Indole 3 Acetic Acid(IAA) CAS 87-51-4

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Indole 3 Acetic Acid(IAA), also known as indoleacetic acid, is a plant auxin with chemical formula C10H9NO2 and 8CAS 7-51-4, White crystalline powder, soluble in ethanol, acetone and ether, slightly soluble in chloroform, insoluble in water. It is used as plant growth stimulator and analytical reagent. Indoleacetic acid is synthesized in the expanded young leaves and apical meristem, and accumulated from top to bottom through the long-distance transportation of phloem. The root can also produce auxin and transport it from bottom to top. The auxin in plants is formed by tryptophan through a series of intermediate products.

Indole-3-acetic acid (IAA), as the earliest discovered natural plant growth hormone, is endowed with unique biological activity by the indole ring and acetic acid side chain in its molecular structure. Since its isolation and purification from plants in 1934, IAA has demonstrated extensive application value in agriculture, horticulture, biotechnology, and basic research fields.

Core regulatory factors of plant growth

 

1. Bi directional regulation of cell division and elongation
IAA promotes cell division by regulating the expression of cyclin genes, while inducing cell elongation by acidifying the cell wall and activating expansin protein. In the meristematic tissue of the stem tip, low concentrations of IAA (0.01-1 μ M) promote longitudinal cell elongation, while high concentrations (>10 μ M) inhibit root cell elongation by inducing ethylene synthesis. This concentration dependent effect was significant in the maize embryo sheath elongation experiment: 0.1 μ M IAA increased embryo sheath elongation by 40%, while 10 μ M treatment resulted in elongation inhibition.

 

2. Organ construction and morphogenesis
Root development: Indole 3 Acetic Acid(IAA) establishes a root meristem gradient by regulating the polarity localization of PIN proteins, promoting the formation of root primordia. In Arabidopsis mutant studies, pin1 deficiency resulted in disrupted distribution of IAA and a 60% reduction in root hair quantity.
Top advantage: IAA produced at the stem tip inhibits lateral bud germination through polar transport, and exogenous application of IAA transport inhibitors (such as NPA) can increase the number of potato lateral buds by 3-5 times.
Flower and fruit development: IAA induces tomato parthenocarpy, and soaking flowers in a 3000 mg/L IAA solution increases seedless fruit yield by 200%; Spraying 20 mg/L IAA during the apple fruit setting period can increase the fruit setting rate by 35%.

 

3. Environmental adaptation response
Phototropism: The accumulation rate of IAA on the backlit side of oat embryo sheaths is 30% faster than on the backlit side, resulting in a difference in cell elongation rate.
Geotropism: The asymmetric distribution of IAA in maize root cap column cells inhibits the elongation of lower cells and accelerates the elongation of upper cells, resulting in negative geotropism of roots.
Adversity response: Under drought stress, the IAA content in wheat roots increased by 2.3 times, enhancing water absorption capacity by promoting root growth.

Key components of plant tissue culture

 

1. Induction of callus tissue
In tobacco leaf mesophyll cell culture, adding 0.1-1 mg/L IAA to MS medium can increase the callus induction rate from 12% to 85%. The ratio of IAA to cytokinins (such as 6-BA) determines the direction of differentiation: high IAA/low 6-BA (10:1) promotes root formation, while low IAA/high 6-BA (1:10) induces bud differentiation.

2. Somatic embryogenesis
In carrot suspension cell culture, the combination of 0.5 mg/L IAA and 2 mg/L 2,4-D can increase the frequency of embryonic development by 40%. IAA regulates the expression of key genes involved in embryonic development, such as LEC1 and FUS3, and initiates the process of somatic embryonic development.

3. Optimization of genetic transformation system
In Agrobacterium mediated cotton genetic transformation, adding 0.01 mg/L IAA to the pre culture medium can increase the transformation efficiency by 25%. IAA maintains cell division activity, prolongs the window period of Agrobacterium infection, and reduces browning phenomenon.

Innovative Application of Modern Agricultural Technology

 

1. Efficient rooting technology
Hard branch cutting: Grape hard branches were treated with 500 mg/L IAA rapid dipping, and the rooting rate reached 92%, which was 58% higher than the control group.
Difficult to root tree species: Red pine tender branches were soaked in 1000 mg/L IAA for 24 hours, and the rooting rate increased from 12% to 67%.
Development of composite formulation: Mixing IAA and fungicide (1:10) to treat rice seedlings resulted in a 40% increase in root number and an 85% effect in preventing and controlling Fusarium wilt.

2. Fruit setting and quality control
Seedless fruit production: Spraying 20 mg/L IAA during the peak flowering period of strawberries increases the proportion of seedless fruits by 70% and the weight of individual fruits by 15%.

 

Fruit uniformity: Spraying 10 mg/L IAA during the young fruit stage of citrus reduced the standard deviation of fruit shape index by 0.2 and increased the commercial fruit rate by 25%.
Sugar accumulation: Applying 5 mg/L IAA during the swelling period of sugar beet tubers increased sugar content by 1.8 percentage points and yield by 12%.
3. Adversity cultivation management
Saline alkali land improvement: Corn seeds treated with a combination of IAA and humic acid showed a 40% increase in germination rate and a 25% increase in seedling dry weight under 0.3% NaCl stress.
Low temperature seedling cultivation: Spraying 5 mg/L IAA on cucumber seedlings during the seedling stage increased survival rate by 35% at 5 ℃ and reduced electrolyte leakage rate by 22%.

