name: Gibberellin A5
• Synonyms: Gibberellin A5;4aα,7-Dihydroxy-1-methyl-8-methylenegibba-2-ene-1α,10β-dicarboxylic acid 1,4a-lactone;4aα,7-Dihydroxy-1β-methyl-8-methylenegibb-2-ene-1α,10β-dicarboxylic acid 1,4a-lactone;4aα,7-Dihydroxy-1β-methyl-8-methylenegibba-2-ene-1α,10β-dicarboxylic acid 1,4a-lactone;Bean factor II;(1R,4aR,4bR,7S,9aS,10S,10aR)-7-hydroxy-1-methyl-8-methylene-13-oxo-1,4,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;GA5
• CAS NO: 561-56-8
• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.37498
• Product Categories: Agro-Products, Chiral Reagents, Heterocycles
• Mol File: 561-56-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 573.8°Cat760mmHg
• Flash Point: 211.3°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1.48E-15mmHg at 25°C
• Refractive Index: 1.639
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: Gibberellin A5(CAS DataBase Reference)
• NIST Chemistry Reference: Gibberellin A5(561-56-8)
• EPA Substance Registry System: Gibberellin A5(561-56-8)

Safety Data

• Hazardous Substances Data: 561-56-8(Hazardous Substances Data)

Usage

Description

Gibberellin A5, a plant hormone, is primarily known for its role in promoting floral development in plants. It is a naturally occurring compound that belongs to the gibberellin family, which are a group of plant hormones that regulate various aspects of plant growth and development. Unlike some other gibberellins, Gibberellin A5 has a minimal impact on stem elongation, making it a more targeted option for specific applications.

Uses

Used in Agricultural Industry:
Gibberellin A5 is used as a growth regulator for promoting floral development in plants. Its application reason is to enhance the reproductive growth of plants, leading to increased fruit and seed production. This can be particularly beneficial for farmers and horticulturists looking to improve crop yields and quality.
Used in Plant Breeding:
Gibberellin A5 is used as a tool in plant breeding for the selection and development of new plant varieties with improved floral characteristics. Its application reason is to facilitate the manipulation of plant growth and development, allowing breeders to create plants with desired traits, such as earlier flowering, larger flowers, or increased resistance to environmental stressors.
Used in Research and Development:
Gibberellin A5 is used as a research tool for studying the molecular mechanisms underlying plant growth and development. Its application reason is to provide scientists with a means to investigate the role of gibberellins in various biological processes, such as cell division, elongation, and differentiation. This can lead to a better understanding of plant growth regulation and the potential development of new plant growth regulators or targeted therapies for specific agricultural applications.

InChI:InChI=1/C19H22O5/c1-10-8-17-9-18(10,23)7-4-11(17)19-6-3-5-16(2,15(22)24-19)13(19)12(17)14(20)21/h3,5,11-13,23H,1,4,6-9H2,2H3,(H,20,21)/t11-,12-,13-,16-,17+,18+,19-/m1/s1

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 
• 78259-50-4 ent-13-hydroxy-20-norgibberell-1,16-diene-7,19-dioic acid 19,10-lactone 
• 78259-47-9 1β-chlorogibberellin A₅ 
• 71472-13-4 ent-3β-chloro-10,13-dihydroxy-20-norgibberella-1,16-diene-7,19-dioic acid 19,10-lactone 
• 15355-45-0 gibberellin A₅ methyl ester 
• 510-50-9 gibberellic acid methyl ester 
• 65003-46-5 Gibberellin A₁ methyl ester 13-acetate 
• 75885-04-0 C₂₉H₃₂O₇S 
• 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 
• 5034-26-4 methyl 3-didehydrogibberellin A₃ 13-acetate 
• 75884-90-1 3-epi-gibberellin A₁ methyl ester 13-acetate 
• 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 
• 123592-49-4 C₁₉H₂₄O₅ 

Downstream Products

• 19147-78-5 Gibberellin A₆ 
• 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 
• 15355-45-0 gibberellin A₅ methyl ester 

Relevant articles and documents

Synthesis of gibberellin GA6 and its role in flowering of Lolium temulentum.

The induction of flowering by one long day (LD) in the grass Lolium temulentum is most closely mimicked by application of the gibberellins (GAs) GA(5) or GA(6), both of which occur naturally. These gibberellins promote floral development but have little effect on stem elongation. Endogenous GA(5) and GA(6) contents in the shoot apex double on the day after the LD and, for GA(5) (and we presume for GA(6) as well) reach a concentration known to be inductive for the excised shoot apex in vitro. They are, therefore, strong candidates as LD floral stimuli in this grass. The synthesis of GA(6) and an examination of its florigenic properties in L. temulentum are described.

A NOVEL EXPEDITIOUS ENTRY INTO GIBBERELLINS. THE TOTAL SYNTHESIS OF (+/-)-GA5

A 16-step synthesis of (+/-)-GA5 (12), starting from m-methoxybenzoic acid, is described.Refunctionalization of the kinetic cycloadduct 4, obtained in 96 percent yield from the Diels-Alder reaction of furan 3 in water in the presence of β-cyclo

Partial Synthesis of Gibberellin A9 and Gibberellin A9; Gibberellin A5 and Gibberellin A5; and Gibberellin A20 and Gibberellin A20

The 3α-alcohols, obtained by reduction of 3-didehydrogibberellin A3 methyl ester 13-acetate with lithium borohydride, borodeuteride, and borotritiide, have been converted into the 3β-chloro-derivatives and, hence, by reduction with tri-n-butylstannane followed by hydrolysis, into gibberellin A20, gibberellin A20, and gibberellin A20. Gibberellin A20 has been prepared from the product of the reduction of the 3-thiobenzoate of the 3α-alcohol with tri-n-butylstannane.The 3β-alcohols, minor products of these reductions, have been dehydrated and hydrolysed to give gibberellin A5 and gibberellin A5.The 3α-alcohol, from the lithium borohydride reduction of 3-didehydrogibberellin A7 has been transformed into the 3β-chloro-derivative and the 3-thiobenzoate which, with tri-n-butylstannane, or with tri-n-butylstannane, followed by hydrolysis, yielded gibberellin A9, gibberellin A9, or gibberellin A9.In an analogous way, the product of reduction of 3-didehydrogibberellin A4 with lithium borodeuteride was converted into gibberellin A9.The mass spectral fragmentation of the methyl esters and methyl ester trimethylsilyl ethers of gibberellins are also discussed.