31:
640:) the proton on the alpha carbon and the proton trapped in the internal hydrogen bridge show a nice pair of doublets instead a singlet (H on alpha-C) and the formentioned broad signal of exchangable protons. So on the NMR-time scale the exchange equilibrium for the alpha-hydroxy group is frozen.
236:
of α-halocarboxylic acids, readily available precursors, to produce 2-hydroxycarboxylic acids. For instance, the production of glycolic acid typically follows this method, utilizing a base-induced reaction, followed by acid workup. Similarly, unsaturated acids and
538:
Kempers S, Katz HI, Wildnauer R, Green B (June 1998). "An evaluation of the effect of an alpha hydroxy acid-blend skin cream in the cosmetic improvement of symptoms of moderate to severe xerosis, epidermolytic hyperkeratosis, and ichthyosis".
1266:
Curson, Andrew R. J.; Liu, Ji; Bermejo Martínez, Ana; Green, Robert T.; Chan, Yohan; Carrión, Ornella; Williams, Beth T.; Zhang, Sheng-Hui; Yang, Gui-Peng; Bulman Page, Philip C.; Zhang, Xiao-Hua; Todd, Jonathan D. (2017).
100:. AHAs serve a dual purpose; industrially, they are utilized as additives in animal feed and as precursors for polymer synthesis. In cosmetics, they are commonly used for their ability to chemically exfoliate the skin and
813:
Herold, B. C.; Scordi-Bello, I.; Cheshenko, N.; Marcellino, D.; Dzuzelewski, M.; Francois, F.; Morin, R.; Casullo, V. Mas; Anderson, R. A.; Chany, C.; Waller, D. P.; Zaneveld, L. J. D.; Klotman, M. E. (2002-11-15).
415:
Alpha hydroxy acids are generally safe when used on the skin as a cosmetic agent using the recommended dosage. The most common side-effects are mild skin irritations, redness and flaking. The United States
899:
Chang, Theresa L.; Teleshova, Natalia; Rapista, Aprille; Paluch, Maciej; Anderson, Robert A.; Waller, Donald P.; Zaneveld, Lourens J.D.; Granelli-Piperno, Angela; Klotman, Mary E. (2007-10-02).
636:-spectrum of these compounds: instead of giving rise to a contribution to the broad signal of rapidly exchanged protons (between COOH, OH, NH, etc) in 2-phenyl-2-hydroxyacetic acid (
148:(PGA), a polymer distinguished by its high crystallinity, thermal stability, and mechanical strength, despite its synthetic origins. Both PLA and PGA are fully biodegradable.
576:
1192:
761:
Samantaray, Paresh Kumar; Little, Alastair; Haddleton, David M.; McNally, Tony; Tan, Bowen; Sun, Zhaoyang; Huang, Weijie; Ji, Yang; Wan, Chaoying (2020).
431:
The FDA has warned consumers that care should be taken when using alpha hydroxy acids after an industry-sponsored study found that they can increase the
1099:
Nwaukwa S, Keehn P (1982). "Oxidative cleavage of α-diols, α-diones, α-hydroxy-ketones and α-hydroxy- and α-keto acids with calcium hypochlorite ".
816:"Mandelic Acid Condensation Polymer: Novel Candidate Microbicide for Prevention of Human Immunodeficiency Virus and Herpes Simplex Virus Entry"
1251:
1221:
736:
396:
182:
1135:
1050:
1017:
1168:
633:
593:
176:
763:"Poly(glycolic acid) (PGA): a versatile building block expanding high performance and sustainable bioplastic applications"
1340:
1335:
417:
164:
30:
424:
expert panels both suggest that alpha hydroxy acids are safe to use as long as they are sold at low concentrations,
421:
400:
209:, playing a role in the industrial-scale preparation of various compounds. These acids are used when synthesizing
1269:"Dimethylsulfoniopropionate biosynthesis in marine bacteria and identification of the key gene in this process"
1320:
517:
Kalla G, Garg A, Kachhawa D (2001). "Chemical peeling--glycolic acid versus trichloroacetic acid in melasma".
250:
205:α-Hydroxy acids, such as glycolic acid, lactic acid, citric acid, and mandelic acid, serve as precursors in
1241:
1211:
881:
716:
318:
133:
471:
Atzori L, Brundu MA, Orru A, Biggio P (March 1999). "Glycolic acid peeling in the treatment of acne".
168:
1130:. Coxon, J. M. (James Morriss), 1941- (3rd. ed.). London: Blackie Academic & Professional.
