1594:. Leucomalachite green causes an "increase in the number and severity of changes". As leucomalachite green is the primary metabolite of malachite green and is retained in fish muscle much longer, most human dietary intake of malachite green from eating fish would be in the leuco form. During the experiment, rats were fed up to 543 ppm of leucomalachite green, an extreme amount compared to the average 5 ppb discovered in fish. After a period of two years, an increase in lung adenomas in male rats was discovered but no incidences of liver tumors. Therefore, it could be concluded that malachite green caused carcinogenic symptoms, but a direct link between malachite green and
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fluorescent molecule to a highly fluorescent molecule. In the fluorogen activating protein tool, established by a group at
Carnegie Mellon University, Malachite green binds a specific fluorogen activating protein to become highly fluorescent. Expression of the fluorogen activating protein as fusions of targeting domains can impart subcellular localization. Its use is similar to that of
1492:
A set of malachite green derivatives is also a key component in a fluorescence microscopy tool called the fluorogen activating protein/fluorogen system. Malachite green is in a class of molecules called fluorophores. When malachite green's rotational freedom is restricted, it transforms from a non
1509:
In 1992, Canadian authorities determined that eating fish contaminated with malachite green posed a significant health risk. Malachite green was classified a Class II Health Hazard. Due to its low manufacturing cost, malachite green is still used in certain countries with less restrictive laws for
1283:
This alcohol is important because it, not MG, traverses cell membranes. Once inside the cell, it is metabolized into LMG. Only the cation MG is deeply colored, whereas the leuco and alcohol derivatives are not. This difference arises because only the cationic form has extended pi-delocalization,
1390:
MG has frequently been used to catch thieves and pilferers. The bait, usually money, is sprinkled with the anhydrous powder. Anyone handling the contaminated money will find that on upon washing the hands, a green stain on the skin that lasts for several days will result.
1610:
7.9x10), several research groups have developed technologies to detect malachite green. For example, Zhao et al., demonstrated the use of malachite green aptamer in microcantilever based sensors to detect low concentration of malachite green.
1119:
516:
1871:"Triphenylmethane dye (C52H54N4O12) is potentially a hazardous substance in edible freshwater fish at trace level: toxicity, hematology, biochemistry, antioxidants, and molecular docking evaluation study"
1537:
Malachite green has been banned in the United States since 1983 in food-related applications. The substance is also banned in the United
Kingdom. It is prohibited from the use in food in Macao.
473:
1534:, where the substance is also banned for use in aquaculture. In June 2007, the FDA blocked the importation of several varieties of seafood due to continued malachite green contamination.
2070:
Cho, Bongsup P.; Yang, Tianle; Blankenship, Lonnie R.; et al. (2003). "Synthesis and
Characterization of N-Demethylated Metabolites of Malachite Green and Leucomalachite Green".
136:
1847:
Wendy C. Andersen, Sherri B. Turnipseed, and José E. Roybal "Quantitative and
Confirmatory Analyses of Malachite Green and Leucomalachite Green Residues in Fish and Shrimp"
578:
425:
1383:, leuco-malachite green (LMG), is found in fish treated with malachite green, and this finding is the basis of controversy and government regulation. See also
2099:
Plakas, S. M.; El Said, K. R.; Stehly, G. R.; et al. (1996). "Uptake, tissue distribution, and metabolism of malachite green in the channel catfish (
651:
2201:
1710:
887:
2221:
363:
1340:
Malachite green is traditionally used as a dye. Kilotonnes of MG and related triarylmethane dyes are produced annually for this purpose.
1473:
between pH 0.2–1.8. However, this use is relatively rare. Leuco-malachite green (LMG) is used as a detection method for latent blood in
2211:
1531:
1497:
but has the added benefit of having a 'dark state' before the malachite green fluorophore is added. This is especially useful for
2154:"In vitro effect of malachite green on Candida albicans involves multiple pathways and transcriptional regulators UPC2 and STP2"
1943:
1776:
1628:
2011:
Babendure, Jeremy R.; Adams, Stephen R.; Tsien, Roger Y. (2003). "Aptamers Switch on
Fluorescence of Triphenylmethane Dyes".
