685:
234:
159:
24:
638:, the occurrence of isovaleraldehyde is not limited to beer. The compound has found to be a flavor component in many different types of foods. It is described as having a malty flavor and has been found in
699:. This is a flavouring agent that can be used in confectionary, tobacco, and other foodstuffs, toothpastes and the like. It is described as imparting a creamy, dairy, vanilla chocolate and berry flavour.
669:
The compound is used as a reactant in the synthesis of a number of compounds. Notably it is used to synthesize 2,3-dimethylbut-2-ene, and is then converted to 2,3-dimethylbutane-2,3-diol and methyl
776:
283:
567:
as a catalyst. A mixture of 3-methylbut-3-en-1-ol and 3-methylbut-2-en-1-ol may also be used. These starting materials are obtained from a reaction between
793:
926:
681:, are synthesized from isovaleraldehyde and its corresponding acid. It is a common reagent or building block in organic synthesis.
472:
248:
410:
677:. Pinacolone itself is then used in synthesis for number of pesticides. Additionally, a range of pharmaceuticals, such as
191:
212:
475:, and found in low concentrations in many types of food. Commercially it is used as a reagent for the production of
437:
872:
Poulsen, Pernille; Overgaard, Mette; Jensen, Kim L.; Jørgensenjournal=Organic
Syntheses, Karl Anker (2014).
386:
154:
36:
684:
229:
62:
96:
752:
Cserháti, T.; Forgács, E. (2003). "Flavor (Flavour) Compounds: Structures and
Characteristics".
951:
789:
946:
885:
852:
839:
Boeckman, Robert; Tusch, Douglas J.; Biegasiewiczjournal=Organic
Syntheses, Kyle F. (2015).
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116:
696:
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431:
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495:
Synthetic routes for the production of isovaleraldehyde vary. One method is by the
785:
180:
23:
695:
Acid-catalyzed cyclic trimerization of
Isovaleraldehyde gives 2,4,6-Triisobutyl-
912:
906:
674:
612:
564:
484:
325:
127:
890:
873:
857:
840:
659:
655:
568:
702:
According to IFF, isovaleraldehyde is used as a food flavorant additive.
678:
468:
647:
635:
615:
480:
343:
167:
841:"Organocatalyzed Direct Asymmetric α-Hydroxymethylation of Aldehydes"
643:
639:
611:
Finally, in beer the compound is produced via a reaction between the
430:
Except where otherwise noted, data are given for materials in their
683:
107:
95:
85:
651:
623:
619:
663:
217:
874:"Enantioselective Organocatalytic α-Arylation of Aldehydes"
380:
Soluble in alcohol and ether, slightly soluble in water
738:(15th ed.). New York, NY: John Wiley. p. 719.
756:(2nd ed.). Elsevier Science. pp. 2509–2517.
455:, also known as 3-methylbutanal, with the formula (CH
916:(1978 to International Flavors and Fragrances Inc).
824:Owuor, P. O. (2003). "Tea: Analysis and Tasting".
809:Bamforth, C. W. (2003). "Chemistry of Brewing".
179:
71:
777:Ullmann's Encyclopedia of Industrial Chemistry
8:
729:
727:
725:
723:
721:
719:
717:
715:
257:InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
826:Encyclopedia of Food Sciences and Nutrition
811:Encyclopedia of Food Sciences and Nutrition
754:Encyclopedia of Food Sciences and Nutrition
267:InChI=1/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3
555:Another method of production involves the
232:
157:
135:
15:
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769:
767:
765:
763:
199:
774:Kohlpaintner, C. "Aliphatic Aldehydes".
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540:
537:A small amount of 2,2-dimethylpropanal (
529:
525:
521:
517:
513:
509:
505:
711:
288:
253:
228:
736:Hawley's Condensed Chemical Dictionary
358:−51 °C (−60 °F; 222 K)
148:
368:92 °C (198 °F; 365 K)
260:Key: YGHRJJRRZDOVPD-UHFFFAOYSA-N
115:
7:
828:(2nd ed.). pp. 5757–5762.
