20109-89-1

Basic information

• Product Name: (2Z,4E)-methyl 5-(1',4'-dihydroxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienoate
• CAS NO: 20109-89-1
• Molecular Weight: 280.364
• Mol File: 20109-89-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (2Z,4E)-methyl 5-(1',4'-dihydroxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z,4E)-methyl 5-(1',4'-dihydroxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienoate(20109-89-1)
• EPA Substance Registry System: (2Z,4E)-methyl 5-(1',4'-dihydroxy-2',6',6'-trimethyl-2'-cyclohexen-1'-yl)-3-methylpenta-2,4-dienoate(20109-89-1)

Safety Data

• Hazardous Substances Data: 20109-89-1(Hazardous Substances Data)

Upstream product

• 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 
• 6901-96-8 abscisic acid methylester 
• 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 
• 6901-90-2 (1'S,2E,4E)-5-(1'-Hydroxy-2',6',6'-trimethyl-4'-oxo-2'-cyclohexenyl)-3-methyl-2,4-pentadiensaeure-methylester 

Downstream Products

• 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 
• 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 
• 19598-75-5 5-<1-Hydroxy-6.6-dimethyl-2-methylen-Δ³-cyclohexenyl-(1)>-3-methyl-pentadien-(2trans.4trans)-saeuremethylester 
• 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 articles and documents

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.

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.

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.