435:
This effect is reversible after stopping the use of alpha hydroxy acids. Other sources suggest that
1268:
958:"Relative effectiveness of methionine hydroxy analog compared to DL-methionine in broiler chickens"
453:
365:
172:
655:"A Perspective on Polylactic Acid-Based Polymers Use for Nanoparticles Synthesis and Applications"
1299:
1186:
790:
496:
458:
214:
62:
901:"SAMMA, a mandelic acid condensation polymer, inhibits dendritic cell-mediated HIV transmission"
1291:
1247:
1217:
1174:
1164:
1141:
1131:
1046:
1013:
979:
938:
920:
853:
835:
782:
732:
694:
676:
589:
548:
526:
488:
448:
284:
206:
1283:
1108:
1079:
1038:
1005:
969:
928:
912:
843:
827:
774:
724:
684:
666:
581:
480:
432:
404:
280:
137:
129:
97:
66:
50:
222:
218:
186:
121:
163:. Early laboratory work performed in 2002 and 2007 against notable pathogens such as the
933:
900:
831:
728:
689:
654:
484:
1112:
848:
815:
1329:
794:
637:
436:
160:
156:
152:
145:
141:
82:
74:
61:
carbon atom away from the acid group. This structural aspect distinguishes them from
54:
1303:
500:
364:
Additionally, α-keto aldehydes can be transformed into α-hydroxy acids through the
254:
93:
17:
916:
96:
compared to their non-alpha hydroxy counterparts, a property enhanced by internal
653:
Casalini, Tommaso; Rossi, Filippo; Castrovinci, Andrea; Perale, Giuseppe (2019).
1237:
1207:
288:
194:
117:
101:
86:
78:
715:
Storti, G.; Lattuada, M. (2017-01-01). Perale, Giuseppe; Hilborn, Jöns (eds.).
1287:
1178:
246:
233:
190:
1042:
1009:
924:
839:
786:
680:
671:
585:
1145:
623:
Handbook of
Chemistry and Physics, CRC Press, 58th edition, page D147 (1977)
210:
1295:
983:
942:
857:
698:
530:
492:
144:
serves as a foundation for the development of poly(glycolic acid), spelled
974:
957:
552:
238:
113:
778:
762:
279:
Another synthetic pathway for α-hydroxy acids involves the addition of
242:
125:
574:
Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic".
1084:
1067:
226:
1033:
Ritzer E, Sundermann R (2000). "Hydroxycarboxylic Acids, Aromatic".
1321:
428:
levels greater than 3.5, and include thorough safety instructions.
717:"8 - Synthesis of bioresorbable polymers for medical applications"
317:
Furthermore, specialized synthetic routes include the reaction of
29:
1243:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
1213:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
632:
The strength of the hydrogen bonding is refelected also in the
473:
Journal of the
European Academy of Dermatology and Venereology
128:, are used in the creation of biodegradable materials such as
1000:
Miltenberger K (2000). "Hydroxycarboxylic Acids, Aliphatic".
1246:(6th ed.), New York: Wiley-Interscience, p. 1864,
880:
Nutrition, Center for Food Safety and
Applied (2022-11-22).
1216:(6th ed.), New York: Wiley-Interscience, p. 813,
425:
217:. α-Hydroxy acids are particularly prone to acid-catalyzed
185:, alpha hydroxy carboxylic acid, is used commercially in a
1068:"Oxidation of some α-hydroxy-acids with lead tetraacetate"
321:
carboxylic acids with oxygen, followed by aqueous workup.
956:
Lemme, A.; Hoehler, D.; Brennan, JJ; Mannion, PF (2002).
519:
Indian
Journal of Dermatology, Venereology and Leprology
171:(HSV) suggest SAMMA warrants further investigation as a
721:Bioresorbable Polymers for Biomedical Applications
159:produces 'SAMMA', obtained via condensation with
155:, another alpha hydroxy acid, when combined with
34:Structural formulae of α-, β- and γ-hydroxy acids
1035:Ullmann's Encyclopedia of Industrial Chemistry
1002:Ullmann's Encyclopedia of Industrial Chemistry
577:Ullmann's Encyclopedia of Industrial Chemistry
439:, in particular, may protect from sun damage.
659:Frontiers in Bioengineering and Biotechnology
8:
1191:: CS1 maint: location missing publisher (
995:
993:
399:is an intermediate in the biosynthesis of
1083:
1072:Bulletin of the Chemical Society of Japan
973:
932:
847:
688:
670:
283:to ketones or aldehydes, followed by the
1161:Organic chemistry:structure and function
383:
356:
352:
348:
339:
335:
331:
327:
310:
306:
302:
271:
267:
263:
232:One common synthesis route involves the
566:
229:or aldehyde, and water as by-products.
