14375-45-2

Basic information

• Product Name: Abscisic acid
• Synonyms: TIMTEC-BB SBB003072;(2-CIS,4-TRANS)-5-(1-HYDROXY-2,6,6-TRIMETHYL-4-OXO-2-CYCLOHEXEN-1-YL)-3-METHYL-2,4-PENTADIENOIC ACID;(+/-)-2-CIS-4-TRANS-ABSCISIC ACID;2-CIS,4-TRANS-ABSCISIC ACID;5-[1-HYDROXY-2,6,6-TRIMETHYL-4-OXOCYCLOHEX-2-EN-1-YL]-3-METHYL-[2Z,4E]-PENTADIENOIC ACID;(+/-)-ABSCISIC ACID;ABSCISIC ACID;ABSCISIC ACID, (+/-)-
• CAS NO: 14375-45-2
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32
• Product Categories: Sesqui-Terpenoids;Biochemistry;Plant Growth Regulators;Plant Growth Trgulators (Others);Terpenes;Terpenes (Others);Pesticide intermediates;Inhibitors
• Mol File: 14375-45-2.mol

Chemical Properties

• Melting Point: 186-188 °C(lit.)
• Boiling Point: 458.74 °C at 760 mmHg
• Flash Point: 120°C
• Appearance: White to pale-yellow powder
• Density: 1.193 g/cm³
• Vapor Pressure: 2.41E-10mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: methanol: 50 mg/mL, may be clear to slightly hazy
• PKA: 4.87±0.33(Predicted)
• Sensitive: Light Sensitive
• Merck: 14,11
• BRN: 4142666
• CAS DataBase Reference: Abscisic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Abscisic acid(14375-45-2)
• EPA Substance Registry System: Abscisic acid(14375-45-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 14375-45-2(Hazardous Substances Data)

Usage

Uses

Used in Plant Tissue Culture:
Abscisic acid is used as a growth retardant to promote the maturation of somatic embryos and the synthesis of storage reserves in embryos during maturation. It also acts as a controlling factor of germination and dormancy in somatic embryos, inducing a quiescent state during plant tissue culture and synthetic seed studies.
Used in Stress Response Regulation:
Abscisic acid is used to regulate stress responses in plants, as the rate of ABA synthesis increases when the plant is under stress. This helps plants adapt to various environmental conditions and maintain their growth and development.
Used in Agricultural Applications:
In agriculture, Abscisic acid is used as an abscission-accelerant, promoting the natural detachment of leaves, branches, flowers, etc., from plants. It is a naturally occurring plant growth inhibitor and one of the five major plant hormones, carrying out important functions in the growth and development of plants.
Used in Anti-transpiration:
Abscisic acid stimulates stomatal closure, reducing transpirational water loss. It is used as an anti-transpiration agent during the acclimatization of tissue culture-raised plants, helping them adapt to new environmental conditions.
Used in Inhibiting Fruit Ripening and Seed Germination:
Abscisic acid is used to inhibit fruit ripening, seed germination, and photosynthesis, as well as kinetin biosynthesis, which are essential processes in plant growth and development.

References

[1] Shintaro Munemasa, Felix Hauser, Jiyoung Park, Rainer Waadt, Benjamin Brandt, Julian I Schroeder (2015) Mechanisms of abscisic acid-mediated control of stomatal aperture, 28, 154-162 [2] Manoj K. Rai, N. S. Shekhawat, Harish, Amit K. Gupta, M. Phulwaria, Kheta Ram, U. Jaiswal (2011) The role of abscisic acid in plant tissue culture: a review of recent progress, 106, 179-190 [3] https://pages.wustl.edu/ipgsa/abscisic-acid

Metabolic pathway

Plant growth regulators: promotion of maturation of the somatic embryo of white spruce Somatic embryo suspension cultures of white spruce containing (?+)-abscisic acid (ABA) metabolize (+?)- ABA almost completely to yield quantitatively phaseic acid with slight further transformation into dihydrophaseic acid within 7 days. (-)-ABA remains essentially unchanged under the same culture conditions, and when the cells are supplied with racemic (±)-ABA, only the (+?) enantiomer is metabolized.

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)/p-1/b6-5+,10-7-/t15-/m1/s1

Upstream product

• 6901-90-2 (S)-methyl abscisate 
• 41944-86-9 (2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal 
• 21293-29-8 (2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic 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 
• 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 
• 220863-62-7 abscisic acid 1-(2-nitrophenyl)ethyl ester 
• 14398-53-9 (R)-(-)-abscisic acid 
• 133-89-1 UDP-glucose 
• 50-99-7 D-glucose 
• 23526-45-6 blumenol A 
• 39763-33-2 (+)-(S)-dehydrovomifoliol 
• 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 
• 52421-93-9 (2Z)-3-methyl-2-penten-4-ynal 

Downstream Products

• 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 
• 130694-63-2 (-) (1'S,2'R)-2',3'-dihydro-abscisic acid 
• 56298-25-0 (+)-abscisyl alcohol 
• 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 

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Study on the regulation of anthocyanin biosynthesis by exogenous Abscisic acid (cas 14375-45-2) in grapevine08/07/2019

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Involvement of Abscisic acid (cas 14375-45-2) in the resistance of citrus fruit to Penicillium digitatum infection08/06/2019

The involvement of hormone abscisic acid (ABA) in citrus fruit resistance to Penicillium digitatum infection was investigated. To this end, the effect of both exogenous ABA and inhibitors of ABA biosynthesis in plants on the resistance of sweet oranges to be infected by this major postharvest pa...detailed

Abscisic acid (cas 14375-45-2) metabolism and transport08/05/2019

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Relevant articles and documents

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

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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.