646:
337:
InChI=1S/C23H25N2.ClH/c1-24(2)21-14-10-19(11-15-21)23(18-8-6-5-7-9-18)20-12-16-22(17-13-20)25(3)4;/h5-17H,1-4H3;1H/q+1;/p-1
1960:
1498:
1485:, converting the colorless LMG into malachite green. Therefore, the appearance of a green color indicates the presence of
347:
InChI=1/C23H25N2.ClH/c1-24(2)21-14-10-19(11-15-21)23(18-8-6-5-7-9-18)20-12-16-22(17-13-20)25(3)4;/h5-17H,1-4H3;1H/q+1;/p-1
2053:
Effect of
Receptor Attachment on Sensitivity of Label Free Microcantilever Based Biosensor Using Malachite Green Aptamer
760:
have no effect on the color. The intense green color of the cation results from a strong absorption band at 621 nm (
2206:
328:
1327:
2266:
1923:
658:
1777:"DNA Analyst Training Laboratory Training Manual Protocol 2.18 Leucomalachite Green Presumptive Test for Blood"
451:
1384:
574:
2131:
DeFina, Steven C.; Dieckmann, Thorsten (2002). "Synthesis of selectively N- or C-labelled malachite green".
1295:
of the MG cation. The alcohol derivative of MG is derived from LMG by replacement of the unique C–H by C–OH.
2241:
1527:
1368:
761:
556:
271:
214:
19:
This article is about the organic dye called "malachite green". For the use of malachite as a pigment, see
507:
1980:
292:
176:
570:
502:
1976:"Mutagenicity and carcinogenicity in relation to DNA adduct formation in rats fed leucomalachite green"
497:
1586:(oral, mouse) is 80 mg/kg. Rats fed malachite green experience "a dose-related increase in liver
1494:
24:
2256:
309:
2251:
1941:
Annual Report on
Surveillance for Veterinary Residues in Food in the UK for 2001, 2002, and 2003
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2246:
2236:
492:
2271:
1553:
530:
485:
1869:
Poopal, Rama-Krishnan; Ashwini, Rajan; Ramesh, Mathan; Li, Bin; Ren, Zongming (2023-03-01).
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1568:
1309:
280:
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59:
716:
and also using in pigment industry. Formally, malachite green refers to the chloride salt
436:
111:
8:
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1210:
748:, although the term malachite green is used loosely and often just refers to the colored
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stained with malachite green (vegetative cells stained pink with safranin counterstain)
713:
1989:
2183:
2087:
2036:
2028:
1993:
1940:
1910:
1898:
1890:
1822:
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1482:
1458:
1405:
1203:
1834:
1731:
Srivastava, S; Sinha, R; Roy, D (2004). "Toxicological effects of malachite green".
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2165:
2140:
2112:
2079:
2020:
1985:
1882:
1852:
1814:
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On the left is leuco-malachite Green (LMG) and on the right are the two equivalent
1125:
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582:
386:
1754:
548:
260:
1947:
1653:
Raducan, Adina; Olteanu, Alexandra; Puiu, Mihaela; Oancea, Dumitru (2008-03-01).
1317:
874:
566:
2216:
1803:"Fluorogen-activating single-chain antibodies for imaging cell surface proteins"
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1654:
611:
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2032:
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1434:
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Numerous niche applications exploit the intense color of MG. It is used as a
1363:
1321:
207:
2116:
2054:
1441:
stains bacteria red or magenta, and malachite green is used as a blue-green
1114:{\displaystyle {\ce {C6H5CHO + C6H5N(CH3)2 -> (C6H5N(CH3)2)2C6H5 + H2O}}}
37:
2187:
2091:
2040:
1997:
1902:
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1313:
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2004:
1802:
1399:
46:
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1606:
Although malachite green has almost no fluorescence in aqueous solution (
1595:
1587:
1549:
1511:
1358:
1353:
1348:
682:
20:
1708:
Thomas
Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in
1560:
1541:
1478:
1422:
1410:
1380:
1373:
685:. Malachite green is traditionally used as a dye for materials such as
466:
409:
187:
2123:
Schoettger, 1970; Smith and Heath, 1979; Gluth and Hanke, 1983. Bills
2083:
2024:
1856:
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2144:
1545:
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counterstain is often used. Malachite green is a part of
Alexander's
1450:
1430:
1305:
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701:
544:
1975:
1818:
628:
Except where otherwise noted, data are given for materials in their
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135:
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Dhamgaye, S; Devaux, F; Manoharlal, R; et al. (Jan 2012).
