51:
42:
332:
712:
707:
1628:
1139:
1074:)-2-methylbutanoic acid has a pervasive, cheesy, sweaty odor. The main use of the materials, and their esters, is therefore as flavours and food additives. The compounds' safety in this application was reviewed by an
720:
967:. The dried root of this plant has been used medicinally since antiquity. The chemical identity of all three compounds was first investigated in the 19th century by oxidation of the components of
687:
798:
1010:. It was the target of the first enantioselective synthesis in 1904 when the German chemist W. Marckwald heated ethyl(methyl)malonic acid with the chiral base
790:
1518:
Mariaca, Raul G.; Imhof, Miroslava I.; Bosset, J. O. (2001). "Occurrence of volatile chiral compounds in dairy products, especially cheese - A review".
1386:
Matteoli, Ugo; Beghetto, Valentina; Scrivanti, Alberto (1999). "Asymmetric hydrogenation by an in situ prepared (S)-BINAP–Ru(II) catalytic system".
578:
1236:
794:
1632:
1090:
Since 2-methylbutanoic acid and its esters are natural components of many foods, they are present in mammals including humans.
1430:
17:
1212:
1197:
526:
1014:
and obtained an optically active product mixture. Either enantiomer of 2-methylbutanoic acid can now be obtained by
855:
778:
929:)-2-methylbutanoic occurs in many fruits such as apples and apricots, as well as in the scent of the orchid
756:
447:
327:
1155:
259:
487:
169:
774:
711:
1156:"Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation"
1135:
339:
1015:
512:
50:
41:
1652:
902:
706:
1554:
1154:
Rettinger, Klaus; Burschka, Christian; Scheeben, Peter; Fuchs, Heike; Mosandl, Armin (1991).
1099:
1062:
Racemic 2-methylbutanoic acid is a slightly volatile, colorless liquid with a pungent cheesy
955:
945:
734:
699:
669:
298:
1230:
309:
980:
475:
464:
126:
69:
1494:
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1446:
1054:
derivatives. The acid chloride is commonly used as the intermediate to obtain the others.
806:
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436:
1038:
The compound and its enantiomers react as typical carboxylic acids: they can form
1082:
panel, who concluded that there were no concerns at the likely levels of intake.
995:
964:
950:
878:
770:
414:
1422:
1190:
Current Topics in
Flavours and Fragrances: Towards a New Millennium of Discovery
1047:
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837:
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1240:. Vol. 27 (11th ed.). Cambridge University Press. p. 859.
814:
786:
1066:. The smell differs significantly between the two enantiomeric forms. (
922:
906:
340:
270:
822:
1023:
748:
1356:
1293:
848:
Except where otherwise noted, data are given for materials in their
1229:
381:
1070:)-2-Methylbutyric acid has a pleasantly sweet, fruity odor while (
830:
168:
1011:
766:
639:
393:
1627:
1103:
931:
242:
1555:"Safety evaluation of certain food additives and contaminants"
1153:
975:. Among the products isolated was a compound which gave a (+)
1043:
1039:
1027:
875:
192:
150:
542:: InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)
492:
1413:
Jenkins, P. R. (1985). "Carboxylic acids and derivatives".
1063:
364:
744:
1385:
1079:
1075:
27:
Carboxylic acid with chemical formula CH3CH2CH(CH3)CO2H
1253:"Could Valerian Have Been the First Anticonvulsant?"
1553:FAO/WHO Expert Committee on food additives (1998).
998:2-methylbutanoic acid can readily be prepared by a
1517:
740:
1639:
1187:
943:2-Methylbutanoic acid is a minor constituent of
435:
424:
413:
1215:, Ed. Alec M. Pridgeon et al., p. 207 (LUISIA).
1181:
136:
125:
114:
1361:Berichte der Deutschen Chemischen Gesellschaft
826:
1600:"Metabocard for Methyl (S)-2-Methylbutanoate"
1140:Institute for Occupational Safety and Health
921:)-2-methylbutanoic acid occurs naturally in
565:: Key: WLAMNBDJUVNPJU-BYPYZUCNSA-N
555:: Key: WLAMNBDJUVNPJU-SCSAIBSYSA-N
1575:"Metabocard for (S)-2-Methylbutanoic acid"
1388:Journal of Molecular Catalysis A: Chemical
818:
330:
308:
297:
286:
1354:
1339:
1268:
474:
463:
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1127:
1125:
1412:
1294:"On the isomeric forms of valeric acid"
654:−90 °C (−130 °F; 183 K)
511:
14:
1640:
1291:
664:176 °C (349 °F; 449 K)
321:
1520:European Food Research and Technology
1250:
1218:
1149:
1147:
1122:
842:83 °C (181 °F; 356 K)
545:Key: WLAMNBDJUVNPJU-UHFFFAOYSA-N
258:
230:
219:
208:
396:
380:
24:
1251:Eadie, Mervyn J. (November 2004).
