Simple method for preparing gibberellin GA1

A gibberellin and gibberellin technology, which is applied in the field of simple preparation of gibberellin GA1, can solve the problems of limited application research, and achieve the effects of mild reaction conditions, low cost and easy operation

Inactive Publication Date: 2006-05-24
YUNNAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

while the homologue GA 1 It is a highly active gibberellin compound with significant plant growth regulation effect, but there is no fermentation method to produce GA 1 , thus limiting its application research

Method used

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  • Simple method for preparing gibberellin GA1
  • Simple method for preparing gibberellin GA1
  • Simple method for preparing gibberellin GA1

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 5.0 g gibberellin GA 3 Dissolve in 50 milliliters of methanol, add 10 milliliters of triethylamine and 0.5 gram of 5% palladium carbon (Pd-C), and flow hydrogen (H 2 ) reaction for several hours to tens of hours, silica gel thin layer chromatography (TLC) detection, after the reaction is complete, filter off palladium carbon (Pd-C), wash the filter residue with a little methanol, combine methanol, recover methanol under reduced pressure, and dissolve the residue In 100 ml of ethyl acetate, acidify to pH = 1.0 with hydrochloric acid, wash the filtrate with saturated brine, dry over anhydrous sodium sulfate, and concentrate to dryness in vacuo to obtain 4.6 g of light white solid (1) (yield 92%). Melting point mp: 165~168℃.

[0016] 1 H-NMR (300MHz, D-Pyridine): δ: 5.51 (1H, brs), 5.48 (1H, brs), 5.10 (1H, brs), 4.70 (1H, brs), 4.00 (2H, brs), 3.50- 3.20 (2H, m), 3.4 (1H, brs), 2.80-2.50 (3H, m), 2.30-2.00 (5H, m), 1.94 (3H, S, CH3).

[0017] 13 C-NMR (75.5MH2, D-Pyr...

Embodiment 2

[0022] 5.0 g gibberellin GA 3 Dissolve in 50 ml of ethyl acetate, add 10 ml of triethylamine and 0.5 g of 5% palladium on carbon (Pd-C), and flow hydrogen (H 2 ) reaction for several hours to tens of hours, silica gel thin layer chromatography (TLC) detection, after the reaction is complete, filter off palladium carbon (Pd-C), wash the filter residue with a little ethyl acetate, combine ethyl acetate, and recover the solvent under reduced pressure , the residue was dissolved in 100 ml of ethyl acetate, acidified with hydrochloric acid to pH = 1.0, and the filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated to dryness in vacuo, and crystallized with acetone / petroleum ether to obtain a light white solid (1) 4.5 g (90% yield).

Embodiment 3

[0024] 8.0 g gibberellin GA 3 Dissolve in 50 ml of ethyl acetate, add 10 ml of pyridine and 0.9 g of 5% palladium on carbon (Pd-C), and flow hydrogen (H 2 ) reaction for several hours to tens of hours, silica gel thin layer chromatography (TLC) detection, after the reaction is complete, filter off palladium carbon (Pd-C), wash the filter residue with a little ethyl acetate, combine ethyl acetate, and recover the solvent under reduced pressure , the residue was dissolved in 100 ml of ethyl acetate, acidified with hydrochloric acid to PH=1.0, and the filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated in vacuo to dryness, and recrystallized with acetone / petroleum ether to obtain a light white solid (1 ) 7.5 g (94% yield).

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Abstract

The invention surfactant a simple and convenient method for preparing gibberellin GA1 (3beta, 10 alpha, 13 alpha-trihydroxyl-20-decarbonized Gibberella-16-alkene-7, 19-diacid-19, 10 inner ester), using the GA3 produced by industrialized fermenting method as initial raw material, and making a series of easy-to-industrialize chemical reactions to synthesize and obtain the GA1. And the invention dissolves the GA3 in the solvent such as alcohol, adds in organic alkali such as triethylamine and Pt / Pd in a certain proportion as catalyst, feeds hydrogen gas (H2) to make reaction at room temperature, then making halogen inner esterification on the hydrogenated products, and recrystallizes the products of the halogen inner esterification, and then eliminating the halogens from the recrystallized products under the condition of Zn and hydrated nickel chloride (Zn / NiCl2.XH2O) or sodium hydrosulfide so as to obtain the target products GA1. And the invention has the advantages of moderate reacting conditions, lower cost, easy operation, and being adaptive to industrialized production.

Description

technical field [0001] The present invention relates to a compound GA with structural formula (I) 1 (3β, 10α, 13α-trihydroxy-20-anorcarb-16-ene-7,19-bisacid-19-10 lactone). [0002] Background technique [0003] Gibberellins (Gibberellins, GA) are tetracyclic diterpenoids, which are endogenous plant growth regulators widely present in plants. So far, 129 such substances have been isolated and identified from plants. Gibberellins have the functions of promoting plant cell division, cell elongation, leaf enlargement, stem elongation, side branch growth, bolting, promoting male flower formation of hermaphrodite flowers, and promoting seed germination and fruit growth. Gibberellic acid GA 3 (Chinese product name 920) has been used in my country for nearly 30 years, and it has the strongest activity in promoting the elongation of plant fruit cells. It has been widely used in the cultivation of various crops, and has remarkable economic benefits. It is still the plant growt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/77
Inventor 张洪彬吴松福陈静波刘建平李良刘小龙杨万松朱洁赵静峰
Owner YUNNAN UNIV
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