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
• Article Data: 16

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

Description

Abscisic Acid (ABA) is a naturally occurring isoprenoid plant hormone (phytohormone) that is synthesized in all parts of plants and plays a crucial role in various plant developmental processes. It is considered an inhibitor of plant growth and is primarily used as a growth retardant in plant tissue culture. ABA is involved in establishing dormancy, regulating stress responses, and controlling stomatal movements, leaf senescence, and bud and seed dormancy. It is a white to light yellow crystalline powder and belongs to the terpenoid family.

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

• 133-89-1 UDP-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 
• 6901-90-2 (S)-methyl abscisate 
• 23069-07-0 4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol 
• 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 
• 123196-49-6 (S)-6-[1-Hydroxy-meth-(Z)-ylidene]-2,2-dimethyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone 
• 123196-53-2 (2Z,4E)-5-((1S,4S)-1,4-Dihydroxy-2,2-dimethyl-6-methylene-cyclohexyl)-3-methyl-penta-2,4-dienal 
• 123196-51-0 (+)-(1'S,4'S)-(2Z,4E)-5-(1',4'-Diydroxy-2',2'-dimethyl-6'-methylenecyclohexyl)-3-methyl-2,5-pentadien-1-ol 
• 123214-38-0 (+)-(S)-2,2-Dimethyl-6-methylene-4-tetrahydropyranyloxy-1-cyclohexanone 

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 
• 1206693-50-6 tetramethylammonium salt of (S)-(+)-abscisic acid 
• 1206693-54-0 tetramethylguanidinium salt of (S)-(+)-abscisic acid 
• 1206792-23-5 rubidium salt of (S)-(+)-abscisic acid 
• 1206792-24-6 cesium salt of (S)-(+)-abscisic acid 
• 1206693-51-7 tetrabutylammonium salt of (S)-(+)-abscisic acid 
• 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 

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