360:
231:
635:
630:
38:
28:
778:
54:
927:
783:
782:
1180:
Glycolic acid is slightly stronger than acetic acid due to the electron-withdrawing power of the terminal hydroxyl group. The carboxylate group can coordinate to metal ions, forming coordination complexes. Of particular note are the complexes with Pb and Cu which are significantly stronger than
1240:). Commercially, important derivatives include the methyl (CAS# 96-35-5) and ethyl (CAS# 623-50-7) esters which are readily distillable (boiling points 147–149 °C and 158–159 °C, respectively), unlike the parent acid. The butyl ester (b.p. 178–186 °C) is a component of some
781:
1299:
United States
National Library of Medicine "Hydroxyacetic Acid" in TOXNET Hazardous Substances Data Bank (HSDB), citing Gerhartz, W. (exec ed.), Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA13
643:
1654:
Sigel, Astrid; Operschall, Bert P.; Sigel, Helmut (2017). "Chapter 11. Complex
Formation of Lead(II) with Nucleotides and Their Constituents". In Astrid, S.; Helmut, S.; Sigel, R. K. O. (eds.).
610:
1685:
729:
784:
1424:
717:
1770:
1454:) was incorrect, because like many chemists at that time, they used the wrong atomic masses for carbon (6 instead of 12) and for oxygen (8 instead of 16).
1388:
940:
1181:
complexes with other carboxylic acids. This indicates that the hydroxyl group is involved in complex formation, possibly with the loss of its proton.
1563:
1912:
1531:— is consistent with the acid whose amide can be regarded as glycocoll and which therefore obtained from Laurent the name "glycolic acid".)
409:
1439:: 17–43. For their production of glycolic acid, see pp. 34–37. Note: Strecker and Sokolov's empirical formula for glycolic acid (viz,
1310:
799:
1633:
806:
725:
1793:"Bile Acid Sodium Symporter BASS6 Can Transport Glycolate and Is Involved in Photorespiratory Metabolism in Arabidopsis thaliana"
1495:
kommt mit der Säure überein, als deren
Amidverbindung man das Glycocoll betrachten kann, und welche daher von Laurent den Namen
1343:
2244:
1689:
1463:(Socoloff and Strecker, 1851), p. 37. In recognition of Laurent's correct surmise, Strecker and Sokolov named glycolic acid:
2288:
1856:
935:
1905:
1791:
South, Paul F.; Walker, Berkley J.; Cavanagh, Amanda P.; Rolland, Vivien; Badger, Murray; Ort, Donald R. (2017-03-28).
1580:
1604:
374:
792:
2305:
1880:
947:
2342:
37:
591:
1762:
2259:
1898:
1421:
709:
27:
2332:
2249:
721:
679:
317:
226:
1257:
1099:
Glycolic acid can be synthesized in various ways. The predominant approaches use a catalyzed reaction of
338:
168:
1172:
Glycolic acid can also be prepared using an enzymatic biochemical process that may require less energy.
705:
2274:
2239:
634:
567:
1043:(1822–1871) and Russian chemist Nikolai Nikolaevich Sokolov (1826–1877). They produced it by treating
2264:
1385:
238:
2066:
355:
2293:
1267:, much effort has been devoted to suppressing its formation. One process converts glycolate into
1205:
Glycolic acid is a useful intermediate for organic synthesis, in a range of reactions including:
128:
2337:
1711:
629:
2254:
1314:
657:
622:
544:
1364:
2269:
326:
66:
737:
713:
8:
2109:
1625:
523:
188:
94:
359:
230:
148:
104:
1952:
1825:
1792:
883:
1732:
53:
2005:
1990:
1885:
1830:
1812:
1737:
1667:
1576:
1335:
1272:
1194:
1115:
2142:
1995:
1947:
1848:
1820:
1804:
1727:
1719:
1659:
1568:
1253:
1119:
1052:
998:
733:
506:
432:
1597:"Glycolic acid, What is Glycolic acid? About its Science, Chemistry and Structure"
1428:
1392:
1040:
1014:
697:
1244:, being desirable because it is nonvolatile and has good dissolving properties.
