Abscisic Acid
Structural Formula Vector Image
Title: Abscisic Acid
CAS Registry Number: 21293-29-8
CAS Name: (2Z,4E)-5-[(1S)-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic acid
Additional Names: abscisin II; dormin; ABA
Molecular Formula: C15H20O4
Molecular Weight: 264.32
Percent Composition: C 68.16%, H 7.63%, O 24.21%
Literature References: Abscission-accelerating plant hormone; naturally occurring as the (+)-cis,trans-form. Regulates seed maturation and germination and mediates the plant response to environmental stress. Isoln from young cotton fruit: K. Ohkuma et al., Science 142, 1592 (1963); from sycamore leaves: J. W. Cornforth et al., Nature 205, 1269 (1965). Identification in sycamore, birch, rose, cabbage, potato, lemon, avocado: eidem, ibid. 210, 627 (1966). Structure and synthesis of (±)-cis,trans-form: eidem, ibid. 206, 715 (1965); and enantiomers: F. Kienzle et al., Helv. Chim. Acta 61, 2616 (1978). Absolute configuration of naturally occurring form: G. Ryback, Chem. Commun. 1972, 1190. Crystal and molecular structure: H. W. Schmalle et al., Acta Crystallogr. B33, 2218 (1977). Review: F. T. Addicott, J. L. Lyon, Annu. Rev. Plant Physiol. 20, 139 (1969). Review of role in root growth regulation: P. E. Pilet, P. W. Barlow, Plant Growth Regul. 6, 217-265 (1987); of metabolism: J. A. D. Zeevaart, R. A. Creelman, Annu. Rev. Plant Physiol. Plant Mol. Biol. 39, 439-473 (1988); of signal transduction: J. Leung, J. Giraudat, ibid. 49, 199-222 (1998).
Properties: Crystals from ethyl acetate + hexane, mp 161-163°. Sublimes at 120°. [a]D20 +411.1° (c = 1 in ethanol). [a]D20 +426.5° (c = 1 in 0.005N methanolic H2SO4). Sol in aq NaHCO3, chloroform, acetone, ethyl acetate, ether; slightly sol in benzene, water; sparingly sol in petr ether. uv max (methanol): 252 nm (e 25200).
Melting point: mp 161-163°
Optical Rotation: [a]D20 +411.1° (c = 1 in ethanol); [a]D20 +426.5° (c = 1 in 0.005N methanolic H2SO4)
Absorption maximum: uv max (methanol): 252 nm (e 25200)
Derivative Type: (-)-cis,trans-Form
CAS Registry Number: 14398-53-9
Additional Names: (R)-(-)-Abscisic acid
Properties: mp 162-163°. [a]D20 -426.2° (c = 1 in 0.005N H2SO4).
Melting point: mp 162-163°
Optical Rotation: [a]D20 -426.2° (c = 1 in 0.005N H2SO4)
Derivative Type: (±)-cis,trans-Form
CAS Registry Number: 14375-45-2
Properties: Crystals, mp 188-190°.
Melting point: mp 188-190°

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