出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/27 10:51:15」(JST)
| Indole-3-acetic acid | |
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IUPAC name
2-(1H-indol-3-yl)acetic acid |
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Other names
Indole-3-acetic acid, |
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| Identifiers | |
| CAS number | 87-51-4 Y |
| PubChem | 802 |
| ChemSpider | 780 Y |
| DrugBank | DB07950 |
| KEGG | C00954 Y |
| ChEBI | CHEBI:16411 Y |
| ChEMBL | CHEMBL82411 Y |
| Jmol-3D images | Image 1 |
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SMILES
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InChI
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| Properties | |
| Molecular formula | C10H9NO2 |
| Molar mass | 175.184 |
| Appearance | white solid |
| Melting point |
168-170 °C (441-443 K) |
| Solubility in water | moderate |
| Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Indole-3-acetic acid (IAA) is the most common, naturally-occurring, plant hormone of the auxin class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists.[1] Chemically, IAA is a carboxylic acid in which the carboxyl group is attached through a methylene group to the C-3 position of an indole ring. In appearance, IAA is a colorless solid.
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IAA is predominantly produced in cells of the apex (bud) and very young leaves of a plant. Plants can synthesize IAA by several independent biosynthetic pathways. Four of them start from tryptophan, but there is also a biosynthetic pathway independent of tryptophan.[2] Plants mainly produce IAA from tryptophan through indole-3-pyruvic acid.[3][4] IAA is also produced from tryptophan through indole-3-acetaldoxime in Arabidopsis.[5]
IAA 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. On a larger scale, IAA serves as signaling molecule necessary for development of plant organs and coordination of growth.
There are less expensive and metabolically stable synthetic auxin analogs on the market for use in horticulture, such as indole-3-butyric acid (IBA) and 1-naphthaleneacetic acid (NAA).[citation needed]
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 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.[citation needed]
Chemically, it can be synthesized by the reaction of indole with glycolic acid in the presence of base at 250 °C:[6]
Many methods for its synthesis have been developed since its original synthesis from indole-3-acetonitrile.[7]
IAA doesn’t have any toxic concerns to humans. It is advised to wear gloves when working with it and to always wear glasses goggles or a face shield to avoided contact to the eye. All bottles are to have a category II label on them for primary eye irritant. It is advised that if IAA does make contact with your eye to wash it out with water and to then contact your doctor.[8]
Studies have been done on mice to see if IAA and similar chemicals have been used in studies to see what affects they have on the development of the cerebral cortex of mice in the early stages of the fetuses. They found that it decreased the locomotor activities of the embryos/fetuses. They also observed that in their study with just IAA that there was a notable drop in brain sizes compared to the other considerations that they used.[9]
Indole-3-acetic acid (IAA) and horseradish peroxidase (HRP) have been proposed on the basis of polymer transfer and gene-direction, they may be useful in cancer therapy. Radical-IAA IAA in the human body will attach to cells with that characterized by HRP. By this means the HRP reaction cells can be selectively killed. But because of the competitive bonding of the IAA-HRP more studies must be done before clinical studies can begin.[10]
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| リンク元 | 「auxin」「インドール酢酸」 |
| 拡張検索 | 「5-hydroxyindoleacetic acid」「hydroxyindoleacetic acid」 |