Gibberellic acid

This article is about the chemical. For its function in plants, see Gibberellin.
Gibberellic acid
Names
IUPAC name
(3S,3aS,4S,4aS,7S,9aR,9bR,12S)-7,12-Dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno[1,2-b]furan-4-carboxylic acid
Identifiers
3D model (JSmol)
54346
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.911 Edit this at Wikidata
EC Number
  • 201-001-0
KEGG
UNII
  • InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16+,17+,18+,19-/m1/s1 checkY
    Key: IXORZMNAPKEEDV-SNTJWBGVSA-N checkY
  • InChI=1/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16+,17+,18+,19-/m1/s1
    Key: IXORZMNAPKEEDV-SNTJWBGVBW
  • O=C1O[C@@]52\C=C/[C@H](O)[C@]1([C@H]5[C@H](C(=O)O)[C@]43[C@H]2CC[C@@](O)(C(=C)C3)C4)C
Properties
C19H22O6
Molar mass 346.379 g·mol−1
Melting point 233 to 235 °C (451 to 455 °F; 506 to 508 K) (decomposition)
5 g/L (20 °C)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H319
P264, P280, P305+P351+P338, P337+P313
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Gibberellic acid (also called gibberellin A3 or GA3) is a hormone found in plants and fungi.[1] Its chemical formula is C19H22O6. When purified, it is a white to pale-yellow solid.

Plants in their normal state produce large amounts of GA3. It is possible to produce the hormone industrially using microorganisms.[2] Gibberellic acid is a simple gibberellin, a pentacyclic diterpene acid promoting growth and elongation of cells. It affects decomposition of plants and helps plants grow if used in small amounts, but eventually plants develop tolerance to it.[citation needed] GA stimulates the cells of germinating seeds to produce mRNA molecules that code for hydrolytic enzymes. Gibberellic acid is a very potent hormone whose natural occurrence in plants controls their development. Since GA regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect.[3] It is usually used in concentrations between 0.01 and 10 mg/L.[citation needed]

GA was first identified in Japan in 1926, as a metabolic by-product of the plant pathogen Gibberella fujikuroi (thus the name), which afflicts rice plants. Fujikuroi-infected plants develop bakanae ("foolish seedling"), which causes them to rapidly elongate beyond their normal adult height. The plants subsequently lodge due to lack of support, and die.[2]

Gibberellins have a number of effects on plant development. They can stimulate rapid stem and root growth, induce mitotic division in the leaves of some plants, and increase seed germination rates.[4]

  1. ^ Silva ALL, Rodrigues C, Costa JL, Machado MP, Penha RO, Biasi LA, Vandenberghe LPS, Soccol CR (2013). "Gibberellic acid fermented extract obtained by solid-state fermentation using citric pulp by Fusarium moniliforme: Influence on Lavandula angustifolia Mill. cultivated in vitro" (PDF). Pakistan Journal of Botany. 45 (6): 2057–2064. Retrieved 26 November 2014.
  2. ^ a b Camara, M. C. et al (2015) General Aspects and Applications of Gibberelins and Gibberellic Acid in Plants. In: Hardy, J.. (Org.). Gibberellins and Gibberellic Acid: Biosynthesis, Regulation and Physiological Effects. 1ed.Hauppauge: Nova Science Publishers, 2015, v., p. 1-21.
  3. ^ Riley, John M. "Gibberellic Acid for Fruit Set and Seed Germination". Archived from the original on 3 March 2008. Retrieved 26 Oct 2012.
  4. ^ Edwards, Miriam (1976). "Dormancy in Seeds of Charlock (Sinapis arvensis L.)". Plant Physiol. 58 (5): 626–630. doi:10.1104/pp.58.5.626. PMC 542271. PMID 16659732.