Gibberellic acid: Difference between revisions

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

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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]

Uses

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.

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.^[5]

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.

References

^ Silva ALL, Rodrigues C, Costa JL, Machado MP, Penha RO, Biasi LA, Vandenberghe LPS, Soccol CR (2013). "Gibberellic acid fermented extract obtained by solid-state fermentation using citric pulp by Fusarium moniliforme: Influence on Lavandula angustifolia Mill. cultivated in vitro" (PDF). Pakistan Journal of Botany. 45 (6): 2057–2064. Retrieved 26 November 2014.
^ ^a ^b 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.
^ ^a ^b Riley, John M. "Gibberellic Acid for Fruit Set and Seed Germination". Archived from the original on 3 March 2008. Retrieved 26 Oct 2012.
^ Edwards, Miriam (1976). "Dormancy in Seeds of Charlock (Sinapis arvensis L.)". Plant Physiol. 58 (5): 626–630. doi:10.1104/pp.58.5.626. PMC 542271. PMID 16659732.
^ Krzymińska-Bródka A, Ulczycka-Walorska M, Łysiak GP, Czuchaj P (December 2023). "The longevity of cut Polygonatum multiflorum (L.) All. shoots depending on postharvest handling". Acta Agrobotanica. 76. Polish Botanical Society: 1–11. doi:10.5586/aa/176280.

[GA3-1] Silva ALL, Rodrigues C, Costa JL, Machado MP, Penha RO, Biasi LA, Vandenberghe LPS, Soccol CR (2013). "Gibberellic acid fermented extract obtained by solid-state fermentation using citric pulp by Fusarium moniliforme: Influence on Lavandula angustifolia Mill. cultivated in vitro" (PDF). Pakistan Journal of Botany. 45 (6): 2057–2064. Retrieved 26 November 2014.

[camara-2] 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.

[riley-3] Riley, John M. "Gibberellic Acid for Fruit Set and Seed Germination". Archived from the original on 3 March 2008. Retrieved 26 Oct 2012.

[4] Edwards, Miriam (1976). "Dormancy in Seeds of Charlock (Sinapis arvensis L.)". Plant Physiol. 58 (5): 626–630. doi:10.1104/pp.58.5.626. PMC 542271. PMID 16659732.

[AA-5] Krzymińska-Bródka A, Ulczycka-Walorska M, Łysiak GP, Czuchaj P (December 2023). "The longevity of cut Polygonatum multiflorum (L.) All. shoots depending on postharvest handling". Acta Agrobotanica. 76. Polish Botanical Society: 1–11. doi:10.5586/aa/176280.

[1]

[2]

[3]

[4]

[5]

@@ Line 1: / Line 1: @@
+{{About|the chemical|its function in plants|Gibberellin}}
-{{Refimprove|date=November 2012}}
 {{chembox
 | Verifiedfields = changed
@@ Line 6: / Line 6: @@
 | ImageFile = Gibberellic acid.svg
 | ImageSize = 240px
+| ImageFile1 = Gibberellic-acid-from-xtal-3D-bs-17.png
-| IUPACName = (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
+| 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
 | OtherNames =
 |Section1={{Chembox Identifiers
+| CASNo = 77-06-5
+| CASNo_Ref = {{cascite|correct|CAS}}
+| Beilstein = 54346
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 7995349
+| 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
 | UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = BU0A7MWB6L
+| 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
 | 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
 | InChIKey = IXORZMNAPKEEDV-SNTJWBGVBW
@@ Line 19: / Line 33: @@
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = IXORZMNAPKEEDV-SNTJWBGVSA-N
-| CASNo = 77-06-5
-| CASNo_Ref = {{cascite|correct|CAS}}
-| EINECS = 201-001-0
-| ChEMBL_Ref = {{ebicite|correct|EBI}}
-| ChEMBL = 566653
-| PubChem = 522636
-| 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
-| ChEBI_Ref = {{ebicite|changed|EBI}}
-| ChEBI = 28833
-| KEGG_Ref = {{keggcite|correct|kegg}}
-| KEGG = C01699
   }}
 |Section2={{Chembox Properties
+| C=19 | H=22 | O=6
-| Formula = C<sub>19</sub>H<sub>22</sub>O<sub>6</sub>
-| MolarMass = 346.37 g/mol
 | Appearance =
 | Density =
@@ Line 39: / Line 41: @@
 | MeltingPt_notes = (decomposition)
 | BoilingPt =
-| Solubility = 5 g/l (20 °C)
+| Solubility = 5 g/L (20 °C)
   }}
 |Section3={{Chembox Hazards
+| GHSPictograms = {{GHS07}}
-| EUClass = Irritant ('''Xi''')
+| GHSSignalWord = Warning
-| RPhrases = {{R36}}
-| SPhrases = {{R26}}, {{S36}}
+| HPhrases = {{H-phrases|319}}
+| PPhrases = {{P-phrases|264|280|305+351+338|337+313}}
 | MainHazards =
 | FlashPt =
@@ Line 51: / Line 54: @@
 }}
-'''Gibberellic acid''' (also called '''Gibberellin A3''', '''GA''', and '''GA<sub>3</sub>''') 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|accessdate=26 November 2014}}</ref>
+'''Gibberellic acid''' (also called '''gibberellin A3''' or '''GA<sub>3</sub>''') 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 C<sub>19</sub>H<sub>22</sub>O<sub>6</sub>. When purified, it is a white to pale-yellow solid.
-.  Its [[chemical formula]] is C<sub>19</sub>H<sub>22</sub>O<sub>6</sub>. When purified, it is a white to pale-yellow solid.
-Plants in their normal state produce low 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> Nowadays, it
+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}}
-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.<ref name="GA3"/>
-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|accessdate=26 Oct 2012}}</ref> It is usually used in concentrations between 0.01 and 10&nbsp;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.<ref name="camara"/>
+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 rate.
+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 bundles and bigger grapes, especially [[Sultana (grape)|Thompson seedless]] grapes. In the [[Okanagan]] and [[Creston Valley|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.
+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==
@@ Line 73: / Line 74: @@
 *[[Plant hormone]]
 *[[6-Benzylaminopurine]]
+*[[Auxin]]
 ==References==
 {{Reflist}}
-==External links==
-* [http://webbook.nist.gov/cgi/cbook.cgi?ID=77-06-5&Units=SI Synonyms at webbook.nist.gov]
-<!--
-'''2,7-dihydroxy-1-methyl-8-methylene-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid''', or '''(3S,3aS,4S,4aS,7S,9aR,12S)-7,12-dihydroxy-3-methyl-6-methyllene-2-oxoperhydro-4a,7-methano-9b,3-propeno[1,2-b]furan-4-carboxylic acid''' ([[IUPAC]]), {{SMILESCAS|CAS=77-06-5|SMILES=[H][C@]12[C@@] (C=C[C@H](O)[C@] ([C@]5=O)3C)(O5) [C@]3([H])[C@H] ([C@@](O)=O)[C@] (C[C@]4=C)1C [C@@]4(O)CC2}} It is also available under names '''Activol''', '''Berelex''', '''Brellin''', '''Cekugib''', 'Gibbrel''', '''Gib-sol''', '''Gib-tabs''', '''Grocel''', and others.
--->
 {{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]]