370:
241:
44:
35:
566:
569:
663:
630:
571:
947:
612:
1308:
Anter, J.; Romero Jiménez, M.; Fernández Bedmar, Z.; Villatoro Pulido, M.; Analla, M.; Alonso Moraga, A.; Muñoz
Serrano, A. (March 2011). "Antigenotoxicity, cytotoxicity, and apoptosis induction by apigenin, bisabolol, and protocatechuic acid".
893:
736:-induced mouse skin tumours. Depending on the amount of PCA and the time before application, PCA could reduce or enhance tumour growth. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural
1226:"A simple phenolic antioxidant protocatechuic acid enhances tumor promotion and oxidative stress in female ICR mouse skin: dose- and timing-dependent enhancement and involvement of bioactivation by tyrosinase"
1588:
Pacheco
Palencia, L. A.; Mertens-Talcott, S; Talcott, S. T. (June 2008). "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Açaí (
570:
823:). Protocatechuic acid also exists in the skins of some strains of onion as an antifungal mechanism, increasing endogenous resistance against smudge fungus. It is also found in
643:
1265:
Guan, S.; Ge, D.; Liu, T. Q.; Ma, X.-H.; Cui, Z.-F. (March 2009). "Protocatechuic acid promotes cell proliferation and reduces basal apoptosis in cultured neural stem cells".
1104:
858:
PCA is regarded as an active component in traditional
Chinese herbal medicine such as Stenoloma chusanum (L.) Ching, Ilex chinensis Sims, Cibotium barometz (L.) J.Sm.
572:
906:
580:
1765:
Pietta, P. G.; Simonetti, P.; Gardana, C.; Brusamolino, A.; Morazzoni, P.; Bombardelli, E. (1998). "Catechin metabolites after intake of green tea infusions".
409:
920:
792:
has been shown to be due to the tanning action of an agent produced by oxidation of a phenolic substance. In the analogous hardening of the cockroach
681:, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in
1858:
1350:
L. and its bioactive constituents exhibit antiviral activity against HSV-2 and anti-enzymatic properties against urease by an ESI–MS based assay"
594:
751:
cells, protocatechuic acid showed an antigenotoxic effect and tumoricidal activity. In two preclinical investigations, protocatechuic acid from
1814:
940:
935:
733:
1911:
1827:
915:
384:
2122:
979:
925:
1627:
120:
2035:
1140:
Liu, C.-L.; Wang, J.-M.; Chu, C.-Y.; Cheng, M.-T.; Tseng, T.-H. (2002). "In vivo protective effect of protocatechuic acid on
1121:
888:
1063:"Apoptotic effect of 3,4-dihydroxybenzoic acid on human gastric carcinoma cells involving JNK/p38 MAPK signaling activation"
1455:
961:
650:
2127:
327:
1851:
758:
348:
990:
529:
732:
cells, as well as malignant HSG1 cells taken from human oral cavities, but PCA was found to have mixed effects on
1987:
1975:
1963:
1957:
248:
1185:
cytotoxicity of protocatechuic acid to cultured human cells from oral tissue: involvement in oxidative stress"
1876:
930:
236:
2022:
1844:
2003:
1949:
1889:
1884:
1011:
781:
678:
178:
1492:
Mallavadhani, U. V.; Mahapatra, A. (2005). "A new aurone and two rare metabolites from the leaves of
1274:
56:
1652:
Delsignore, A; Romeo., F.; Giaccio, M. (1997). "Content of phenolic substances in basidiomycetes".
775:
753:
365:
86:
2132:
1790:
1521:
138:
1836:
1823:
1782:
1747:
1706:
1609:
1570:
1513:
1436:
1381:
1326:
1290:
1247:
1206:
1161:
1117:
1084:
946:
851:
845:
606:
717:
testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection
1774:
1737:
1696:
1661:
1601:
1560:
1552:
1505:
1426:
1416:
1371:
1361:
1318:
1282:
1237:
1224:
Nakamura, Y.; Torikai, K.; Ohto, Y.; Murakami, A.; Tanaka, T.; Ohigashi, H. (October 2000).
