It is a member of the class of compounds known as auxins and a chlorinated analogue of the more common indole-3-acetic acid (IAA) auxin. 4-Cl-IAA is found in the seeds of a variety of plants, particularly legumes such as peas and broad beans.[2][3][4][5] In one study it is written that the substance is "mainly found in reproductive structures" and "is thought to be restricted to members of the leguminous tribe Fabeae, specifically "the genera Vicia, Pisum, Lathyrus, Lens, and Vavilovia".[6] In Pisum sativum, 4-Cl-IAA biosynthesis diverges from IAA biosynthesis when the amino acid tryptophan is chlorinated to form 4-chlorotryptophan (4-Cl-Trp); the biosynthesis of 4-Cl-IAA then precedes parallel to that of IAA.[7]
Engvild hypothesized in 1996 that 4-Cl-IAA may be a "death hormone" that maturing seeds use to trigger death of the parent plant by mobilizing nutrients to be stored in the seed.[8]
^Reinecke, Dennis M. (1999). "4-Chloroindole-3-acetic acid and plant growth". Plant Growth Regulation. 27 (1): 3–13. doi:10.1023/A:1006191917753. ISSN 0167-6903. S2CID 23683065.
^Pless, Tanja; Boettger, Michael; Hedden, Peter; Graebe, Jan (1984). "Occurrence of 4-Cl-indoleacetic acid in broad beans and correlation of its levels with seed development". Plant Physiology. 74 (2): 320–3. doi:10.1104/pp.74.2.320. PMC1066676. PMID 16663416.
^Ernstsen, Arild; Sandberg, Goeran (1986). "Identification of 4-chloroindole-3-acetic acid and indole-3-aldehyde in seeds of Pinus sylvestris". Physiologia Plantarum. 68 (3): 511–18. doi:10.1111/j.1399-3054.1986.tb03390.x.
^Katayama, Masato; Thiruvikraman, Singanallore V.; Marumo, Shingo (1987). "Identification of 4-chloroindole-3-acetic acid and its methyl ester in immature seeds of Vicia amurensis (the tribe Vicieae), and their absence from three species of Phaseoleae". Plant and Cell Physiology. 28 (2): 383–386. ISSN 0032-0781. Archived from the original on 16 October 2013. Retrieved 16 October 2013.
^Magnus, Volker; Ozga, Jocelyn A.; Reinecke, Dennis M.; Pierson, Gerald L.; Larue, Thomas A.; Cohen, Jerry D.; Brenner, Mark L (1997). "4-chloroindole-3-acetic and indole-3-acetic acids in Pisum sativum". Phytochemistry. 46 (4): 675–681. doi:10.1016/S0031-9422(97)00229-X.
^ abLam, H. K.; McAdam, S. A.; McAdam, E. L.; Ross, J. J. (2015). "Evidence That Chlorinated Auxin is Restricted to the Fabaceae but Not to the Fabeae". Plant Physiology. 168 (3): 798–803. doi:10.1104/pp.15.00410. PMC4741347. PMID 25971549.
^Tivendale, N.D.; Davidson, S. E.; Davies, N. W.; Smith, J. A.; Dalmais, M.; Bendahmane, A. I.; Quittenden, L. J.; Sutton, L.; Bala, R. K.; Signor, C. Le; Thompson, R.; Horne, J.; Reid, J. B.; Ross, J. J. (2012). "Biosynthesis of the Halogenated Auxin, 4-Chloroindole-3-Acetic Acid". Plant Physiology. 159 (3): 1055–1063. doi:10.1104/pp.112.198457. PMC3387693. PMID 22573801.
^Engvild, Kjeld C. (1996). "Herbicidal activity of 4-chloroindoleacetic acid and other auxins on pea, barley and mustard". Physiologia Plantarum. 96 (2): 333–337. doi:10.1111/j.1399-3054.1996.tb00222.x.
