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
CAS Number	77-06-5 Y
3D model (JSmol)	Interactive image
Beilstein Reference	54346
ChEBI	CHEBI:28833 N
ChEMBL	ChEMBL566653 Y
ChemSpider	7995349 Y
DrugBank	DB07814
ECHA InfoCard	100.000.911
EC Number	201-001-0
KEGG	C01699 Y
PubChem CID	6466
UNII	BU0A7MWB6L Y
CompTox Dashboard (EPA)	DTXSID0020656
InChI 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 Y Key: IXORZMNAPKEEDV-SNTJWBGVSA-N Y 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
SMILES 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
Chemical formula	C19H22O6
Molar mass	346.379 g·mol−1
Melting point	233 to 235 °C (451 to 455 °F; 506 to 508 K) (decomposition)
Solubility in water	5 g/L (20 °C)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	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 YN ?) Infobox references

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]

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.