35:
297:
202:
526:
521:
26:
631:
1025:
enzymes could not easily digest hair, nails, feathers, and such. He realized that while the disulfide bonds, which stabilize proteins by cross-linking, were broken, the structures containing these proteins could be reshaped easily, and that they would retain this shape after the disulfide bonds were
1056:
dermal for rabbit is 848 mg/kg. Mercaptoacetic acid in hair waving and depilatory products containing other mercapto acids can be identified by using thin-layer chromatography and gas chromatography. MAA also has been identified by using potentiometric titration with
501:
1665:
Lee CW, Phil M. The detection of iron traces on hands by ferrozine sparys: a report on the sensitivity and interference of the method and recommended procedure in forensic science investigation.
734:
processing. It is also used as an acidity indicator, manufacturing of thioglycolates, and in bacteriology for preparation of thioglycolate media. Thioglycolysis reactions are used on
1149:
571:
1482:
Gregorí Valdes, B. S., Serro, A. P., Gordo, P. M., Silva, A., Gonçalves, L., Salgado, A., Marto, J., Baltazar, D., Santos, R. G. dos, Bordado, J. M., Ribeiro, H. M. (2017).
644:
993:. Thioglycolic acid reacts with diethyl acetylmalonate to form acetylmercaptoacetic acid and diethyl malonate, the reducing agent in the conversion of Fe(III) to Fe(II).
1175:
810:
Thioglycolic acid is prepared by reaction of sodium or potassium chloroacetate with alkali metal hydrosulfide in aqueous medium. It can be also prepared via the
346:
1249:"Characterization of oxidized tannins: comparison of depolymerization methods, asymmetric flow field-flow fractionation and small-angle X-ray scattering"
1737:
Vandeputte M, Dryon L, Van Den Winkel P, Mertens J, Massart DL. Determination of thioglycolic acid using a silver sulfide single crystal electrode.
34:
1640:
Cosmetic, Toiletry, and
Fragrance Association (CTFA). Thioglycolic Acid. 1987;(1987a). Submission of unpublished data by CTFA Code No. 3-25-2
726:
bonds in the cortex of hair. One reforms these broken bonds in giving hair a "perm". Alternatively and more commonly, the process leads to
1189:
1566:
311:
1792:
1304:"Detection and Identification of Oxidation Markers of the Reaction of Grape Tannins with Volatile Thiols Commonly Found in Wine"
1721:
Goetz N, Gataud P, Bore P. Gas-chromatographic determination of mercaptoacetic acid in hair-waving and diplatory products.
1164:
254:
275:
874:
651:
595:
582:
1787:
1484:"New Polyurethane Nail Lacquers for the Delivery of Terbinafine: Formulation and Antifungal Activity Evaluation"
790:, a special bacterial growth media. It is also used in so-called "fallout remover" or "wheel cleaner" to remove
540:
1693:
1398:"Phenolic compounds of Moroccan red press wines: Influence of fining agents and micro-oxygenation treatments"
1617:
484:
520:
197:
1521:
1070:
715:
1681:
1205:, 14th ed.; O’Neil, Maryadele J., Ed.; Merck & Co., Inc.: Whitehouse Station, NJ, 2006; p. 9342.
159:
1782:
1705:
Goetz N, Gataud P, Bore P. Determination of mercaptoacetic acid in hair waving and depilatory products.
534:
525:
513:
1359:"Douglas bark dry fractionation for polyphenols isolation: From forestry waste to added value products"
119:
1397:
1358:
47:
974:
787:
292:
85:
1464:
1339:
1284:
1046:
1039:
940:
Thioglycolic acid is a reducing agent, especially at higher pH. It oxidizes to the corresponding
815:
746:
1649:
Saeed M. Hameed N. Madan V. Mansoor S. Preparation and
Mechanisms studies of Thioglycolic Acid.
1599:
1562:
1503:
1456:
1417:
1378:
1331:
1323:
1276:
1268:
1170:
819:
1591:
1495:
1448:
1409:
1370:
1315:
1260:
1230:
1002:
735:
711:
671:
462:
369:
263:
1777:
1080:
695:
691:
561:
179:
1682:
National
Academies Press:Biographical Memoirs:David Rockwell Goddard:by Ralph O. Erickson
1247:
Vernhet A, Dubascoux S, Cabane B, Fulcrand H, Dubreucq E, Poncet-Legrand C (2011-09-01).
