37:
429:
288:
1303:
28:
797:
792:
880:
883:
885:
1020:
884:
1773:
Hardy, Gordon E.; Kaska, William C.; Chandra, B. P.; Zink, Jeffrey I. (March 1981). "Triboluminescence-structure relationships in polymorphs of hexaphenylcarbodiphosphorane and anthranilic acid, molecular crystals, and salts".
805:
772:
2105:
851:
1033:
2098:
1102:. Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. The anion , obtained by the deprotonation of anthranilic acid, is called
2053:
Angelos SA, Meyers JA (1985). "The isolation and identification of precursors and reaction products in the clandestine manufacture of methaqualone and mecloqualone".
886:
1614:
1609:[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
894:
998:
2091:
478:
1662:
Hardy, Mark R. (1997). "Glycan
Labeling with the Flurophores 2-Aminobenzamide and Antranilic Acid". In Townsend, R. Reid; Hotchkiss, Arland T. Jr. (eds.).
908:
2300:
1561:
1544:
741:
2613:
2204:
1392:
1362:
1142:
form with space group Pbca, which is not triboluminescent; a non-triboluminescent monoclinic phase with similar structure is also known.
2209:
36:
1602:
1575:
901:
1893:
1673:
1646:
443:
2435:
983:
1818:
2464:
1610:
1606:
847:
1040:
2594:
1288:
837:
386:
2772:
2305:
407:
796:
2862:
1528:
1080:
667:
2661:
2569:
2295:
2244:
2219:
295:
1411:
are derived from fenamic acid or anthranilic acid and are called "anthranilic acid derivatives" or "fenamates".
2782:
2589:
2445:
2224:
1706:
931:
859:
2229:
1607:"RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"
2628:
2584:
2412:
2185:
703:
791:
283:
2837:
2716:
2693:
2531:
2440:
2367:
2272:
2160:
2120:
1457:
2653:
2329:
1473:
1453:
1277:
1199:
819:
784:
644:
225:
155:
68:
2128:
2117:
1856:
1736:
855:
633:
56:
2829:
2618:
2310:
2290:
1525:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1504:
1499:
1494:
1348:
424:
121:
2239:
1752:
1432:
1151:
185:
2083:
173:
1847:
Sheibley, Fred E. (1943). "Carl Julius
Fritzsche and the discovery of anthranilic acid, 1841".
1302:
2777:
2735:
2070:
2033:
1976:
1923:
1889:
1885:
1814:
1702:
1669:
1642:
1571:
1540:
1447:
1408:
1384:
1060:
970:
2165:
2062:
2005:
1952:
1904:
Auburn
University course material. Jack DeRuiter, Principles of Drug Action 2, Fall 2002 1:
1864:
1806:
1783:
1744:
1532:
1135:
1095:
716:
594:
501:
395:
2579:
2387:
1404:
1400:
1087:
314:
1590:
1106:. Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L
245:
131:
1860:
1740:
1729:
Proceedings of the Royal
Society of London. Series A. Mathematical and Physical Sciences
428:
287:
205:
2574:
2214:
2175:
1420:
1396:
1380:
1352:
1336:
1273:
1011:
657:
1150:
Many routes to anthranilic acid have been described. Industrially it is produced from
1122:. Solid anthranilic acid typically consists of both the amino-carboxylic acid and the
2856:
2759:
2726:
2688:
2546:
2430:
1428:
1340:
1056:
583:
573:
276:
1756:
2797:
2675:
2551:
2382:
2315:
2180:
2170:
2150:
1489:
1477:
1372:
1280:. In organisms capable of tryptophan synthesis, anthranilate is a precursor to the
1203:
1139:
843:
27:
2234:
1905:
1663:
1636:
2527:
2024:
1971:
1918:
1536:
1292:
1254:
1250:
976:
958:
920:
628:
359:
2807:
2683:
2648:
2638:
2623:
2604:
2503:
2498:
2493:
2392:
2280:
2259:
2132:
2114:
1436:
1344:
1284:
1281:
1258:
1127:
1123:
1119:
1099:
611:
605:
532:
236:
2009:
1956:
1810:
1110:
in that context, but it is now known to be non-essential in human nutrition.
829:
2707:
2523:
2488:
2421:
2407:
1567:
1476:
because of its use in making the now-widely outlawed euphoric sedative drug
1356:
1320:
1748:
1264:
Anthranilic acid was first obtained by base-induced degradation of indigo.
2074:
2763:
2750:
2697:
2519:
2483:
2474:
2378:
2339:
2155:
1456:
of anthranilic acid gives the 2,4-dichloro derivative, which can undergo
1443:
1376:
1257:
in aqueous sodium hydroxide, followed by neutralization. In the era when
907:
900:
893:
866:
825:
615:
256:
1787:
1306:
Anthranilate is the biosynthetic precursor to the amino acid tryptophan.
