2112-08-5

Basic information

• Product Name: GIBBERELLIN A9 METHYL ESTER
• Synonyms: 4aalpha,4bbeta-Gibbane-1alpha,10beta-dicarboxylic acid, 4a-hydroxy-1-methyl-8-methylene-, 1,4a-lactone, methyl ester;GA9, methyl ester;Gibbane-1,10-dicarboxylic acid, 4a-hydroxy-1-methyl-8-methylene-, 1,4a-lactone, 10-methyl ester, (1alpha,4aalpha,4bbeta,10beta)-;Gibberelline GA9, methyl ester;GIBBERELLIN A9 METHYL ESTER;(4bβ)-1α,4aα-(Carbonyloxy)-1-methyl-8-methylenegibbane-10β-carboxylic acid 10-methyl ester;1-Methyl-8-methylene-13-oxo-4aα,1α-(epoxymethano)gibbane-10β-carboxylic acid methyl ester;(1R,4aR,4bR,7R,9aR,10S,10aR)-methyl 1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate
• CAS NO: 2112-08-5
• Molecular Formula: C20H26O4
• Molecular Weight: 330.42
• Product Categories: Miscellaneous Plant Growth Regulators;Plant Growth Regulators;Plant Tissue Culture
• Mol File: 2112-08-5.mol

Chemical Properties

• Appearance: /
• Refractive Index: 1.566
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• Stability: Light Sensitive
• CAS DataBase Reference: GIBBERELLIN A9 METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: GIBBERELLIN A9 METHYL ESTER(2112-08-5)
• EPA Substance Registry System: GIBBERELLIN A9 METHYL ESTER(2112-08-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2112-08-5(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Gibberellin A9 Methyl Ester is used as a plant growth regulator for promoting growth, increasing fruit size, and improving crop yield. It can also be used to break dormancy in seeds and stimulate germination, as well as to prevent fruit drop and promote fruit setting.
Used in Plant Research:
Gibberellin A9 Methyl Ester is used as a research tool for studying the role of Gibberellin in plant growth and development. It can be used to investigate the molecular mechanisms underlying Gibberellin signaling and its interactions with other plant hormones.
Used in Commercial Plant Production:
Gibberellin A9 Methyl Ester is used in commercial plant production to enhance the growth and quality of ornamental plants, as well as to improve the yield and quality of agricultural crops. It can be applied as a foliar spray or soil drench to provide a controlled release of the hormone to the plants.
Used in Seed Germination:
Gibberellin A9 Methyl Ester is used to promote seed germination, particularly in seeds that require specific hormonal conditions for germination. It can be applied to seeds to break dormancy and stimulate germination, leading to faster and more uniform seedling growth.
Used in Fruit Ripening:
Gibberellin A9 Methyl Ester is used to promote fruit ripening and improve fruit quality. It can be applied to fruits to stimulate the ripening process, leading to improved color, texture, and flavor.
Used in Turfgrass Management:
Gibberellin A9 Methyl Ester is used in turfgrass management to control the growth of grass and improve its overall appearance. It can be applied to turfgrass to reduce the growth rate, promote a more compact and uniform growth, and improve the overall quality of the turf.
Used in Plant Tissue Culture:
Gibberellin A9 Methyl Ester is used in plant tissue culture to manipulate plant growth and development during in vitro propagation. It can be used to regulate the growth of plantlets and improve the success rate of plant tissue culture techniques.
Used in Plant Stress Management:
Gibberellin A9 Methyl Ester is used to manage plant stress, particularly in response to environmental factors such as drought, salinity, and temperature fluctuations. It can be applied to plants to enhance their stress tolerance and improve their overall health and productivity.

InChI:InChI=1/C20H26O4/c1-11-9-19-10-12(11)5-6-13(19)20-8-4-7-18(2,17(22)24-20)15(20)14(19)16(21)23-3/h12-15H,1,4-10H2,2-3H3/t12-,13-,14-,15?,18-,19+,20-/m1/s1

Upstream product

• 2074-29-5 gibberellin A₄ methyl ester 
• 186581-53-3 diazomethane 
• 427-77-0 GA₉ 
• 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 
• 75885-06-2 C₂₇H₃₀O₅S 
• 2074-29-5 3-epi-gibberellin A₄ methyl ester 
• 510-50-9 gibberellic acid methyl ester 
• 2270-55-5 ent-10β,16β-dihydroxy-13-methyl-17,20-bisnor-8,13-isogibberellane-7,19-dioic acid 19,10β-lactone 7-methyl ester 
• 78097-94-6 ent-3α,13-dichloro-10β-hydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10β-lactone 7-methyl ester 
• 75885-05-1 ent-3α-chloro-10β-hydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10β-lactone 7-methyl ester 
• 92134-58-2 C₂₇H₃₄O₇S 
• 87667-58-1 C₂₁H₃₀O₇S 
• 427-77-0 Gibberellin-A⁽⁹⁾ 

Downstream Products

• 55812-47-0 15β-hydroxy-GA₉ 
• 55812-47-0 15α-hydroxy-GA₉ 
• 15355-41-6 gibberellin A₂₀ methyl ester 
• 95721-71-4 12α-hydroxy-GA₉-Me 
• 95721-72-5 12β-hydroxy-GA₀-Me 
• 427-77-0 Gibberellin-A⁽⁹⁾ 

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.

A New Method for the Deoxygenation of Tertiary and Secondary Alcohols

The derivatisation of alcohols as their methyl oxalyl esters is shown to be a convenient and selective method for deoxygenation by stannyl radicals.

The Partial Synthesis of Beyergibberellin A4 and A9 Methyl Esters

Beyergibberellins A4 and A9 methyl esters were synthesized from methyl gibberellate via gibberellin A1 methyl ester and its 3-epimer.The C/D ring junction of the 3-epimer was isomerized to afford the 16-oxo-8,13-isogibberellin and 3-hydroxy group removed by tributyltin hydride reduction of the corresponding chloride.Alternatively the C/D ring junction of the gibberellin A1 methyl ester was isomerized and the 3-hydroxy group was converted into its trimethylsilylethoxymethyl derivative.Reduction of the 16-ketones and elimination of the corresponding 16-sulphonate esters over alumina or with collidine afforded the title compounds.

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.