296:
201:
139:
95:
1058:
1010:
719:
622:
544:
473:
1436:
1190:"Thioglycolic acid :Understanding the risk of specific chemicals of interest - PREVOR"
1771:
1452:
1343:
1075:
451:
441:
190:
1303:
755:
derivatives of thioglycolic acid isooctyl esters are widely used as stabilizers for
714:, including calcium thioglycolate and sodium thioglycolate. TGA is the precursor to
1468:
1288:
742:
727:
1374:
1556:
243:
1483:
881:
551:
25:
1499:
1413:
1264:
1145:
1114:
1027:
982:
811:
791:
707:
400:
170:
1603:
1421:
1382:
1327:
1319:
1272:
1234:
1757:
Okada K, Okada E. Novel treatment using thioglycolic acid for pincer nails.
1248:
941:
752:
723:
687:
1507:
1460:
1335:
1280:
1694:
http://www.sigmaaldrich.com/safety-center.html?cm_sp=Search-_-MSDS-_-MSDS1
802:
iron combines with thioglycolate to form red-violet ferric thioglycolate.
1026:
allowed to re-form. TGA was developed in the 1940s for use as a chemical
1022:
1595:
1018:
1014:
799:
731:
431:
230:
986:
795:
682:
H. TGA is often called mercaptoacetic acid (MAA). It contains both a
150:
1582:
Lyons E (1927-08-01). "Thioglycolic Acid as a Color Test for Iron".
977:
with metal ions. Such complexes have been used for the detection of
621:
Except where otherwise noted, data are given for materials in their
218:
1396:
Ben Aziz M, Mouls L, Fulcrand H, Douieb H, Hajjaj H (2017-05-01).
1357:
Trivelato P, Mayer C, Barakat A, Fulcrand H, Aouf C (2016-08-01).
1006:
683:
130:
118:
108:
1561:. Vol. 12: Corrosion to Cottonseed. CRC Press. p. 103.
978:
608:
421:
209:
990:
756:
1005:, in the early 1930s, identified TGA as a useful reagent for
694:
functional groups. It is a colorless liquid with a strongly
280:
1437:"Novel treatment using thioglycolic acid for pincer nails"
741:
TGA has also been used to soften nails, either to reshape
1225:
639:
1150:
National
Institute for Occupational Safety and Health
1163:
973:Thioglycolic acid, usually as its dianion, forms
880:of 3.83 is an acid about 10 times stronger than
242:
1696:(accessed Nov 10, 2013). Product Number – T3758
698:. TGA is miscible with polar organic solvents.
556:> 110 °C; 230 °F; 383 K
456:96 °C (205 °F; 369 K) at 5 mmHg
94:
1558:Encyclopedia of Chemical Processing and Design
1545:"SONAX Xtreme Wheel Cleaner" Safety data sheet
1227:Ullmann's Encyclopedia of Industrial Chemistry
1052:inhalation for rat is 21 mg/m for 4 h, and LD
8:
320:InChI=1S/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4)
1308:Journal of Agricultural and Food Chemistry
944:(2-acetic acid or dithiodiglycolic acid):
330:InChI=1/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4)
295:
200:
178:
17:
1221:
1219:
1217:
1215:
1213:
1211:
710:and is still used as such, especially in
262:
1584:Journal of the American Chemical Society
1144:NIOSH Pocket Guide to Chemical Hazards.
1092:
786:Sodium thioglycolate is a component of
351:
316:
291:
1302:Suc L, Rigou P, Mouls L (2021-03-17).
1253:Analytical and Bioanalytical Chemistry
1139:
1137:
1135:
1133:
1131:
1129:
1127:
1125:
1123:
1115:NIOSH Pocket Guide to Chemical Hazards
191:
745:into the correct position or to help
323:Key: CWERGRDVMFNCDR-UHFFFAOYSA-N
158:
138:
7:
722:. TGA and its derivatives break the
446:−16 °C (3 °F; 257 K)
1021:(hair protein), while studying why
333:Key: CWERGRDVMFNCDR-UHFFFAOYAP
233:
217:
1488:Journal of Pharmaceutical Sciences
759:. These species have the formula R
14:
1453:10.1111/j.1346-8138.2012.01670.x
1178:from the original on 2022-05-07.
