Indole-3-acetic acid
Encyclopedia : I : IN : IND : Indole-3-acetic acid
| Indole-3-acetic acid | |
|---|---|
|
| |
| General | |
| Systematic name | 1H-indole-3-acetic acid |
| Other names | indole-3-acetic acid indoleacetic acid heteroauxin IAA |
| Molecular formula | C10H9NO2 |
| SMILES | C1=CC=C2C(=C1)C(=CN2)CC(=O)O |
| Molar mass | 175.18 g/mol |
| Appearance | White powder (unstable) |
| CAS number | [87-51-4] |
| Properties | |
| Density and phase | ? g/cm3, ? |
| Solubility in water | sparingly sol. |
| Melting point | 168-170 °C (? K) |
| Boiling point | ? °C (? K) |
| Acidity (pKa) | 4.75 |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | 171 °C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties | n, εr, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds | auxin indolebutyric acid 1-naphthaleneacetic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) [Chemical infoboxInfobox disclaimer and references] | |
Indole-3-acetic acid, also known as IAA, is a member of the group of phytohormones called auxins. IAA is generally considered to be the most important native auxin.
Auxin
It is produced in cells in the apex (bud) of a plant. Plant cells synthesize IAA from tryptophan. It has many different effects, as all auxins do, such as inducing cell elongation and cell division with all subsequent results for plant growth and development. There are less expensive and more stable synthetic auxin analogs on the market for use in horticulture, such as indole-3-butyric acid (IBA) and 1-naphthaleneacetic acid (NAA).
Studies of IAA in the 1940s led to the development of the phenoxy herbicides 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 chemically stable analogs of IAA. However, when sprayed on broad-leaf 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
External links
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
| Plant hormones | [edit] |
| Abscisic acid - Auxins - Cytokinins - Ethylene (Ethene) - Gibberellins |
From Wikipedia, the Free Encyclopedia. Original article here. Support Wikipedia by contributing or donating.
All text is available under the terms of the GNU Free Documentation License See Wikipedia Copyrights for details.