6755-41-5

Usage

Uses

Used in Pharmaceutical Industry:
5-(1-HYDROXY-2,6,6-TRIMETHYL-4-OXOCYCLOHEX-2-EN-1-YL)-3-METHYL-(2E,4E)-PENTADIENOIC ACID is used as an active pharmaceutical ingredient for its potential therapeutic properties. 5-(1-HYDROXY-2,6,6-TRIMETHYL-4-OXOCYCLOHEX-2-EN-1-YL)-3-METHYL-(2E,4E)-PENTADIENOIC ACID's unique structure may allow it to interact with specific biological targets, making it a candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, 5-(1-HYDROXY-2,6,6-TRIMETHYL-4-OXOCYCLOHEX-2-EN-1-YL)-3-METHYL-(2E,4E)-PENTADIENOIC ACID can be utilized as a starting material for the synthesis of other complex organic molecules. Its reactivity and functional groups may enable the creation of novel compounds with various applications.
Used in Material Science:
5-(1-HYDROXY-2,6,6-TRIMETHYL-4-OXOCYCLOHEX-2-EN-1-YL)-3-METHYL-(2E,4E)-PENTADIENOIC ACID may also find applications in material science, where its unique structure could be exploited to develop new materials with specific properties. These materials could be used in a range of industries, from electronics to aerospace.
Used in Agricultural Industry:
5-(1-HYDROXY-2,6,6-TRIMETHYL-4-OXOCYCLOHEX-2-EN-1-YL)-3-METHYL-(2E,4E)-PENTADIENOIC ACID can be used for the biological study and analysis of antioxidant properties and major components of plant extracts. This application can contribute to the understanding of the plant's potential benefits and uses in agriculture and the development of new products derived from these plants.

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-/m1/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 
• 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 
• 14398-53-9 (R)-(-)-abscisic acid 
• 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 
• 6153-05-5 (Z)-3-methylpent-2-en-4-ynol 
• 6901-90-2 (S)-methyl abscisate 
• 85718-96-3 (2Z,4E)-5-((1S,4S)-1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid 
• 123196-50-9 (1'S,4'S)-(Z)-5-(1'-Hydroxy-2',2'-dimethyl-6'-methylene-4'-tetrahydropyranyloxycyclohexyl)-3-methyl-2-penten-5-yl tetrahydropyranyl ether 
• 123196-50-9 (1'R,4'S)-(Z)-5-(1'-Hydroxy-2',2'-dimethyl-6'-methylene-4'-tetrahydropyranyloxycyclohexyl)-3-methyl-2-penten-5-yl tetrahydropyranyl ether 
• 123196-52-1 (-)-(1'R,4'S)-(Z)-5-(1',4'-Dihydroxy-2',2'-dimethyl-6'-methylenecyclohexyl)-3-methyl-2-penten-5-yn-1-ol 
• 123196-48-5 (+)-(4R)-2,2-Dimethyl-4-tetrahydropyranyloxy-1-cyclohexanone 
• 131319-96-5 (+)-(R)-4-Hydroxy-2,2-dimethyl-1-cyclohexanone 
• 851040-82-9 (+)-(2Z,4E)-methyl trans-1',4'-dihydroxy-γ-ionylideneacetate 

Downstream Products

• 6901-90-2 (S)-methyl abscisate 
• 24394-14-7 Phaseic-Saeure 
• 91897-25-5 (S)-7'-hydroxyabscisic acid 
• 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 
• 1559077-99-4 (S)-4-hydroxy-3,5,5-trimethyl-4-((1E,3Z)-5,5,5-trifluoro-3-methylpenta-1,3-dien-1-yl)cyclohex-2-enone 

Relevant academic research and scientific papers

Lignosulfonate Improves Photostability and Bioactivity of Abscisic Acid under Ultraviolet Radiation

Abscisic acid (ABA), as a commonly used plant growth regulator, is easy to be degraded and lose its bioactivity under sunshine. To select an eco-friendly and efficient photoprotectant for the improvement of photostability and bioactivity of ABA when exposed to ultraviolet (UV) light, we tested the effects of three biodegradable natural-derived high polymers, sodium lignosulfonates 3A [molecular weight (MW) > 50000, with degree of sulfonation (DS) of 0.48] and NA (20000 a high MW and low DS had a stronger UV absorption and the hollow aggregate micelles formatted by lignosulfonate protect ABA from UV damage. Approximately 50% more ABA was kept when 280 mg/L ABA aqueous solution was irradiated by UV light for 2 h in the presence of 2000 mg/L lignosulfonate 3A. The bioactivity on wheat (JIMAI 22) seed germination was greatly kept by 3A in comparison to that of ABA alone. The 300 times diluent of 280 mg/L ABA plus 2000 mg/L 3A after 2 h of irradiation showed 20.8, 19.3, and 9.3% more inhibition on shoot growth, root growth, and root numbers of wheat seed, separately, in comparison to ABA diluent alone. We conclude that lignosulfonate 3A was an eco-friendly and efficient agent to keep ABA activity under UV radiation. This research could be used in UV-sensitive and water-soluble agrichemicals and to optimize the application times and dosages of ABA products.

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.