1196:
1153:
1109:
1074:
494:
432:
336:
43:
2008:
833:
808:
1278:
369:
240:
198:
158:
96:
2092:
1894:
1565:
1540:
1431:
1400:
1376:
1345:
969:
804:
789:
621:
34:
1201:
1180:
1157:
2116:
2097:
2087:
2082:
2066:
1969:
1930:
1867:
517:
483:
229:
1794:
1725:
1525:
1631:
705:
Protocatechuic acid (PCA) is antioxidant and anti-inflammatory. PCA extracted from
1509:
2056:
2030:
1471:
1242:
1225:
825:
1102:
Ritzer, Edwin; Sundermann, Rudolf (2000). "Hydroxycarboxylic Acids, Aromatic".
300:
17:
2061:
1665:
1421:
1366:
1286:
867:
507:
455:
189:
1751:
1113:
1819:
1778:
871:
737:
725:
1742:
1710:
1613:
1574:
1517:
1440:
1385:
1330:
1294:
1251:
1210:
1165:
1088:
1786:
1322:
2051:
1401:"Biological evaluation and molecular docking of protocatechuic acid from
983:
965:
748:
729:
694:
683:
593:
586:
579:
552:
209:
1701:
1680:
218:
793:
689:
662:
522:
513:
473:
287:
249:
1724:
Li, Xican; Wang, Xiaozhen; Chen, Dongfeng; Chen, Shuzhi (2011-07-31).
1605:
1556:
1079:
1062:
757:
showed an excellent ability to effectively inhibit the replication of
762:
169:
1726:"Antioxidant Activity and Mechanism of Protocatechuic Acid in vitro"
1344:
Hassan, S. T. S.; Švajdlenka, E.; Berchová-Bímová, K. (April 2017).
620:
Except where otherwise noted, data are given for materials in their
275:
1679:
Lee, Y.-S.; Kang, Y. H.; Jung, J. Y.; et al. (October 2008).
945:
902:)-3,4-dihydroxycyclohexa-1,5-diene-1,4-dicarboxylate dehydrogenase
745:
661:
311:
149:
119:
109:
587:
1061:
Lin, H.-H.; Chen, J.-H.; Huang, C.-C.; Wang, C.-J. (June 2007).
266:
1840:
721:
was measured by chemical markers and histological assessment.
393:
InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
1179:
Babich, H.; Sedletcaia, A.; Kenigsberg, B. (November 2002).
353:
796:, the phenolic substance concerned is protocatechuic acid.
1405:
L. as a potent urease inhibitor by an ESI–MS based method"
773:
Protocatechuic acid can be isolated from the stem bark of
1454:
Alemika, T. E.; Onawunmi, G. O.; Olugbade, T. O. (2006).
564:
1681:"Protein glycation inhibitors from the fruiting body of
843:
Protocatechuic acid is also found in mushrooms such as
638:
1541:"The occurrence of phenolic substances in arthropods"
761:
and to potently deactivate the catalytic activity of
709:
protected against chemically induced liver toxicity
2075:
2044:
2021:
1996:
1948:
1923:
1904:
1875:
840:), which is used worldwide as a food and beverage.
1539:Hackman, R. H.; Pryor, M. G.; Todd, A. R. (1948).
1464:Nigerian Journal of Natural Products and Medicines
1144:-butyl hydroperoxide-induced rat hepatotoxicity".
1399:Hassan, S. T. S.; Švajdlenka, E. (October 2017).
