| Revision as of 19:34, 6 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit |
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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 413867470 |
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| Watchedfields = changed |
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| ImageFile = Anthranilic acid 2.svg |
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| verifiedrevid = 443392717 |
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| ImageSize = 160px |
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| ImageFileL1 = Anthranilsäure.svg |
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| ImageName = Skeletal formula |
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| ImageSizeL1 = 125 |
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| ImageFile1 = 2-Aminobenzoic-acid-3D-balls-B.png |
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| ImageClassL1 = skin-invert |
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| ImageSize1 = 170px |
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| ImageAltL1 = Skeletal formula of anthranilic acid |
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| ImageName1 = Ball-and-stick model |
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| IUPACName = 2-aminobenzoic acid |
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| ImageFileR1 = 2-Aminobenzoic-acid-3D-balls.png |
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| ImageSizeR1 = 125 |
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| OtherNames = vitamin L<sub>1</sub>, Anthranilate |
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| ImageNameR1 = C=black, H=white, O=red, N=blue |
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| Section1 = {{Chembox Identifiers |
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| ImageAltR1 = Ball-and-stick model of the anthranilic acid molecule |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| PIN = 2-Aminobenzoic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 748 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> |
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| SystematicName = 2-Aminobenzenecarboxylic acid |
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| OtherNames = {{Unbulleted list |
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| Anthranilic acid |
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| ''o''-Aminobenzoic acid |
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| 2-Aminobenzoic acid |
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| Vitamin L<sub>1</sub> |
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| Anthranilate (conjugate base) |
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|2-AA, 2AA, AA |
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}} |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C00108 |
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| KEGG = C00108 |
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| InChI = 1/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) |
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| InChI = 1/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 30754 |
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| ChEBI = 30754 |
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| DrugBank_Ref = {{drugbankcite|changed|??}} |
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| DrugBank = DB04166 |
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| SMILES = O=C(O)c1ccccc1N |
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| SMILES = O=C(O)c1ccccc1N |
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| InChIKey = RWZYAGGXGHYGMB-UHFFFAOYAS |
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| InChIKey = RWZYAGGXGHYGMB-UHFFFAOYAS |
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| SMILES1 = c1ccc(c(c1)C(=O)O)N |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 14173 |
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| ChEMBL = 14173 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 118-92-3 |
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| CASNo = 118-92-3 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 222 |
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| ChemSpiderID = 222 |
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| PubChem = 227 |
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}} |
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| EINECS = 204-287-5 |
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| Section2 = {{Chembox Properties |
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| 3DMet = B00027 |
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|C=7|H=7|N=1|O=2 |
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| Gmelin = 3397 |
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| Solubility = 5.7 g/L (25 °C) |
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| Beilstein = 471803 |
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| Solvent = |
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| UNII = 0YS975XI6W |
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| SolubleOther = Hot water,ethanol and ether |
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<!-- | DrugBank = DB04056 (comment: can not have two drugbank values in Chembox)--> |
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| Appearance = white or yellow solid |
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| RTECS = CB2450000 |
