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Revision as of 12:21, 25 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL', 'ChEBI', 'StdInChI', 'StdInChIKey').← Previous edit Latest revision as of 17:07, 12 January 2024 edit undoAverixus (talk | contribs)Extended confirmed users739 edits →Use and regulation: Fixed WP:SEAOFBLUE 
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{{chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 443646143 | verifiedrevid = 477199155
| Name = 1-Naphthaleneacetic acid | Name = 1-Naphthaleneacetic acid
| ImageFile = Kwas_naftylooctowy.svg | ImageFile = Kwas_naftylooctowy.svg
| ImageSize = 200px
| ImageName = 1-Naphthaleneacetic acid | ImageSize = 180
| ImageName = 1-Naphthaleneacetic acid
⚫ | ImageFile1 = 1-Naphthaleneacetic-acid-3D-balls.png
⚫ | IUPACName = 2-(1-Naphthyl)acetic acid
| ImageSize1 = 220
⚫ | OtherNames = 1-Naphthaleneacetic acid<br/>α-Naphthaleneacetic acid<br />Naphthylacetic acid<br />NAA
| ImageAlt1 = 1-Naphthaleneacetic acid molecule
⚫ | Section1 = {{Chembox Identifiers
⚫ | PIN = 2-(Naphthalen-1-yl)acetic acid
⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | OtherNames = 1-Naphthaleneacetic acid<br/>α-Naphthaleneacetic acid<br/>Naphthylacetic acid<br/>NAA<br/>Napthoxy acetic acid<br/>2-(1-Naphthyl)acetic acid
⚫ | DrugBank = <!-- blanked - oldvalue: DB01750 -->
⚫ |Section1={{Chembox Identifiers
⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank = DB01750
| SMILES = O=C(O)Cc2cccc1ccccc12 | SMILES = O=C(O)Cc2cccc1ccccc12
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = <!-- blanked - oldvalue: 32918 --> | ChEBI = 32918
| ChemSpiderID = 6601 | ChemSpiderID = 6601
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
Line 20: Line 24:
| InChIKey = PRPINYUDVPFIRX-UHFFFAOYAF | InChIKey = PRPINYUDVPFIRX-UHFFFAOYAF
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 428495 --> | ChEMBL = 428495
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = <!-- blanked - oldvalue: 1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14) --> | StdInChI = 1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = <!-- blanked - oldvalue: PRPINYUDVPFIRX-UHFFFAOYSA-N --> | StdInChIKey = PRPINYUDVPFIRX-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 6862 | PubChem = 6862
| CASNo = 86-87-3 | CASNo = 86-87-3
| UNII_Ref = {{fdacite|correct|FDA}}
| References = <ref></ref>
| RTECS = | UNII = 33T7G7757C
| RTECS =
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=12 | H=10 | O=2
| Formula = C<sub>12</sub>H<sub>10</sub>O<sub>2</sub>
⚫ | Appearance = White powder
| MolarMass = 186.2066 g/mol
⚫ | Density =
⚫ | Appearance = White powder
⚫ | Solubility = 0.42 g/L (20 °C)
⚫ | Density =
⚫ | MeltingPt = {{convert|135|C|F}}
⚫ | Solubility = 0.38 g/L (17 °C)
⚫ | BoilingPt =
⚫ | MeltingPt = 135 °C
| pKa = 4.24<ref>{{cite journal |title= Chemical Constitution and the Dissociation Constants of Monocarboxylic Acids. Part XIV. Monomethylcyclohexanecarboxylic Acids |last1= Dippy |first1= J. F. J. |last2= Hughes |first2= S. R. C. |last3= Laxton |first3= J. W. |journal= Journal of the Chemical Society (Resumed) |year= 1954 |volume= 1954 |pages= 4102–4106 |doi= 10.1039/JR9540004102 }}</ref>
⚫ | BoilingPt =
⚫ | Viscosity =
| pKa = 4.24 (25 °C)<ref>''J. Chem. Soc.'' (1954) 4102</ref>
⚫ | Viscosity =
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| MolShape = | MolShape =
| Dipole = | Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| RPhrases =
| SPhrases =
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherAnions = | OtherAnions =
| OtherCations = | OtherCations =
| Function = ]s | OtherFunction_label = ]s
| OtherFunctn = ] | OtherFunction = ]
| OtherCpds = | OtherCompounds =
}} }}
}} }}


'''1-Naphthaleneacetic acid''', commonly abbreviated NAA, is an ] with the ] C<sub>10</sub>H<sub>7</sub>CH<sub>2</sub>CO<sub>2</sub>H. This colourless solid is soluble in organic solvents. It features a carboxylmethyl group (CH<sub>2</sub>CO<sub>2</sub>H) linked to the "1-position" of ]. '''1-Naphthaleneacetic acid''' ('''NAA''') is an ] with the ] C<sub>10</sub>H<sub>7</sub>CH<sub>2</sub>CO<sub>2</sub>H. This colorless solid is soluble in organic solvents. It features a carboxylmethyl group (CH<sub>2</sub>CO<sub>2</sub>H) linked to the "1-position" of ].


==Use and regulation== ==Use and regulation==
NAA is a ] in the ] family and is an ingredient in many commercial ] ] products; it is a rooting agent and used for the ] of plants from stem and leaf cutting. It is also used for ].<ref></ref> NAA is a synthetic ] in the ] family and is an ingredient in many commercial ] products; it is a rooting agent and used for the ] of plants from stem and leaf ]. It is also used for ].<ref>{{cite patent |country= US |status= patent |number= 6800482 |title= Cultured cells of Australian laurel, Pittosporaceae and a method for culturing tissues by using said cultured cells |gdate= 2004-10-05 |inventor= Morikawa, H.; Takahashi, M.}}</ref>

⚫ The hormone NAA does not occur naturally, and, like all auxins, is toxic to plants at high concentrations. In the United States, under the ] (FIFRA), products containing NAA require registration with the ] (EPA) as ]s.

==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&nbsp;mg/kg.<ref>Tomlin, C.D.S., 2006. The Pesticide Manual, 14th ed. UK</ref> 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&nbsp;μg/mL.<ref>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</ref> 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.<ref>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</ref>

In ] 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 ]-tandem mass spectrometry (HPLC-MS/MS).<ref>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</ref>

==Derivative uses==
*RSD 1000


⚫ The hormone 1-Naphthyl acetic acid (NAA) does not occur naturally. Under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), products containing NAA require registration with the Environmental Protection Agency (EPA) as pesticides.
==See also== ==See also==
*] *]
*] *]
*] *]
*] - Another chemical used as a plant rooting agent.
*]


==References== ==References==
{{Reflist}} {{Reflist}}

==External links==
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