Indole-3-acetic acid 2027822 205934322 2008-04-16T02:22:38Z WriterHound 266293 formatting {{Chembox new |ImageFile=Indol-3-ylacetic acid2.svg |ImageSize= |IUPACName=2-(1H-indol-3-yl)acetic acid |OtherNames=Indole-3-acetic acid,<br>indolylacetic acid,<br>indoleacetic acid,<br>heteroauxin,<br>IAA |Section1= {{Chembox Identifiers | CASNo=87-51-4 | PubChem=802 | SMILES=C1=CC=C2C(=C1) C(=CN2)CC(=O)O }} |Section2= {{Chembox Properties | Formula=C<sub>10</sub>H<sub>9</sub>NO<sub>2</sub> | MolarMass=175.184 | Appearance= | Density= | MeltingPt=168-170 °C (441-443 K) | BoilingPt= | Solubility= }} |Section3= {{Chembox Hazards | MainHazards= | FlashPt= | Autoignition= }} }} '''Indole-3-acetic acid''', also known as IAA, is a member of the group of [[phytohormone]]s called [[auxin]]s. IAA is generally considered to be the most important native auxin. == Auxin == {{main|Auxin}} It is produced in cells in the [[apex]] ([[bud]]) and young leaves of a [[plant]]. Plant cells synthesize IAA from [[tryptophan]]. It has many different effects, as all auxins do, such as inducing [[Cell (biology)|cell]] elongation and [[cell division]] with all subsequent results for plant growth and development. There are less expensive and [[metabolism|metabolically]] stable synthetic [[auxin]] analogs on the market for use in [[horticulture]], such as [[indole-3-butyric acid]] (IBA) and [[1-Naphthaleneacetic acid|1-naphthaleneacetic acid]] (NAA). Studies of IAA in the 1940s led to the development of the [[phenoxy herbicide]]s [[2,4-dichlorophenoxyacetic acid]] (2,4-D) and [[2,4,5-trichlorophenoxyacetic acid]] (2,4,5-T). Like IBA and NAA, 2,4-D and 2,4,5-T are metabolically and environmentally more stable analogs of IAA. However, when sprayed on broad-leaf dicot plants, they induce rapid, uncontrolled growth, eventually killing them. First introduced in 1946, these herbicides were in widespread use in [[agriculture]] by the middle of the [[1950s]]. == Chemical properties of IAA == IAA can be produced by the reaction of [[indole]] with potassium glycolate at 250 C, but this compound is chemically unstable in particular when exposed to light or changing temperature. == See also == * [[Auxin]] * [[Phytohormone]] * [[Indole]] * [[Acetic acid]] ==Additional images== <gallery> Image:Indol2.svg|[[Indole]] Image:Acetic-acid-2D-skeletal.svg|[[Acetic acid]] </gallery> ==External links== {{Plant_hormones}} [[Category:Auxins]] [[Category:Plant physiology]] [[Category:Aromatic compounds]] [[Category:Carboxylic acids]] [[Category:Indoles]] [[de:Indol-3-essigsäure]] [[es:Ácido indolacético]] [[fr:Acide indole 3-acétique]] [[pl:Kwas indolilooctowy]] [[ru:Гетероауксин]]