629:
524:
519:
381:
33:
24:
625:(at 25 °C , 100 kPa).
912:The second ionization has a pK
393:
387:
375:
1:
1494:(6). Elsevier BV: 1570–1577.
1435:Okada, K., Okada, E. (2012).
1375:10.1016/j.indcrop.2016.03.014
1363:Industrial Crops and Products
1229:, 2012, Wiley-VCH, Weinheim.
576:(US health exposure limits):
1555:McKetta JJ Jr (1981-01-01).
1165:"What exactly is Mercaptan?"
1522:"What is a fallout remover"
1809:
1500:10.1016/j.xphs.2017.02.017
1441:The Journal of Dermatology
1045:(oral, rat) is 261 mg/kg,
738:to study their structure.
706:TGA is used as a chemical
1414:10.1016/j.lwt.2016.12.034
1265:10.1007/s00216-011-5076-2
873:Thioglycolic acid with a
730:, as is done commonly in
619:
602:TWA 1 ppm (4 mg/m)
570:
500:
495:
362:
342:
307:
78:
58:
46:
41:
32:
23:
1320:10.1021/acs.jafc.0c07163
1235:10.1002/14356007.a16_265
814:obtained by reaction of
416:colorless, clear liquid
1793:Foul-smelling chemicals
1764:volume 39, pp. 996-999.
1723:Cosmet Sci Technol Ser.
485:Magnetic susceptibility
478:10 mmHg (17.8 °C)
1651:Pak. J. Sci. Ind. Res.
1447:(12). Wiley: 996–999.
1071:Ammonium thioglycolate
716:ammonium thioglycolate
426:strong, disagreeable
63:2-Mercaptoacetic acid
61:2-Sulfanylacetic acid
1692:Sigma-Aldrich MSDS.
1618:"Limit Test of Iron"
1192:. 11 September 2014.
1034:Safety and detection
749:penetrate the nail.
718:, which is used for
48:Preferred IUPAC name
1596:10.1021/ja01407a010
1174:. 22 January 2013.
788:thioglycolate broth
747:topical antifungals
463:Solubility in water
408: g·mol
69:Mercaptoacetic acid
52:Sulfanylacetic acid
20:
816:sodium thiosulfate
652:Infobox references
611:(Immediate danger)
19:Thioglycolic acid
18:
1314:(10): 3199–3208.
1171:Independent.co.uk
820:chloroacetic acid
736:condensed tannins
664:Thioglycolic acid
660:Chemical compound
658:
657:
535:Hazard statements
276:CompTox Dashboard
120:Interactive image
71:Thioglycolic acid
1800:
1788:Chelating agents
1745:
1735:
1729:
1719:
1713:
1703:
1697:
1690:
1684:
1679:
1673:
1663:
1657:
1647:
1641:
1638:
1632:
1631:
1629:
1628:
1614:
1608:
1607:
1590:(8): 1916–1920.
1579:
1573:
1572:
1552:
1546:
1543:
1537:
1536:
1534:
1533:
1518:
1512:
1511:
1479:
1473:
1472:
1432:
1426:
1425:
1393:
1387:
1386:
1354:
1348:
1347:
1299:
1293:
1292:
1259:(5): 1559–1569.
1244:
1238:
1223:
1206:
1200:
1194:
1193:
1186:
1180:
1179:
1167:
1160:
1154:
1153:
1141:
1118:
1112:
1106:
1102:, 11th Edition,
1097:
1003:David R. Goddard
672:organic compound
642:
636:
633:
632:
562:Explosive limits
546:
542:
528:
523:
491:−50.0·10 cm/mol
407:
395:
389:
383:
377:
370:Chemical formula
300:
299:
284:
282:
266:
246:
235:
221:
204:
193:
182:
162:
142:
122:
98:
65:Acetyl mercaptan
37:
28:
21:
1808:
1807:
1803:
1802:
1801:
1799:
1798:
1797:
1768:
1767:
1754:
1752:Further reading
1749:
1748:
1736:
1732:
1720:
1716:
1704:
1700:
1691:
1687:
1680:
1676:
1667:J Forensic Sci.
