| Revision as of 12:55, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476049195 of page Gibberellic_acid for the Chem/Drugbox validation project (updated: 'ChEBI'). |
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{{About|the chemical|its function in plants|Gibberellin}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 461120291 |
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| verifiedrevid = 476997249 |
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| ImageFile = Gibberellic acid.svg |
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| ImageFile = Gibberellic acid.svg |
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| ImageSize = 240px |
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| ImageSize = 240px |
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| ImageFile1 = Gibberellic-acid-from-xtal-3D-bs-17.png |
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| IUPACName = (3S,3aS,4S,4aS,7S,9aR,9bR,12S)-7,12-dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazulenofuran-4-carboxylic acid |
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| 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-propenoazulenofuran-4-carboxylic acid |
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| IUPACName_hidden = yes |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 77-06-5 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Beilstein = 54346 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7995349 |
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| ChemSpiderID = 7995349 |
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| DrugBank = DB07814 |
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| EINECS = 201-001-0 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 566653 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 28833 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C01699 |
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| PubChem = 6466 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = BU0A7MWB6L |
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| UNII = BU0A7MWB6L |
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| SMILES = O=C1O52\C=C/(O)1(5(C(=O)O)432CC(O)(C(=C)C3)C4)C |
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| 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 |
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| 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 |
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| InChIKey = IXORZMNAPKEEDV-SNTJWBGVBW |
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| InChIKey = IXORZMNAPKEEDV-SNTJWBGVBW |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IXORZMNAPKEEDV-SNTJWBGVSA-N |
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| StdInChIKey = IXORZMNAPKEEDV-SNTJWBGVSA-N |
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| CASNo = 77-06-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| EINECS = 201-001-0 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 566653 |
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| PubChem = 522636 |
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| SMILES = O=C1O52\C=C/(O)1(5(C(=O)O)432CC(O)(C(=C)\C3)C4)C |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = <!-- blanked - oldvalue: 28833 --> |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C01699 |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>19</sub>H<sub>22</sub>O<sub>6</sub> |
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| MolarMass = 346.37 g/mol |
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| Appearance = |
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| Density = |
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| MeltingPt = 233 - 235 °C (decomposition) |
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| BoilingPt = |
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| Solubility = 5 g/l (20 °C) |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section2={{Chembox Properties |
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| C=19 | H=22 | O=6 |
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| EUClass = Irritant ('''Xi''') |
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| RPhrases = {{R36}} |
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| Appearance = |
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| Density = |
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| SPhrases = {{R26}}, {{S36}} |
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| MeltingPtC = 233 to 235 |
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| MeltingPt_notes = (decomposition) |
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| Solubility = 5 g/L (20 °C) |
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}} |
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|Section3={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|319}} |
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| PPhrases = {{P-phrases|264|280|305+351+338|337+313}} |
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'''Gibberellic acid''' (also called '''gibberellin A3''' or '''GA<sub>3</sub>''') is a ] 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 ] is C<sub>19</sub>H<sub>22</sub>O<sub>6</sub>. When purified, it is a white to pale-yellow solid. |
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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 ], a ] ] 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 ] molecules that code for ]. 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 mg/L.{{Citation needed|date=March 2019}} |
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GA was first identified in Japan in 1926, as a metabolic by-product of the plant pathogen '']'' (thus the name), which afflicts ] plants. ''Fujikuroi''-infected plants develop '']'' ("foolish seedling"), which causes them to rapidly elongate beyond their normal adult height. The plants subsequently ] due to lack of support, and die.<ref name="camara"/> |
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Gibberellins have a number of effects on plant development. They can stimulate rapid stem and root growth, induce ] 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> |
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==Uses== |
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Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger ] in seeds that would otherwise remain ].<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 ] grapes. In the ] and ] valleys, it is also used as a ] 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. |
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It can be used to extend the shelf life of flowers and cut greens in ]. The ] of cut shoots of '']'' 'Variegatum' kept in water is about 7 days. To extend their life after cutting, conditioning with gibberellic acid or ] 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> |
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GA is widely used in the barley ] 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. |
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==See also== |
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*] (ABA) |
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==References== |
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