chloroindole, acetic, acid, organic, compound, that, functions, plant, hormone, namespreferred, iupac, name, chloro, indol, acetic, acidother, names, chloro, indol, acetic, acididentifierscas, number, 2519, model, jsmol, interactive, imagechebi, chebi, 20339, . 4 Chloroindole 3 acetic acid 4 Cl IAA is an organic compound that functions as a plant hormone 1 4 Chloroindole 3 acetic acid NamesPreferred IUPAC name 4 Chloro 1H indol 3 yl acetic acidOther names 2 4 Chloro 1H indol 3 yl acetic acidIdentifiersCAS Number 2519 61 1 N3D model JSmol Interactive imageChEBI CHEBI 20339 YChEMBL ChEMBL309993 YChemSpider 90727 YECHA InfoCard 100 255 860PubChem CID 100413UNII RF78HU5XXV YCompTox Dashboard EPA DTXSID10179857InChI InChI 1S C10H8ClNO2 c11 7 2 1 3 8 10 7 6 5 12 8 4 9 13 14 h1 3 5 12H 4H2 H 13 14 YKey WNCFBCKZRJDRKZ UHFFFAOYSA N YInChI 1 C10H8ClNO2 c11 7 2 1 3 8 10 7 6 5 12 8 4 9 13 14 h1 3 5 12H 4H2 H 13 14 Key WNCFBCKZRJDRKZ UHFFFAOYAYSMILES Clc1cccc2c1c c nH 2 CC O OPropertiesChemical formula C 10H 8Cl N O 2Molar mass 209 63 g mol 1Except 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 referencesSynopsis EditIt is a member of the class of compounds known as auxins and a chlorinated analogue of the more common indole 3 acetic acid IAA auxin 4 Cl IAA is found in the seeds of a variety of plants particularly legumes such as peas and broad beans 2 3 4 5 In one study it is written that the substance is mainly found in reproductive structures and is thought to be restricted to members of the leguminous tribe Fabeae specifically the genera Vicia Pisum Lathyrus Lens and Vavilovia 6 In Pisum sativum 4 Cl IAA biosynthesis diverges from IAA biosynthesis when the amino acid tryptophan is chlorinated to form 4 chlorotryptophan 4 Cl Trp the biosynthesis of 4 Cl IAA then precedes parallel to that of IAA 7 Engvild hypothesized in 1996 that 4 Cl IAA may be a death hormone that maturing seeds use to trigger death of the parent plant by mobilizing nutrients to be stored in the seed 8 Lam et al found the substance in the seeds of Medicago truncatula Melilotus indicus and three species of Trifolium 6 References Edit Reinecke Dennis M 1999 4 Chloroindole 3 acetic acid and plant growth Plant Growth Regulation 27 1 3 13 doi 10 1023 A 1006191917753 ISSN 0167 6903 S2CID 23683065 Pless Tanja Boettger Michael Hedden Peter Graebe Jan 1984 Occurrence of 4 Cl indoleacetic acid in broad beans and correlation of its levels with seed development Plant Physiology 74 2 320 3 doi 10 1104 pp 74 2 320 PMC 1066676 PMID 16663416 Ernstsen Arild Sandberg Goeran 1986 Identification of 4 chloroindole 3 acetic acid and indole 3 aldehyde in seeds of Pinus sylvestris Physiologia Plantarum 68 3 511 18 doi 10 1111 j 1399 3054 1986 tb03390 x Katayama Masato Thiruvikraman Singanallore V Marumo Shingo 1987 Identification of 4 chloroindole 3 acetic acid and its methyl ester in immature seeds of Vicia amurensis the tribe Vicieae and their absence from three species of Phaseoleae Plant and Cell Physiology 28 2 383 386 ISSN 0032 0781 Archived from the original on 16 October 2013 Retrieved 16 October 2013 Magnus Volker Ozga Jocelyn A Reinecke Dennis M Pierson Gerald L Larue Thomas A Cohen Jerry D Brenner Mark L 1997 4 chloroindole 3 acetic and indole 3 acetic acids in Pisum sativum Phytochemistry 46 4 675 681 doi 10 1016 S0031 9422 97 00229 X a b Lam H K McAdam S A McAdam E L Ross J J 2015 Evidence That Chlorinated Auxin is Restricted to the Fabaceae but Not to the Fabeae Plant Physiology 168 3 798 803 doi 10 1104 pp 15 00410 PMC 4741347 PMID 25971549 Tivendale N D Davidson S E Davies N W Smith J A Dalmais M Bendahmane A I Quittenden L J Sutton L Bala R K Signor C Le Thompson R Horne J Reid J B Ross J J 2012 Biosynthesis of the Halogenated Auxin 4 Chloroindole 3 Acetic Acid Plant Physiology 159 3 1055 1063 doi 10 1104 pp 112 198457 PMC 3387693 PMID 22573801 Engvild Kjeld C 1996 Herbicidal activity of 4 chloroindoleacetic acid and other auxins on pea barley and mustard Physiologia Plantarum 96 2 333 337 doi 10 1111 j 1399 3054 1996 tb00222 x This article about a heterocyclic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 4 Chloroindole 3 acetic acid amp oldid 1136087089, wikipedia, wiki, book, books, library,
