Title: Gibberellic Acid
CAS Registry Number: 77-06-5
CAS Name: (1a,2b,4aa,4bb,10b)-2,4a,7-Trihydroxy-1-methyl-8-methylenegibb-3-ene-1,10-dicarboxylic acid 1,4a-lactone
Synonyms: gibberellin X; gibberellin A3
Trademarks: Activol (Zeneca); Gibrel (AgriDyne)
Molecular Formula: C19H22O6
Molecular Weight: 346.37
Percent Composition: C 65.88%, H 6.40%, O 27.71%
Literature References: Plant hormone; most outstanding of the plant-growth promoting metabolites of
Gibberella fujikuroi. Isoln: P. J. Curtis, B. E. Cross,
Chem. Ind. (London) 1954, 1066; B. E. Cross,
J. Chem. Soc. 1954, 4670; P. W. Brian
et al., US 2842051; C. T. Calam, P. J. Curtis,
US 2950288; A. J. Birch
et al., US 2977285 (1958, 1960, 1961, all to ICI). Stereochemistry and structure: G. Stork, H. Newman,
J. Am. Chem. Soc. 81, 5518 (1959); B. E. Cross
et al., Proc. Chem. Soc. London 1959, 302; F. McCapra
et al., ibid. 1962, 185; D. C. Aldridge
et al., J. Chem. Soc. 1963, 143; P. M. Bourn
et al., ibid. 1963, 154. Partial synthesis: E. J. Corey
et al., J. Am. Chem. Soc. 93, 7316 (1971). Stereospecific total synthesis:
eidem, ibid. 100, 8034 (1978). Promotes growth of seedlings: M. J. Bukovac, S. H. Wittwer,
Q. Bull. Mich. Agric. Exp. Stn. 39, 307 (1956); J. M. Merritt,
J. Agric. Food Chem. 6, 184 (1958).
Reviews: B. E. Cross
et al. in
Adv. Chem. Ser. 28, entitled "Gibberellins," J. M. Merritt, Ed. (ACS, Washington DC, 1961) p 13; series of articles in
Plant Growth Subst., Proc. 7th Int. Conf., D. J. Carr, Ed. (Springer-Verlag, Berlin, 1972).
Properties: Crystals from ethyl acetate, mp 233-235° (effervescence). [a]D19 +86° (c = 2.12). pK 4.0. Slightly sol in water, ether. Freely sol in methanol, ethanol, acetone. Moderately sol in ethyl acetate. Sol in aq solns of sodium bicarbonate and sodium acetate.
Melting point: mp 233-235° (effervescence)
pKa: pK 4.0
Optical Rotation: [a]D19 +86° (c = 2.12)
Derivative Type: Methyl ester
Molecular Formula: C20H24O6
Molecular Weight: 360.40
Percent Composition: C 66.65%, H 6.71%, O 26.64%
Properties: Needles from benzene + methanol, mp 209-210°. [a]D20 +75° (c = 0.5).
Melting point: mp 209-210°
Optical Rotation: [a]D20 +75° (c = 0.5)
Use: Plant growth regulator.
