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and is still used today. 2-Methylundecanal is synthesized in industry by two main routes. The first route, like
Darzens, involves converting methyl nonyl ketone to its glycidate by allowing it to react with alkyl chloroacetate. The glycidate then undergoes
1281:
Dieter Enders; Hubert Dyker, Synthesis and
Properties of Enantiomers of the Two Artificial Fragrances Lilial and Methylundecanal. Institut für Organische Chemie der Rheinisch-Westfälischen Technischen Hochschule. 1990, 1107–1110,
516:
1046:. This process involves starting with simple achiral aldehydes and converting them either to their SAMP or RAMP chiral hydrazones using SAMP or RAMP as a chiral auxiliary. The chiral hydrazones are then
483:
582:
1086:
notes, fir in particular, but is also used in fantasy compositions. This aldehyde was one of the first synthetics to be used in a prestigious perfume, namely
682:
868:
The second method for the synthesis of 2-methylundecanal begins with the conversion of undecanal to 2-methyleneundecanal by allowing it to react with
1043:
369:
720:-like. At high dilution it has a flavor similar to honey and nuts. It is a colorless or pale yellow liquid that is soluble in organic
677:
1062:. Testing of the enantiomers by a professional perfumer indicated only a slight difference in odor quality and intensity.
1255:
Burdock, George A., Fenorali, Giovanni. Fenorali’s
Handbook of Flavor Ingredients, 5th ed.; CRC Press: Boca Raton, 2004.
1265:
Ullmann’s
Encyclopedia of Industrial Chemistry 7th Ed: Fragrances and Flavors, John Wiley & Sons Inc, Hoboken 2009.
23:
1260:
334:
689:
884:
of this compound is hydrogenated and the resulting 2-methylundecanal is separated from the by-products using
1278:
Darzens, Georges; Comptes Rendus
Hebdomadaires des séances de l’Académie des Sciences. 1904, 139, 1214-1217.
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1114:. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records
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594:
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1212:
Synthesis and
Properties of Enantiomers of the Two Artificial Fragrances Lilial and Methylundecanal
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135:
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150:
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128:
36:
8:
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745:
64:
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to give 2-methylundecanal. The resulting solution is over 50% 2-methyleneundecanal. The
319:
180:
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1300:
1270:
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169:
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869:
732:. It is used as a fragrance component in soaps, detergents, and perfumes.
888:. The required undecanal in the first step is generated from 1-decene by
881:
621:
586:
578:
1055:
1047:
1039:
713:
417:
189:
119:
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659:
Except where otherwise noted, data are given for materials in their
343:
InChI=1S/C12H24O/c1-3-4-5-6-7-8-9-10-12(2)11-13/h11-12H,3-10H2,1-2H3
1293:
Ramsden, E. N. A-Level
Chemistry. 4th ed. Nelson Thornes: UK, 2000.
1178:
Comptes Rendus
Hebdomadaires des séances de l'Académie des Sciences
753:
353:
InChI=1/C12H24O/c1-3-4-5-6-7-8-9-10-12(2)11-13/h11-12H,3-10H2,1-2H3
614:
87:
1083:
729:
721:
709:
562:
540:
438:
207:
752:. This method of synthesis can be used to produce a variety of
650:
570:
99:
602:
261:
77:
303:
1275:
CRC Handbook of
Chemistry and Physics. 89th ed. 2008-2009.
1075:
1042:
can be synthesized with high enantiomeric purity using the
1199:(7th ed.). Hoboken: John Wiley & Sons Inc. 2009.
740:
The first synthesis of 2-methylundecanal was recorded by
1244:
Molecule of the Month: Chanel No 5 and 2-methylundecanal
1151:
Molecule of the Month: Chanel No 5 and 2-methylundecanal
536:
1298:
241:
226:
219:
610:
63:
1197:Ullmann's Encyclopedia of Industrial Chemistry
1082:as well as in the perfume industry to give
712:peel oil. This compound smells herbaceous,
626:93.4 °C (200.1 °F; 366.5 K)
318:
179:
149:
134:
127:
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1189:
1187:
1138:Fenorali's Handbook of Flavor Ingredients
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314:
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1165:(89th ed.). CRC Press. 2008–2009.
1140:(5th ed.). Boca Raton: CRC Press.
1126:
1108:"2-Methylundecanal - Compound Summary"
1070:2-Methylundecanal is used widely as a
170:
1209:
1203:
1163:CRC Handbook of Chemistry and Physics
453:171 °C; 340 °F; 444 K
346:Key: NFAVNWJJYQAGNB-UHFFFAOYSA-N
107:
1229:(4th ed.). UK: Nelson Thornes.
876:. The 2-methyleneundecanal is then
356:Key: NFAVNWJJYQAGNB-UHFFFAOYAB
210:
13:
1249:
1155:
1144:
14:
1328:
1237:
1030:)-2-Methylundecanal (above) and (
667:
506:
501:
404:
22:
1065:
1015:2-Methylundecanal contains one
663:(at 25 °C , 100 kPa).
1100:
735:
410:
398:
1:
1093:
1010:
7:
1136:Fenorali, Giovanni (2004).
1034:)-2-Methylundecanal (below)
708:that is found naturally in
10:
1333:
1288:10.1002/jlac.1990199001200
1044:SAMP/RAMP hydrazone method
1176:Darzens, Georges (1904).