866:Protocatechuic acid is one of the main catechins
137:
299:
568:
95:
1105:Ullmann's Encyclopedia of Industrial Chemistry
1852:
8:
921:4-hydroxybenzoate 3-monooxygenase (NAD(P)H)
2041:
1993:
1901:
1859:
1845:
1837:
1594:Journal of Agricultural and Food Chemistry
788:The hardening of the protein component of
693:studies. It is produced commercially from
666:UV visible spectrum of protocatechuic acid
368:
239:
197:
26:
1741:
1700:
1564:
1430:
1420:
1375:
1365:
1241:
1200:
1078:
335:
1689:Biological & Pharmaceutical Bulletin
1023:
414:
389:
364:
217:
1730:Functional Foods in Health and Disease
1135:
1133:
964:uses 3,4-dihydroxybenzoate to produce
488:202 °C (396 °F; 475 K)
230:
1815:CRC Handbook of Chemistry and Physics
1029:
1027:
870:found in humans after consumption of
396:Key: YQUVCSBJEUQKSH-UHFFFAOYSA-N
177:
157:
7:
941:4,5-dihydroxyphthalate decarboxylase
936:3,4-dihydroxyphthalate decarboxylase
815:), is rich in protocatechuic acid (
290:
274:
25:
1202:10.1034/j.1600-0773.2002.910505.x
916:3-hydroxybenzoate 4-monooxygenase
807:, obtained from the fruit of the
1812:Haynes, William M., ed. (2016).
950:Protocatechuic acid biosynthesis
724:PCA has been reported to induce
628:
42:
33:
1067:International Journal of Cancer
982:uses 3,4-dihydroxybenzoate and
980:protocatechuate 3,4-dioxygenase
926:4-sulfobenzoate 3,4-dioxygenase
624:(at 25 °C , 100 kPa).
2036:Phloroglucinol carboxylic acid
1915:-Hydroxybenzoic acid glucoside
1456:"Antibacterial phenolics from
889:3-dehydroshikimate dehydratase
1:
1189:Pharmacology & Toxicology
1158:10.1016/s0278-6915(02)00002-9
962:protocatechuate decarboxylase
1870:(C6-C1) and their glycosides
1510:10.1080/14786410410001704705
1146:Food and Chemical Toxicology
1980:3,4-Dihydroxybenzoic acid (
1968:2,5-Dihydroxybenzoic acid (
759:herpes simplex virus type 2
2149:
911:-dihydrodiol dehydrogenase
460:154.12 g/mol
1988:3,5-Dihydroxybenzoic acid
1976:2,6-Dihydroxybenzoic acid
1964:2,4-Dihydroxybenzoic acid
1958:2,3-Dihydroxybenzoic acid
1666:10.1017/S0953756296003206
1470:: 108–110. Archived from
1422:10.3390/molecules22101696
1367:10.3390/molecules22050722
1311:Journal of Medicinal Food
1287:10.1016/j.tiv.2008.11.008
1243:10.1093/carcin/21.10.1899
618:
546:
425:
405:
380:
79:
70:3,4-Dihydroxybenzoic acid
67:
61:3,4-Dihydroxybenzoic acid
55:
50:
41:
32:
1877:Monohydroxybenzoic acids
1498:Natural Product Research
1114:10.1002/14356007.a13_519
2023:Trihydroxybenzoic acids
1897:(2-Hydroxybenzoic acid)
1779:10.1002/biof.5520080119
1545:The Biochemical Journal
1108:. Weinheim: Wiley-VCH.
931:vanillate monooxygenase
417:C1=CC(=C(C=C1C(=O)O)O)O
2123:Dihydroxybenzoic acids
1950:Dihydroxybenzoic acids
1743:10.31989/ffhd.v1i7.127
951:
667:
575:
2004:Ethyl protocatechuate
1937:-hydroxybenzoic acid)
1890:4-Hydroxybenzoic acid
1885:3-Hydroxybenzoic acid
1494:Diospyros melanoxylon
1323:10.1089/jmf.2010.0139
1012:Ethyl protocatechuate
949:
782:Diospyros melanoxylon
779:. and from leaves of
679:dihydroxybenzoic acid
665:
574:
1654:Mycological Research
883:Biosynthesis enzymes
769:Occurrence in nature
557:(fire diamond)
57:Preferred IUPAC name
28:Protocatechuic acid
2128:Phenol antioxidants
1982:Protocatechuic acid
1702:10.1248/bpb.31.1968
1458:Boswellia dalzielii
1403:Hibiscus sabdariffa
1348:Hibiscus sabdariffa
1279:2009ToxVi..23..201G
1267:Toxicology in Vitro
955:Degradation enzymes
838:Hibiscus sabdariffa
829:(17,540 ppm).
