Indol-2-acetic acid

Pyrano[3,4-b]indol-3-ones are the most useful equivalents of the indol-2,3-quinodimethane synthon which are currently available for synthetic application. These compounds can be synthesized readily from indole-3-acetic acids and carboxylic anhydrides[5,6]. On heating with electrophilic alkenes or alkynes, adducts are formed which undergo decarboxylation to 1,2-dihydro-carbazoles or carbazoles, respectively. 

The mode of action is by inhibiting 5-enolpymvyl-shikimate-3-phosphate synthase. Roundup shuts down the production of the aromatic amino acids phenylalanine, tyrosine, and tryptophane (30). Whereas all these amino acids are essential to the survival of the plant, tryptophane is especially important because it is the progenitor for indole-3-acetic acid, or auxin, which plays an important role in growth and development, and controls cell extension and organogenesis. 

Naturally Occurring Compounds. Many derivatives of iadole are found ia plants and animals where they are derived from the amino acid tryptophan. Several of these have important biological function or activity. Serotonin [50-67-9] (12) functions as a neurotransmitter and vasoconstrictor (35). Melatonin [73-31-4] (13) production is controlled daily by the circadian cycle and its physiological level iafluences, and seasonal rhythms ia humans and other species (36). Indole-3-acetic acid [87-51-4] (14) is a plant growth stimulant used ia several horticultural appHcations (37). 

H-Indole, 3,3-dichloro-synthesis, 4, 369 3H-Indole, 3,3-dimethyl-synthesis, 4, 224 3H-Indole, 3-hydroperoxy-autoxidation, 4, 247 rearrangement, 4, 249 3H-Indole, 3-oximino-synthesis, 4, 209, 210 3H-Indole, 3-oximino-2-phenyl Beckmann rearrangement, 4, 210 Indoleacetic acid synthesis, 4, 337 Indole-3-acetic acid as growth regulator, 4, 372 synthesis, 4, 346 Indole alkaloids, 4, 373 synthesis, 4, 276... 

Indole-3-acetic acid [87-51-4] M 175.2, m 167-169 , pK -6.13 (aq H2SO4), pK 4 5 4 (CO2H). Recrystd from EtOH/water [James and Ware J Phys Chem 89 5450 7985]. 

Coupling reactions of indole-3-acetic acid derivatives have also p ovided convenient routes to indolo[2,3-a]carbazoles (Scheme 5). An iodine-p-omoted coupling... 

Hydroxyindoles carrying a side chain containing a free NH2, OH, or COOH functional group are unstable. Therefore, 1-hydroxytryptophan, -tryptamine, and -indole-3-acetic acid have not been prepared yet. 

Tm-mediated-radical cyclizadon of isonitnles provides a usefid strategy for the preparadon of indoles (Tukuyama reacdoni This radical cyclizadon is used for synthesis of 6-hydroxy-indole-3-acetic acid, which is thearomadc subunit of Nephdatoxin The reqidsite isotdtnles are prepared from rdtroarenes via amines fEq 10 66 ... 

Dichlorophenoxy acetic acid (555ng) 12/ Indole-3-acetic acid ethyl ester (445ng)... 

CN I -(4-chlorobenzoyl)-5-methoxy-2-methyl-1 //-indole-3-acetic acid carboxymethyl ester... 

CN ( )-l-(4-chlorobenzoyl)-5-methoxy-2-methyl-lH-indole-3-acetic acid 2-I4-[3-[[4-(benzoylamino)-5-(dipropylamino)-1,5-dioxopentyl]oxy]propyl]-1 -piperazinyl]ethyl ester... 

Jensen JB, H Egsgaard, H van Onckelen, BU Jochknsen (1995) Catabolism of indole-3-acetic acid and 4- and 5-chloroindole-3-acetic acid in Bradyrhizobium japonicum. J Bacterial 111 5762-5766. 

J. E. Loper and M. N. Schroth, Influence of bacterial sources of indole-3-acetic acid on root elongation of sugar beet. Phytopathology 76 386 (1986). 

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