14398-53-9

Usage

Uses

Used in Plant Growth and Development:
(-)-CIS, TRANS-ABSCISIC ACID is used as a growth regulator for promoting seed maturation and germination. It plays a crucial role in the plant's life cycle by ensuring proper development and growth.
Used in Environmental Stress Adaptation:
(-)-CIS, TRANS-ABSCISIC ACID is used as a stress response modulator for helping plants adapt to various environmental stresses, such as drought, high salinity, and cold temperatures. It aids in the plant's survival and resilience against unfavorable conditions.
Used in Agricultural Applications:
(-)-CIS, TRANS-ABSCISIC ACID is used as a bioactive compound in the agricultural industry for improving crop yield and quality. By enhancing the plant's stress tolerance and growth regulation, it contributes to better crop performance and increased productivity.
Used in Plant Biotechnology:
(-)-CIS, TRANS-ABSCISIC ACID is used as a research tool in plant biotechnology for understanding the molecular mechanisms underlying plant growth, development, and stress responses. It helps scientists develop genetically modified plants with improved traits, such as enhanced stress tolerance and higher yield potential.
Used in Plant Hormone Research:
(-)-CIS, TRANS-ABSCISIC ACID is used as a subject of study in plant hormone research to explore its role in various physiological processes and interactions with other plant hormones. This knowledge can be applied to develop new strategies for crop improvement and stress management in agriculture.

InChI:InChI=1/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-/t15-/m0/s1

Upstream product

• 41944-86-9 (2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal 
• 6153-05-5 (Z)-3-methylpent-2-en-4-ynol 
• 69350-44-3 (2Z,4E)-5-((R)-1-Hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-3-methyl-penta-2,4-dienal 
• 6901-90-2 (S)-methyl abscisate 
• 19041-17-9 methyl 4-bromo-3-methylbut-2-enoate 
• 51318-62-8 ethyl 4-bromo-3-methylcrotonate 
• 50-99-7 D-glucose 
• 21293-29-8 (2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid 
• 133-89-1 UDP-glucose 
• 124744-00-9 (2Z,4E)-5-<(1S,4S)-1,4-Dihydroxy-2,6,6-trimethyl-2-cyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal 
• 94618-21-0 (2Z)-3-methylpent-2-en-4-ynal dimethyl acetal 
• 52421-93-9 (2Z)-3-methyl-2-penten-4-ynal 
• 20109-89-1 (2Z,4E)-methyl 5-(1',4'-dihydroxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienoate 
• 20109-89-1 (2Z,4E)-methyl 5-(1',4'-dihydroxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienoate 

Downstream Products

• 6901-90-2 (S)-methyl abscisate 
• 24394-14-7 Phaseic-Saeure 
• 91897-25-5 (S)-7'-hydroxyabscisic acid 
• 721948-65-8 [3',5',5',7',7',7'-2H₆]-(+)-abscisic acid 
• 39701-87-6 methyl (2Z,4E)-5-((1S,4S)-1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid 
• 50464-90-9 methyl cis-1',4'-dihydroxy-α-ionylideneacetate 
• 1042697-12-0 (S)-(+)-abscisic acid sodium salt 
• 1042697-13-1 potassium salt of (S)-(+)-abscisic acid 
• 1042697-10-8 (S)-(+)-abscisic acid lithium salt 
• 1042432-69-8 (S)-(+)-abscisic acid ethanolamine salt 

Relevant academic research and scientific papers

A new megastigmane sulphoglycoside and polyphenolic constituents from pericarps of Garcinia mangostana

A megastigmane sulphoglycoside together with three phenolic compounds were isolated from the water-soluble fraction of the pericarps of Garcinia mangostana. The structure of the new compound was determined as 4-O-sulpho-β-d-glucopyranosyl abscisate (1) by spectroscopic data. Proanthocyanidin A2 (2) showed potent α-glucosidase inhibitory and DPPH scavenging activities with IC50values of 3.46 and 11.6 μM, respectively.

Synthesis and biological activity of abscisic acid esters

Abstract 16 ABA esters including 11 new compounds were prepared by two different esterification routes. All the structures of ABA esters were confirmed by 1H NMR, 13C NMR and HRMS. Their biological activity and hydrolysis stability were investigated. Fortunately, there were 15 and 9 compounds which displayed much better or nearly the same inhibition activity for rice seedling growth and Arabidopsis thaliana seed germination compared to ABA, respectively. Especially, compounds 2d and 2g showed better biological activities than ABA in the three tests. Moreover, we found that chemical hydrolysis ability of the esters in vitro had little relationship to their biological activity.

