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951:
CAPB has been claimed to cause allergic reactions in some users, but a controlled pilot study has found that these cases may represent irritant reactions rather than true allergic reactions. Furthermore, results of human studies have shown that CAPB has a low sensitizing potential if impurities with
942:
The impurities AA and DMAPA are most critical, as they have been shown to be responsible for skin sensitization reactions. These by-products can be avoided by a moderate excess chloroacetate and the exact adjustment of pH value during betainization reaction accompanied by regular analytical control.
1351:
Fowler Jr, J. F.; Zug, K. M.; Taylor, J. S.; Storrs, F. J.; Sherertz, E. A.; Sasseville, D. A.; Rietschel, R. L.; Pratt, M. D.; Mathias, C. G.; Marks, J. G.; Maibach, H. I.; Fransway, A. F.; Deleo, V. A.; Belsito, D. V. (2004).
470:
442:
1323:
Shaffer, K. K.; Jaimes, J. P.; Hordinsky, M. K.; Zielke, G. R.; Warshaw, E. M. (2006). "Allergenicity and cross-reactivity of coconut oil derivatives: A double-blind randomized controlled pilot study".
1418:
Foti, C.; Bonamonte, D.; Mascolo, G.; Corcelli, A.; Lobasso, S.; Rigano, L.; Angelini, G. (2003). "The role of 3-dimethylaminopropylamine and amidoamine in contact allergy to cocamidopropylbetaine".
661:, or its methyl ester, is the main constituent). The primary amine in DMAPA is more reactive than the tertiary amine, leading to its selective addition to form an amide. In the second step
960:(DMAPA) are low and tightly controlled. Other studies have concluded that most apparent allergic reactions to CAPB are more likely due to amidoamine. Cocamidopropyl betaine was voted 2004
583:
525:
533:
297:
1461:
Fowler, J. F.; Fowler, L. M.; Hunter, J. E. (1997). "Allergy to cocamidopropyl betaine may be due to amidoamine: A patch test and product use test study".
112:
105:
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1084:
23:
1506:
1239:"Morphology and dynamics of self-assembled structures in mixed surfactant systems (SDS + CAPB) in the context of methane hydrate growth"
540:
1383:
Korting, H. C.; Parsch, E. M.; Enders, F.; Przybilla, B. (1992). "Allergic contact dermatitis to cocamidopropyl betaine in shampoo".
1284:
Bhattacharjee, Gaurav; Kushwaha, Omkar Singh; Kumar, Asheesh; Khan, Muzammil Yusuf; Patel, Jay
Narayan; Kumar, Rajnish (2017-04-05).
1529:
262:
860:
Cocamidopropyl betaine is used as a foam booster in shampoos. It is a medium-strength surfactant also used in bath products like
836:
containing a long hydrocarbon chain at one end and a polar group at the other. This allows CAPB to act as a surfactant and as a
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InChI=1S/C19H38N2O3/c1-4-5-6-7-8-9-10-11-12-14-18(22)20-15-13-16-21(2,3)17-19(23)24/h4-17H2,1-3H3,(H-,20,22,23,24)
281:
InChI=1/C19H38N2O3/c1-4-5-6-7-8-9-10-11-12-14-18(22)20-15-13-16-21(2,3)17-19(23)24/h4-17H2,1-3H3,(H-,20,22,23,24)
162:
957:
929:
650:
618:
1110:
De Groot, A. C.; Van Der Walle, H. B.; Weyland, J. W. (1995). "Contact allergy to cocamidopropyl betaine".
665:
reacts with the remaining tertiary amine to form a quaternary ammonium center (a quaternization reaction).
150:
1156:
Brand, R.; Delaney, T. A. (1998). "Allergic contact dermatitis to cocamidopropylbetaine in hair shampoo".
900:
484:
454:
40:
1035:
Christian Nitsch, Hans-Joachim
Heitland, Horst Marsen, Hans-Joachim Schlüussler, "Cleansing Agents" in
1534:
1238:
1079:. Surfactant Science Series. Vol. 68 (2nd ed.). New York: Marcel Dekker, Inc. p. 359.