1664:
1660:
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1644:
1639:
1635:
1626:
1624:
1616:
1615:
1611:
1581:
1580:
1576:
1569:
1554:
1553:
1549:
1544:
1540:
1531:
1529:
1520:
1519:
1515:
1481:
1480:
1476:
1434:
1433:
1429:
1395:
1394:
1390:
1356:
1355:
1351:
1301:
1300:
1296:
1246:
1245:
1241:
1224:
1209:
1203:The Merck index
1201:
1197:
1188:
1187:
1183:
1162:
1161:
1157:
1143:
1142:
1121:
1113:
1109:
1098:
1094:
1089:
1081:Thiolactic acid
1067:
1055:
1050:
1043:
1036:
1011:disulfide bonds
999:
971:
969:With metal ions
963:
959:
955:
951:
935:
931:
927:
923:
915:
907:
903:
899:
895:
887:
878:
871:
864:
860:
856:
852:
845:
841:
837:
833:
829:
808:
782:
778:
774:
770:
766:
762:
704:
696:unpleasant odor
692:carboxylic acid
681:
677:
661:
654:
649:
648:
647: ?)
638:
634:
630:
626:
612:
599:
586:
537:
516:
488:
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269:
249:
236:
224:
185:
165:
145:
125:
112:
101:
88:
74:
72:
70:
68:
67:Mercaptoacetate
66:
64:
62:
54:
53:
12:
11:
5:
1806:
1804:
1796:
1795:
1790:
1785:
1780:
1770:
1769:
1766:
1765:
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1714:
1698:
1685:
1674:
1658:
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1567:
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1427:
1388:
1349:
1294:
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1207:
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1107:
1091:
1090:
1088:
1085:
1084:
1083:
1078:
1073:
1066:
1063:
1059:silver nitrate
1053:
1048:
1041:
1035:
1032:
998:
995:
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967:
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961:
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953:
949:
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623:standard state
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547:
541:H301+H311+H331
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474:Vapor pressure
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100:
99:
91:
89:
84:
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76:
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73:Thiovanic acid
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50:
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30:
29:
13:
10:
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1712:104:1062-1069
1711:
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1568:9780824724627
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1526:DetailingWiki
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1254:
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1214:
1212:
1208:
1204:
1199:
1196:
1191:
1185:
1182:
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1173:
1172:
1166:
1159:
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1147:
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1134:
1132:
1130:
1128:
1126:
1124:
1120:
1116:
1111:
1108:
1105:
1101:
1096:
1093:
1086:
1082:
1079:
1077:
1076:Glycolic acid
1074:
1072:
1069:
1068:
1064:
1062:
1060:
1051:
1044:
1033:
1031:
1029:
1024:
1020:
1016:
1012:
1008:
1004:
996:
994:
992:
988:
984:
980:
976:
968:
947:
946:
945:
943:
919:
918:
917:
891:
890:
889:
883:
879:
868:
848:
825:
824:
823:
821:
817:
813:
805:
803:
801:
797:
794:residue from
793:
789:
784:
758:
754:
750:
748:
744:
739:
737:
733:
729:
725:
721:
717:
713:
709:
701:
699:
697:
693:
689:
685:
673:
669:
665:
653:
646:
641:
624:
618:
614:
610:
606:
605:
601:
598:(Recommended)
597:
593:
592:
588:
585:(Permissible)
584:
580:
579:
575:
574:
569:
565:
563:
560:
559:
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553:
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452:Boiling point
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442:Melting point
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1783:Acetic acids
1761:
1759:J. Dermatol.
1758:
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1725:
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1709:
1706:
1701:
1688:
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1636:
1625:. Retrieved
1622:Web Formulas
1621:
1612:
1587:
1583:
1577:
1557:
1550:
1541:
1530:. Retrieved
1528:. 2016-03-17
1525:
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1037:
1017:, including
1000:
972:
939:
911:
872:
809:
785:
751:
743:pincer nails
740:
705:
667:
663:
662:
572:
502:
160:ChEMBL116455
79:Identifiers
59:Other names
15:
1672:31:920-930.
1656:35: 131-132
1408:: 143–150.
1100:Merck Index
882:acetic acid
846:→ Na + NaCl
552:Flash point
413:Appearance
363:Properties
198:100.000.616
140:CHEBI:30065
1772:Categories
1744:3:500-504.
1627:2016-06-14
1532:2016-06-14
1087:References
1061:solution.