290:
2299:
2124:
1985:
1264:
1218:
1214:
918:
901:
689:
557:
1663:
1542:
862:
842:
685:
2326:
2061:
2028:
1957:
1921:
1890:
1816:
1712:"Glycolate and glyoxylate metabolism by isolated peroxisomes or chloroplasts"
1572:
1233:
1230:
1226:
1126:
1108:
1104:
1084:
1044:
701:
537:
495:
485:
219:
2167:
2114:
2104:
2099:
2056:
1962:
1942:
1925:
1834:
1741:
1671:
1658:. Metal Ions in Life Sciences. Vol. 17. de Gruyter. pp. 319–402.
1142:
1100:
1060:
1596:
1083:; also benzoyl glycolic acid). They boiled the ester for days with dilute
805:
2203:
2187:
2172:
2080:
2075:
2070:
2046:
2038:
2013:
1972:
1808:
1283:
Glycolic acid is an irritant to the skin. It occurs in all green plants.
1146:
1138:
1130:
1048:
979:
905:
889:
818:
741:
532:
1723:
1256:. It is recycled by conversion to glycine within the peroxisomes and to
791:
208:
2177:
1934:
1162:
1154:
1134:
1018:
986:
798:
517:
457:
239:
179:
749:
2223:
2182:
2162:
2137:
2119:
2018:
1561:
Karlheinz
Miltenberger (2005). "Hydroxycarboxylic Acids, Aliphatic".
1268:
1206:
1158:
1150:
990:
667:
917:
Except where otherwise noted, data are given for materials in their
2213:
2208:
2154:
2132:
1763:"New protein can increase yields, save farmers millions every year"
1149:-free. Glycolic acid can be isolated from natural sources, such as
909:
764:
265:
199:
1431:("Investigation of some products that arise from hippuric acid"),
1263:
Because photorespiration is a wasteful side reaction in regard to
757:
127:
2218:
2091:
2051:
2023:
1516:
contained in the barium salt — or considered as the acid hydrate
1241:
1222:
1021:
982:
693:
527:
475:
277:
1853:
ICSC:NENG1537 International
Chemical Safety Cards (WHO/IPCS/ILO)
1686:"DuPont Glycolic Acid Leather Dyeing & Tanning Applications"
1422:"Untersuchung einiger aus der Hippursäure entstehenden Producte"
1190:
159:
1013:
The name "glycolic acid" was coined in 1848 by French chemist
500:
100 °C (212 °F; 373 K) Decomposes above 100 °C
1210:
1166:
1056:
1029:
1002:
301:
139:
117:
343:
1237:
1039:
Glycolic acid was first prepared in 1851 by German chemist
256:
1790:
1271:
without using the conventional BASS6 and PLGG1 route; see
1032:
of a hypothetical acid, which he called "glycolic acid" (
1560:
1653:
1087:, thereby obtaining benzoic acid and glycolic acid (
1189:Glycolic acid is used in the textile industry as a
993:products. Glycolic acid is widespread in nature. A
1395:("On aminated acids and the sugar of gelatine "),
663:
2324:
1411:" ("Let us call the latter 'glycolic acid' ...")
671:
289:
1420:Socoloff, Nicolaus and Strecker, Adolph (1851)
1386:"Sur les acides amidés et le sucre de gélatine"
780:
103:
1920:
1564:Ullmann's Encyclopedia of Industrial Chemistry
1125:Other methods, not noticeably in use, include
753:
1906:
1534:
1311:"DuPont Glycolic Acid Technical Information"
1656:Lead: Its Effects on Environment and Health
1079:), which they called "benzoglycolic acid" (
1913:
1899:
745:
383:InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
358:
229:
187:
1824:
1731:
1709:
1556:
1554:
1552:
393:InChI=1/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
325:
1465:"Die in dem Barytsalz enthaltene Säure
1114:It is also prepared by the reaction of
354:
207:
2325:
2245:Clindamycin/adapalene/benzoyl peroxide
1549:
1328:
997:(sometimes spelled "glycollate") is a
823:300 °C (572 °F; 573 K)
220:
1894:
1841:
1760:
1303:
1145:. Some of today's glycolic acids are
490:75 °C (167 °F; 348 K)
386:Key: AEMRFAOFKBGASW-UHFFFAOYSA-N
167:
147:
41:Ball-and-stick model of glycolic acid
1357:
1252:Plants produce glycolic acid during
1200:
1111:of formaldehyde), for its low cost.