265:
2455:
2374:
2353:
2344:
2263:
2249:
2195:
1424:
1388:
1332:
1328:
1316:
1315:
Industrially, anthranilic acid is an intermediate in the production of
637:
620:
563:
346:
296:
2066:
1868:
1079:
H) and has a sweetish taste. The molecule consists of a benzene ring,
2560:
2358:
2141:
1461:
1296:
1198:
The resulting sodium salt of phthalamic acid is decarbonylated via a
216:
1261:
was obtained from plants, it was degraded to give anthranilic acid.
1010:
Except where otherwise noted, data are given for materials in their
1801:
Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and
Derivatives".
334:
1727:
Brown, C. J. (1968). "The crystal structure of anthranilic acid".
1324:
1301:
1091:
624:
370:
196:
154:
144:
2023:
Atkinson, Edward R.; Murphy, Donald M.; Lufkin, James E. (1951).
1375:
is a derivative of anthranilic acid, which in turn is a nitrogen
1366:
1138:. Above 81 °C (178 °F; 354 K), it converts to an
553:
325:
2087:
1996:
Wagner, E. C.; Fegley, Marion F. (1947). "Isatoic anhydride".
1837:, (B. S. Furniss et al., Eds.) (1978), p.666, London: Longman.
412:
35:
26:
578:
146 to 148 °C (295 to 298 °F; 419 to 421 K)
452:
InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
462:
InChI=1/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
1641:(2013 ed.). Atlanta: ScholarlyEditions. p. 23.
878:
1943:
Atkinson, E. R.; Lawler, H. J. (1927). "Diphenic Acid".
1835:
Vogel's
Textbook of Practical Organic Chemistry, 4th Ed.
992:
1638:
Aminobenzoic Acids—Advances in
Research and Application
1028:
2828:
2821:
2795:
2758:
2748:
2725:
2706:
2637:
2603:
2559:
2544:
2512:
2473:
2454:
2420:
2405:
2352:
2337:
2328:
2258:
2194:
2140:
2127:
1917:Logullo, F. M.; Seitz, A. H.; Friedman, L. (1968).
1118:Although not usually referred to as such, it is an
1094:. As a result of containing both acidic and basic
588:200 °C (392 °F; 473 K) (sublimes)
172:
939:> 530 °C (986 °F; 803 K)
925:> 150 °C (302 °F; 423 K)
358:
1419:Anthranilic acid can be diazotized to give the
882:
130:
1803:Ullmann's Encyclopedia of Industrial Chemistry
2099:
1919:"Benzenediazonium-2-carboxy- and Biphenylene"
1906:Non-Steroidal Antiinflammatory Drugs (NSAIDS)
8:
1295:. After then, cyclization occurs to produce
2825:
2755:
2556:
2417:
2349:
2334:
2137:
2106:
2092:
2084:
427:
286:
244:
15:
1880:
1878:
394:
1776:Journal of the American Chemical Society
1768:
1766:
1272:Anthranilic acid is biosynthesized from
1515:
1365:have been proposed as replacements for
483:
448:
423:
264:
1691:(1983), p.62., Rahway: Merck & Co.
1435:reactions such as in the synthesis of
1423:. This cation can be used to generate
1126:ammonium carboxylate forms, and has a
277:
2301:2-Amino-3-carboxymuconic semialdehyde
1970:Clarke, H. T.; Kirner, W. R. (1922).
1563:CRC Handbook of Chemistry and Physics
1393:non-steroidal anti-inflammatory drugs
1130:crystal structure with space group P2
455:Key: RWZYAGGXGHYGMB-UHFFFAOYSA-N
224:
204:
7:
2614:2,3-Dihydroxy-3-methylpentanoic acid
2029:-4,4',6,6'-Tetrachlorodiphenic Acid"
1363:Anthranilate-based insect repellents
1703:"Anthranilic Acid (Vitamin L)]"
1668:. Marcel Dekker, Inc. p. 360.
1249:A related method involves treating
465:Key: RWZYAGGXGHYGMB-UHFFFAOYAS
349:
333:
14:
1888:. Pearson Education India, 2010.
1886:Medicinal Chemistry, 2nd Edition
1560:Haynes, William M., ed. (2016).
1018:
795:
790:
519:
513:
2436:Imidazol-4-one-5-propionic acid
1617:from the original on 2023-08-03
1202:of the amide group, induced by
1014:(at 25 °C , 100 kPa).