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| Density = 1.4 g/cm<sup>3</sup> |
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}} |
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| MeltingPt = 146–148 °C<ref></ref> |
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|Section2={{Chembox Properties |
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| BoilingPt = |
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| C=7 | H=7 | N=1 | O=2 |
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}} |
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| Solubility = 0.572 g/100 mL (25 °C) |
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| Section7 = {{Chembox Hazards |
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| SolubleOther = very soluble in ], ] <br> soluble in ], ], ] <br> slightly soluble in ], ] |
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| ExternalMSDS = |
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| Appearance = white or yellow solid |
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| EUClass = |
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| Odor = odorless |
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| RPhrases = {{R36}} {{R37}} |
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| Density = 1.412 g/cm<sup>3</sup> |
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| SPhrases = {{S26}} {{S39}} |
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| NFPA-H = 2 |
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| MeltingPtC = 146 to 148 |
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| MeltingPt_ref = <ref></ref> |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| BoilingPtC = 200 |
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| BoilingPt_notes = (sublimes) |
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| FlashPt = >150 °C |
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| pKa = {{Unbulleted list |
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}} |
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| 2.17 (amino; H<sub>2</sub>O) |
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| 4.85 (carboxyl; H<sub>2</sub>O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = ] | isbn = 978-1498754286 | pages=5–89 | title-link = CRC Handbook of Chemistry and Physics }}</ref> |
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}} |
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| LogP = 1.21 |
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| VaporPressure = 0.1 Pa (52.6 °C) |
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| RefractIndex = 1.578 (144 °C) |
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| MagSus = -77.18·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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|Section4={{Chembox Thermochemistry |
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| DeltaHf = -380.4 KJ/mol |
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}} |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| GHSPictograms = {{GHS05}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|318|319}} |
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| PPhrases = {{P-phrases|264|280|305+351+338|310|337+313}} |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| AutoignitionPt = > |
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| AutoignitionPtC = 530 |
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| FlashPt = > |
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| FlashPtC = 150 |
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| LD50 = 1400 mg/kg (oral, rat) |
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}} |
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|Section8={{Chembox Legal status |
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| legal_AU = |
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| legal_BR = D1 |
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| 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> |
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| legal_US = |
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'''Anthranilic acid''' is the ] with the ] C<sub>6</sub>H<sub>4</sub>(NH<sub>2</sub>)COOH. This amino acid is a white solid when pure, although commercial samples may appear yellow. The molecule consists of a benzene ring with two adjacent functional groups, a ] and an ]. It is sometimes referred to as ] L. |
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it has a sweetish taste, it is flammable and will produce nitrogen oxide fumes when burning, it maybe sensitive to prolonged exposure to air and light |
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'''Anthranilic acid''' is an ] with the ] C<sub>6</sub>H<sub>4</sub>(NH<sub>2</sub>)(CO<sub>2</sub>H) and has a sweetish taste.<ref>{{Cite book|url=https://books.google.com/books?id=sa2_I2GD2pUC|title=Aminobenzoic Acids—Advances in Research and Application|last=Acton|first=Q. Ashton|publisher=ScholarlyEditions|year=2013|isbn=9781481684842|edition=2013|location=Atlanta|pages=23|via=Google Books}}</ref><ref>{{Cite book|url=https://books.google.com/books?id=mk-V2w6kHRgC|title=Techniques in Glycobiology|last=Hardy|first=Mark R.|publisher=Marcel Dekker, Inc.|year=1997|isbn=9780824798222|editor-last=Townsend|editor-first=R. Reid|pages=360|chapter=Glycan Labeling with the Flurophores 2-Aminobenzamide and Antranilic Acid|editor2-last=Hotchkiss|editor2-first=Arland T. Jr.|via=Google Books}}</ref><ref>''The Merck Index, 10th Ed.'' (1983), p.62., Rahway: Merck & Co.</ref> The molecule consists of a benzene ring, ] with a ] and an ]. As a result of containing both acidic and basic ]s, the compound is ]. Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. The anion <sup>−</sup>, obtained by the deprotonation of anthranilic acid, is called '''anthranilate'''. Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L<sub>1</sub> in that context, but it is now known to be non-essential in human nutrition.<ref>{{Cite web | author = Davidson, Michael W. | date = 2004 | url = http://micro.magnet.fsu.edu/vitamins/pages/anthranilic.html | title = Anthranilic Acid (Vitamin L)] | publisher = ] | access-date = November 20, 2019 }}</ref> |