776:Boswellia dalzielii
754:Hibiscus sabdariffa
707:Hibiscus sabdariffa
671:Protocatechuic acid
495:Solubility in water
29:
952:
907:terephthalate 1,2-
701:Biological effects
668:
651:Infobox references
576:
478:1.524 g/cm (4 °C)
468:light brown solid
27:
2110:
2109:
2106:
2105:
2017:
2016:
1960:(Hypogallic acid)
1944:
1943:
1818:(97th ed.).
1683:Phellinus linteus
1606:10.1021/jf800161u
1600:(12): 4631–4636.
1557:10.1042/bj0430474
1236:(10): 1899–1907.
1080:10.1002/ijc.22571
1073:(11): 2306–2316.
852:Phellinus linteus
846:Agaricus bisporus
659:Chemical compound
657:
656:
607:Safety data sheet
542:4.48, 8.83, 12.6
349:CompTox Dashboard
121:Interactive image
16:(Redirected from
2140:
2042:
1994:
1902:
1861:
1854:
1847:
1838:
1833:
1799:
1798:
1773:(1–2): 111–118.
1762:
1756:
1755:
1745:
1721:
1715:
1714:
1704:
1676:
1670:
1669:
1649:
1643:
1642:
1640:
1639:
1630:. Archived from
1628:"Chemical Query"
1624:
1618:
1617:
1590:Euterpe oleracea
1585:
1579:
1578:
1568:
1536:
1530:
1529:
1489:
1483:
1482:
1480:
1479:
1451:
1445:
1444:
1434:
1424:
1396:
1390:
1389:
1379:
1369:
1341:
1335:
1334:
1305:
1299:
1298:
1262:
1256:
1255:
1245:
1221:
1215:
1214:
1204:
1176:
1170:
1169:
1137:
1128:
1127:
1099:
1093:
1092:
1082:
1058:
1052:
1049:
1043:
1042:Haynes, p. 5.148
1040:
1034:
1033:Haynes, p. 3.190
1031:
822:
820:
813:Euterpe oleracea
641:
635:
632:
631:
596:
589:
582:
567:
502:271 g/L (80 °C)
433:Chemical formula
373:
372:
357:
355:
339:
303:
292:
278:
251:
243:
232:
221:
201:
181:
161:
141:
123:
99:
46:
37:
30:
21:
2148:
2147:
2143:
2142:
2141:
2139:
2138:
2137:
2113:
2112:
2111:
2102:
2071:
2040:
2013:
2009:Orsellinic acid
1992:
1940:
1919:
1900:
1871:
1865:
1830:
1811:
1808:
1803:
1802:
1764:
1763:
1759:
1723:
1722:
1718:
1695:(10): 1968–72.
1678:
1677:
1673:
1651:
1650:
1646:
1637:
1635:
1626:
1625:
1621:
1587:
1586:
1582:
1538:
1537:
1533:
1491:
1490:
1486:
1477:
1475:
1453:
1452:
1448:
1398:
1397:
1393:
1343:
1342:
1338:
1307:
1306:
1302:
1264:
1263:
1259:
1223:
1222:
1218:
1178:
1177:
1173:
1139:
1138:
1131:
1124:
1101:
1100:
1096:
1060:
1059:
1055:
1051:Haynes, p. 5.91
1050:
1046:
1041:
1037:
1032:
1025:
1020:
1008:
987:
973:
880:
864:
818:
816:
802:
771:
703:
660:
653:
648:
647:
646: ?)
