1-Naphthaleneacetic acid

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1-Naphthaleneacetic acid
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Names
Preferred IUPAC name
2-(Naphthalen-1-yl)acetic acid
Other names
1-Naphthaleneacetic acid
α-Naphthaleneacetic acid
Naphthylacetic acid
NAA
Napthoxy acetic acid
2-(1-Naphthyl)acetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
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KEGG
PubChem CID
UNII
  • InChI=1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14) Yes check.svgY
    Key: PRPINYUDVPFIRX-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)
    Key: PRPINYUDVPFIRX-UHFFFAOYAF
  • O=C(O)Cc2cccc1ccccc12
Properties
C12H10O2
Molar mass 186.210 g·mol−1
AppearanceWhite powder
Melting point 135 °C (275 °F)
0.42 g/L (20 °C)
Acidity (pKa)4.24 [1]
Hazards
Safety data sheet (SDS) SIRI.org sciencelab.com
Related compounds
Related Auxins
Indole-3-acetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-Naphthaleneacetic acid (NAA) is an organic compound with the formula C10H7CH2CO2H. This colorless solid is soluble in organic solvents. It features a carboxylmethyl group (CH2CO2H) linked to the "1-position" of naphthalene.

Contents

Use and regulation

NAA is a synthetic plant hormone in the auxin family and is an ingredient in many commercial horticultural products; it is a rooting agent and used for the vegetative propagation of plants from stem and leaf cuttings. It is also used for plant tissue culture. [2]

The hormone NAA does not occur naturally, and, like all auxins, is toxic to plants at high concentrations. In the United States, under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), products containing NAA require registration with the Environmental Protection Agency (EPA) as pesticides.

Use and analysis

NAA is widely used in agriculture for various purposes. It is considered to be only slightly toxic but when at higher concentrations it can be toxic to animals. This was shown when tested on rats via oral ingestion at 1000–5900 mg/kg. [3] NAA has been shown to greatly increase cellulose fiber formation in plants when paired with another phytohormone called gibberellic acid. Because it is in the auxin family it has also been understood to prevent premature dropping and thinning of fruits from stems. It is applied after blossom fertilization. Increased amounts can actually have negative effects however, and cause growth inhibition to the development of plant crops. It has been used on many different crops including apples, olives, oranges, potatoes, and various other hanging fruits. In order for it to obtain its desired effects it must be applied in concentrations ranging from 20–100 μg/mL. [4] NAA present in the environment undergoes oxidation reactions with hydroxyl radicals and sulfate radicals. Radical reactions of NAA were studied using pulse radiolysis technique. Hydroxyl adduct radical was formed as the intermediate during the reaction of hydroxyl radical with NAA. The intermediate naphthyl methyl radical was formed during the reaction of sulfate radical anion with NAA. [5]

In micropropagation of various plants, NAA is typically added to a medium containing nutrients essential to the plants' survival. It is added to help induce root formation in various plant types. It can also be applied by spraying it onto plants and which is typical in agricultural use. It is prohibited in many areas to use it in high concentrations due to the health concerns towards humans and other animals.

NAA can be detected by HPLC-tandem mass spectrometry (HPLC-MS/MS). [6]

Derivative uses

See also

Related Research Articles

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Plant hormones are signal molecules, produced within plants, that occur in extremely low concentrations. Plant hormones control all aspects of plant growth and development, including embryogenesis, the regulation of organ size, pathogen defense, stress tolerance and reproductive development. Unlike in animals each plant cell is capable of producing hormones. Went and Thimann coined the term "phytohormone" and used it in the title of their 1937 book.

<span class="mw-page-title-main">Auxin</span> Plant hormone

Auxins are a class of plant hormones with some morphogen-like characteristics. Auxins play a cardinal role in coordination of many growth and behavioral processes in plant life cycles and are essential for plant body development. The Dutch biologist Frits Warmolt Went first described auxins and their role in plant growth in the 1920s. Kenneth V. Thimann became the first to isolate one of these phytohormones and to determine its chemical structure as indole-3-acetic acid (IAA). Went and Thimann co-authored a book on plant hormones, Phytohormones, in 1937.