1293:
470:White powder or colorless crystals
396:Key: AEMRFAOFKBGASW-UHFFFAOYAR
280:
264:
31:Chemical structure of glycolic acid
13:
1017:(1807–1853). He proposed that the
776:
36:
26:
14:
2354:
1874:
1433:Annalen der Chemie und Pharmacie
1397:Annales de Chimie et de Physique
989:in water. It is used in various
925:
633:
628:
52:
1859:from the original on 2005-09-21
1784:
1773:from the original on 2017-04-07
1761:Gerea, Alexandra (2017-04-03).
1754:
1703:
1678:
1647:
1636:from the original on 2017-08-25
1618:
1607:from the original on 2018-04-12
1589:
1346:from the original on 2020-07-27
1184:
978:) is a colorless, odorless and
921:(at 25 °C , 100 kPa).
1886:Hazardous Substances Data Bank
1457:
1414:
1378:
1122:followed by re-acidification.
1094:
592:Occupational safety and health
1:
2260:Erythromycin/benzoyl peroxide
1480:oder als Säurehydrat gedacht
1286:
1247:
1175:
2250:Clindamycin/benzoyl peroxide
1630:thaipolychemicals.weebly.com
7:
1710:Kisaki, T.; Tolbert, N. E.
1258:tartronic acid semialdehyde
831:or concentration (LD, LC):
22:
10:
2359:
2275:Tretinoin/benzoyl peroxide
2240:Adapalene/benzoyl peroxide
1403:: 110–123. From p. 112: "
1008:
2283:
2265:Erythromycin/isotretinoin
2232:
2196:
2153:
2090:
2037:
2004:
1971:
1933:
1881:Glycolic acid MS Spectrum
1664:10.1515/9783110434330-011
1384:Laurent, Auguste (1848).
1278:
1260:within the chloroplasts.
915:
875:
827:
609:
589:
584:
462:76.05 g/mol
425:
405:
370:
87:
77:
65:
60:
51:
21:
1573:10.1002/14356007.a13_507
680:Precautionary statements
1567:. Weinheim: Wiley-VCH.
1024:—which was then called
851:2040 mg/kg (rat, oral)
562:1.051 kPa (80 °C)
2343:Anti-acne preparations
1225:in the preparation of
849:1950 mg/kg (rat, oral)
787:
82:2-Hydroxyethanoic acid
42:
32:
2255:Clindamycin/tretinoin
1543:U.S. patent 2,152,852
1367:. University of Akron
786:
40:
30:
2270:Sulfacetamide/sulfur
1849:"Glycolic Acid MSDS"
1809:10.1105/tpc.16.00775
1718:. pp. 242–250.
1405:Appelons ce dernier
1365:"Glycolic Acid MSDS"
863:median concentration
769:(fire diamond)
67:Preferred IUPAC name
2333:Alpha hydroxy acids
2110:Cyproterone acetate
1724:10.1104/pp.44.2.242
1063:and glycolic acid (
966:; chemical formula
507:Solubility in water
18:
2310:Never to phase III
1958:Blue light therapy
1953:8-Hydroxyquinoline
1924:-treating agents (
1427:2020-07-27 at the
1391:2020-07-27 at the
1221:. It is used as a
1005:of glycolic acid.
