Gibberellic acid

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.

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
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).
☒N verify (what is checkY☒N ?)
Infobox references

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. 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.

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]

Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger germination in seeds that would otherwise remain dormant.[3] It is also widely used in the grape-growing industry as a hormone to induce the production of larger bunches and bigger grapes, especially Thompson seedless grapes. In the Okanagan and Creston valleys, it is also used as a growth regulator in the cherry industry. It is used on Clementine Mandarin oranges, which may otherwise cross-pollinate with other citrus and produce undesirable seeds. Applied directly on the blossoms as a spray, it allows for Clementines to produce a full crop of seedless fruit.

GA is widely used in the barley malting industry. A GA solution is sprayed on the barley after the steeping process is completed. This stimulates growth in otherwise partly dormant kernels and produces a uniform and rapid growth.

See also

References
  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. 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". 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.
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