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<span class="mw-page-title-main">Micropropagation</span> Practice in plant tissue culture

Micropropagation or tissue culture is the practice of rapidly multiplying plant stock material to produce many progeny plants, using modern plant tissue culture methods.

<span class="mw-page-title-main">Indole-3-acetic acid</span> Chemical compound

Indole-3-acetic acid 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. IAA is a derivative of indole, containing a carboxymethyl substituent. It is a colorless solid that is soluble in polar organic solvents.

<span class="mw-page-title-main">Phenylacetic acid</span> Chemical compound

Phenylacetic acid, also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogenously, it is a catabolite of phenylalanine. As a commercial chemical, because it can be used in the illicit production of phenylacetone, it is subject to controls in countries including the United States and China.

<span class="mw-page-title-main">Indole-3-butyric acid</span> Chemical compound

Indole-3-butyric acid (1H-indole-3-butanoic acid, IBA) is a white to light-yellow crystalline solid, with the molecular formula C12H13NO2. It melts at 125 °C in atmospheric pressure and decomposes before boiling. IBA is a plant hormone in the auxin family and is an ingredient in many commercial horticultural plant rooting products.

<span class="mw-page-title-main">Trifluoroacetic acid</span> Chemical compound

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<span class="mw-page-title-main">Fenoprop</span> Chemical compound

Fenoprop, also called 2,4,5-TP, is the organic compound 2-(2,4,5-trichlorophenoxy)propionic acid. It is a phenoxy herbicide and a plant growth regulator, an analog of 2,4,5-T in which the latter's acetic acid sidechain is replaced with a propionate group (with an extra CH3). The addition of this extra methyl group creates a chiral centre in the molecule and useful biological activity is found only in the (2R)-isomer. The compound's mechanism of action is to mimic the auxin growth hormone indoleacetic acid (IAA). When sprayed on plants it induces rapid, uncontrolled growth. As with 2,4,5-T, fenoprop is toxic to shrubs and trees.

<span class="mw-page-title-main">Plant tissue culture</span> Growing cells under lab conditions

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<span class="mw-page-title-main">Atractyloside</span> Chemical compound

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References

  1. Dippy, J. F. J.; Hughes, S. R. C.; Laxton, J. W. (1954). "Chemical Constitution and the Dissociation Constants of Monocarboxylic Acids. Part XIV. Monomethylcyclohexanecarboxylic Acids". Journal of the Chemical Society (Resumed). 1954: 4102–4106. doi:10.1039/JR9540004102.
  2. USpatent 6800482,Morikawa, H.; Takahashi, M.,"Cultured cells of Australian laurel, Pittosporaceae and a method for culturing tissues by using said cultured cells",issued 2004-10-05
  3. Tomlin, C.D.S., 2006. The Pesticide Manual, 14th ed. UK
  4. A. Navalón, R. Blanc, J.L. Vilchez Determination of 1-naphthylacetic acid in commercial formulations and natural waters by solid-phase spectrofluorimetry Mikcrochim. Acta, 126 (1997), pp. 33–38
  5. Naduvilpurakkal B. Shibin, Radhakrishnan Sreekanth, Usha K. Aravind, Kadavilpparampu M. Afsal Mohammed, Narayana V. Chandrashekhar, Jayan Joseph, Sisir K. Sarkar, Devidas B. Naik and Charuvila T. Aravindakumar. Radical chemistry of glucosamine naphthalene acetic acid and naphthalene acetic acid: a pulse radiolysis study. J. Phys. Org. Chem., 2014
  6. M.J. Benotti, F.P. Lee, R.A. Rieger, C.R. Iden, C.E. Heine, B.J. Brownawell HPLC/TOF-MS: an alternative to LC/MS/MS for sensitive and selective determination of polar organic contaminants in the aquatic environment Ferrer Imma, E.M. Thurman (Eds.), Liquid Chromatography/Mass Spectrometry, MS/MS and Time of Flight MS, American Chemical Society, New York (2003), pp. 109–127