Gibberellic acid

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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	54346
ChEBI	CHEBI:28833 ;
ChEMBL	ChEMBL566653 ;
ChemSpider	7995349 ;
DrugBank	DB07814;
ECHA InfoCard	100.000.911
EC Number	201-001-0;
KEGG	C01699 ;
PubChem CID	6466;
UNII	BU0A7MWB6L ;
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 Key: IXORZMNAPKEEDV-SNTJWBGVSA-N ; 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). verify (what is ?) Infobox references

Gibberellic acid (also called gibberellin A3 or GA₃) is a hormone found in plants and fungi. 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. 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. 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.

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.