270:Key: YGHRJJRRZDOVPD-UHFFFAOYAE
170:
780:. Weinheim: Wiley-VCH. p. 9.
14:
904:Donald Arthur Withycombe, et al.
813:(2nd ed.). pp. 440–447.
552:side product is also generated.
22:
673:-butyl ketone, better known as
559:of 3-methylbut-3-en-1-ol using
434:(at 25 °C , 100 kPa).
50:Isovaleral, Isovaleric Aldehyde
734:Lewis, R. J. Sr., ed. (2007).
411:Occupational safety and health
1:
786:10.1002/14356007.a01_321.pub3
968:
634:As it can be derived from
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348:0.785 g/mL at 20 °C
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279:
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55:
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35:
30:
21:
891:10.15227/orgsyn.091.0175
858:10.15227/orgsyn.092.0320
471:, a colorless liquid at
387:Magnetic susceptibility
692:
913:U.S. patent 4,191,785
907:U.S. patent 4,093,752
687:
630:Occurrences and uses
37:Preferred IUPAC name
375:Solubility in water
330:86.13
18:
693:
688:2,4,6-Triisobutyl-
438:Infobox references
16:
878:Organic Syntheses
845:Organic Syntheses
446:Chemical compound
444:
443:
338:Colorless Liquid
213:CompTox Dashboard
97:Interactive image
17:Isovaleraldehyde
959:
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453:organic compound
450:Isovaleraldehyde
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307:Chemical formula
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927:"LMR Naturals"
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697:1,3,5-trioxane
690:1,3,5-trioxane
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499:of isobutene:
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467:CHO. It is an
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557:isomerization
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149:ECHA InfoCard
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424:Combustible
420:Main hazards
409:
56:Identifiers
48:Other names
884:: 175–184.
851:: 320–327.
520:+ CO → (CH
414:(OHS/OSH):
335:Appearance
300:Properties
155:100.008.811
117:CHEBI:16638
941:Categories
706:References
675:pinacolone
620:reductones
613:amino acid
547:C−C(CHO)CH
485:pesticides
326:Molar mass
201:69931RWI96
128:ChemSpider
84:3D model (
63:CAS Number
660:olive oil
656:chocolate
569:isobutene
491:Synthesis
291:CC(C)CC=O
952:Alkanals
679:butizide
595:O → (CH
481:perfumes
469:aldehyde
404:Hazards
389:(χ)
320:O
73:590-86-3
947:Flavors
648:chicken
636:leucine
622:in the
616:leucine
344:Density
168:PubChem
792:
662:, and
644:coffee
640:cheese
284:SMILES
31:Names
394:−57.5
249:InChI
181:11552
137:11065
108:ChEBI
86:JSmol
790:ISBN
671:tert
652:fish
624:malt
618:and
603:CHCH
591:+ CH
571:and
528:C−CH
516:+ H
512:C=CH
483:and
463:CHCH
192:UNII
886:doi
853:doi
782:doi
664:tea
607:CHO
587:CCH
565:ZnO
561:CuO
539:(CH
532:CHO
504:(CH
473:STP
218:EPA
171:CID
943::
910:,
882:91
880:.
876:.
849:92
847:.
843:.
788:.
762:^
744:^
714:^
666:.
658:,
654:,
650:,
646:,
642:,
626:.
583:CH
579:CH
575::
487:.
479:,
318:10
929:.
894:.
888::
861:.
855::
798:.
784::
605:2
601:2
599:)
597:3
593:2
589:2
585:3
581:3
563:–
549:3
545:2
543:)
541:3
530:2
526:2
524:)
522:3
518:2
514:2
510:2
508:)
506:3
465:2
461:2
459:)
457:3
396:×
316:H
314:5
312:C
220:)
216:(
88:)
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