40:C=black, H=white, O=red, N=blue
2250:β-Hydroxy β-methylglutaryl-CoA
2205:β-Hydroxy β-methylbutyric acid
1529:The Royal Society of Chemistry
522:
507:
1:
2465:1-Pyrroline-5-carboxylic acid
2210:β-Hydroxy β-methylbutyryl-CoA
1849:Journal of Chemical Education
1701:Davidson, Michael W. (2004).
1347:) and UV-absorber as well as
103:Anthranilate (conjugate base)
73:2-Aminobenzenecarboxylic acid
2595:2-Methyl-3-oxopropanoic acid
2055:Journal of Forensic Sciences
1289:phosphoribosyl pyrophosphate
1154:, beginning with amination:
2773:4-Hydroxyphenylpyruvic acid
2306:2-Aminomuconic semialdehyde
1537:10.1039/9781849733069-FP001
947:or concentration (LD, LC):
22:
2879:
2649:generation of homocysteine
1665:Techniques in Glycobiology
2296:3-Hydroxyanthranilic acid
1689:The Merck Index, 10th Ed.
1678:– via Google Books.
1651:– via Google Books.
1635:Acton, Q. Ashton (2013).
1008:
943:
771:
766:
734:
494:
474:
439:
114:
79:
67:
55:
50:
21:
2783:4-Maleylacetoacetic acid
2590:3-Hydroxyisobutyric acid
2446:Glutamate-1-semialdehyde
2010:10.15227/orgsyn.027.0045
1957:10.15227/orgsyn.007.0030
1884:Sriram D, Yogeeswari P.
1811:10.1002/14356007.a03_555
1707:Florida State University
1613:(published 2023-04-04).
838:Precautionary statements
2629:2-Methylacetoacetyl-CoA
2585:3-Hydroxyisobutyryl-CoA
2121:metabolic intermediates
1611:Diário Oficial da União
1450:, a versatile reagent.
965:1400 mg/kg (oral, rat)
704:Magnetic susceptibility
600:0.572 g/100 mL (25 °C)
2838:Cysteine sulfinic acid
2684:conversion to cysteine
2441:Formiminoglutamic acid
2368:3-Phosphoglyceric acid
2245:β-Methylglutaconyl-CoA
1749:10.1098/rspa.1968.0003
1327:are used in preparing
1307:
1287:via the attachment of
889:
548:white or yellow solid
41:
31:
2570:α-Ketoisovaleric acid
2225:β-Ketoisocaproic acid
2220:α-Ketoisocaproic acid
1531:. 2014. p. 748.
1480:(Quaalude, Mandrax).
1468:Safety and regulation
1305:
1278:anthranilate synthase
1200:Hofmann rearrangement
888:
69:Systematic IUPAC name
39:
30:
2657:-Adenosyl methionine
2240:β-Methylcrotonyl-CoA
2230:β-Ketoisocaproyl-CoA
2186:β-Hydroxybutyryl-CoA
1427:, dimerized to give
1349:corrosion inhibitors
871:(fire diamond)
634:trifluoroacetic acid
632:slightly soluble in
57:Preferred IUPAC name
2830:Cysteine metabolism
2619:2-Methylbutyryl-CoA
2311:2-Aminomuconic acid
2291:3-Hydroxykynurenine
1861:1943JChEd..20..115S
1788:10.1021/ja00395a014
1741:1968RSPSA.302..185B
1505:Methyl anthranilate
1500:4-Aminobenzoic acid
1495:3-Aminobenzoic acid
1474:DEA List I Chemical
1460:coupling to form a
1339:, pharmaceuticals (
595:Solubility in water
540: g·mol
186:Beilstein Reference
94:2-Aminobenzoic acid
61:2-Aminobenzoic acid
18:
2717:α-Ketobutyric acid
2694:α-Ketobutyric acid
2532:γ-Glutamylcysteine
2276:′-Formylkynurenine
2161:α-Aminoadipic acid
1433:diazonium coupling
1308:
1152:phthalic anhydride
1098:, the compound is
1041:Infobox references
890:
91:-Aminobenzoic acid
42:
32:
16:
2863:Anthranilic acids
2850:
2849:
2846:
2845:
2817:
2816:
2791:
2790:
2778:Homogentisic acid
2744:
2743:
2736:Methylmalonyl-CoA
2540:
2539:
2401:
2400:
2324:
2323:
2067:10.1520/JFS11044J
2034:Organic Syntheses
1977:Organic Syntheses
1945:Organic Syntheses
1924:Organic Syntheses
1869:10.1021/ed020p115
1735:(1469): 185–199.
1570:. pp. 5–89.
1566:(97th ed.).