961:
243:
64:
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1443:
1266:
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1135:
633:
group, is derived from coconut oil. Cocamidopropyl betaine to a significant degree has replaced
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Hande, Vrushali; Choudhary, Nilesh; Chakrabarty, Suman; Kumar, Rajnish (2020-12-01).
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907:. CAPB, as an additive, helps to scale up the gas hydrates' formation process.
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649:. Instead it is produced in a two step manner, beginning with the reaction of
645:
Despite the name cocamidopropyl betaine, the molecule is not synthesized from
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621:. CAPB is available as a viscous pale yellow solution and it is used as a
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910:
CAPB is obtained as an aqueous solution in concentrations of about 30%.
385:
181:
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490:
29:
Lauramidopropyl betaine, the major component of cocamidopropyl betaine
560:
Except where otherwise noted, data are given for materials in their
1354:"Allergy to cocamidopropyl betaine and amidoamine in North America"
111:
104:
97:
87:
1286:"Effects of Micellization on Growth Kinetics of Methane Hydrate"
889:
629:. The name reflects that the major part of the molecule, the
231:
517:
578:
1202:
Mowad, C. (2001). "Cocamidopropyl betaine allergy".
896:. However, some studies indicate it is an allergen.
913:Typical impurities of leading manufacturers today:
876:, and to reduce the irritation that purely ionic
410:> 100 °C (212 °F; 373 K)
193:
1358:Dermatitis: Contact, Atopic, Occupational, Drug
1326:Dermatitis: Contact, Atopic, Occupational, Drug
1290:Industrial & Engineering Chemistry Research
521:
400:< −10 °C (14 °F; 263 K)
73:
1385:Journal of the American Academy of Dermatology
1075:. In Martin M. Rieger; Linda D. Rhein (eds.).
1058:Amines: Synthesis, Properties and Applications
1037:Ullmann’s Encyclopedia of Industrial Chemistry
8:
964:by the American Contact Dermatitis Society.
1060:. Cambridge University Press. p. 281.
899:CAPB is also used as a co-surfactant with
246:
153:
131:
15:
1105:
1103:
653:(DMAPA) with fatty acids from coconut or
213:
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1158:The Australasian Journal of Dermatology
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1204:American Journal of Contact Dermatitis
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888:, which most often does not irritate
274:Key: MRUAUOIMASANKQ-UHFFFAOYSA-N
7:
284:Key: MRUAUOIMASANKQ-UHFFFAOYAL
184:
1475:10.1111/j.1600-0536.1997.tb02464.x
1170:10.1111/j.1440-0960.1998.tb01264.x
1124:10.1111/j.1600-0536.1995.tb02078.x
1009:"Cocoamidopropyl-Betaine-CAPB-SDS"
880:would cause. It also serves as an
609:) is a mixture of closely related
14:
1432:10.1034/j.1600-0536.2003.00078.x
568:
460:
348:
342:
315:C(=O)C(CCCNC(=O)CCCCCCCCCCC)(C)C
310:CCCCCCCCCCCC(=O)NCCC(C)(C)CC(=O)
305:CCCCCCCCCCCC(=O)NCCC(C)(C)CC()=O
22:
1504:History of Allergen of the Year
903:for promoting the formation of
564:(at 25 °C , 100 kPa).
974:Cocamidopropyl hydroxysultaine
625:in personal care products and
380:Clear to slight yellow liquid
354:
336:
1:
1550:Quaternary ammonium compounds
1397:10.1016/S0190-9622(08)80270-8
1039:, 2005, Wiley-VCH, Weinheim.
856:Specifications and properties
1255:10.1016/j.molliq.2020.114296
1243:Journal of Molecular Liquids
1056:Stephen A. Lawrence (2004).
1571:
846:quaternary ammonium cation
44:{(dimethyl)ammonio}acetate
932:(DMAPA) < 15 ppm
558:
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21:
1530:Zwitterionic surfactants
1302:10.1021/acs.iecr.7b00328
1077:Surfactants in Cosmetics
1045:10.1002/14356007.a07_137
958:dimethylaminopropylamine
930:Dimethylaminopropylamine
918:Sodium monochloroacetate
651:dimethylaminopropylamine
619:dimethylaminopropylamine
17:Lauramidopropyl betaine
1216:10.1053/ajcd.2001.29549
1071:Reich, Charles (1997).