Research tools for plant physiological mechanisms

 

1. Analysis of transportation routes
By using radioactive labeling to track the movement path of IAA in plants, the "co transport model" of polar transport was revealed: IAA and H ⁺ were transported in the same direction, and a membrane potential gradient was established to drive transport.
2. Research on signal transduction
Indole 3 Acetic Acid(IAA) is used as a model molecule to elucidate the interaction mechanism between auxin receptor TIR1/AFB and AUX/IAA proteins. Yeast two hybrid experiments showed that 10 nM IAA can induce the formation of TIR1-AUX/IAA complexes and activate ARF transcription factors.
3. Elucidation of metabolic pathways
Isotope tracing technology combined with LC-MS analysis has identified the main metabolic pathways of IAA in plants: 70% is stored in the form of indole-3-acetic acid aspartic acid complexes, and 20% is degraded by IAA oxidase to oxidized indole-3-acetic acid.

Extended application of industry and biotechnology

 

1. Microbial engineering production
Recombinant Escherichia coli expresses tryptophan monooxygenase (iaAM) and indole-3-aldehyde dehydrogenase (iaAH), resulting in an IAA production of 1.2 g/L in the fermentation broth, which is 40% lower than the cost of chemical synthesis.
2. Development of biological dyes
IAA forms a red complex with iron ions, which can be used for microscopic localization of auxin distribution in plant tissue sections, with a sensitivity of 0.1 μ g/g tissue.
3. Environmental monitoring indicators
As a plant stress biomarker, changes in IAA content can reflect the degree of heavy metal pollution: the decrease in IAA content in rice roots under Cd ² ⁺ stress is significantly negatively correlated with the pollution index (r=-0.87).

The synthesis route of IAA: the reaction of indole, formaldehyde and potassium cyanide at 150 ℃, 0.9~1MPa to produce 3-indole acetonitrile, and then hydrolysis under the action of potassium hydroxide. Or from the reaction of indole and glycolic acid. In a 3L stainless steel autoclave, add 270g (4.1mol) 85% potassium hydroxide, 351g (3mol) indole, and then slowly add 360g (3.3mol) 70% hydroxyacetic acid aqueous solution. Heat it to 250 ℃ and stir for 18 h. Cool to below 50 ℃, add 500mL of water, and stir at 100 ℃ for 30min to dissolve indole-3-potassium acetate. Cool to 25 ℃, pour autoclave materials into water, and add water to a total volume of 3L. Extract with 500mL ether, separate the water layer, acidify with hydrochloric acid at 20-30 ℃, and precipitate indole-3-acetic acid. Filter, wash in cold water and dry in dark to obtain 455-490g of product.

Principle of action: Indoleacetic acid is synthesized in the expanded young leaves and apical meristem, and accumulated from top to bottom through the long-distance transportation of phloem. The root can also produce auxin and transport it from bottom to top. The auxin in plants is formed by tryptophan through a series of intermediate products. Its main pathway is through indole acetaldehyde. Indole acetaldehyde can be formed from the oxidation and deamination of tryptophan to indole pyruvic acid and then decarboxylation, or from the oxidation and deamination of tryptophan to tryptophan. Then indolealdehyde is oxidized to indoleacetic acid. Another possible synthesis pathway is the conversion of tryptophan from indole acetonitrile to indole acetic acid. In plants, IAA can combine with other substances to lose its activity, such as combining with aspartic acid to form IAA, inositol to form IAA, glucose to form glucoside, and protein to form IAA-protein complex. The bound indoleacetic acid usually accounts for 50~90% of indoleacetic acid in plants. It may be a storage form of auxin in plant tissues. They can be hydrolyzed to produce free indoleacetic acid. Indoleacetic acid oxidase, which is ubiquitous in plant tissues, can oxidize and decompose indoleacetic acid.

Discovery process of indole 3 acetic acid(IAA): auxin is the earliest discovered plant hormone. In 1880, when studying the phototropism of plants, C. Darwin of the United Kingdom found that unidirectional illumination of the coleoptile would cause the phototropism bending of the coleoptile. Cut off the tip of the coleoptile or cover the coleoptile with an opaque tin foil cap. Phototropic bending will not occur when irradiated with unilateral light. Therefore, Darwin believed that the coleoptile produced a downward moving substance under unilateral light, which caused the growth speed of the back-light surface and the light-facing surface of the coleoptile to be different, making the coleoptile bend to the light. In 1910, the experiment of P. Boysen-Jense proved that the effect produced by the tip of the coleoptile can be transmitted to the lower part through the agar plate. In 1914, the experiment of A. Paal proved that the curved growth of coleoptile was caused by the uneven distribution of the influence produced by the tip in its lower part. In 1928, F.W. Went of the Netherlands placed the tip of the cut oat coleoptile on the agar block. After a period of time, the tip of the coleoptile was removed and these agar pieces were placed on the side of the pointed coleoptile. As a result, the side with the agar grew faster and bent in the opposite direction. This experiment confirmed that a substance produced by the coleoptile tip diffused into the agar and then placed on the coleoptile can transfer to the lower part of the coleoptile and promote the growth of the lower part. Later, Winter separated the growth-related substances produced by the sheath tip for the first time, and named this substance auxin. In 1931, Kogl and others in the Netherlands isolated a compound from human urine and added it to agar, which can also induce coleoptile bending. The compound was proved to be indoleacetic acid. Then in 1946, Kogl and others also found indoleacetic acid, phenylacetic acid (PAA), indolebutyric acid (IBA), etc. in plant tissues.

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