657:
630:
482:
477:
385:
365:
330:
47:
35:
30:
21:
1271:10.1002/14356007.a11_141
1058:with a slight excess of
1052:lithium diisopropylamide
756:and became known as the
553:Precautionary statements
886:fractional distillation
637:Related alkyl aldehydes
1225:Ramsden, E.N. (2000).
1210:Dyker, Hubert (1990).
1035:
1025:
642:Hexyl cinnamaldehyde
37:Preferred IUPAC name
872:in the presence of
750:ethyl chloroacetate
746:methyl nonyl ketone
425: g·mol
18:
1036:
690:Infobox references
631:Related compounds
433:Colourless liquid
17:2-Methylundecanal
16:
1227:A-Level Chemistry
1017:asymmetric carbon
702:2-Methylundecanal
698:Chemical compound
696:
695:
531:Hazard statements
299:CompTox Dashboard
253:
238:
161:
146:
89:Interactive image
41:2-Methylundecanal
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1112:PubChem Compound
1104:
1060:dimethyl sulfate
890:hydroformylation
758:Darzens reaction
706:organic compound
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647:Isobutyraldehyde
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460:Refractive index
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393:Chemical formula
377:CCCCCCCCCC(C)C=O
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1307:Fatty aldehydes
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947:CHO + HCHO → CH
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1137:
1116:. Retrieved
1111:
1102:
1088:Chanel No. 5
1069:
1066:Applications
1037:
1031:
1027:
1014:
878:hydrogenated
870:formaldehyde
867:
765:followed by
739:
701:
700:
645:
522:
484:
463:
443:830.3 mg cm
262:RTECS number
249:
234:
157:
142:
48:Identifiers
1074:element in
1040:enantiomers
882:double bond
736:Preparation
622:Flash point
517:Signal word
430:Appearance
386:Properties
177:100.003.424
1301:Categories
1118:12 October
1094:References
1080:detergents
1054:(LDA) and
496:Pictograms
418:Molar mass
287:S94QNS2VY5
252:)-2-methyl
237:)-2-methyl
160:)-2-methyl
145:)-2-methyl
120:ChemSpider
76:3D model (
55:CAS Number
1072:fragrance
1056:alkylated
1048:metalated
1011:Chirality
920:+ CO → CH
860:)CHO + CO
754:aldehydes
718:ambergris
599:P337+P313
595:P333+P313
591:P332+P313
579:P302+P352
487:labelling
269:YQ1509000
198:203-765-0
190:EC Number
1317:Alkanals
1312:Perfumes
986:)CHO + H
963:)CHO + H
817:R) + HCl
724:such as
722:solvents
478:Hazards
65:110-41-8
1084:conifer
813:)OCH(CO
730:ethanol
710:kumquat
683:what is
681: (
523:Warning
439:Density
423:184.323
228:6915922
208:PubChem
136:5291693
1259:
1019:atom.
844:O → CH
797:R → CH
789:+ ClCH
785:C(O)CH
716:, and
714:orange
704:is an
678:verify
675:
651:Lilial
473:1.432
370:SMILES
246:
243:637522
231:
154:
151:553128
139:
100:ChEMBL
31:Names
1076:soaps
1050:with
1002:CH(CH
864:+ ROH
856:CH(CH
840:R + H
809:CH(CH
726:ether
335:InChI
221:61031
129:54990
78:JSmol
1257:ISBN
1120:2011
1078:and
1038:The
1006:)CHO
990:→ CH
982:C(CH
959:C(CH
874:base
836:OCCO
748:and
728:and
615:P501
611:P391
607:P363
603:P362
587:P321
575:P280
571:P273
567:P272
563:P264
559:P261
545:H410
541:H317
537:H315
278:UNII
1284:doi
1267:doi
994:(CH
974:(CH
951:(CH
939:(CH
932:CHO
924:(CH
916:+ H
912:=CH
900:(CH
892:.
848:(CH
832:CCH
824:(CH
801:(CH
777:(CH
485:GHS
304:EPA
211:CID
1303::
1186:^
1128:^
1110:.
1090:.
970:CH
945:10
935:CH
930:10
908:CH
896:CH
820:CH
793:CO
773:CH
769:.
613:,
609:,
605:,
601:,
597:,
593:,
589:,
585:,
581:,
577:,
573:,
569:,
565:,
561:,
543:,
539:,
489::
408:24
402:12
248:(2
233:(2
156:(2
141:(2
1290:.
1286::
1269::
1214:.
1180:.
1122:.
1032:S
1028:R
1026:(
1004:3
1000:8
998:)
996:2
992:3
988:2
984:2
980:8
978:)
976:2
972:3
967:O
965:2
961:2
957:8
955:)
953:2
949:3
943:)
941:2
937:3
928:)
926:2
922:3
918:2
914:2
910:2
906:7
904:)
902:2
898:3
862:2
858:3
854:8
852:)
850:2
846:3
842:2
838:2
834:3
830:8
828:)
826:2
822:3
815:2
811:3
807:8
805:)
803:2
799:3
795:2
791:2
787:3
783:8
781:)
779:2
775:3
673:N
469:)
467:D
464:n
462:(
411:O
405:H
399:C
306:)
302:(
250:S
235:R
158:S
143:R
80:)
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