844:, consisting of both a
901:Sodium dodecyl sulfate
864:. It is also used in
603:Cocamidopropyl betaine
528:
1391:(6 Pt 1): 1013–1015.
527:
962:Allergen of the Year
779:H + NaOH → CH
510:(fire diamond)
1540:Cosmetics chemicals
432:< 100 cP (30°C)
417:Solubility in water
372: g·mol
18:
1509:2014-04-25 at the
1463:Contact Dermatitis
1420:Contact Dermatitis
1112:Contact Dermatitis
926:(AA) < 0.3%
591:Infobox references
529:
16:
1555:Fatty acid amides
1545:Antistatic agents
1513:. contactderm.org
1296:(13): 3687–3698.
1086:978-0-8247-9805-5
886:hair conditioners
870:emulsifying agent
663:chloroacetic acid
611:organic compounds
599:Chemical compound
597:
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485:Hazard statements
227:CompTox Dashboard
113:Interactive image
106:Interactive image
99:Interactive image
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627:animal husbandry
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1090:. Retrieved
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1019:. Retrieved
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909:
905:gas hydrates
898:
859:
831:
644:
635:cocamide DEA
606:
602:
601:
506:
476:
443:
58:Identifiers
50:Other names
1535:Antiseptics
878:surfactants
850:carboxylate
840:. It is a
659:lauric acid
631:lauric acid
615:coconut oil
471:Signal word
377:Appearance
324:Properties
151:100.057.308
1524:Categories
1364:(1): 5–6.
1249:: 114296.
1092:9 December
980:References
954:amidoamine
924:Amidoamine
920:< 5 ppm
862:hand soaps
842:zwitterion
832:CAPB is a
641:Production
623:surfactant
455:Pictograms
390:1.05 g/cm
365:Molar mass
215:5OCF3O11KX
124:ChemSpider
86:3D model (
75:61789-40-0
65:CAS Number
41:IUPAC name
1310:0888-5885
1271:224848279
1263:0167-7322
956:(AA) and
874:thickener
866:cosmetics
838:detergent
828:Chemistry
446:labelling
428:Viscosity
172:263-058-8
164:EC Number
52:2-acetate
1507:Archived
1440:12786723
1370:15573641
1338:16956456
1224:11753899
1140:42960180
968:See also
936:Glycerol
681:COOH + H
507:NFPA 704
437:Hazards
422:Soluble
1491:7933812
1483:9455630
1448:9944011
1405:1479082
1186:9381720
1178:9611386
1132:8706401
938:< 3%
771:+ ClCH
647:betaine
584:what is
582: (
477:Warning
386:Density
370:342.524
182:PubChem
1489:
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1438:
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1021:26 May
947:Safety
868:as an
848:and a
791:CONHCH
751:CONHCH
717:CONHCH
579:verify
576:
298:SMILES
35:Names
1487:S2CID
1444:S2CID
1267:S2CID
1182:S2CID
1136:S2CID
1012:(PDF)
263:InChI
195:20280
133:19106
88:JSmol
1479:PMID
1436:PMID
1401:PMID
1366:PMID
1334:PMID
1306:ISSN
1259:ISSN
1220:PMID
1174:PMID
1128:PMID
1094:2012
1081:ISBN
1023:2021
890:skin
872:and
803:N(CH
763:N(CH
729:N(CH
705:→ CH
697:N(CH
617:and
607:CAPB
499:H400
495:H319
491:H315
206:UNII
1471:doi
1428:doi
1393:doi
1298:doi
1251:doi
1247:319
1212:doi
1166:doi
1120:doi
1041:doi
892:or
884:in
783:(CH
743:(CH
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685:NCH
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232:EPA
185:CID
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799:CH
795:CH
789:10
775:CO
759:CH
755:CH
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739:CH
725:CH
721:CH
715:10
693:CH
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679:10
669:CH
637:.
497:,
493:,
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346:38
340:19
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765:3
761:2
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731:3
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719:2
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699:3
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691:2
687:2
683:2
677:)
675:2
671:3
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574:N
548:0
541:1
534:2
358:3
355:O
352:2
349:N
343:H
337:C
234:)
230:(
90:)
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