15355-41-6

Basic information

• Product Name: Gibberellin I
• Synonyms: Gibberellin I;7-Hydroxy-1-methyl-8-methylene-4aα,1α-(oxycarbonyl)gibbane-10β-carboxylic acid methyl ester
• CAS NO: 15355-41-6
• Molecular Formula: C20H26O5
• Molecular Weight: 346.41744
• Mol File: 15355-41-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Gibberellin I(CAS DataBase Reference)
• NIST Chemistry Reference: Gibberellin I(15355-41-6)
• EPA Substance Registry System: Gibberellin I(15355-41-6)

Safety Data

• Hazardous Substances Data: 15355-41-6(Hazardous Substances Data)

Upstream product

• 139113-38-5 ent-13-acetoxy-3,10β-dihydroxy-20-norgibberell-16-ene-17,19-dioic acid 7-methyl ester 19,10-lactone 3-S-methyl dithiocarbonate 
• 75885-03-9 gibberellin A₂₀ methyl ester 13-acetate 
• 139113-43-2 15α-hydroxygibberellin A₂₀ 7,15-lactone 
• 78148-91-1 C₂₀H₂₅ClO₅ 
• 2112-08-5 gibberellin A₉ methyl ester 
• 25274-39-9 3-epi-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 
• 75884-90-1 3-epi-gibberellin A₁ methyl ester 13-acetate 
• 5034-26-4 methyl 3-didehydrogibberellin A₃ 13-acetate 
• 75885-04-0 C₂₉H₃₂O₇S 
• 75885-01-7 3β-chloro-gibberellin A₂₀ methyl ester 13-acetate 
• 510-50-9 gibberellic acid methyl ester 

Relevant articles and documents

Hydrolysis of Gibberellin 7-Methyl Esters: Anchimeric Assistance by a 15-Alcohol

The neighbouring group effects of 15α- and 15β-hydroxy groups on the rate of hydrolysis of gibberellin 7-methyl esters are described.The presence of a 15-alcohol increases the rate of ester hydrolysis and a 15α- has a greater influence than a 15β-alcohol.The 15α-alcohol may be effective either through hydrogen bonding between the hydroxy proton and the ester carbonyl thus stabilising the tetrahedral intermediate formed on hydrolysis of the ester, or via 7,15α-lactonisation followed by hydrolysis of the lactone.The 15β-hydroxy may act through hydrogen bonding of a water molecule between the proton of the 15β-alcohol and the 7-carbonyl function.The effect is enhanced by the presence of a 13-acetate.

Metabolism of GA9 Methyl Ester in a Culture of Prothallia of Lygodium japonicum

GA9 methyl ester (GA9-Me) fed to a culture of prothallia of Lygodium japonicum was metabolized into three monohydroxy-GA9-Me after three weeks.One of these was identified as GA20-Me and the structures of the other two were defined to be 12α- and 12β-hydroxy-GA9-Me by spectroscopic analyses.

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.

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.