4-Chloroindole-3-acetic acid

4-Chloroindole-3-acetic acid
4-Chloroindole-3-acetic acid
IUPAC name
2-(4-chloro-1H-indol-3-yl)acetic acid
Identifiers
CAS number 2519-61-1
PubChem 100413
ChemSpider 90727 YesY
ChEBI CHEBI:20339 YesY
ChEMBL CHEMBL309993 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C10H8ClNO2
Molar mass 209.63 g mol−1
 YesY acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

4-Chloroindole-3-acetic acid (4-Cl-IAA) is a natural plant hormone.[1] It is a member of the class of compounds known as auxins and a chlorinated derivative of the more common auxin indole-3-acetic acid (IAA). 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] It is hypothosized 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.[6]

References

  1. ^ Reinecke, Dennis M. 4-Chloroindole-3-acetic acid and plant growth. Plant Growth Regulation (1999), 27(1), 3-13.
  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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1066676. 
  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. 
  5. ^ Magnus, Volker; Ozga, Jocelyn A.; Reinecke, Dennis M.; Pierson, Gerald L.; Larue, Thomas A.; Cohen, Jerry D.; Brenner, Mark L. 4-chloroindole-3-acetic and indole-3-acetic acids in Pisum sativum. Phytochemistry (1997), 46(4), 675-681.
  6. ^ 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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