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81:
Aniline green; Basic green 4; Diamond green B; Victoria green B
1523:
1486:
757:
694:
619:
147:
125:
2098:
712:
Malachite green is classified in the dyestuff industry as a
297:
1655:"Influence of surfactants on the fading of malachite green"
686:
226:
1974:
Culp, S J; Beland, FA; Heflich, R H; et al. (2002).
1961:"Food Safety Information - Prohibited Substances in Food"
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1049:
1036:
1015:
1002:
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968:
947:
934:
915:
902:
1652:
1571:= 10 days) than is the parent molecule (HL = 2.8 days).
2069:
1973:
540:
2217:
Malachite green - endospore staining technique (video)
2133:
Journal of
Labelled Compounds and Radiopharmaceuticals
1530:(FDA) detected malachite green in seafood from China,
1868:
1124:
Second, this colorless leuco compound, a relative of
890:
2019:(48). American Chemical Society (ACS): 14716–14717.
704:; the name just comes from the similarity of color.
697:. Despite its name the dye is not prepared from the
2010:
1924:
Chinese fish crisis shows seafood safety challenges
1284:which allows the molecule to absorb visible light.
869:Malachite green is prepared by the condensation of
1730:
1113:
536:
2228:
259:
2130:
110:
102:
1711:Ullmann's Encyclopedia of Industrial Chemistry
1693:
1320:in the molecular ratio 1:2 in the presence of
1308:form of malachite green was first prepared by
72:-dimethylcyclohexa-2,5-dien-1-iminium chloride
1800:
1782:. National Forensic Science Technology Center
371:CN(C)c1ccc(cc1)C(=C2C=CC(=(C)C)C=C2)c3ccccc3.
1875:Environmental Science and Pollution Research
707:
681:and controversially as an antimicrobial in
435:
1775:
586:
312:
217:
195:
2177:
2055:https://doi.org/10.1016/j.snb.2019.126963
1670:
1366:. It is a very popular treatment against
279:
2013:Journal of the American Chemical Society
1461:. Malachite green can also be used as a
1398:
1352:, which infects fish eggs in commercial
1286:
1128:, is oxidized to the cation that is MG:
1481:catalyzes the reaction between LMG and
308:
2229:
1698:. Jai Sai Publications. pp. 2/37.
414:364.911 g/mol (chloride)
208:
340:Key: FDZZZRQASAIRJF-UHFFFAOYSA-M
175:
155:
1801:Szent-Gyorgyi, Christopher (2007).
1518:found traces of malachite green in
775:Malachite green (second transition)
350:Key: FDZZZRQASAIRJF-REWHXWOFAA
250:
234:
13:
2202:U.S. National Institutes of Health
2063:
1445:. Malachite green is also used in
1326:
824:Malachite green (first transition)
25:Basic copper carbonate § Uses
14:
2283:
2207:U.S. Food and Drug Administration
2195:
636:
506:
501:
496:
491:
45:
36:
2047:
1967:
1953:
1939:Veterinary Residues Committee.
1933:
1917:
1851:2006, volume 54, pp. 4517–4523.
1696:Principles of organic chemistry
1514:purposes. In 2005, analysts in
1453:within bacterial cells; here a
632:(at 25 °C , 100 kPa).
1862:
1841:
1794:
1769:
1724:
1702:
1687:
1646:
1621:
1449:, since it can directly stain
1299:
1052:
1039:
1023:
989:
984:
971:
955:
452:Occupational safety and health
1:
1990:10.1016/S0027-5107(02)00152-5
1755:10.1016/j.aquatox.2003.09.008
1614:
1526:. In 2006, the United States
1504:
1394:
1385:Antimicrobials in aquaculture
1202:A typical oxidizing agent is
1601:
1528:Food and Drug Administration
1369:Ichthyophthirius multifiliis
1356:, MG has been used to treat
1331:Synthesis of malachite green
7:
2158:Antimicrob Agents Chemother
1574:
756:salt is also marketed. The
600:or concentration (LD, LC):
10:
2288:
1887:10.1007/s11356-022-24206-y
1714:2002, Wiley-VCH, Weinheim.