964:hydroxyacetic acid
948:Infobox references
876:Related compounds
871:3.6 ppm (rat, 4h)
788:
520:in other solvents
71:Hydroxyacetic acid
43:
33:
16:
2320:
2319:
2029:Red light therapy
2006:Anti-inflammatory
1273:glycerate pathway
1227:polyglycolic acid
1201:Organic synthesis
1116:chloroacetic acid
983:crystalline solid
956:Chemical compound
954:
953:
897:Related compounds
869:7.7 ppm (rat, 4h)
658:Hazard statements
339:CompTox Dashboard
129:Interactive image
47:
46:
2350:
2143:Ethinylestradiol
1996:Benzoyl peroxide
1948:Benzoyl peroxide
1915:
1908:
1901:
1892:
1891:
1868:
1867:
1865:
1864:
1845:
1839:
1838:
1828:
1788:
1782:
1781:
1779:
1778:
1758:
1752:
1751:
1749:
1748:
1735:
1716:Plant Physiology
1707:
1701:
1700:
1698:
1697:
1688:. Archived from
1682:
1676:
1675:
1651:
1645:
1644:
1642:
1641:
1622:
1616:
1615:
1613:
1612:
1593:
1587:
1586:
1558:
1547:
1545:
1538:
1532:
1530:
1515:
1494:
1479:
1461:
1455:
1453:
1418:
1412:
1407:acide glycolique
1382:
1376:
1375:
1373:
1372:
1361:
1355:
1354:
1352:
1351:
1332:
1326:
1325:
1323:
1322:
1313:. Archived from
1307:
1301:
1297:
1254:photorespiration
1120:sodium hydroxide
1081:Benzoglykolsäure
1078:
1053:nitrogen dioxide
1034:acide glycolique
977:
938:
932:
929:
928:
808:
801:
794:
779:
759:
755:
751:
747:
743:
739:
735:
731:
727:
723:
719:
715:
711:
707:
703:
699:
695:
691:
687:
673:
669:
665:
637:
632:
451:
433:Chemical formula
363:
362:
347:
345:
329:
293:
282:
268:
241:
233:
222:
211:
191:
171:
151:
131:
107:
80:Hydroacetic acid
56:
23:
19:
15:
2358:
2357:
2353:
2352:
2351:
2349:
2348:
2347:
2323:
2322:
2321:
2316:
2315:
2300:Clinical trials
2279:
2228:
2192:
2149:
2086:
2033:
2000:
1967:
1929:
1919:
1877:
1872:
1871:
1862:
1860:
1847:
1846:
1842:
1789:
1785:
1776:
1774:
1759:
1755:
1746:
1744:
1708:
1704:
1695:
1693:
1684:
1683:
1679:
1652:
1648:
1639:
1637:
1626:"Glycolic acid"
1624:
1623:
1619:
1610:
1608:
1595:
1594:
1590:
1583:
1559:
1550:
1541:
1539:
1535:
1529:
1525:
1521:
1517:
1514:
1510:
1506:
1502:
1493:
1489:
1485:
1481:
1478:
1474:
1470:
1466:
1462:
1458:
1452:
1448:
1444:
1440:
1429:Wayback Machine
1419:
1415:
1393:Wayback Machine
1383:
1379:
1370:
1368:
1363:
1362:
1358:
1349:
1347:
1340:www.chemsrc.com
1336:"Glycolic acid"
1334:
1333:
1329:
1320:
1318:
1309:
1308:
1304:
1298:
1294:
1289:
1281:
1250:
1217:and long chain
1203:
1187:
1178:
1097:
1076:
1072:
1068:
1064:
1041:Adolph Strecker
1015:Auguste Laurent
1011:
975:
971:
967:
957:
950:
945:
944:
943: ?)
