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

Uses

Gibberellin A5 is a plant hormone which promotes floral development but have little effect on stem elongation.

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

• 78259-47-9 1β-chlorogibberellin A₅ 
• 123592-49-4 C₁₉H₂₄O₅ 
• 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 
• 75884-90-1 3-epi-gibberellin A₁ methyl ester 13-acetate 
• 5034-26-4 methyl 3-didehydrogibberellin A₃ 13-acetate 
• 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 
• 65003-46-5 Gibberellin A₁ methyl ester 13-acetate 
• 510-50-9 gibberellic acid methyl ester 
• 15355-45-0 gibberellin A₅ methyl ester 
• 71472-13-4 ent-3β-chloro-10,13-dihydroxy-20-norgibberella-1,16-diene-7,19-dioic acid 19,10-lactone 
• 78259-50-4 ent-13-hydroxy-20-norgibberell-1,16-diene-7,19-dioic acid 19,10-lactone 
• 75885-02-8 ent-13-acetoxy-10-hydroxy-20-norgobberella-2,16-diene-7,19-dioic acid 19,10-lactone 7-methyl ester 
• 129082-39-9 C₁₉H₂₃IO₅ 

Downstream Products

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

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.