1209:Hydrolysis of MG gives an
465:Moderately toxic, Extreme
18:
2212:U.K. Department of Health
1672:10.2478/s11532-007-0066-0
1343:MG is active against the
822:
773:
708:Structures and properties
626:
596:
472:
449:
444:
418:
379:
359:
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86:
78:
58:
53:
44:
35:
2105:Can. J. Fish. Aquat. Sci
1720:10.1002/14356007.a27_179
557:Precautionary statements
64:4-{(phenyl)methylidene}-
2267:Dimethylamino compounds
2117:10.1139/cjfas-53-6-1427
1859:and references therein
1544:malachite green to its
1522:and fish imported from
1435:Gimenez staining method
1335:
881:malachite green (LMG):
1552:(the leuco form has a
1414:
1332:
1312:in 1877 by condensing
1296:
1115:
762:extinction coefficient
1598:was not established.
1402:
1330:
1290:
1116:
107: (chloride salt)
2222:Malachite Green Dyes
2170:10.1128/AAC.00574-11
1849:J. Agric. Food Chem.
1807:Nature Biotechnology
1694:Dr. M Vishwanathan.
1293:resonance structures
888:
115: (oxalate salt)
60:Preferred IUPAC name
21:Malachite § Use
2242:Triarylmethane dyes
2101:Ictalurus punctatus
1881:(11): 28759–28779.
1747:2004AqTox..66..319S
1629:"C&L Inventory"
1106:
1090:
1077:
1064:
1051:
1038:
1017:
1004:
983:
970:
949:
936:
917:
904:
32:
2072:Chem. Res. Toxicol
1984:. 506–507: 55–63.
1946:2012-02-11 at the
1734:Aquatic Toxicology
1590:" along with lung
1463:saturable absorber
1447:endospore staining
1415:
1362:and is used as an
1333:
1297:
1111:
1094:
1078:
1065:
1026:
1021:
1005:
992:
987:
958:
953:
937:
924:
905:
892:
714:triarylmethane dye
677:that is used as a
659:Infobox references
30:
2084:10.1021/tx0256679
2025:10.1021/ja037994o
1981:Mutation Research
1857:10.1021/jf0532258
1483:hydrogen peroxide
1406:Bacillus subtilis
1403:A preparation of
1204:manganese dioxide
1109:
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1029:
1020:
1008:
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908:
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867:
866:
818:
817:
667:Chemical compound
665:
664:
531:Hazard statements
404:(chloride)
293:CompTox Dashboard
137:Interactive image
2279:
2191:
2181:
2148:
2145:10.1002/jlcr.554
2120:
2111:(6): 1427–1433.
2095:
2057:
2051:
2045:
2044:
2008:
2002:
2001:
1971:
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1475:forensic science
1419:biological stain
1379:. The principal
1279:
1198:
1126:triphenylmethane
1120:
1118:
1117:
1112:
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675:organic compound
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387:Chemical formula
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31:Malachite green
29:
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2257:Aromatic amines
2227:
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2064:Further reading
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2005:
1972:
1968:
1959:
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1948:Wayback Machine
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1604:
1584:
1577:
1567:muscle longer (
1563:is retained in
1507:
1397:
1338:
1318:dimethylaniline
1310:Hermann Fischer
1302:
1277:
1273:
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875:dimethylaniline
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671:Malachite green
668:
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654: ?)
645:
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633:
618:80mg/kg (oral,
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2196:External links
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2164:(1): 495–506.
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2139:(3): 241–248.
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2078:(3): 285–294.
