20109-89-1

Upstream product

• 6901-90-2 (1'S,2E,4E)-5-(1'-Hydroxy-2',6',6'-trimethyl-4'-oxo-2'-cyclohexenyl)-3-methyl-2,4-pentadiensaeure-methylester 
• 6901-96-8 abscisic acid methylester 
• 186581-53-3 diazomethane 
• 20110-02-5 (+/-)-abscisic acid cis-1',4'-diol 
• 21293-29-8 (2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid 
• 122346-87-6 C₁₈H₂₆O₅ 
• 79434-13-2 (+)-(S)-5-(1'-Hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-3-methylpenta-2,4-diensaeure-methylester 

Downstream Products

• 19598-75-5 5-<1-Hydroxy-6.6-dimethyl-2-methylen-Δ³-cyclohexenyl-(1)>-3-methyl-pentadien-(2trans.4trans)-saeuremethylester 
• 2228-72-0 Abscisic acid 
• 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 
• 19598-74-4 5-<1-Hydroxy-6.6-dimethyl-2-methylen-Δ³-cyclohexenyl-(1)>-3-methyl-pentadien-(2cis.4trans)-saeuremethylester 
• 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 
• 6901-90-2 (S)-methyl abscisate 
• 130847-04-0 (3'R,4'S)-5-(3',4'-Dihydroxy-2',6',6'-trimethylcyclohex-1'-enyl)-3-methylpenta-2,4-diensaeure-methylester 
• 130930-83-5 (3'S,4'S)-5-(3',4'-Dihydroxy-2',6',6'-trimethylcyclohex-1'-enyl)-3-methylpenta-2,4-diensaeure-methylester 
• 130847-03-9 (3'RS,4'S)-5-(3',4'-Diacetoxy-2',6',6'-trimethylcyclohex-1'-enyl)-3-methylpenta-2,4-diensaeure-methylester 
• 130856-61-0 (+)-(1'S,4'S)-5-(4'-Acetoxy-1'-hydroxy-2',6',6'-trimethylcyclohex-2-enyl)-3-methylpenta-2',4'-diensaeure-methylester 
• 130856-62-1 (+)-(1'S,4'R)-5-(4'-Acetoxy-1'-hydroxy-2',6',6'-trimethylcyclohex-2-enyl)-3-methylpenta-2',4'-diensaeure-methylester 

Relevant academic research and scientific papers

Synthesis, structural characterization and effect on human granulocyte intracellular cAMP levels of abscisic acid analogs

The phytohormone abscisic acid (ABA), in addition to regulating physiological functions in plants, is also produced and released by several mammalian cell types, including human granulocytes, where it stimulates innate immune functions via an increase of the intracellular cAMP concentration ([cAMP]i). We synthesized several ABA analogs and evaluated the structure-activity relationship, by the systematical modification of selected regions of these analogs. The resulting molecules were tested for their ability to inhibit the ABA-induced increase of [cAMP]i in human granulocytes. The analogs with modified configurations at C-2′ and C-3′ abrogated the ABA-induced increase of the [cAMP]i and also inhibited several pro-inflammatory effects induced by exogenous ABA on granulocytes and monocytes. Accordingly, these analogs could be suitable as novel putative anti-inflammatory compounds.

Asymmetrical ligand binding by abscisic acid 8′-hydroxylase

Abscisic acid (ABA), a plant stress hormone, has a chiral center (C1′) in its molecule, yielding the enantiomers (1′S)-(+)-ABA and (1′R)-(-)-ABA during chemical synthesis. ABA 8′-hydroxylase (CYP707A), which is the major and key P450 enzyme in ABA catabol

Biosynthesis of Abscisic Acid by the Non-mevalonate Pathway in Plants, and by the Mevalonate Pathway in Fungi

The biosynthetic pathways to abscisic acid (ABA) were investigated by feeding [1-13C]-D-glucose to cuttings from young tulip tree shoots and to two ABA-producing phytopathogenic fungi. 13C-NMR spectra of the ABA samples isolated showed that the carbons at 1, 5, 6, 4′, 7′ and 9′ of ABA from the tulip tree were labeled with 13C, while the carbons at 2, 4, 6, 1′, 3′, 5′, 7′, 8′ and 9′ of ABA from the fungi were labeled with 13C.The former corresponds to C-1 and -5 of isopentenyl pyrophosphate, and the latter to C-2, -4 and -5 of isopentenyl pyrophosphate. This finding reveals that ABA was biosynthesized by the non-mevalonate pathway in the plant, and by the mevalonate pathway in the fungi. 13C-Labeled ss;-carotene from the tulip tree showed that the positions of the labeled carbons were the same as those of ABA, being consistent with the biosynthesis of ABA via carotenoids. Lipiferolide of the tulip tree was also biosynthesized by the non-mevalonate pathway.

Preparation and analysis of some acetosugar esters of abscisic acid and derivatives

Racemic abscisic acid (ABA), the cis and trans 1′, 4′-diols (ABA diols) derived from ABA by reduction of the 4′ ketone, and the corresponding 4′-O-acetates were converted into various acetosugar esters by reaction of their cesium salts with the 1-chloroacetosugars derived from glucose, galactose, lactose, and maltose. Analytical separations of the acetosugar esters using high-performance liquid chromatography (LC) on reverse-phase columns were developed. Continuous flow secondary ion mass spectra (CFSIMS) of the various acetosugar esters were obtained and an LC/CFSIMS protocol employing multiple reaction monitoring was used to detect ABA acetoglucose ester in an acetylated extract obtained from plant cells that had been treated with ABA.

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.

Synthese der (3S,4R,3'S,4'R)- und (3S,4S,3'S,4'S)-Crustaxanthine sowie weiterer Verbindungen mit 3,4-Dihydroxy-β-Endgruppen

Starting from 3, the enantiomerically pure title compounds were synthesized in eight steps.Spectra and HPLC systems are presented that allow a distinction between these isomers.