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==Biological role== |
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Anthranilic acid is biosynthesized from ]. It is the precursor to the ] ] via the attachment of ] to the ]. |
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==Structure== |
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Although not usually referred to as such, it is an ]. Solid anthranilic acid typically consists of both the amino-carboxylic acid and the ]ic ammonium carboxylate forms, and has a ] crystal structure with space group P2<sub>1</sub>.<ref>{{Cite journal | doi = 10.1098/rspa.1968.0003| title = The crystal structure of anthranilic acid| journal = Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences| volume = 302| issue = 1469| pages = 185–199| year = 1968| bibcode = 1968RSPSA.302..185B| last1 = Brown| first1 = C. J.| s2cid = 93221347}}</ref> It is ].<ref name="hardy"/> Above {{convert|81|C|F K}}, it converts to an ] form with space group Pbca, which is not triboluminescent; a non-triboluminescent monoclinic phase with similar structure is also known.<ref name="hardy">{{cite journal |last1=Hardy |first1=Gordon E. |last2=Kaska |first2=William C. |last3=Chandra |first3=B. P. |last4=Zink |first4=Jeffrey I. |title=Triboluminescence-structure relationships in polymorphs of hexaphenylcarbodiphosphorane and anthranilic acid, molecular crystals, and salts |journal=Journal of the American Chemical Society |date=March 1981 |volume=103 |issue=5 |pages=1074–1079 |doi=10.1021/ja00395a014}}</ref> |
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== History and etymology == |
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In 1840-1841, ] was able to extract and crystallize two acids from the products of reaction of ] with ], which he called chrysanilic and anthranilic acids after their colors before purification (golden yellow and black respectively) and the plant anil ('']'').<ref>{{Cite journal |last=Fritzsche |first=J. |date=1841 |title=Ueber die Producte der Einwirkung des Kali auf das Indigblau |url=https://books.google.com/books?id=-l42AQAAMAAJ&pg=PA67 |journal=Journal für Praktische Chemie |language=en |volume=23 |issue=1 |pages=67–83 |doi=10.1002/prac.18410230104 |issn=0021-8383}}</ref><ref>{{Cite journal |last=Fritzsche |first=J. |date=1841 |title=Ueber die Produkte der Einwirkung von Kali auf Indigblau |url=https://books.google.com/books?id=OsMwAAAAYAAJ&pg=PA76 |journal=Justus Liebigs Annalen der Chemie |language=en |volume=39 |issue=1 |pages=76–91 |doi=10.1002/jlac.18410390104 |issn=0075-4617}}</ref> The former was identified as ortho-carboxy anil of indoxyl-2-aldehyde only in 1910<ref>{{Cite journal |last=Sheibley |first=Fred E. |date=March 1943 |title=Carl Julius Fritzsche and the discovery of anthranilic acid, 1841 |url=https://pubs.acs.org/doi/abs/10.1021/ed020p115 |journal=Journal of Chemical Education |language=en |volume=20 |issue=3 |pages=115 |doi=10.1021/ed020p115 |issn=0021-9584}}</ref> while the latter was identified as salicylamide already in 1843 by ].<ref>{{Cite book |url=https://books.google.com/books?id=DAcAAAAAMAAJ&pg=PA536 |title=The Chemical Gazette |date=1843 |language=en}}</ref> |
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==Production== |
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Many routes to anthranilic acid have been described. Industrially it is produced from ], beginning with amination: |
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:C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>O + NH<sub>3</sub> + NaOH → C<sub>6</sub>H<sub>4</sub>(C(O)NH<sub>2</sub>)CO<sub>2</sub>Na + H<sub>2</sub>O |
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The resulting sodium salt of phthalamic acid is decarbonylated via a ] of the amide group, induced by ]:<ref>{{Cite book | doi = 10.1002/14356007.a03_555| chapter = Benzoic Acid and Derivatives| title = Ullmann's Encyclopedia of Industrial Chemistry| year = 2000| last1 = Maki| first1 = Takao| last2 = Takeda| first2 = Kazuo| isbn = 3527306730}}.</ref> |
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:C<sub>6</sub>H<sub>4</sub>(C(O)NH<sub>2</sub>)CO<sub>2</sub>Na + HOCl → C<sub>6</sub>H<sub>4</sub>NH<sub>2</sub>CO<sub>2</sub>H + NaCl + CO<sub>2</sub> |
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A related method involves treating ] with sodium ] in aqueous sodium hydroxide, followed by neutralization.<ref>''Vogel's Textbook of Practical Organic Chemistry, 4th Ed.'', (B. S. Furniss et al., Eds.) (1978), p.666, London: Longman.</ref> In the era when ] was obtained from plants, it was degraded to give anthranilic acid. |