637:
633:
629:
625:
601:
600:
599:
598:
591:
584:
577:
573:
565:
538:
520:
501:
497:
449:
445:
441:
435:
421:
418:
413:
412:
401:
398:
397:
394:
388:
387:
376:
358:
351:
342:
322:
306:
293:
281:
261:
224:
204:
184:
164:
144:
126:
113:
102:
89:
75:
74:Protocatechuate
73:
71:
63:
62:
23:
22:
18:Protocatechuate
15:
12:
11:
5:
2146:
2144:
2136:
2135:
2130:
2125:
2115:
2114:
2108:
2107:
2104:
2103:
2101:
2100:
2095:
2093:Methyl gallate
2090:
2085:
2079:
2077:
2073:
2072:
2070:
2069:
2064:
2059:
2054:
2048:
2046:
2039:
2038:
2033:
2027:
2025:
2019:
2018:
2015:
2014:
2012:
2011:
2006:
2000:
1998:
1991:
1990:
1985:
1978:
1973:
1966:
1961:
1954:
1952:
1946:
1945:
1942:
1941:
1939:
1938:
1927:
1925:
1921:
1920:
1918:
1917:
1908:
1906:
1899:
1898:
1895:Salicylic acid
1892:
1887:
1881:
1879:
1873:
1872:
1868:Phenolic acids
1866:
1864:
1863:
1856:
1849:
1841:
1835:
1834:
1828:
1807:
1804:
1801:
1800:
1757:
1716:
1671:
1660:(5): 552–556.
1644:
1619:
1580:
1551:(3): 474–477.
1531:
1484:
1446:
1391:
1336:
1317:(3): 276–283.
1300:
1273:(2): 201–208.
1257:
1230:Carcinogenesis
1216:
1195:(5): 245–253.
1171:
1129:
1122:
1094:
1053:
1044:
1035:
1022:
1021:
1019:
1016:
1015:
1014:
1007:
1004:
1003:
1002:
985:
976:
971:
957:
956:
944:
943:
938:
933:
928:
923:
918:
913:
904:
891:
885:
884:
879:
876:
863:
860:
832:PCA occurs in
801:
798:
790:insect cuticle
770:
767:
702:
699:
658:
655:
654:
649:
627:
626:
622:standard state
619:
616:
615:
610:
603:
602:
592:
585:
578:
563:
562:
561:
560:
558:
549:
548:
544:
543:
540:
536:
526:
525:
510:
504:
503:
500:18 g/L (14 °C)
498:
493:
490:
489:
486:
480:
479:
476:
470:
469:
466:
462:
461:
458:
452:
451:
447:
443:
439:
436:
431:
428:
427:
423:
422:
420:
419:
416:
408:
407:
406:
403:
402:
400:
399:
395:
392:
391:
383:
382:
381:
378:
377:
375:
374:
361:
359:
347:
344:
343:
341:
340:
332:
330:
324:
323:
321:
320:
316:
314:
308:
307:
305:
304:
296:
294:
286:
283:
282:
280:
279:
271:
269:
263:
262:
260:
259:
255:
253:
245:
244:
234:
226:
225:
223:
222:
214:
212:
206:
205:
203:
202:
194:
192:
186:
185:
183:
182:
174:
172:
166:
165:
163:
162:
154:
152:
146:
145:
143:
142:
134:
132:
128:
127:
125:
124:
116:
114:
107:
104:
103:
101:
100:
92:
90:
85:
82:
81:
77:
76:
69:
65:
64:
60:
59:
53:
52:
48:
47:
39:
38:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2145:
2134:
2131:
2129:
2126:
2124:
2121:
2120:
2118:
2099:
2098:Syringic acid
2096:
2094:
2091:
2089:
2088:Eudesmic acid
2086:
2084:
2083:Ethyl gallate
2081:
2080:
2078:
2074:
2068:
2067:Chebulic acid
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2049:
2047:
2043:
2037:
2034:
2032:
2029:
2028:
2026:
2024:
2020:
2010:
2007:
2005:
2002:
2001:
1999:
1995:
1989:
1986:
1983:
1979:
1977:
1974:
1971:
1970:Gentisic acid
1967:
1965:
1962:
1959:
1956:
1955:
1953:
1951:
1947:
1936:
1932:
1931:Methylparaben
1929:
1928:
1926:
1922:
1916:
1914:
1910:
1909:
1907:
1903:
1896:
1893:
1891:
1888:
1886:
1883:
1882:
1880:
1878:
1874:
1869:
1862:
1857:
1855:
1850:
1848:
1843:
1842:
1839:
1831:
1829:9781498754293
1825:
1821:
1817:
1816:
1810:
1809:
1806:Cited sources
1805:
1796:
1792:
1788:
1784:
1780:
1776:
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669:
553:
533:
312:RTECS number
80:Identifiers
68:Other names
2057:Norbergenin
2031:Gallic acid
989:to produce
978:The enzyme
960:The enzyme
874:infusions.