1028:depilatory
1001:Scientist
983:molybdenum
956:H + "O" →
812:Bunte salt
806:Production
792:iron oxide
728:depilation
720:permanents
712:salt forms
708:depilatory
514:Pictograms
436:1.32 g/cm
401:Molar mass
354:C(C(=O)O)S
264:7857H94KHM
171:ChemSpider
107:3D model (
86:CAS Number
1739:Analysis.
1604:0002-7863
1422:0023-6438
1383:0926-6690
1369:: 12–15.
1344:232112725
1328:0021-8561
1273:1618-2650
975:complexes
942:disulfide
869:Reactions
861:H + NaHSO
753:Organotin
724:disulfide
688:mercaptan
670:) is the
505:labelling
468:miscible
1728:4:65-79.
1707:Analyst.
1508:28263845
1461:22963208
1336:33657810
1281:21573842
1176:Archived
1152:(NIOSH).
1065:See also
1023:protease
1015:proteins
1007:reducing
916:of 9.3:
900:H → HSCH
853:O → HSCH
496:Hazards
487:(χ)
1469:7413716
1289:4645218
1146:"#0610"
1019:keratin
997:History
888:4.76):
800:Ferrous
732:leather
645:what is
643: (
432:Density
231:PubChem
96:68-11-1
1778:Thiols
1602:
1565:
1506:
1467:
1459:
1420:
1381:
1342:
1334:
1326:
1287:
1279:
1271:
1117:. CDC.
989:, and
987:silver
948:2 HSCH
849:Na + H
834:H + Na
796:wheels
763:Sn(SCH
690:) and
640:verify
637:
347:SMILES
219:C02086
151:ChEMBL
42:Names
1762:2012,
1742:1975,
1726:1985,
1710:1979,
1670:1986,
1654:1992,
1465:S2CID
1340:S2CID
1285:S2CID
928:→ SCH
818:with
684:thiol
615:N.D.
589:none
573:NIOSH
566:5.9%
406:92.11
312:InChI
131:ChEBI
109:JSmol
1600:ISSN
1563:ISBN
1504:PMID
1457:PMID
1418:ISSN
1379:ISSN
1332:PMID
1324:ISSN
1277:PMID
1269:ISSN
1104:9265
1038:The
1009:the
979:iron
920:HSCH
892:HSCH
826:ClCH
702:Uses
674:HSCH
609:IDLH
545:H314
422:Odor
255:UNII
244:1133
210:KEGG
180:1101
1592:doi
1496:doi
1492:106
1449:doi
1410:doi
1402:LWT
1371:doi
1316:doi
1261:doi
1257:401
1231:doi
1013:in
991:tin
960:+ H
936:+ H
908:+ H
884:(pK
757:PVC
668:TGA
596:REL
583:PEL
503:GHS
281:EPA
234:CID
1774::
1620:.
1598:.
1588:49
1586:.
1524:.
1502:.
1490:.
1486:.
1463:.
1455:.
1445:39
1443:.
1439:.
1416:.
1406:78
1404:.
1400:.
1377:.
1367:86
1365:.
1361:.
1338:.
1330:.
1322:.
1312:69
1310:.
1306:.
1283:.
1275:.
1267:.
1255:.
1251:.
1210:^
1168:.
1148:.
1122:^
1054:50
1049:50
1047:LC
1042:50
1040:LD
1030:.
985:,
981:,
952:CO
932:CO
924:CO
904:CO
896:CO
875:pK
857:CO
830:CO
822::
798:.
783:.
777:17
767:CO
678:CO
543:,
507::
1630:.
1606:.
1594::
1571:.
1535:.
1510:.
1498::
1471:.
1451::
1424:.
1412::
1385:.
1373::
1346:.
1318::
1291:.
1263::
1237:.
1233::
964:O
962:2
958:2
954:2
950:2
934:2
930:2
926:2
922:2
914:a
906:2
902:2
898:2
894:2
886:a
877:a
863:4
859:2
855:2
851:2
844:3
842:O
840:2
838:S
836:2
832:2
828:2
781:2
779:)
775:H
773:8
771:C
769:2
765:2
761:2
686:(
680:2
676:2
666:(
635:Y
394:S
391:2
388:O
385:4
382:H
379:2
376:C
283:)
279:(
111:)
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