4-Chloroindole-3-acetic acid

Last updated
4-Chloroindole-3-acetic acid
4-chloroindole-3-acetic acid.png
Names
Preferred IUPAC name
(4-Chloro-1H-indol-3-yl)acetic acid
Other names
2-(4-Chloro-1H-indol-3-yl)acetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.255.860 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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) Yes check.svgY
    Key: WNCFBCKZRJDRKZ-UHFFFAOYSA-N Yes check.svgY
  • InChI=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-UHFFFAOYAY
  • Clc1cccc2c1c(c[nH]2)CC(=O)O
Properties
C10H8ClNO2
Molar mass 209.63 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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4-Chloroindole-3-acetic acid (4-Cl-IAA) is an organic compound that functions as a plant hormone. [1]

Synopsis

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]

Lam et al found the substance in the seeds of Medicago truncatula , Melilotus indicus , and three species of Trifolium . [6]

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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 .
  6. 1 2 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.
  7. ↑ 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.
  8. ↑ 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.
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