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Wikipedia

Gibberellic acid

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.

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
  • 77-06-5 Y
3D model (JSmol)
  • Interactive image
54346
ChEBI
  • CHEBI:28833 N
ChEMBL
  • ChEMBL566653 Y
ChemSpider
  • 7995349 Y
DrugBank
  • DB07814
ECHA InfoCard 100.000.911
EC Number
  • 201-001-0
KEGG
  • C01699 Y
  • 6466
UNII
  • BU0A7MWB6L Y
  • DTXSID0020656
  • 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
  • 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
C19H22O6
Molar mass 346.379 g·mol−1
Melting point 233 to 235 °C (451 to 455 °F; 506 to 508 K) (decomposition)
5 g/L (20 °C)
Hazards
GHS labelling:
Warning
H319
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).
N verify (what is YN ?)

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]

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.

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 edit

References edit

  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.
  2. ^ 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.
  3. ^ a b Riley, John M. "Gibberellic Acid for Fruit Set and Seed Germination". 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.

gibberellic, acid, this, article, about, chemical, function, plants, gibberellin, also, called, gibberellin, hormone, found, plants, fungi, chemical, formula, c19h22o6, when, purified, white, pale, yellow, solid, namesiupac, name, dihydroxy, methyl, methylene,. This article is about the chemical For its function in plants see Gibberellin 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 Gibberellic acid NamesIUPAC 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 acidIdentifiersCAS Number 77 06 5 Y3D model JSmol Interactive imageBeilstein Reference 54346ChEBI CHEBI 28833 NChEMBL ChEMBL566653 YChemSpider 7995349 YDrugBank DB07814ECHA InfoCard 100 000 911EC Number 201 001 0KEGG C01699 YPubChem CID 6466UNII BU0A7MWB6L YCompTox Dashboard EPA DTXSID0020656InChI 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 YKey IXORZMNAPKEEDV SNTJWBGVSA N YInChI 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 s1Key IXORZMNAPKEEDV SNTJWBGVBWSMILES 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 CPropertiesChemical formula C 19H 22O 6Molar mass 346 379 g mol 1Melting point 233 to 235 C 451 to 455 F 506 to 508 K decomposition Solubility in water 5 g L 20 C HazardsGHS labelling PictogramsSignal word WarningHazard statements H319Precautionary statements P264 P280 P305 P351 P338 P337 P313Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 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 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 editAbscisic acid ABA Gibberellin Plant hormone 6 Benzylaminopurine AuxinReferences edit 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 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 Retrieved from https en wikipedia org w index php title Gibberellic acid amp oldid 1146820807, wikipedia, wiki, book, books, library,

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