1184:
1159:Vollhardt KP, Schore NE (2018-01-29).
508:"Alpha Hydroxy Acids for Skin Care".
7:
875:
873:
871:
869:
867:
808:
806:
804:
756:
754:
710:
708:
648:
646:
397:2-Hydroxy-4-(methylthio)butyric acid
183:2-Hydroxy-4-(methylthio)butyric acid
73:carbon atoms. Notable AHAs include
832:10.1128/JVI.76.22.11236-11244.2002
729:10.1016/b978-0-08-100262-9.00008-2
485:10.1111/j.1468-3083.1999.tb01000.x
245:esters undergo hydration to yield
25:
634:Proton nuclear magnetic resonance
112:The synthesis and utilization of
723:. Woodhead Publishing: 153–179.
510:Cosmetic Dermatology, Supplement
1128:Principles of organic synthesis
609:Dawson RM, et al. (1959).
373:R−C(O)CHO + 2OH → R−CH(OH)CO
296:R−CHO + HCN → R−CH(OH)CN
177:sexually-transmitted infection
39:Alpha hydroxy carboxylic acids
1:
1113:10.1016/S0040-4039(00)88578-0
917:10.1016/j.febslet.2007.08.048
611:Data for Biochemical Research
249:derivatives from esters, and
418:Food and Drug Administration
401:3-dimethylsulfoniopropionate
165:human immunodeficiency virus
124:(PLA) and its cyclic ester
27:Class of chemical compounds
1357:
1163:(8th ed.). New York.
613:. Oxford: Clarendon Press.
422:Cosmetic Ingredient Review
43:α-hydroxy carboxylic acids
1288:10.1038/nmicrobiol.2017.9
1043:10.1002/14356007.a13_519
1010:10.1002/14356007.a13_507
672:10.3389/fbioe.2019.00259
586:10.1002/14356007.a13_507
580:. Weinheim: Wiley-VCH.
433:likelihood of sunburns.
403:, precursor to natural
251:3-hydroxypropionic acid
201:Synthesis and reactions
35:
882:"Alpha Hydroxy Acids"
355:Li + H → R−CH(OH)CO
134:drug delivery systems
33:
1126:Chandler NR (1993).
512:: 1–6. October 1994.
169:herpes simplex virus
92:α-Hydroxy acids are
1341:Cosmetics chemicals
1336:Alpha hydroxy acids
1276:Nature Microbiology
1236:Smith, Michael B.;
1206:Smith, Michael B.;
1101:Tetrahedron Letters
975:10.1093/ps/81.6.838
826:(22): 11236–11244.
820:Journal of Virology
454:Hydroxybutyric acid
366:Cannizzaro reaction
175:to prevent vaginal
173:topical microbicide
18:Alpha hydroxy acids
779:10.1039/D0GC01394C
459:Omega hydroxy acid
305:O → R−CH(OH)CO
270:O → R−CH(OH)CO
215:oxidative cleavage
189:to substitute for
63:beta hydroxy acids
49:), are a group of
36:
1253:978-0-471-72091-1
1223:978-0-471-72091-1
1107:(31): 3135–3138.
911:(24): 4596–4602.
773:(13): 4055–4081.
738:978-0-08-100262-9
449:Beta hydroxy acid
301:R−CH(OH)CN + 2H
285:acidic hydrolysis
207:organic synthesis
69:are separated by
67:functional groups
16:(Redirected from
1348:
1308:
1307:
1273:
1263:
1257:
1256:
1233:
1227:
1226:
1203:
1197:
1196:
1190:
1182:
1156:
1150:
1149:
1123:
1117:
1116:
1096:
1090:
1089:
1087:
1085:10.1246/bcsj.9.8
1063:
1057:
1056:
1030:
1024:
1023:
997:
988:
987:
977:
953:
947:
946:
936:
896:
890:
889:
877:
862:
861:
851:
810:
799:
798:
758:
749:
748:
746:
745:
712:
703:
702:
692:
674:
650:
641:
630:
624:
621:
615:
614:
606:
600:
599:
571:
556:
534:
513:
504:
405:dimethyl sulfide
387:
381:
380:
377:
360:
343:
313:
297:
281:hydrogen cyanide
275:
130:medical implants
98:hydrogen bonding
51:carboxylic acids
21:
1356:
1355:
1351:
1350:
1349:
1347:
1346:
1345:
1326:
1325:
1317:
1312:
1311:
1271:
1265:
1264:
1260:
1254:
1235:
1234:
1230:
1224:
1205:
1204:
1200:
1183:
1171:
1158:
1157:
1153:
1138:
1125:
1124:
1120:
1098:
1097:
1093:
1066:Ôeda H (1934).