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1659:Open Chemistry
1645:
1633:echa.europa.eu
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1559:of 5.70), the
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912:
899:
865:
864:
859:
854:
848:
847:
842:
840:
834:
833:
816:
815:
810:
805:
799:
798:
793:
791:
785:
784:
743:
739:
735:
731:
727:
723:
719:
709:
706:
666:
663:
662:
657:
635:
634:
630:standard state
627:
624:
623:
616:
607:
605:
602:
601:
594:
593:
579:P305+P351+P338
560:
555:
552:
551:
534:
529:
526:
525:
520:
515:
512:
511:
489:
484:
481:
480:
470:
469:
463:
460:
457:
456:
447:
446:
442:
441:
429:
424:
421:
420:
416:
415:
412:
406:
405:
401:
397:
393:
390:
385:
382:
381:
377:
376:
374:
373:
370:
362:
361:
360:
357:
356:
354:
353:
349:
346:
345:
343:
339:
336:
335:
327:
326:
325:
322:
321:
319:
318:
305:
303:
291:
288:
287:
285:
284:
276:
274:
268:
267:
265:
264:
256:
254:
246:
243:
242:
240:
239:
231:
229:
223:
222:
212:
204:
203:
201:
200:
192:
190:
184:
183:
181:
180:
172:
170:
164:
163:
161:
160:
152:
150:
144:
143:
141:
140:
132:
130:
123:
120:
119:
117:
116:
108:
99:
97:
92:
89:
88:
84:
83:
80:
76:
75:
63:
62:
56:
55:
51:
50:
42:
41:
15:
9:
6:
4:
3:
2:
2284:
2273:
2270:
2268:
2265:
2263:
2262:Fish medicine
2260:
2258:
2255:
2253:
2250:
2248:
2247:Staining dyes
2245:
2243:
2240:
2238:
2237:PH indicators
2235:
2234:
2232:
2223:
2220:
2218:
2215:
2213:
2210:
2208:
2205:
2203:
2200:
2199:
2189:
2185:
2180:
2175:
2171:
2167:
2163:
2159:
2155:
2150:
2146:
2142:
2138:
2134:
2129:
2126:
2122:
2118:
2114:
2110:
2106:
2102:
2097:
2093:
2089:
2085:
2081:
2077:
2073:
2068:
2067:
2056:
2050:
2042:
2038:
2034:
2030:
2026:
2022:
2018:
2014:
2007:
1999:
1995:
1991:
1987:
1983:
1982:
1977:
1970:
1962:
1956:
1949:
1945:
1942:
1936:
1929:
1925:
1920:
1912:
1908:
1904:
1900:
1896:
1892:
1888:
1884:
1880:
1876:
1872:
1865:
1858:
1854:
1850:
1844:
1836:
1832:
1828:
1824:
1820:
1816:
1812:
1808:
1804:
1797:
1778:
1772:
1764:
1760:
1756:
1752:
1748:
1744:
1741:(3): 319–29.
1740:
1736:
1735:
1727:
1721:
1717:
1713:
1712:
1705:
1697:
1690:
1682:
1678:
1673:
1668:
1664:
1660:
1656:
1649:
1634:
1630:
1624:
1620:
1612:
1609:
1608:quantum yield
1599:
1597:
1593:
1589:
1585:
1572:
1570:
1566:
1562:
1558:
1557:
1551:
1547:
1543:
1538:
1535:
1533:
1529:
1525:
1521:
1517:
1513:
1502:
1500:
1496:
1490:
1488:
1484:
1480:
1476:
1472:
1468:
1464:
1460:
1456:
1452:
1448:
1444:
1440:
1436:
1432:
1428:
1424:
1420:
1412:
1408:
1407:
1401:
1392:
1388:
1386:
1382:
1378:
1375:
1371:
1370:
1365:
1364:antibacterial
1361:
1360:
1355:
1351:
1350:
1346:
1341:
1329:
1325:
1323:
1322:sulfuric acid
1319:
1315:
1311:
1307:
1294:
1289:
1285:
1216:
1215:
1214:
1212:
1207:
1205:
1131:
1130:
1129:
1127:
1099:
1091:
1083:
1070:
1057:
1044:
1031:
1010:
997:
976:
963:
942:
929:
921:
910:
897:
884:
883:
882:
880:
876:
872:
863:
860:
858:
855:
853:
850:
849:
846:
843:
841:
839:
836:
835:
830:
825:
821:
814:
811:
809:
806:
804:
801:
800:
797:
796:above pH 13.2
794:
792:
790:
789:below pH 11.5
787:
786:
781:
776:
772:
769:
763:
759:
755:
751:
715:
705:
703:
700:
696:
692:
688:
684:
680:
676:
672:
660:
653:
648:
631:
625:
621:
617:
613:
604:
603:
599:
595:
561:
558:
554:
553:
535:
532:
528:
527:
524:
521:
518:
514:
513:
509:
504:
499:
494:
490:
487:
483:
482:
478:
476:
471:
468:
464:
459:
458:
454:
453:
448:
443:
438:
433:
430:
427:
423:
422:
419:Pharmacology
417:
413:
411:
408:
407:
391:
388:
384:
383:
378:
369:
368:
365:
358:
344:
334:
333:
330:
323:
315:
311:
310:DTXSID1025512
307:
306:
304:
294:
290:
289:
282:
278:
277:
275:
273:
270:
269:
262:
258:
257:
255:
249:
245:
244:
237:
233:
232:
230:
228:
225:
224:
220:
216:
213:
211:
209:ECHA InfoCard
206:
205:
198:
194:
193:
191:
189:
186:
185:
178:
174:
173:
171:
169:
166:
165:
158:
154:
153:
151:
149:
146:
145:
138:
134:
133:
131:
127:
122:
121:
113:
109:
105:
101:
100:
98:
95:
91:
90:
85:
77:
71:
67:
61:
57:
52:
48:
43:
39:
34:
26:
22:
2272:Carbocations
2161:
2157:
2136:
2132:
2124:
2108:
2104:
2100:
2075:
2071:
2049:
2016:
2012:
2006:
1979:
1969:
1955:
1935:
1927:
1919:
1878:
1874:
1864:
1848:
1843:
1810:
1806:
1796:
1784:. Retrieved
1771:
1738:
1732:
1726:
1709:
1704:
1695:
1689:
1665:(1): 89–92.
1662:
1658:
1648:
1636:. Retrieved
1632:
1623:
1605:
1578:
1555:
1548:form. Being
1539:
1536:
1532:among others
1508:
1491:
1471:pH indicator
1459:pollen stain
1443:counterstain
1427:cell biology
1425:analysis of
1416:
1404:
1389:
1367:
1357:
1347:
1342:
1339:
1314:benzaldehyde
1303:
1282:
1208:
1201:
1123:
871:benzaldehyde
868:
861:
856:
851:
845:above pH 1.8
844:
838:below pH 0.2
837:
829:pH indicator
823:
812:
807:
802:
795:
788:
780:pH indicator
774:
711:
670:
669:
597:
522:
474:
461:Main hazards
450:
177:ChEMBL186357
87:Identifiers
79:Other names
69:
65:
1638:27 December
1596:liver tumor
1588:DNA adducts
1550:lipophillic
1512:aquaculture
1423:microscopic
1359:Saprolegnia
1354:aquaculture
1349:Saprolegnia
1300:Preparation
1161:+ HCl + ½ O
683:aquaculture
612:median dose
598:Lethal dose
517:Signal word
455:(OHS/OSH):
426:ATCvet code
380:Properties
215:100.008.476
157:CHEBI:72449
16:Organic dye
2231:Categories
1930:, 7/1/2007
1615:References
1561:metabolite
1542:metabolize
1505:Regulation
1479:Hemoglobin
1469:, or as a
1467:dye lasers
1451:endospores
1411:endospores
1395:Niche uses
1381:metabolite
1374:freshwater
486:Pictograms
410:Molar mass
281:12058M7ORO
188:ChemSpider
124:3D model (
94:CAS Number
2033:0002-7863
1928:USA Today
1911:253671609
1895:1614-7499
1786:8 January
1681:2391-5420
1602:Detection
1554:log
1516:Hong Kong
1501:studies.
1433:. In the
985:⟶
702:malachite
575:P301+P312
477:labelling
112:2437-29-8
2188:22006003
2092:12641428
2041:14640641
1998:12351145
1944:Archived
1903:36401692
1835:21815631
1827:18157118
1763:15129773
1592:adenomas
1575:Toxicity
1540:Animals
1455:safranin
1437:, basic
1409:showing
1345:oomycete
1165:→ [C
877:to give
679:dyestuff
467:irritant
445:Hazards
440:)
432:QP53AX16
104:569-64-2
2179:3256066
1743:Bibcode
1565:catfish
1439:fuchsin
1377:aquaria
1258:C(OH)(C
1246:]Cl + H
1211:alcohol
1193:]Cl + H
766:10 M cm
754:oxalate
699:mineral
691:leather
652:what is
650: (
434: (
248:PubChem
2186:
2176:
2127:(1977)
2125:et al.
