Oxanilic acid

• CAT Number: I034035
• CAS Number: 500-72-1
• Molecular Formula: C8H7NO3
• Molecular Weight: 165.15
• Purity: 98%
• Synonyms: Oxanilic acid; Anilino(oxo)acetic acid; Kyselina oxalanilova
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Acetic acid, 2-oxo-2-(phenylamino)-
• InChI: InChI=1S/C8H7NO3/c10-7(8(11)12)9-6-4-2-1-3-5-6/h1-5H,(H,9,10)(H,11,12)
• InChIKey: PQJZHMCWDKOPQG-UHFFFAOYSA-N
• SMILES: O=C(O)C(NC1=CC=CC=C1)=O

Oxanilic acid（Cat No.:I034035） is a chemical compound that is formed by the reaction of oxalic acid and aniline, resulting in the formation of a mono-amide. It consists of an oxalic acid moiety and an aniline moiety connected by an amide bond. This compound has applications in various fields, including organic synthesis, and as a building block for the production of dyes and pigments. Oxanilic acid can also be used as a reagent in chemical reactions or as a precursor for the synthesis of other organic compounds.

Reference

1: Heberle SA, Aga DS, Hany R, Müller SR. Simultaneous quantification of acetanilide herbicides and their oxanilic and sulfonic acid metabolites in natural waters. Anal Chem. 2000 Feb 15;72(4):840-5. PubMed PMID: 10701271.
2: Scarfe GB, Wilson ID, Warne MA, Holmes E, Nicholson JK, Lindon JC. Structure-metabolism relationships of substituted anilines: prediction of N-acetylation and N-oxanilic acid formation using computational chemistry. Xenobiotica. 2002 Apr;32(4):267-77. PubMed PMID: 12028661.
3: Dagnac T, Jeannot R, Mouvet C, Baran N. Determination of oxanilic and sulfonic acid metabolites of acetochlor in soils by liquid chromatography-electrospray ionisation mass spectrometry. J Chromatogr A. 2002 May 24;957(1):69-77. PubMed PMID: 12102314.
4: Wilson ID, Macdonald CM, Fromson JM, Troke JA, Hillbeck D. Species differences in the metabolism of 14C-p-trifluoromethylaniline: production of an oxanilic acid as the major metabolite by the rat. Biochem Pharmacol. 1985 Jun 1;34(11):2025-8. PubMed PMID: 4004918.
5: Zimmerman LR, Schneider RJ, Thurman EM. Analysis and detection of the herbicides dimethenamid and flufenacet and their sulfonic and oxanilic acid degradates in natural water. J Agric Food Chem. 2002 Feb 27;50(5):1045-52. PubMed PMID: 11853478.
6: Huang SB, Mayer TJ, Yokley RA. Direct aqueous injection LC-ESI/MS/MS analysis of water for 11 chloro- and thiomethyltriazines and metolachlor and its ethanesulfonic and oxanilic acid degradates. J Agric Food Chem. 2008 Apr 23;56(8):2595-602. doi: 10.1021/jf800086a. Epub 2008 Mar 29. PubMed PMID: 18373350.
7: Sellstedt JH, Guinosso CJ, Begany AJ, Bell SC, Rosenthale M. Oxanilic acids, a new series of orally active antiallergic agents. J Med Chem. 1975 Sep;18(9):926-33. PubMed PMID: 1159715.
8: Artico M, Ross WC. Aryl-2-halogenoalkylamines. 23. Derivatives of oxanilic acid and salicylic acid: synthesis and antineoplastic activities. Biochem Pharmacol. 1968 Jun;17(6):883-91. PubMed PMID: 5661351.
9: Viegas CA, Costa C, André S, Viana P, Ribeiro R, Moreira-Santos M. Does S-metolachlor affect the performance of Pseudomonas sp. strain ADP as bioaugmentation bacterium for atrazine-contaminated soils? PLoS One. 2012;7(5):e37140. doi: 10.1371/journal.pone.0037140. Epub 2012 May 15. PubMed PMID: 22615921; PubMed Central PMCID: PMC3352881.
10: Iskra J, Titan P, Meglič V. The effect of fluorine atom on the synthesis and composition of gametocidal ethyl oxanilates. Acta Chim Slov. 2013;60(3):561-8. PubMed PMID: 24169710.
11: Hostetler KA, Thurman EM. Determination of chloroacetanilide herbicide metabolites in water using high-performance liquid chromatography-diode array detection and high-performance liquid chromatography/mass spectrometry. Sci Total Environ. 2000 Apr 5;248(2-3):147-55. PubMed PMID: 10805235.
12: Hancock TC, Sandstrom MW, Vogel JR, Webb RM, Bayless ER, Barbash JE. Pesticide fate and transport throughout unsaturated zones in five agricultural settings, USA. J Environ Qual. 2008 May 2;37(3):1086-100. doi: 10.2134/jeq2007.0024. Print 2008 May-Jun. PubMed PMID: 18453430.
13: Seybold CA, Mersie W, McNamee C. Anaerobic degradation of atrazine and metolachlor and metabolite formation in wetland soil and water microcosms. J Environ Qual. 2001 Jul-Aug;30(4):1271-7. PubMed PMID: 11476505.
14: Klein C, Schneider RJ, Meyer MT, Aga DS. Enantiomeric separation of metolachlor and its metabolites using LC-MS and CZE. Chemosphere. 2006 Mar;62(10):1591-9. Epub 2005 Aug 2. PubMed PMID: 16081137.
15: Shoemaker JA. Novel chromatographic separation and carbon solid-phase extraction of acetanilide herbicide degradation products. J AOAC Int. 2002 Nov-Dec;85(6):1331-7. PubMed PMID: 12477196.
16: Elsayed OF, Maillard E, Vuilleumier S, Millet M, Imfeld G. Degradation of chloroacetanilide herbicides and bacterial community composition in lab-scale wetlands. Sci Total Environ. 2015 Jul 1;520:222-31. doi: 10.1016/j.scitotenv.2015.03.061. Epub 2015 Mar 25. PubMed PMID: 25817759.
17: Mersie W, McNamee C, Seybold C, Wu J, Tierney D. Degradation of metolachlor in bare and vegetated soils and in simulated water-sediment systems. Environ Toxicol Chem. 2004 Nov;23(11):2627-32. PubMed PMID: 15559277.
18: Mai H, Gonzalez P, Pardon P, Tapie N, Budzinski H, Cachot J, Morin B. Comparative responses of sperm cells and embryos of Pacific oyster (Crassostrea gigas) to exposure to metolachlor and its degradation products. Aquat Toxicol. 2014 Feb;147:48-56. doi: 10.1016/j.aquatox.2013.11.024. Epub 2013 Dec 7. PubMed PMID: 24378469.
19: Baran N, Mouvet C, Dagnac T, Jeannot R. Infiltration of acetochlor and two of its metabolites in two contrasting soils. J Environ Qual. 2004 Jan-Feb;33(1):241-9. PubMed PMID: 14964378.
20: Baran N, Gourcy L. Sorption and mineralization of S-metolachlor and its ionic metabolites in soils and vadose zone solids: consequences on groundwater quality in an alluvial aquifer (Ain Plain, France). J Contam Hydrol. 2013 Nov;154:20-8. doi: 10.1016/j.jconhyd.2013.07.009. Epub 2013 Aug 13. PubMed PMID: 24055953.