1065:
1064:
1060:
1053:
1032:
1031:
1027:
1020:
999:
998:
991:
962:Poultry Science
955:
954:
950:
898:
897:
893:
879:
878:
865:
812:
811:
802:
767:Green Chemistry
760:
759:
752:
743:
741:
739:
714:
713:
706:
652:
651:
644:
631:
627:
622:
618:
608:
607:
603:
596:
573:
572:
568:
563:
537:
516:
507:
470:
467:
465:Further reading
445:
413:
394:
385:
378:
375:
374:
372:
358:
354:
350:
346:
341:
337:
333:
329:
325:
312:
308:
304:
300:
295:
273:
269:
265:
261:
223:carbon monoxide
219:decarbonylation
203:
187:racemic mixture
122:polylactic acid
110:
28:
23:
22:
15:
12:
11:
5:
1354:
1352:
1344:
1343:
1338:
1328:
1327:
1324:
1323:
1316:
1315:External links
1313:
1310:
1309:
1258:
1252:
1228:
1222:
1198:
1169:
1151:
1137:978-0751401264
1136:
1118:
1091:
1058:
1052:978-3527306732
1051:
1025:
1019:978-3527306732
1018:
989:
968:(6): 838–845.
948:
891:
863:
800:
750:
737:
704:
642:
625:
616:
601:
594:
565:
564:
562:
559:
558:
557:
535:
514:
505:
466:
463:
462:
461:
456:
451:
444:
441:
412:
409:
393:
390:
389:
388:
362:
361:
344:
315:
314:
298:
291:intermediate.
277:
276:
202:
199:
179:transmission.
167:(HIV) and the
109:
106:
94:stronger acids
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1353:
1342:
1339:
1337:
1334:
1333:
1331:
1322:
1319:
1318:
1314:
1305:
1301:
1297:
1293:
1289:
1285:
1281:
1277:
1270:
1262:
1259:
1255:
1249:
1245:
1244:
1239:
1232:
1229:
1225:
1219:
1215:
1214:
1209:
1202:
1199:
1194:
1188:
1180:
1176:
1172:
1170:9781319079451
1166:
1162:
1155:
1152:
1147:
1143:
1139:
1133:
1129:
1122:
1119:
1114:
1110:
1106:
1102:
1095:
1092:
1086:
1081:
1077:
1073:
1069:
1062:
1059:
1054:
1048:
1044:
1040:
1036:
1029:
1026:
1021:
1015:
1011:
1007:
1003:
996:
994:
990:
985:
981:
976:
971:
967:
963:
959:
952:
949:
944:
940:
935:
930:
926:
922:
918:
914:
910:
906:
902:
895:
892:
887:
883:
876:
874:
872:
870:
868:
864:
859:
855:
850:
845:
841:
837:
833:
829:
825:
821:
817:
809:
807:
805:
801:
796:
792:
788:
784:
780:
776:
772:
768:
764:
757:
755:
751:
740:
734:
730:
726:
722:
718:
711:
709:
705:
700:
696:
691:
686:
682:
678:
673:
668:
664:
660:
656:
649:
647:
643:
639:
638:mandelic acid
635:
629:
626:
620:
617:
612:
605:
602:
597:
591:
587:
583:
579:
578:
570:
567:
560:
554:
550:
547:(6): 347–50.
546:
542:
536:
532:
528:
524:
520:
515:
511:
506:
502:
498:
494:
490:
486:
482:
479:(2): 119–22.
478:
474:
469:
468:
464:
460:
457:
455:
452:
450:
447:
446:
442:
440:
438:
437:glycolic acid
434:
429:
427:
423:
419:
410:
408:
406:
402:
398:
391:
371:
370:
369:
367:
359:H + 2Li + ...
345:
324:
323:
322:
320:
299:
294:
293:
292:
290:
286:
282:
260:
259:
258:
256:
252:
248:
244:
240:
235:
230:
228:
224:
220:
216:
212:
208:
200:
198:
196:
192:
188:
184:
180:
178:
174:
170:
166:
162:
161:sulfuric acid
158:
157:sulfuric acid
154:
153:mandelic acid
151:Furthermore,
149:
147:
146:polyglycolide
143:
142:glycolic acid
140:. Similarly,
139:
135:
131:
127:
123:
119:
115:
107:
105:
103:
99:
95:
90:
88:
84:
83:mandelic acid
80:
76:
75:glycolic acid
72:
68:
64:
60:
56:
55:hydroxy group
52:
48:
44:
40:
32:
19:
1282:(5): 17009.