868:metabolites
826:Allium cepa
512:soluble in
465:Appearance
426:Properties
237:100.002.509
179:ChEMBL37537
159:CHEBI:36062
2117:Categories
2062:Theogallin
2045:Glycosides
1905:Glycosides
1767:BioFactors
1736:(7): 232.
1638:2011-09-25
1478:2013-07-30
1360:(5): 722.
1123:3527306730
1018:References
991:3-carboxy-
862:Metabolism
738:stem cells
508:Solubility
456:Molar mass
337:36R5QJ8L4B
190:ChemSpider
108:3D model (
87:CAS Number
2133:Catechols
2076:Alkylated
1997:Alkylated
1924:Alkylated
1820:CRC Press
1752:2160-3855
1592:Mart.)".
1409:Molecules
1354:Molecules
999:-muconate
872:green tea
809:açaí palm
740:. In an
728:of human
726:apoptosis
319:UL0560000
258:202-760-0
250:EC Number
2052:Bergenin
1933:(Methyl-
1795:37684286
1711:18827365
1614:18522407
1575:16748434
1526:35200920
1518:15700652
1441:29019930
1386:28468298
1331:21182433
1295:19095056
1252:11023549
1211:12570031
1183:In vitro
1166:11955669
1089:17304508
1006:See also
966:catechol
805:Açaí oil
800:In foods
749:leukemia
742:in vitro
730:leukemia
715:In vitro
695:vanillin
684:in vitro
554:NFPA 704
547:Hazards
210:DrugBank
1787:9699018
1566:1274717
1432:6151788
1377:6154344
1275:Bibcode
878:Enzymes
834:roselle
794:ootheca
719:in vivo
711:in vivo
690:in vivo
677:) is a
644:what is
642: (
530:Acidity
523:benzene
514:ethanol
474:Density
450:
288:PubChem
219:DB03946
97:99-50-3
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763:urease
639:verify
636:
609:(SDS)
410:SMILES
276:C00230
170:ChEMBL
139:B00064
131:3DMet
51:Names
1791:S2CID
1522:S2CID
746:HL-60
518:ether
385:InChI
150:ChEBI
110:JSmol
1824:ISBN
1783:PMID
1748:ISSN
1707:PMID
1610:PMID
1571:PMID
1514:PMID
1437:PMID
1382:PMID
1327:PMID
1291:PMID
1248:PMID
1207:PMID
1162:PMID
1142:tert
1118:ISBN
1085:PMID
968:and
687:and
613:MSDS
328:UNII
267:KEGG
1775:doi
1738:doi
1697:doi
1662:doi
1658:101
1602:doi
1561:PMC
1553:doi
1506:doi
1496:".
1427:PMC
1417:doi
1372:PMC
1362:doi
1319:doi
1283:doi
1238:doi
1197:doi
1154:doi
1110:doi
1075:doi
1071:120
997:cis
993:cis
909:cis
849:or
817:630
734:TPA
675:PCA
354:EPA
291:CID
72:PCA
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