Concise enantioselective synthesis of abscisic acid and a new analogue

Short and high-yielding syntheses of enantiomerically pure (S)-(+) and (R)-(-)-abscisic acid are described. The syntheses proceed through key intermediates that preferentially recrystallise as single diastereoisomers for each enantiomer. This route allows the preparation of either enantiomer of abscisic acid in ca. 30% overall yield, and as demonstrated, gives access to an enantiomerically pure abscisic acid analogue. The Royal Society of Chemistry 2006.

Resolution of (+)-abscisic acid using an Arabidopsis glycosyltransferase

Abscisic acid (ABA) can exist as two enantiomers, with (+)-ABA as the naturally occurring form. Typically, both enantiomers occur in chemical preparations and both can be modified in the plant to their respective glucose esters. To identify glycosyltransferases capable of discriminating between the different forms of ABA, the Family 1 enzymes of Arabidopsis thaliana were screened for activity towards (±)-ABA. Eight enzymes were found to recognise the plant hormone, with one UGT71B6 showing enantioselective glucosylation towards (+)-ABA. UGT71B6 was used in a whole-cell biocatalysis system as a means of separating (+)- and (-)-ABA, thereby offering an alternative to chemical synthesis for the production of pure (+)-ABA.

Crop-selective herbicide

An agricultural chemical composition which comprises a first component having herbicidal activity selected from the group consisting of glyphosate and the like and a second component selected from the group consisting of phosphorus acid derivatives and the like and may further comprise a third component selected from maleic hydrazide and the like; and use of it as a plant growth retardant and crop selective herbicide.

Synthesis, Biological Activity, and Metabolism of 8′,8′,8′-Trideuteroabscisic Acid

An 8′,8′,8′-trideuterated analog of abscisic acid (ABA) was diastereoselectively synthesized as a new analog of ABA that is resistant to 8′-hydroxylation, the first metabolic reaction of ABA, owing to the primary kinetic isotope effect. (+)-8′,8′,8′-Trideutero-ABA showed long-term activity in the rice elongation assay. The rate of metabolism of this analog in rice cell suspension culture was about two fold slower than that of (+)-ABA. The concentration of 8′,8′-dideuterophaseic acid produced was about 1/3 that of phaseic acid converted from (+)-ABA. This result indicated that the long-lasting activity of the (+)-trideutero-ABA in the rice assay was the result of the delayed 8′-hydroxylation as expected.

Facile Preparation of Chiral Abscisic Acid

The asymmetric epoxidation of (+/-)-methyl (2Z,4E)-1',4'-dihydroxy-α-ionylideneacetates is described for the preparation of chiral abscisic acid.A conventional Sharpless kinetic resolution of (+/-)-1',4'-cis-dihydroxyacetate with diethyl L-tartrate and then two simple steps of conversion gave (S)-abscisic acid, which was also obtained by combination of (+/-)-1',4'-trans-dihydroxyacetate with diethyl D-tartrate.Finally, (S)-abscisic acid was obtained in a 25percent overall yield from the racemic mixture.

Convenient Syntheses of Optically Active Abscisic Acid and Xanthoxin

The Reformatzky reaction of 3-(bromomethyl)crotonate with an optically active epoxycyclohexane aldehyde derivative (3), followed by dehydration, gave the chiral dienoic acid (6) stereospecifically.The product was derived to optically active abscisic acid (1) and xanthoxin (2) successfully.

Syntheses of Chiral 4'-Hydroxy and 1',4'-Dihydroxy-γ-ionylideneacetic Acids, Fungal Biosynthetic Intermediates of Abscisic Acid

Both chiral 4'-hydroxy and 1',4'-dihydroxy-γ-ionylideneacetic acids (3, 4 and 5), biosynthetic intermediates of abscisic acid produced by Cercospora cruenta, were synthesized from a chiral starting material, (R)- or (S)-4-hydroxy-2,2-dimethyl-1-cyclohexanone (7). -Sigmatropic rearrangement of (S)-1-chloromethyl-3,3-dimethyl-5-tetrahydropyranyl(THP)oxy-1-cyclohexene (8), followed by the Reformatsky reaction with 4-bromo-3-methyl-2-butenoate (10) gave (1'R,4'S)-4.The diastereomeric isomer, (1'R,4'R)-3, was synthesized in the same manner.The reaction of (S)-2,2-dimethyl-5-methylene-4-THPoxy-1-cyclohexanone (14) with a Grignard reagent prepared from (Z)-3-methyl-2-penten-4-ynyl THP ether (15) and subsequent conversion of the side chain gave (1'S,4'S)-5.These synthetic compounds confirmed the stereochemistry of natural 3, 4 and 5.