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Revision as of 08:18, 20 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI', 'CASNo').← Previous edit Latest revision as of 14:25, 17 December 2024 edit undoArthurfragoso (talk | contribs)Extended confirmed users2,076 edits Fixes image on dark mode 
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{{DISPLAYTITLE:''N''-Acetylanthranilic acid}} {{DISPLAYTITLE:''N''-Acetylanthranilic acid}}
{{chembox {{Chembox
| Verifiedfields = changed
| verifiedrevid = 453511542
| Watchedfields = changed
| Name=''N''-Acetylanthranilic acid
| verifiedrevid = 456483862
| ImageFile = N-acetylanthranilic_acid.svg
| Name = ''N''-Acetylanthranilic acid
| ImageSize = 120px
| ImageFileL1 = N-acetylanthranilic_acid.svg
| ImageName = N-acetylanthranilic Acid
| ImageSizeL1 = 120px
|IUPACName=2-acetamidobenzoic acid
| ImageClassL1 = skin-invert
|OtherNames=2-acetamidobenzoic acid, 2-Carboxyacetanilide, o-Acetoaminobenozic acid, Acetylanthranilic acid, 2-(Acetylamino)benzoic acid
| ImageNameL1 = N-acetylanthranilic Acid
|Section1= {{Chembox Identifiers
| ImageFileR1 = N-Acetylanthranilic-acid-from-xtal-Mercury-3D-bs.png
| CASNo = <!-- blanked - oldvalue: 89-52-1 -->
| ImageNameR1 = Ball-and-stick model of N-Acetylanthranilic acid
| ChEBI = 36555
| PIN = 2-Acetamidobenzoic acid
| PubChem=6971
| OtherNames = 2-Acetamidobenzoic acid; 2-Carboxyacetanilide; ''o''-Acetoaminobenozic acid; Acetylanthranilic acid; 2-(Acetylamino)benzoic acid
| SMILES=CC(=O)NC1=CC=CC=C1C(=O)O
|Section1={{Chembox Identifiers
| ChEBI = 36555
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 89-52-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P1IE9J75C2
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 36555
| PubChem = 6971 | PubChem = 6971
| SMILES = CC(=O)NC1=CC=CC=C1C(=O)O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6705 | ChemSpiderID = 6705
| InChI = 1/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13) | InChI = 1/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)
| InChIKey = QSACCXVHEVWNMX-UHFFFAOYAX | InChIKey = QSACCXVHEVWNMX-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13) | StdInChI = 1S/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QSACCXVHEVWNMX-UHFFFAOYSA-N | StdInChIKey = QSACCXVHEVWNMX-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=9 | H=9 | N=1 | O=3
| Appearance = Slightly beige solid
| Density = 1.36 g/mL
| MeltingPtC = 184 to 186
| MeltingPt_notes =
| BoilingPtC = 399
| BoilingPt_notes =
| Solubility =
| pKa =
| pKb =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

| Section4 = {{Chembox Thermochemistry
| DeltaGf =
| DeltaHc =
| DeltaHf =
| Entropy =
| HeatCapacity =
}} }}
|Section2= {{Chembox Properties | Section7 = {{Chembox Hazards
| AutoignitionPt =
| Formula=| C=9 | H=9 | N=1 | O=3
| ExploLimits =
| MolarMass= 179.17 g/mol
| FlashPt =
| Appearance=
| LD50 = Oral, mouse = 1114 mg/kg
| Density=
| LC50 =
| MeltingPt=184-186 °C
| MainHazards =
| BoilingPt=
| NFPA-F =
| Solubility=
| pKa = | NFPA-H =
| pKb = | NFPA-R =
| NFPA-S =
}}
| PEL =
|Section3= {{Chembox Hazards
| MainHazards= | REL =
| ExternalSDS =
| FlashPt=
| GHSPictograms = {{GHS07}}
| Autoignition=
| GHSSignalWord =
}}
| HPhrases =
| Section8 = {{Chembox Related
| OtherCpds = | PPhrases =
}} }}
|Section8={{Chembox Legal status
| legal_AU =
| legal_BR = D1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_US =
| legal_UK =
| legal_UN =
}}
|Section9={{Chembox Related
| OtherCompounds =
}}
}} }}


'''''N''-Acetylanthranilic acid''' is an organic compound with the molecular formula C<sub>9</sub>H<sub>9</sub>NO<sub>3</sub>. It is an intermediate product in ] of ] in ], and is further metabolized to ].<ref> '''''N''-Acetylanthranilic acid''' is an organic compound with the molecular formula C<sub>9</sub>H<sub>9</sub>NO<sub>3</sub>. It is an intermediate product in ] of ] in ], and is further metabolized to ].<ref>
{{cite journal {{cite journal
| author = Hund HK, de Beyer A, Lingens F. | vauthors = Hund HK, de Beyer A, Lingens F
| date = 1990 | date = 1990
| title = Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp | title = Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp
| journal = ] | journal = ]
| volume= 371 |issue =10 |pages = 1005–1008 | volume= 371 |issue =10 |pages = 1005–1008
| doi = 10.1515/bchm3.1990.371.2.1005 | doi = 10.1515/bchm3.1990.371.2.1005
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}}</ref><ref> }}</ref><ref>
{{cite journal {{cite journal
| author = Overhage J et al. |vauthors=Overhage J, etal | date = 2005
| date = 2005
| title = Identification of large linear plasmids in Arthrobacter spp. encoding the degradation of quinaldine to anthranilate | title = Identification of large linear plasmids in Arthrobacter spp. encoding the degradation of quinaldine to anthranilate
| journal = ] | journal = ]
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| doi = 10.1099/mic.0.27521-0 | doi = 10.1099/mic.0.27521-0
| pmid = 15699198 | pmid = 15699198
| doi-access = free
}}</ref>
}}</ref>


''N''-Acetylanthranilic acid can be synthesized from 2-bromoacetanilide via ]-] ] in tri-n-butylamine-water at 110-130 °C, under 3 ] of ].<ref> ''N''-Acetylanthranilic acid can be synthesized from 2-bromoacetanilide via ]-] ] in ]-water at 110–130&nbsp;°C, under 3 ] of ].<ref>
{{cite journal {{cite journal
| author = Donald Valentine, Jefferson W. Tilley, Ronald A. LeMahieu | author = Donald Valentine
| author2 = Jefferson W. Tilley
| author3 = Ronald A. LeMahieu
| date = 1981 | date = 1981
| title = Practical, catalytic synthesis of anthranilic acids | title = Practical, catalytic synthesis of anthranilic acids
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| doi = 10.1021/jo00335a075 | doi = 10.1021/jo00335a075
| pmid = | pmid =
}}</ref> In the laboratory, it can be easily synthesized from ] and ].
}}</ref>

''N''-Acetylanthranilic acid exhibits ] when crushed.<ref>{{cite journal | vauthors = Erikson J | title = N-acetylanthranilic acid. A highly triboluminescent material | journal = J Chem Educ | date = Oct 1972 | volume = 49 | issue = 10 | pages = 688 | doi = 10.1021/ed049p688 }}</ref> The fractured crystals have large electrical potentials between areas of high and low charge. When the electrons suddenly migrate to neutralize these potentials, flashes of deep blue light are created.

In the United States, it is a ]-controlled ],<ref>{{cite web|url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1310/1310_02.htm |title=PART 1310 - Section 1310.02 Substances covered |website=www.deadiversion.usdoj.gov}}</ref> because it has been used in the synthesis of ].


==See also== ==See also==