1546:978-0-85404-182-4
1448:isatoic anhydride
1409:meclofenamic acid
1385:active metabolite
1276:by the action of
1096:functional groups
1049:Chemical compound
1047:
1046:
1001:(Drug precursors)
996:
971:Safety data sheet
820:Hazard statements
710:-77.18·10 cm/mol
690:4.85 (carboxyl; H
662:0.1 Pa (52.6 °C)
408:CompTox Dashboard
156:Interactive image
46:
45:
17:Anthranilic acid
2870:
2826:
2756:
2670:
2669:
2557:
2418:
2350:
2335:
2286:Anthranilic acid
2166:2-Oxoadipic acid
2138:
2108:
2101:
2094:
2085:
2079:
2078:
2061:(4): 1022–1047.
2050:
2044:
2042:
2020:
2014:
2013:
1993:
1987:
1985:
1967:
1961:
1960:
1940:
1934:
1932:
1914:
1908:
1902:
1896:
1882:
1873:
1872:
1844:
1838:
1832:
1826:
1824:
1798:
1792:
1791:
1782:(5): 1074–1079.
1770:
1761:
1760:
1724:
1718:
1717:
1715:
1713:
1698:
1692:
1686:
1680:
1679:
1659:
1653:
1652:
1632:
1626:
1625:
1623:
1622:
1599:
1593:
1588:
1582:
1581:
1557:
1551:
1550:
1523:"Front Matter".
1520:
1421:diazonium cation
1136:triboluminescent
1053:Anthranilic acid
1031:
1025:
1022:
1021:
994:
991:
910:
903:
896:
881:
861:
857:
853:
849:
845:
831:
827:
799:
794:
758:
735:Thermochemistry
717:Refractive index
610:very soluble in
539:
524:
521:
515:
509:
502:Chemical formula
432:
431:
416:
414:
398:
362:
351:
337:
315:Gmelin Reference
298:
290:
279:
268:
248:
228:
208:
176:
158:
134:
85:Anthranilic acid
23:
19:
2878:
2877:
2873:
2872:
2871:
2869:
2868:
2867:
2853:
2852:
2851:
2842:
2813:
2787:
2740:
2721:
2702:
2667:
2666:
2633:
2599:
2580:Methacrylyl-CoA
2550:
2536:
2508:
2469:
2450:
2413:α-ketoglutarate
2411:
2397:
2388:Phosphocreatine
2357:
2343:
2320:
2254:
2190:
2123:
2112:
2082:
2052:
2051:
2047:
2022:
2021:
2017:
1995:
1994:
1990:
1969:
1968:
1964:
1942:
1941:
1937:
1916:
1915:
1911:
1903:
1899:
1883:
1876:
1846:
1845:
1841:
1833:
1829:
1821:
1800:
1799:
1795:
1772:
1771:
1764:
1726:
1725:
1721:
1711:
1709:
1700:
1699:
1695:
1687:
1683:
1676:
1661:
1660:
1656:
1649:
1634:
1633:
1629:
1620:
1618:
1601:
1600:
1596:
1589:
1585:
1578:
1559:
1558:
1554:
1547:
1522:
1521:
1517:
1513:
1486:
1470:
1442:It reacts with
1417:
1405:flufenamic acid
1401:tolfenamic acid
1383:, which is the
1353:mold inhibitors
1351:for metals and
1313:
1270:
1245:
1241:
1237:
1233:
1229:
1225:
1221:
1217:
1213:
1193:
1189:
1185:
1181:
1177:
1173:
1169:
1165:
1161:
1148:
1133:
1116:
1109:
1088:carboxylic acid
1078:
1074:
1070:
1066:
1050:
1043:
1038:
1037:
1036: ?)