2090:
2039:
2031:
1996:
1909:
1901:
1893:
1833:
1825:
1761:
1679:
1218:[C
758:anions
752:. The
750:cation
718:[C
693:, and
673:is an
647:verify
644:
523:Danger
364:SMILES
236:C18367
168:ChEMBL
54:Names
23:, and
1907:S2CID
1831:S2CID
1780:(PDF)
1546:leuco
1524:China
1487:blood
1306:leuco
1278:+ HCl
1250:O → C
879:leuco
695:paper
620:mouse
545:H361d
329:InChI
261:11294
197:10820
148:ChEBI
126:JSmol
2184:PMID
2103:)".
2088:PMID
2037:PMID
2029:ISSN
1994:PMID
1899:PMID
1891:ISSN
1823:PMID
1788:2018
1759:PMID
1677:ISSN
1640:2021
1579:The
1520:eels
1510:non
1499:FRET
1429:and
1421:for
1336:Uses
1316:and
1304:The
1266:N(CH
1234:N(CH
1181:N(CH
1149:N(CH
1141:CH(C
873:and
813:13.2
803:11.5
734:N(CH
687:silk
591:P501
587:P330
583:P310
571:P280
567:P270
563:P264
549:H410
541:H318
537:H302
272:UNII
227:KEGG
2174:PMC
2166:doi
2141:doi
2113:doi
2080:doi
2021:doi
2017:125
1986:doi
1883:doi
1853:doi
1815:doi
1751:doi
1716:doi
1667:doi
1495:GFP
1465:in
1372:in
1226:C(C
1173:C(C
919:CHO
862:1.8
852:0.2
768:).
764:of
746:]Cl
726:C(C
475:GHS
437:WHO
400:ClN
298:EPA
251:CID
2233::
2182:.
2172:.
2162:56
2160:.
2156:.
2137:45
2135:.
2109:53
2107:.
2086:.
2076:16
2074:.
2035:.
2027:.
2015:.
1992:.
1978:.
1926:,
1905:.
1897:.
1889:.
1879:30
1877:.
1873:.
1829:.
1821:.
1811:26
1809:.
1805:.
1757:.
1749:.
1739:66
1737:.
1675:.
1661:.
1657:.
1631:.
1583:50
1581:LD
1569:HL
1489:.
1477:.
1387:.
1324:.
1213::
1206:.
1028:CH
960:CH
689:,
622:)
608:50
606:LD
589:,
585:,
581:,
577:,
573:,
569:,
565:,
547:,
543:,
539:,
479::
398:25
394:23
2190:.
2168::
2147:.
2143::
2119:.
2115::
2094:.
2082::
2043:.
2023::
2000:.
1988::
1963:.
1950:.
1913:.
1885::
1855::
1837:.
1817::
1790:.
1765:.
1753::
1745::
1718::
1683:.
1669::
1663:6
1642:.
1556:P
1276:2
1274:)
1272:2
1270:)
1268:3
1264:4
1262:H
1260:6
1256:5
1254:H
1252:6
1248:2
1244:2
1242:)
1240:2
1238:)
1236:3
1232:4
1230:H
1228:6
1224:5
1222:H
1220:6
1197:O
1195:2
1191:2
1189:)
1187:2
1185:)
1183:3
1179:4
1177:H
1175:6
1171:5
1169:H
1167:6
1163:2
1159:2
1157:)
1155:2
1153:)
1151:3
1147:4
1145:H
1143:6
1139:5
1137:H
1135:6
1133:C
1108:O
1100:2
1096:H
1092:+
1084:5
1080:H
1071:6
1067:C
1058:2
1053:)
1045:2
1040:)
1032:3
1024:(
1019:N
1011:5
1007:H
998:6
994:C
990:(
977:2
972:)
964:3
956:(
951:N
943:5
939:H
930:6
926:C
922:+
911:5
907:H
898:6
894:C
857:⇌
831:)
827:(
808:⇌
782:)
778:(
744:2
742:)
740:2
738:)
736:3
732:4
730:H
728:6
724:5
722:H
720:6
642:Y
614:)
610:(
402:2
396:H
392:C
300:)
296:(
128:)
70:N
68:,
66:N
27:.
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