7200-31-9

Upstream product

• 186581-53-3 diazomethane 
• 2228-72-0 Abscisic acid 
• 851040-82-9 (+)-(2Z,4E)-methyl trans-1',4'-dihydroxy-γ-ionylideneacetate 
• 23069-06-9 4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-carbonsaeure-ethylester 
• 21293-29-8 (2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid 
• 14398-53-9 (R)-(-)-abscisic acid 
• 122346-87-6 C₁₈H₂₆O₅ 
• 122346-75-2 (+)-(1R,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-methanol 
• 122346-85-4 (-)-(1S,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-carbaldehyd 
• 23069-07-0 4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol 
• 6755-41-5 (2-trans,4-trans)-abscisic acid 
• 2228-72-0 (±)-2-trans,4-trans-abscisic acid 
• 77-78-1 dimethyl sulfate 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 132340-89-7 (2E,4E)-5-((1R,4R)-1,4-Dihydroxy-2,6,6-trimethyl-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid methyl ester 
• 153630-65-0 methyl (2Z,4E)-5-(1'-hydroxy-4'-methoxycarbonyloxy-2',6',6'-trimethylcyclohexa-2',4'-dienyl)-3-methylpenta-2,4-dienoate 

Relevant academic research and scientific papers

(S)-3′-methyl-abscisic acid and esters thereof

The invention relates to (S)-3′-methyl-abscisic acid, and esters thereof, and methods of using and making these compounds.

3'-SUBSTITUTED-ABSCISIC ACID DERIVATIVES

The invention relates to a novel class of (S)-3′-substituted-abscisic acid derivatives and (±)-3′-substituted-abscisic acid derivatives, and methods of synthesizing the derivatives.

(S)-2′-vinyl-abscisic acid derivatives

The invention relates to a novel class of (S)-2′-vinyl-substituted-abscisic acid derivatives, and to methods of synthesizing and using the derivatives.

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.

(S)-3'-METHYL-ABSCISIC ACID AND ESTERS THEREOF

The invention relates to (S)-3′-methyl-abscisic acid, and esters thereof, and methods of using and making these compounds.

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.

Electrolytic reduction of abscisic acid methyl ester and its free acid

Abscisic acid (ABA, 1), a plant hormone, has electrophilicity derived almost entirely from the side-chain, 3-methylpenta-2,4-dienoic acid. The electrochemical property of ABA was investigated by analysis of its cathodic reaction. ABA methyl ester (1-Me) w

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

Mechanism of the formation of a dehydrated ion by an unusual loss of oxygen at the 4′-carbonyl group of abscisic acid methyl ester in electron ionization mass spectrometry

Methyl ester of abscisic acid (ABA), a plant hormone, gives a dehydrated ion at m/z 260 in electron ionization mass spectrometry (EI-MS). This dehydrated ion had been considered to be derived only from the elimination of the tertiary hydroxyl group at C-1′. We found that 34% of the dehydrated ion was formed by elimination of the oxygen atom at the 4′-carbonyl group, and the remaining 66% by elimination of the 1′-hydroxyl group. This unusual elimination of the carbonyl oxygen was shown with [4′-18O]ABA methyl ester. Involvement of the 4′-carbonyl oxygen in dehydration was observed in methyl ester of phaseic acid (PA), a natural metabolite of ABA, but not in 1′-deoxy-ABA methyl ester or isophorone. This suggested that the 1′-hydroxyl group was necessary for the elimination of the 4′-carbonyl oxygen. ABA methyl esters labeled with stable isotopes showed that hydrogen atoms at the 1′-hydroxyl group and at C-4 or -5 or -3′ or - 5′ or -7′ were eliminated with the 4′-carbonyl oxygen. These results allow us to propose a formation mechanism of the dehydrated ion derived from the elimination of 4′-carbonyl oxygen and hydrogen atoms at C-4 and 1′-oxygen in ABA methyl ester as follows: first, ionization at the 1′-hydroxyl group occurs to give an ion radical, and the proton at the 1′-oxygen migrates to the 4′-carbonyl oxygen after the bond fission between C-1′-C-6′; second, migration of the proton at C-4 to the 1′-oxygen is followed by migration of the protons at C-5 and C-7′ to C-4 and C-5, respectively; finally, the proton at the 1′-oxygen migrates to the 4′-hydroxyl group, and H2O at C-4′ is eliminated to give the dehydrated ion. Our findings point out that a dehydrated ion is not always derived from the elimination of a hydroxyl group. Copyright

3′-Azidoabscisic acid as a photoaffinity reagent for abscisic acid binding proteins

3′-Azidoabscisic acid was synthesized as a potential photoaffinity reagent for abscisic acid binding proteins. This compound was stable in organic and aqueous solutions in the dark, but was decomposed by UV irradiation. Its biological activity was equivalent to that of abscisic acid, suggesting that it may be an effective photoaffinity reagent.