934:
930:
926:
922:
908:
904:
898:
886:
884:α-hydroxy acids
870:
866:
860:
850:
846:
840:
813:
812:
811:
810:
803:
796:
789:
785:
777:
682:
660:
646:
625:
602:
576:
536:
531:
509:
450:
446:
442:
438:
435:
421:
418:
413:
412:
401:
398:
397:
394:
388:
387:
384:
378:
377:
366:
348:
341:
332:
312:
296:
283:
271:
251:
214:
194:
174:
154:
134:
121:
110:
97:
83:
81:
73:
72:
12:
11:
5:
2356:
2346:
2345:
2340:
2335:
2318:
2317:
2314:
2313:
2312:
2311:
2308:
2297:
2291:
2285:
2284:
2281:
2280:
2278:
2277:
2272:
2267:
2262:
2257:
2252:
2247:
2242:
2236:
2234:
2230:
2229:
2227:
2226:
2221:
2216:
2211:
2206:
2200:
2198:
2194:
2193:
2191:
2190:
2185:
2180:
2175:
2170:
2165:
2159:
2157:
2151:
2150:
2148:
2147:
2146:
2145:
2140:
2130:
2129:
2128:
2125:Spironolactone
2122:
2117:
2112:
2107:
2096:
2094:
2088:
2087:
2085:
2084:
2078:
2073:
2064:
2059:
2054:
2049:
2043:
2041:
2035:
2034:
2032:
2031:
2026:
2021:
2016:
2010:
2008:
2002:
2001:
1999:
1998:
1993:
1988:
1986:Salicylic acid
1983:
1977:
1975:
1969:
1968:
1966:
1965:
1960:
1955:
1950:
1945:
1939:
1937:
1931:
1930:
1918:
1917:
1910:
1903:
1895:
1889:
1888:
1883:
1876:
1875:External links
1873:
1870:
1869:
1840:
1803:(4): 808–823.
1797:The Plant Cell
1783:
1753:
1702:
1677:
1646:
1617:
1601:www.3dchem.com
1588:
1582:978-3527306732
1581:
1548:
1533:
1527:
1523:
1519:
1512:
1508:
1504:
1499:erhalten hat."
1491:
1487:
1483:
1476:
1472:
1468:
1456:
1450:
1446:
1442:
1413:
1399:, 3rd series,
1377:
1356:
1327:
1302:
1291:
1290:
1288:
1285:
1280:
1277:
1265:photosynthesis
1249:
1246:
1219:polymerization
1215:esterification
1202:
1199:
1186:
1183:
1177:
1174:
1096:
1093:
1074:
1070:
1066:
1028:—might be the
1010:
1007:
973:
969:
955:
952:
951:
946:
924:
923:
919:standard state
916:
913:
912:
902:Glycolaldehyde
899:
896:
893:
892:
887:
881:
878:
877:
873:
872:
867:
858:
856:
853:
852:
847:
838:
836:
833:
832:
825:
824:
821:
815:
814:
804:
797:
790:
775:
774:
773:
772:
770:
761:
760:
730:P305+P351+P338
718:P303+P361+P353
714:P301+P330+P331
683:
678:
675:
674:
661:
656:
653:
652:
647:
642:
639:
638:
626:
621:
618:
617:
607:
606:
603:
600:
597:
596:
587:
586:
582:
581:
578:
574:
564:
563:
560:
558:Vapor pressure
554:
553:
550:
541:
540:
521:
514:
513:
510:
505:
502:
501:
498:
492:
491:
488:
482:
481:
478:
472:
471:
468:
464:
463:
460:
454:
453:
448:
444:
440:
436:
431:
428:
427:
423:
422:
420:
419:
416:
408:
407:
406:
403:
402:
400:
399:
395:
392:
391:
389:
385:
382:
381:
373:
372:
371:
368:
367:
365:
364:
351:
349:
337:
334:
333:
331:
330:
322:
320:
314:
313:
311:
310:
306:
304:
298:
297:
295:
294:
286:
284:
276:
273:
272:
270:
269:
261:
259:
253:
252:
250:
249:
245:
243:
235:
234:
224:
216:
215:
213:
212:
204:
202:
196:
195:
193:
192:
184:
182:
176:
175:
173:
172:
164:
162:
156:
155:
153:
152:
144:
142:
136:
135:
133:
132:
124:
122:
115:
112:
111:
109:
108:
100:
98:
93:
90:
89:
85:
84:
79:
75:
74:
70:
69:
63:
62:
58:
57:
49:
48:
45:
44:
34:
17:Glycolic acid
9:
6:
4:
3:
2:
2355:
2344:
