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 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28833 N
ChEMBL	ChEMBL566653 Y
ChemSpider	7995349 Y
ECHA InfoCard	100.000.911
EC Number	201-001-0
KEGG	C01699 Y
PubChem	522636
UNII	BU0A7MWB6L Y
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	346.37 g/mol
Melting point	233 to 235 °C (451 to 455 °F; 506 to 508 K) (decomposition)
Solubility in water	5 g/l (20 °C)
Hazards
EU classification (DSD)	Irritant (Xi)
R-phrases	R36
S-phrases	R26, S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Gibberellic acid (also called Gibberellin A3, GA, and GA₃) is a hormone found in plants and fungi . Its chemical formula is C₁₉H₂₂O₆. When purified, it is a white to pale-yellow solid.

However, plants produce low amounts of GA3, therefore this hormone can be produced industrially by microorganisms. Nowadays, it is produced by submerse fermentation, but this process presented low yield with high production costs and hence higher sale value. One alternative process to reduce costs of the GA3 production is Solid-State Fermentation (SSF) that allows the use of agro-industrial residues. 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 grow so much taller than normal that they die from no longer being sturdy enough to support their own weight.

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 rate.

Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger germination in seeds that would otherwise remain dormant. It is also widely used in the grape-growing industry as a hormone to induce the production of larger bundles and bigger grapes, especially Thompson seedless grapes. In the Okanagan and Creston valleys, it is also used as a growth replicator in the cherry industry. It is used on Clementine Mandarin oranges, which may otherwise cross-pollinate with other citrus and grow undesirable seeds. Applied directly on the blossoms as a spray, it allows for Clementines to produce a full crop of fruit without seeds.