4-Chloroindole-3-acetic acid

4-Chloroindole-3-acetic acid

Names
Preferred IUPAC name (4-Chloro-1H-indol-3-yl)acetic acid
Other names 2-(4-Chloro-1H-indol-3-yl)acetic acid
Identifiers
CAS Number	2519-61-1
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:20339
ChEMBL	ChEMBL309993
ChemSpider	90727
PubChem	100413
InChI 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) Key: WNCFBCKZRJDRKZ-UHFFFAOYSA-N 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
SMILES OC(CC1=CNC2=CC=CC(Cl)=C21)=O Clc1cccc2c1c(cn2)CC(=O)O
Properties
Chemical formula	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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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 hypothesized 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. (1999). "4-Chloroindole-3-acetic acid and plant growth". Plant Growth Regulation. 27 (1): 3–13. doi:10.1023/A:1006191917753. ISSN 0167-6903.
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. 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. 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.