1279:
1275:
1261:
1242:
1238:March, Jerry
1231:
1212:
1208:March, Jerry
1201:
1160:
1154:
1127:
1121:
1104:
1100:
1094:
1075:
1071:
1061:
1034:
1028:
1001:
965:
961:
951:
908:
905:FEBS Letters
904:
894:
885:
823:
819:
770:
766:
742:. Retrieved
720:
662:
658:
628:
619:
610:
604:
575:
569:
544:
540:
522:
518:
509:
476:
472:
430:
414:
395:
363:
316:
278:
255:acrylic acid
231:
204:
181:
150:
120:, including
111:
91:
70:
65:, where the
58:
53:featuring a
46:
42:
38:
37:
1078:(1): 8–14.
525:(2): 82–4.
319:dilithiated
289:cyanohydrin
221:, yielding
195:animal feed
118:lactic acid
87:citric acid
79:lactic acid
1330:Categories
1179:1007924903
744:2023-04-01
595:3527306730
561:References
420:(FDA) and
392:Occurrence
262:R−CH(Cl)CO
247:malic acid
234:hydrolysis
191:methionine
102:moisturize
1187:cite book
925:0014-5793
840:0022-538X
795:219749282
787:1463-9262
681:2296-4185
211:aldehydes
116:based on
1304:21460292
1296:28191900
1240:(2007),
1210:(2007),
1146:27813843
984:12079051
943:17825297
858:12388683
699:31681741
531:17664715
493:10343939
443:See also
334:→ R−CH(O
326:R−CHLiCO
309:H + NH
274:H + HCl
239:fumarate
213:through
114:polymers
57:located
934:2018605
690:6797553
665:: 259.
553:9640557
501:9721678
287:of the
266:H + H
243:maleate
138:sutures
126:lactide
1302:
1294:
1250:
1220:
1177:
1167:
1144:
1134:
1049:
1016:
982:
941:
931:
923:
856:
849:136750
846:
838:
793:
785:
735:
697:
687:
679:
592:
551:
529:
499:
491:
411:Safety
347:R−CH(O
330:Li + O
227:ketone
136:, and
85:, and
1300:S2CID
1272:(PDF)
791:S2CID
541:Cutis
497:S2CID
351:Li)CO
338:Li)CO
253:from
41:, or
1292:PMID
1248:ISBN
1218:ISBN
1193:link
1175:OCLC
1165:ISBN
1142:OCLC
1132:ISBN
1047:ISBN
1014:ISBN
980:PMID
939:PMID
921:ISSN
854:PMID
836:ISSN
783:ISSN
733:ISBN
695:PMID
677:ISSN
590:ISBN
549:PMID
527:PMID
489:PMID
241:and
225:, a
108:Uses
47:AHAs
1284:doi
1109:doi
1080:doi
1039:doi
1006:doi
970:doi
929:PMC
913:doi
909:581
886:FDA
844:PMC
828:doi
775:doi
725:doi
685:PMC
667:doi
582:doi
481:doi
382:+ H
193:in
71:two
59:one
1332::
1298:.
1290:.
1278:.
1274:.
1189:}}
1185:{{
1173:.
1140:.
1105:23
1103:.
1074:.
1070:.
1045:.
1037:.
1012:.
1004:.
992:^
978:.
966:81
964:.
960:.
937:.
927:.
919:.
907:.
903:.
884:.
866:^
852:.
842:.
834:.
824:76
822:.
818:.
803:^
789:.
781:.
771:22
769:.
765:.
753:^
731:.
719:.
707:^
693:.
683:.
675:.
661:.
657:.
645:^
588:.
545:61
543:.
523:67
521:.
495:.
487:.
477:12
475:.
426:pH
407:.
368:.
342:Li
257:.
197:.
132:,
104:.
89:.
81:,
77:,
1306:.
1286::
1280:2
1195:)
1181:.
1148:.
1115:.
1111::
1088:.
1082::
1076:9
1055:.
1041::
1022:.
1008::
986:.
972::
945:.
915::
888:.
860:.
830::
797:.
777::
747:.
727::
701:.
669::
663:7
598:.
584::
555:.
533:.
503:.
483::
386:O
384:2
379:2
376:−
357:2
353:2
349:2
340:2
336:2
332:2
328:2
311:3
307:2
303:2
272:2
268:2
264:2
45:(
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