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Anthranilic acid was first obtained by base-induced degradation of indigo.<ref>{{Cite journal | doi = 10.1021/ed020p115| title = Carl Julius Fritzsche and the discovery of anthranilic acid, 1841| journal = Journal of Chemical Education| volume = 20| issue = 3| pages = 115| year = 1943| last1 = Sheibley| first1 = Fred E.| bibcode = 1943JChEd..20..115S}}</ref> |
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===Biosynthesis=== |
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Anthranilic acid is biosynthesized from ] by the action of ]. In organisms capable of tryptophan synthesis, anthranilate is a precursor to the ] ] via the attachment of ] to the ]. After then, cyclization occurs to produce ]. |
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]{{clear-left}} |
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==Uses== |
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==Uses== |
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Anthranilic acid is used as an intermediate for production of ]s, ]s, and ]. It and its ]s are used in preparing ]s to imitate jasmine and orange, pharmaceuticals (loop diuretics e.g. furosemide) and UV-absorber as well as ]s for metals and ]s in ]. |
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Industrially, anthranilic acid is an intermediate in the production of ]s and ]. It and its ]s are used in preparing ]s to mimic ] and ], pharmaceuticals (]s, such as ]) and UV-absorber as well as ]s for metals and ]s in ]. |
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] have been proposed as replacements for ]. |
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Anthranilic acid can be used in ] to generate the ] intermediate.<ref>{{OrgSynth | author = Logullo, F. M.; Seitz, A. H.; Friedman, L. | title = Benzenediazonium-2-carboxy- and Biphenylene | collvol = 5 | collvolpages = 54 | year = 1973 | prep = cv5p0054}}</ref> |
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] is a derivative of anthranilic acid,<ref name=Sriram>Sriram D, Yogeeswari P. . Pearson Education India, 2010. {{ISBN|9788131731444}}</ref>{{rp|235}} which in turn is a nitrogen ] of ], which is the ] of ].<ref name=Sriram/>{{rp|235}} Several ]s, including ], ], ], and ] are derived from fenamic acid or anthranilic acid and are called "anthranilic acid derivatives" or "fenamates".<ref>Auburn University course material. Jack DeRuiter, Principles of Drug Action 2, Fall 2002 1: </ref>{{rp|17}} |
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It is also a ] because of its use in making the now-widely outlawed euphoric sedative drug ] (Quaalud, Mandrax).<ref>Angelos SA, Meyers JA. The isolation and identification of precursors and reaction products in the clandestine manufacture of methaqualone and mecloqualone. ''Journal of Forensic Sciences''. 1985 Oct;30(4):1022-47. PMID 3840834</ref> |
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==Reactions== |
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Anthranilic acid can be diazotized to give the ] <sup>+</sup>. This cation can be used to generate ],<ref>{{OrgSynth| last1= Logullo |first1= F. M. |last2= Seitz |first2= A. H. |last3= Friedman |first3= L. | title = Benzenediazonium-2-carboxy- and Biphenylene | page= 12 | volume= 48 | year = 1968| prep= CV5P0054}}</ref> dimerized to give ],<ref>{{cite journal|doi=10.15227/orgsyn.007.0030|first1=E. R.|last1=Atkinson|first2=H. J.|last2=Lawler|title=Diphenic Acid|journal=Organic Syntheses|volume=7|pages=30|year=1927}}</ref> or undergo ] reactions such as in the synthesis of ].<ref>{{OrgSynth |first1= H. T. |last1= Clarke |first2= W. R. |last2= Kirner |title= Methyl Red |year= 1922 |volume= 2 |page= 47 |prep= cv1p0374}}</ref> |
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It reacts with ] to give ], a versatile reagent.<ref>{{cite journal|journal=Org. Synth. |year=1947|volume=27|page=45 |doi=10.15227/orgsyn.027.0045|title=Isatoic anhydride|first1=E. C. |last1=Wagner |first2=Marion F. |last2=Fegley}}</ref> |
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] of anthranilic acid gives the 2,4-dichloro derivative, which can undergo ] coupling to form a ] compound.<ref>{{OrgSynth |first1=Edward R. |last1=Atkinson |first2=Donald M. |last2=Murphy |first3=James E. |last3=Lufkin |title= ''dl''-4,4',6,6'-Tetrachlorodiphenic Acid |year=1951 |volume=31 |page=96 |prep=CV4P0872}}</ref> |
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==Safety and regulation== |
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It is also a ] because of its use in making the now-widely outlawed euphoric sedative drug ] (Quaalude, Mandrax).<ref>{{cite journal | author = Angelos SA, Meyers JA | title = The isolation and identification of precursors and reaction products in the clandestine manufacture of methaqualone and mecloqualone | journal = Journal of Forensic Sciences | date = 1985 | volume = 30 | issue = 4 | pages = 1022–1047 | doi = 10.1520/JFS11044J | pmid=3840834}}</ref> |
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==See also== |
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==See also== |
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* ] |
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==References== |
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==References== |
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{{Amino acid metabolism intermediates}} |
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{{Amino acid metabolism intermediates}} |
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