1027:
1023:
1019:
1015:
1004:
962:
956:
936:
933:
915:
914:
913:
912:
905:
898:
891:
887:
879:
840:
822:
808:
787:
759:
756:
750:
746:
743:
742:Std enthalpy of
730:1.578 (144 °C)
727:
725:
707:
697:
693:
686:
676:
631:
618:
597:
537:
527:
518:
512:
504:
490:
487:
486:O=C(O)c1ccccc1N
482:
481:
470:
467:
466:
463:
457:
456:
453:
447:
446:
435:
417:
410:
401:
381:
365:
352:
340:
317:
308:
271:
251:
231:
211:
188:
179:
161:
148:
137:
124:
110:
109:
100:
75:
74:
63:
62:
12:
11:
5:
2876:
2874:
2866:
2865:
2855:
2854:
2848:
2847:
2844:
2843:
2841:
2840:
2834:
2832:
2823:
2819:
2818:
2815:
2814:
2812:
2811:
2802:
2800:
2793:
2792:
2789:
2788:
2786:
2785:
2780:
2775:
2769:
2767:
2753:
2746:
2745:
2742:
2741:
2739:
2738:
2732:
2730:
2723:
2722:
2720:
2719:
2713:
2711:
2704:
2703:
2701:
2700:
2691:
2679:
2678:
2673:
2659:
2644:
2642:
2635:
2634:
2632:
2631:
2626:
2621:
2616:
2610:
2608:
2601:
2600:
2598:
2597:
2592:
2587:
2582:
2577:
2575:Isobutyryl-CoA
2572:
2566:
2564:
2554:
2542:
2541:
2538:
2537:
2535:
2534:
2516:
2514:
2510:
2509:
2507:
2506:
2501:
2496:
2491:
2486:
2480:
2478:
2471:
2470:
2468:
2467:
2461:
2459:
2452:
2451:
2449:
2448:
2443:
2438:
2433:
2427:
2425:
2415:
2403:
2402:
2399:
2398:
2396:
2395:
2390:
2385:
2371:
2370:
2364:
2362:
2347:
2332:
2326:
2325:
2322:
2321:
2319:
2318:
2313:
2308:
2303:
2298:
2293:
2288:
2283:
2278:
2269:
2267:
2256:
2255:
2253:
2252:
2247:
2242:
2237:
2232:
2227:
2222:
2217:
2215:Isovaleryl-CoA
2212:
2207:
2201:
2199:
2192:
2191:
2189:
2188:
2183:
2178:
2176:Glutaconyl-CoA
2173:
2168:
2163:
2158:
2153:
2147:
2145:
2135:
2125:
2124:
2113:
2111:
2110:
2103:
2096:
2088:
2081:
2080:
2045:
2015:
1988:
1962:
1935:
1909:
1897:
1874:
1839:
1827:
1819:
1793:
1762:
1719:
1693:
1681:
1674:
1654:
1647:
1627:
1605:(2023-03-31).
1594:
1583:
1577:978-1498754286
1576:
1552:
1545:
1514:
1512:
1509:
1508:
1507:
1502:
1497:
1492:
1485:
1482:
1469:
1466:
1416:
1413:
1397:mefenamic acid
1381:salicylic acid
1341:loop diuretics
1312:
1309:
1274:chorismic acid
1269:
1266:
1247:
1246:
1243:
1239:
1235:
1231:
1227:
1223:
1219:
1215:
1211:
1196:
1195:
1191:
1187:
1183:
1179:
1175:
1171:
1167:
1163:
1159:
1147:
1144:
1131:
1115:
1112:
1107:
1076:
1072:
1068:
1064:
1048:
1045:
1044:
1039:
1017:
1016:
1012:standard state
1009:
1006:
1005:
1003:
1002:
988:
986:
980:
979:
974:
967:
966:
963:
954:
952:
949:
948:
941:
940:
937:
930:
927:
926:
923:
917:
916:
906:
899:
892:
877:
876:
875:
874:
872:
863:
862:
852:P305+P351+P338
841:
836:
833:
832:
823:
818:
815:
814:
809:
804:
801:
800:
788:
783:
780:
779:
769:
768:
764:
763:
762:-380.4 KJ/mol
760:
754:
748:
740:
737:
736:
732:
731:
728:
723:
715:
712:
711:
708:
702:
699:
698:
696:
695:
691:
688:
684:
683:2.17 (amino; H
680:
678:
674:
664:
663:
660:
658:Vapor pressure
654:
653:
650:
641:
640:
608:
602:
601:
598:
593:
590:
589:
586:
580:
579:
576:
570:
569:
566:
560:
559:
556:
550:
549:
546:
542:
541:
535:
529:
528:
525:
516:
510:
505:
500:
497:
496:
492:
491:
489:
488:
485:
477:
476:
475:
472:
471:
469:
468:
464:
461:
460:
458:
454:
451:
450:
442:
441:
440:
437:
436:
434:
433:
420:
418:
406:
403:
402:
400:
399:
391:
389:
383:
382:
380:
379:
375:
373:
367:
366:
364:
363:
355:
353:
345:
342:
341:
339:
338:
330:
328:
322:
321:
318:
313:
310:
309:
307:
306:
302:
300:
292:
291:
281:
273:
272:
270:
269:
261:
259:
253:
252:
250:
249:
241:
239:
233:
232:
230:
229:
221:
219:
213:
212:
210:
209:
201:
199:
193:
192:
189:
184:
181:
180:
178:
177:
169:
167:
163:
162:
160:
159:
151:
149:
142:
139:
138:
136:
135:
127:
125:
120:
117:
116:
112:
111:
108:
107:
104:
101:
98:
95:
92:
86:
82:
81:
77:
76:
72:
71:
65:
64:
60:
59:
53:
52:
48:
47:
44:
43:
33:
13:
10:
9:
6:
4:
3:
2:
2875:
2864:
2861:
2860:
2858:
2839:
2836:
2835:
2833:
2831:
2827:
2824:
2820:
2810:
2809:
2804:
2803:
2801:
2799:
2794:
2784:
2781:
2779:
2776:
2774:
2771:
2770:
2768:
2765:
2761:
2760:phenylalanine
2757:
2754:
2752:
2747:
2737:
2734:
2733:
2731:
2728:
2727:propionyl-CoA
2724:
2718:
2715:
2714:
2712:
2709:
2705:
2699:
2695:
2692:
2690:
2689:Cystathionine
2687:
2685:
2681:
2680:
2677:
2674:
2672:
2671:-homocysteine
2664:
2660:
2658:
2656:
2652:
2650:
2646:
2645:
2643:
2640:
2636:
2630:
2627:
2625:
2622:
2620:
2617:
2615:
2612:
2611:
2609:
2606:
2602:
2596:
2593:
2591:
2588:
2586:
2583:
2581:
2578:
2576:
2573:
2571:
2568:
2567:
2565:
2562:
2558:
2555:
2553:
2548:
2547:propionyl-CoA
2543:
2533:
2529:
2525:
2521:
2518:
2517:
2515:
2511:
2505:
2502:
2500:
2497:
2495:
2492:
2490:
2487:
2485:
2482:
2481:
2479:
2476:
2472:
2466:
2463:
2462:
2460:
2457:
2453:
2447:
2444:
2442:
2439:
2437:
2434:
2432:
2431:Urocanic acid
2429:
2428:
2426:
2423:
2419:
2416:
2414:
2409:
2404:
2394:
2391:
2389:
2386:
2384:
2380:
2376:
2373:
2372:
2369:
2366:
2365:
2363:
2360:
2355:
2351:
2348:
2346:
2341:
2336:
2333:
2331:
2327:
2317:
2314:
2312:
2309:
2307:
2304:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2275:
2271:
2270:
2268:
2265:
2261:
2257:
2251:
2248:
2246:
2243:
2241:
2238:
2236:
2233:
2231:
2228:
2226:
2223:
2221:
2218:
2216:
2213:
2211:
2208:
2206:
2203:
2202:
2200:
2197:
2193:
2187:
2184:
2182:
2179:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2149:
2148:
2146:
2143:
2139:
2136:
2134:
2130:
2126:
2122:
2119:
2116:
2109:
2104:
2102:
2097:
2095:
2090:
2089:
2086:
2076:
2072:
2068:
2064:
2060:
2056:
2049:
2046:
2040:
2036:
2035:
2030:
2028:
2019:
2016:
2011:
2007:
2003:
1999:
1992:
1989:
1983:
1979:
1978:
1973:
1966:
1963:
1958:
1954:
1950:
1946:
1939:
1936:
1930:
1926:
1925:
1920:
1913:
1910:
1907:
1901:
1898:
1895:
1894:9788131731444
1891:
1887:
1881:
1879:
1875:
1870:
1866:
1862:
1858:
1854:
1850:
1843:
1840:
1836:
1831:
1828:
1822:
1816:
1812:
1808:
1804:
1797:
1794:
1789:
1785:
1781:
1777:
1769:
1767:
1763:
1758:
1754:
1750:
1746:
1742:
1738:
1734:
1730:
1723:
1720:
1708:
1704:
1697:
1694:
1690:
1685:
1682:
1677:
1675:9780824798222
1671:
1667:
1666:
1658:
1655:
1650:
1648:9781481684842
1644:
1640:
1639:
1631:
1628:
1616:
1612:
1608:
1604:
1598:
1595:
1592:
1587:
1584:
1579:
1573:
1569:
1565:
1564:
1556:
1553:
1548:
1542:
1538:
1534:
1530:
1527:. Cambridge:
1526:
1519:
1516:
1510:
1506:
1503:
1501:
1498:
1496:
1493:
1491:
1488:
1487:
1483:
1481:
1479:
1475:
1472:It is also a
1467:
1465:
1463:
1459:
1455:
1451:
1449:
1445:
1440:
1438:
1434:
1431:, or undergo
1430:
1429:diphenic acid
1426:
1422:
1414:
1412:
1410:
1406:
1402:
1398:
1394:
1390:
1386:
1382:
1378:
1374:
1370:
1368:
1364:
1360:
1358:
1354:
1350:
1346:
1342:
1338:
1334:
1330:
1326:
1323:. It and its
1322:
1318:
1310:
1304:
1300:
1298:
1294:
1290:
1286:
1283:
1279:
1275:
1267:
1265:
1262:
1260:
1256:
1252:
1242:H + NaCl + CO
1226:Na + HOCl → C
1209:
1208:
1207:
1205:
1201:
1157:
1156:
1155:
1153:
1145:
1143:
1141:
1137:
1129:
1125:
1121:
1113:
1111:
1105:
1101:
1097:
1093:
1089:
1085:
1083:
1062:
1058:
1057:aromatic acid
1054:
1042:
1035:
1030:
1013:
1007:
1000:
990:
989:
987:
985:
982:
981:
978:
977:External MSDS
975:
972:
969:
968:
964:
960:
951:
950:
946:
942:
938:
935:
929:
928:
924:
922:
919:
918:
911:
904:
897:
873:
870:
869:
865:
864:
842:
839:
835:
834:
824:
821:
817:
816:
813:
810:
807:
803:
802:
798:
793:
789:
786:
782:
781:
777:
775:
770:
765:
761:
753:
745:
739:
738:
733:
729:
722:
718:
714:
713:
709:
705:
701:
700:
689:
682:
681:
679:
673:
669:
666:
665:
661:
659:
656:
655:
651:
649:
648:
643:
642:
639:
635:
630:
626:
622:
617:
613:
609:
607:
604:
603:
599:
596:
592:
591:
587:
585:
584:Boiling point
582:
581:
577:
575:
574:Melting point
572:
571:
567:
565:
562:
561:
557:
555:
552:
551:
547:
544:
543:
536:
534:
531:
530:
506:
503:
499:
498:
493:
484:
480:
473:
459:
449:
445:
438:
430:
426:
425:DTXSID8020094
422:
421:
419:
409:
405:
404:
397:
393:
392:
390:
388:
385:
384:
377:
376:
374:
372:
369:
368:
361:
357:
356:
354:
348:
344:
343:
336:
332:
331:
329:
327:
324:
323:
319:
316:
312:
311:
304:
303:
301:
299:
294:
293:
289:
285:
282:
280:
278:ECHA InfoCard
275:
274:
267:
263:
262:
260:
258:
255:
254:
247:
243:
242:
240:
238:
235:
234:
227:
223:
222:
220:
218:
215:
214:
207:
203:
202:
200:
198:
195:
194:
190:
187:
183:
182:
175:
171:
170:
168:
165:
164:
157:
153:
152:
150:
146:
141:
140:
133:
129:
128:
126:
123:
119:
118:
113:
106:2-AA, 2AA, AA
105:
102:
96:
93:
90:
87:
84:
83:
78:
70:
66:
58:
54:
49:
38:
34:
29:
25:
24:
20:
2805:
2798:oxaloacetate
2682:
2676:Homocysteine
2662:
2654:
2647:
2552:succinyl-CoA
2383:Glycocyamine
2316:Glutaryl-CoA
2285:
2273:
2181:Crotonyl-CoA
2171:Glutaryl-CoA
2151:Saccharopine
2058:
2054:
2048:
2038:
2032:
2026:
2018:
2001:
1997:
1991:
1981:
1975:
1972:"Methyl Red"
1965:
1948:
1944:
1938:
1928:
1922:
1912:
1900:
1852:
1848:
1842:
1834:
1830:
1802:
1796:
1779:
1775:
1732:
1728:
1722:
1712:November 20,
1710:. Retrieved
1696:
1688:
1684:
1664:
1657:
1637:
1630:
1619:. Retrieved
1597:
1586:
1562:
1555:
1524:
1518:
1490:Kynureninase
1478:methaqualone
1471:
1454:Chlorination
1452:
1441:
1418:
1395:, including
1373:Fenamic acid
1371:
1361:
1314:
1271:
1268:Biosynthesis
1263:
1253:with sodium
1248:
1204:hypochlorite
1197:
1149:
1140:orthorhombic
1124:zwitterionic
1117:
1104:anthranilate
1103:
1084:-substituted
1081:
1052:
1051:
984:Legal status
944:
932:Autoignition
867:
811:
773:
751:
720:
671:
646:
371:RTECS number
115:Identifiers
88:
80:Other names
2528:glutathione
1293:amine group
1255:hypobromite
1251:phthalimide
959:median dose
945:Lethal dose
934:temperature
921:Flash point
806:Signal word
629:ethyl ether
619:soluble in
568:1.412 g/cm
545:Appearance
495:Properties
284:100.003.898
226:ChEMBL14173
206:CHEBI:30754
2808:urea cycle
2665:-Adenosyl-
2639:methionine
2624:Tiglyl-CoA
2605:isoleucine
2504:Putrescine
2499:Cadaverine
2494:Citrulline
2393:Creatinine
2281:Kynurenine
2260:tryptophan
2133:acetyl-CoA
2118:metabolism
2115:Amino acid
1998:Org. Synth
1855:(3): 115.
