4-Chloroindole-3-acetic acid

4-Chloroindole-3-acetic acid (4-Cl-IAA) is an organic compound that functions as a plant hormone.^[1]

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 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:20339 Y
ChEMBL	ChEMBL309993 Y
ChemSpider	90727 Y
ECHA InfoCard	100.255.860
PubChem CID	100413
UNII	RF78HU5XXV Y
CompTox Dashboard (EPA)	DTXSID10179857
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) Y Key: WNCFBCKZRJDRKZ-UHFFFAOYSA-N Y 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 Clc1cccc2c1c(c[nH]2)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). N verify (what is YN ?) Infobox references

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]