Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Gibberellic acid: Difference between pages

{{About|the chemical|its function in plants|Gibberellin}}

| Watchedfields = changed

| verifiedrevid = 476997249

| ImageFile1 = Gibberellic-acid-from-xtal-3D-bs-17.png

| IUPACName = (3''S'',3a''S'',4''S'',4a''S'',7''S'',9a''R'',9b''R'',12''S'')-7,12-Dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno[1,2-''b'']furan-4-carboxylic acid

|Section1={{Chembox Identifiers

| CASNo = 77-06-5

| CASNo_Ref = {{cascite|correct|CAS}}

| Beilstein = 54346

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| DrugBank = DB07814

| EINECS = 201-001-0

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 566653

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 28833

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C01699

| PubChem = 6466

| 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

|Section2={{Chembox Properties

| C=19 | H=22 | O=6

| Appearance =

| Density =

| MeltingPtC = 233 to 235

| MeltingPt_notes = (decomposition)

| BoilingPt =

| Solubility = 5 g/L (20 °C)

|Section3={{Chembox Hazards

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|319}}

| PPhrases = {{P-phrases|264|280|305+351+338|337+313}}

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

'''Gibberellic acid''' (also called '''gibberellin A3''' or '''GA₃''') is a [[Plant hormone|hormone]] found in plants and fungi.<ref name="GA3">{{cite journal|vauthors=((Silva ALL)), Rodrigues C, Costa JL, Machado MP, Penha RO, Biasi LA, ((Vandenberghe LPS)), Soccol CR|title=Gibberellic acid fermented extract obtained by solid-state fermentation using citric pulp by Fusarium moniliforme: Influence on Lavandula angustifolia Mill. cultivated in vitro|journal=Pakistan Journal of Botany|date=2013|volume=45|issue=6|pages=2057–2064|url=http://www.pakbs.org/pjbot/PDFs/45(6)/30.pdf|access-date=26 November 2014}}</ref> 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.<ref name="camara">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.</ref> Gibberellic acid is a simple [[gibberellin]], a [[Polycyclic compound|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|date=October 2012}} GA stimulates the cells of germinating seeds to produce [[messenger RNA|mRNA]] molecules that code for [[Hydrolase|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.<ref name=riley>{{cite web|last=Riley|first=John M.|title=Gibberellic Acid for Fruit Set and Seed Germination|url=http://www.crfg.org/tidbits/gibberellic.html|access-date=26 Oct 2012|archive-date=3 March 2008|archive-url=https://web.archive.org/web/20080303034828/http://www.crfg.org/tidbits/gibberellic.html|url-status=dead}}</ref> It is usually used in concentrations between 0.01 and 10&nbsp;mg/L.{{Citation needed|date=March 2019}}

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 [[Lodging (agriculture)|lodge]] due to lack of support, and die.<ref name="camara"/>

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.<ref>{{cite journal|last1=Edwards|first1=Miriam|title=Dormancy in Seeds of Charlock (Sinapis arvensis L.)|journal=Plant Physiol.|date=1976|volume=58|issue=5|pages=626–630|doi=10.1104/pp.58.5.626|pmc=542271|pmid=16659732}}</ref>

==Uses==

Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger [[germination]] in seeds that would otherwise remain [[Dormancy|dormant]].<ref name=riley /> It is also widely used in the grape-growing industry as a hormone to induce the production of larger bunches and bigger grapes, especially [[Sultana (grape)|Thompson seedless]] grapes. In the [[Okanagan]] and [[Creston Valley|Creston]] valleys, it is also used as a [[plant hormone|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.

It can be used to extend the shelf life of flowers and cut greens in [[floristry]]. The [[shelf life]] of cut shoots of ''[[Polygonatum multiflorum]]'' 'Variegatum' kept in water is about 7 days. To extend their life after cutting, conditioning with gibberellic acid or [[benzyladenine]] is used. This doubles their possible use.<ref name="AA">{{cite journal | vauthors = Krzymińska-Bródka A, Ulczycka-Walorska M, Łysiak GP, Czuchaj P | title = The longevity of cut ''Polygonatum multiflorum'' (L.) All. shoots depending on postharvest handling| url = https://www.journalssystem.com/agb/The-longevity-of-cut-Polygonatum-multiflorum-L-All-shoots-depending-on-postharvest,176280,0,2.html | journal = Acta Agrobotanica | volume = 76 | issue = | pages = 1–11 | date = December 2023 | pmid = | doi = 10.5586/aa/176280| publisher = Polish Botanical Society | s2cid = | doi-access = free }}</ref>

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==

*[[Abscisic acid]] (ABA)

*[[Gibberellin]]

*[[Plant hormone]]

*[[6-Benzylaminopurine]]

*[[Auxin]]

==References==

{{Reflist}}

{{Authority control}}

[[Category:Plant hormones]]

[[Category:Cyclohexenols]]

[[Category:Tertiary alcohols]]

[[Category:Lactones]]

[[Category:Heterocyclic compounds with 5 rings]]

[[Category:Vinylidene compounds]]

[[Category:Plant growth regulators]]