2341:
2339:
2338:Preservatives
2336:
2334:
2331:
2330:
2328:
2309:
2307:
2304:
2303:
2301:
2298:
2295:
2292:
2290:
2287:
2286:
2282:
2276:
2273:
2271:
2268:
2266:
2263:
2261:
2258:
2256:
2253:
2251:
2248:
2246:
2243:
2241:
2238:
2237:
2235:
2231:
2225:
2222:
2220:
2217:
2215:
2212:
2210:
2207:
2205:
2202:
2201:
2199:
2195:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2160:
2158:
2156:
2152:
2144:
2141:
2139:
2136:
2135:
2134:
2131:
2126:
2123:
2121:
2118:
2116:
2113:
2111:
2108:
2106:
2103:
2102:
2101:
2100:Antiandrogens
2098:
2097:
2095:
2093:
2089:
2082:
2079:
2077:
2074:
2072:
2068:
2067:Tetracyclines
2065:
2063:
2062:Sulfacetamide
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2044:
2042:
2040:
2036:
2030:
2027:
2025:
2022:
2020:
2017:
2015:
2012:
2011:
2009:
2007:
2003:
1997:
1994:
1992:
1989:
1987:
1984:
1982:
1981:Glycolic acid
1979:
1978:
1976:
1974:
1970:
1964:
1961:
1959:
1956:
1954:
1951:
1949:
1946:
1944:
1941:
1940:
1938:
1936:
1935:Antibacterial
1932:
1927:
1923:
1916:
1911:
1909:
1904:
1902:
1897:
1896:
1893:
1887:
1884:
1882:
1879:
1878:
1858:
1855:. CDC/NIOSH.
1854:
1850:
1844:
1836:
1832:
1827:
1822:
1818:
1814:
1810:
1806:
1802:
1798:
1794:
1787:
1772:
1768:
1764:
1757:
1743:
1739:
1734:
1729:
1725:
1721:
1717:
1713:
1706:
1692:on 2013-05-22
1691:
1687:
1681:
1673:
1669:
1665:
1661:
1657:
1650:
1635:
1631:
1627:
1621:
1606:
1602:
1598:
1592:
1584:
1578:
1574:
1570:
1566:
1565:
1557:
1555:
1553:
1544:
1537:
1500:
1496:
1460:
1438:
1434:
1430:
1426:
1423:
1417:
1410:
1406:
1402:
1398:
1394:
1390:
1387:
1381:
1366:
1360:
1345:
1341:
1337:
1331:
1317:on 2006-07-14
1316:
1312:
1306:
1296:
1292:
1284:
1276:
1274:
1270:
1266:
1261:
1259:
1255:
1245:
1243:
1239:
1235:
1232:
1231:biocompatible
1228:
1224:
1220:
1216:
1212:
1208:
1198:
1196:
1192:
1182:
1173:
1170:
1168:
1164:
1160:
1156:
1152:
1148:
1144:
1141:derived from
1140:
1136:
1132:
1128:
1127:hydrogenation
1123:
1121:
1117:
1112:
1110:
1109:carbonylation
1106:
1105:synthesis gas
1102:
1092:
1090:
1086:
1085:sulfuric acid
1082:
1062:
1058:
1054:
1050:
1046:
1045:hippuric acid
1042:
1037:
1035:
1031:
1027:
1023:
1020:
1016:
1006:
1004:
1000:
996:
992:
988:
984:
981:
965:
961:
960:Glycolic acid
949:
942:
937:
920:
914:
911:
907:
903:
900:
895:
894:
891:
888:
885:
880:
879:
874:
868:
864:
855:
854:
848:
844:
835:
834:
830:
826:
822:
820:
817:
816:
809:
802:
795:
771:
768:
767:
763:
762:
684:
681:
677:
676:
662:
659:
655:
654:
651:
648:
645:
641:
640:
636:
631:
627:
624:
620:
619:
615:
613:
608:
604:
599:
598:
594:
593:
588:
583:
579:
573:
569:
566:
565:
561:
559:
556:
555:
551:
549:
548:
543:
542:
539:
538:ethyl acetate
534:
529:
525:
522:
519:
516:
515:
512:70% solution
511:
508:
504:
503:
499:
497:
496:Boiling point
494:
493:
489:
487:
486:Melting point
484:
483:
479:
477:
474:
473:
469:
466:
465:
461:
459:
456:
455:
437:
434:
430:
429:
424:
415:
414:
411:
404:
390:
380:
379:
376:
369:
361:
357:
356:DTXSID0025363
353:
352:
350:
340:
336:
335:
328:
324:
323:
321:
319:
316:
315:
308:
307:
305:
303:
300:
299:
292:
288:
287:
285:
279:
275:
274:
267:
263:
262:
260:
258:
255:
254:
247:
246:
244:
242:
237:
236:
232:
228:
225:
223:
221:ECHA InfoCard
218:
217:
210:
206:
205:
203:
201:
198:
197:
190:
186:
185:
183:
181:
178:
177:
170:
166:
165:
163:
161:
158:
157:
150:
146:
145:
143:
141:
138:
137:
130:
126:
125:
123:
119:
114:
113:
106:
102:
101:
99:
96:
92:
91:
86:
76:
68:
64:
59:
55:
50:
39:
35:
29:
25:
24:
20:
2233:Combinations
2168:Isotretinoin
2115:Drospirenone
2105:Bicalutamide
2057:Erythromycin
1980:
1963:Tea tree oil
1943:Azelaic acid
1861:. Retrieved
1852:
1843:
1800:
1796:
1786:
1775:. Retrieved
1766:
1756:
1745:. Retrieved
1715:
1705:
1694:. Retrieved
1690:the original
1680:
1655:
1649:
1638:. Retrieved
1629:
1620:
1609:. Retrieved
1600:
1591:
1562:
1540:D.J. Loder,
1536:
1498:
1464:
1459:
1436:
1432:
1416:
1408:
1404:
1400:
1396:
1380:
1369:. Retrieved
1359:
1348:. Retrieved
1339:
1330:
1319:. Retrieved
1315:the original
1305:
1295:
1282:
1262:
1251:
1204:
1188:
1185:Applications
1179:
1171:
1143:formaldehyde
1124:
1113:
1101:formaldehyde
1098:
1088:
1080:
1061:benzoic acid
1038:
1033:
1025:
1012:
994:
963:
959:
958:
828:
765:
649:
611:
601:Main hazards
590:
571:
546:
302:RTECS number
169:ChEMBL252557
88:Identifiers
78:Other names
2296:from market
2204:Epristeride
2188:Trifarotene
2173:Motretinide
2081:Doxycycline
2076:Minocycline
2071:Lymecycline
2047:Clindamycin
2039:Antibiotics
2014:Niacinamide
1973:Keratolytic
1767:ZME Science
1497:Glycolsäure
1165:and unripe
1155:sugar beets
1147:formic acid
1139:cyanohydrin
1131:oxalic acid
1095:Preparation
1089:Glykolsäure
1055:to form an
1049:nitric acid
980:hygroscopic
906:Acetic acid
890:Lactic acid
843:median dose
829:Lethal dose
819:Flash point
644:Signal word
595:(OHS/OSH):
533:acetic acid
467:Appearance
426:Properties
227:100.001.073
149:CHEBI:17497
2327:Categories
2178:Tazarotene
1863:2006-06-08
1777:2017-04-06
1747:2023-08-24
1696:2013-04-11
1640:2017-05-02
1611:2018-04-11
1501:(The acid
1371:2006-09-18
1350:2018-05-16
1321:2006-07-06
1287:References
1248:Occurrence
1234:copolymers
1229:and other
1176:Properties
1163:cantaloupe
1135:hydrolysis
1026:glycocolle
1019:amino acid
623:Pictograms
605:Corrosive
518:Solubility
480:1.49 g/cm
458:Molar mass
327:0WT12SX38S
180:ChemSpider
116:3D model (
95:CAS Number
2306:Phase III
2294:Withdrawn
2224:Tioxolone
2183:Tretinoin
2163:Adapalene
2155:Retinoids
2138:Estradiol
2133:Estrogens
2120:Flutamide
2019:Ibuprofen
1817:1532-298X
1269:glycerate
1242:varnishes
1211:reduction
1207:oxidation
1159:pineapple
1151:sugarcane
995:glycolate
991:skin-care
985:, highly
726:P304+P340
722:P304+P312
710:P301+P312
614:labelling
309:MC5250000
248:201-180-5
240:EC Number
2214:Pelretin
2209:Mesulfen
2092:Hormonal
1857:Archived
1835:28351992
1771:Archived
1742:16657053
1672:28731304
1634:Archived
1605:Archived
1425:Archived
1389:Archived
1344:Archived
1197:agent.