1820:3527306730
1621:2023-08-15
1511:References
1464:compound.
1437:methyl red
1391:. Several
1345:furosemide
1343:, such as
1285:tryptophan
1282:amino acid
1259:indigo dye
1174:+ NaOH → C
1146:Production
1128:monoclinic
1120:amino acid
1100:amphoteric
785:Pictograms
612:chloroform
606:Solubility
533:Molar mass
396:0YS975XI6W
237:ChemSpider
143:3D model (
122:CAS Number
2708:threonine
2524:glutamate
2489:Ornithine
2422:histidine
2408:glutamate
2235:β-Leucine
1568:CRC Press
1458:reductive
1415:Reactions
1357:soy sauce
1331:to mimic
1321:saccharin
1114:Structure
1059:with the
860:P337+P313
776:labelling
744:formation
558:odorless
378:CB2450000
305:204-287-5
297:EC Number
97:Vitamin L
2857:Category
2764:tyrosine
2751:fumarate
2698:Cysteine
2520:cysteine
2484:Agmatine
2475:arginine
2379:creatine
2340:pyruvate
2156:Allysine
1757:93221347
1615:Archived
1484:See also
1446:to give
1444:phosgene
1377:isostere
1329:perfumes
1317:azo dyes
1134:. It is
999:Class D1
868:NFPA 704
767:Hazards
706:(χ)
616:pyridine
257:DrugBank
132:118-92-3
2456:proline
2375:glycine
2354:glycine
2345:citrate
2264:alanine
2196:leucine
2075:3840834
1857:Bibcode
1737:Bibcode
1425:benzyne
1389:aspirin
1333:jasmine
1291:to the
1218:(C(O)NH
1182:(C(O)NH
1090:and an
1086:with a
1061:formula
1034:what is
1032: (
668:Acidity
638:benzene
621:ethanol
564:Density
538:137.138
347:PubChem
266:DB04166
191:471803
2561:valine
2359:serine
2142:lysine
2073:
2004:: 45.
1951:: 30.
1892:
1817:
1755:
1672:
1645:
1603:Anvisa
1574:
1543:
1462:biaryl
1407:, and
1337:orange
1325:esters
1297:indole
1190:Na + H
1170:O + NH
1055:is an
1029:verify
1026:
997:
973:(SDS)
812:Danger
479:SMILES
335:C00108
217:ChEMBL
174:B00027
166:3DMet
51:Names
2822:Other
2513:other
1753:S2CID
1092:amine
1082:ortho
652:1.21
625:ether
444:InChI
320:3397
197:ChEBI
145:JSmol
2806:see
2071:PMID
2041:: 96
1984:: 47
1931:: 12
1890:ISBN
1815:ISBN
1714:2019
1670:ISBN
1643:ISBN
1591:IPCS
1572:ISBN
1541:ISBN
1367:DEET
1335:and
1319:and
1311:Uses
1166:(CO)
1075:)(CO
856:P310
848:P280
844:P264
830:H319
826:H318
645:log
554:Odor
387:UNII
326:KEGG
2063:doi
2006:doi
1953:doi
1865:doi
1807:doi
1784:doi
1780:103
1745:doi
1733:302
1533:doi
1387:of
1379:of
1355:in
1222:)CO
1206::
1186:)CO
1071:(NH
774:GHS
755:298
413:EPA
360:227
350:CID
246:222
2859::
2796:G→
2749:G→
2696:+
2545:G→
2530::
2406:G→
2381::
2342:→
2338:G→
2069:.
2059:30
2057:.
2039:31
2037:.
2031:.
2027:dl
2002:27
2000:.
1980:.
1974:.
1947:.
1929:48
1927:.
1921:.
1877:^
1863:.
1853:20
1851:.
1813:.
1805:.
1778:.
1765:^
1751:.
1743:.
1731:.
1705:.
1539:.
1439:.
1403:,
1399:,
1369:.
1359:.
1299:.
1238:CO
1234:NH
993:BR
955:50
953:LD
858:,
854:,
850:,
846:,
828:,
778::
747:(Δ
694:O)
687:O)
677:)
670:(p
636:,
627:,
623:,
614:,
2766:→
2762:→
2729:→
2710:→
2686::
2668:L
2663:S
2655:S
2651::
2641:→
2607:→
2563:→
2549:→
2526:→
2522:+
2477:→
2458:→
2424:→
2410:→
2377:→
2361:→
2356:→
2330:G
2274:N
2266:→
2262:→
2198:→
2144:→
2131:→
2129:K
2107:e
2100:t
2093:v
2077:.
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