1073:C(=O)OCH
910:Glycerol
882:Related
766:NFPA 704
585:Hazards
524:Alcohols
417:OC(=O)CO
200:DrugBank
2219:Stridex
2052:Dapsone
2024:Aspirin
1826:5435425
1546:(1939).
1223:monomer
1195:tanning
1137:of the
1022:glycine
1009:History
987:soluble
941:what is
939: (
568:Acidity
528:acetone
476:Density
452:
278:PubChem
209:DB03085
105:79-14-1
2289:WHO-EM
1991:Sulfur
1833:
1823:
1815:
1740:
1733:396069
1730:
1670:
1579:
1279:Safety
1236:(e.g.
1191:dyeing
1167:grapes
1133:, and
936:verify
933:
650:Danger
552:−1.05
410:SMILES
266:C00160
160:ChEMBL
61:Names
2197:Other
1118:with
1103:with
1057:ester
1047:with
1030:amine
1003:ester
580:3.83
375:InChI
140:ChEBI
118:JSmol
1922:Acne
1831:PMID
1813:ISSN
1738:PMID
1668:PMID
1577:ISBN
1409:...
1300:509.
1238:PLGA
1193:and
1077:COOH
1051:and
1036:).
999:salt
968:HOCH
962:(or
758:P501
754:P405
750:P363
746:P330
742:P321
738:P312
734:P310
706:P280
702:P271
698:P270
694:P264
690:P261
686:P260
672:H332
668:H314
664:H302
545:log
318:UNII
257:KEGG
1926:D10
1821:PMC
1805:doi
1728:PMC
1720:doi
1660:doi
1569:doi
1129:of
1091:).
1059:of
1001:or
612:GHS
535:and
344:EPA
291:757
281:CID
189:737
2329::
2302::
1851:.
1829:.
1819:.
1811:.
1801:29
1799:.
1795:.
1769:.
1765:.
1736:.
1726:.
1714:.
1666:.
1632:.
1628:.
1603:.
1599:.
1575:.
1551:^
1437:80
1435:,
1401:23
1342:.
1338:.
1275:.
1213:,
1169:.
1161:,
1157:,
1153:,
972:CO
859:50
857:LC
839:50
837:LD
756:,
752:,
748:,
744:,
740:,
736:,
732:,
728:,
724:,
720:,
716:,
712:,
708:,
704:,
700:,
696:,
692:,
688:,
670:,
666:,
616::
577:)
570:(p
526:,
2127:)
2083:)
2069:(
1928:)
1914:e
1907:t
1900:v
1866:.
1837:.
1807::
1780:.
1750:.
1722::
1699:.
1674:.
1662::
1643:.
1614:.
1585:.
1571::
1528:6
1526:O
1524:4
1522:H
1520:4
1518:C
1513:5
1511:O
1509:3
1507:H
1505:4
1503:C
1492:6
1490:O
1488:4
1486:H
1484:4
1482:C
1477:5
1475:O
1473:3
1471:H
1469:4
1467:C
1451:6
1449:O
1447:4
1445:H
1443:4
1441:C
1374:.
1353:.
1324:.
1209:-
1107:(
1075:2
1071:5
1069:H
1067:6
1065:C
976:H
974:2
970:2
931:N
865:)
861:(
845:)
841:(
807:1
800:1
793:3
575:a
572:K
547:P
530:,
449:3
447:O
445:4
443:H
441:2
439:C
346:)
342:(
120:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