1144:
949:and the perennial flowering plant
49:
40:
25:
1664:
1621:
971:, which includes the five-carbon
1626:
1417:. Vol. 7. pp. 96–160.
1270:10.1111/j.0013-9580.2004.27904.x
710:
705:
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1567:
1546:
1511:
1487:
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1439:
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1298:Journal of the Chemical Society
852:(at 25 °C , 100 kPa).
1357:"Ueber asymmetrische Synthese"
1348:
1316:
1285:
1244:
1206:
990:
13:
1:
1415:General and Synthetic Methods
1400:10.1016/S1381-1169(98)00235-0
1175:10.1016/S0957-4166(00)86137-6
1115:
1033:
983:, indicating it to be the (2
7:
1423:10.1039/9781847556196-00096
1324:"dl-Methylethylacetic acid"
1093:
959:), where it co-occurs with
917:)-2-methylbutanoic acid. (
36:
10:
1669:
1495:"(R)-2-methylbutyric acid"
1471:"(S)-2-methylbutyric acid"
1292:Pedler, Alexander (1868).
1213:Genera Orchidacearum Vol 6
1085:
938:
1604:Human Metabolome Database
1579:Human Metabolome Database
1188:Karl A. D. Swift (1999).
1136:GESTIS Substance Database
846:
686:
681:
601:
574:
522:
90:
80:
68:
63:
35:
1373:10.1002/cber.19040370165
1341:10.15227/orgsyn.005.0075
1192:. Springer. p. 52.
1016:asymmetric hydrogenation
757:Precautionary statements
1499:The Good Scents Company
1475:The Good Scents Company
1451:The Good Scents Company
1237:Encyclopædia Britannica
1057:
634:Clear colorless liquid
1447:"2-Methylbutyric acid"
1163:Tetrahedron: Asymmetry
903:short-chain fatty acid
85:Methylethylacetic acid
54:
45:
31:2-Methylbutanoic acid
1635:at Wikimedia Commons
1633:2-Methylbutanoic acid
1532:10.1007/s002170000250
1355:Marckwald, W (1904).
1100:3-Methylbutanoic acid
956:Valeriana officinalis
946:Angelica archangelica
868:2-Methylbutanoic acid
74:2-Methylbutanoic acid
53:
44:
1310:10.1039/JS8682100074
1231:"Valeric Acid"
874:is a branched-chain
872:2-methylbutyric acid
83:2-Methylbutyric acid
70:Preferred IUPAC name
18:2-methylbutyric acid
905:. It exists in two
901:H, classified as a
593:: CCC(C)C(=O)O
182:Beilstein Reference
32:
856:Infobox references
644:0.94 g/cm (20 °C)
55:
46:
30:
1631:Media related to
1432:978-0-85186-884-4
1328:Organic Syntheses
1263:(11): 1338–1343.
1000:Grignard reaction
864:Chemical compound
862:
861:
735:Hazard statements
488:CompTox Dashboard
170:Interactive image
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356:: 204-145-2
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1169:(10): 965–968.
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993:
981:polarised light
965:isovaleric acid
941:
932:Luisia curtisii
900:
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879:carboxylic acid
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1653:Alkanoic acids
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1622:External links
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1004:2-chlorobutane
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850:standard state
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799:P305+P351+P338
791:P303+P361+P353
783:P301+P330+P331
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1625:
1608:. Retrieved
1606:. 2019-07-23
1603:
1594:
1583:. Retrieved
1581:. 2019-07-23
1578:
1569:
1558:. Retrieved
1548:
1523:
1519:
1513:
1502:. Retrieved
1498:
1489:
1478:. Retrieved
1474:
1465:
1454:. Retrieved
1450:
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1334:: 75. 1925.
1331:
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1220:
1208:
1189:
1183:
1166:
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1109:Valeric acid
1089:
1071:
1067:
1061:
1037:
994:
984:
961:valeric acid
954:
944:
942:
930:
926:
918:
914:
910:
907:enantiomeric
871:
867:
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91:Identifiers
81:Other names
1367:: 349–354.
1111:, an isomer
1020:tiglic acid
991:Preparation
923:cocoa beans
838:Flash point
721:Signal word
631:Appearance
602:Properties
328:100.003.769
232:CHEBI:38655
221:CHEBI:45525
210:CHEBI:37070
1642:Categories
1610:2020-09-30
1585:2020-09-30
1560:2020-09-30
1504:2020-09-30
1480:2020-09-30
1456:2020-09-30
1116:References
1030:catalyst.
987:) isomer.
700:Pictograms
476:5N31513I0N
465:PX7ZNN5GXK
271:ChemSpider
149:3D model (
127:32231-50-8
98:CAS Number
1304:: 74–76.
1257:Epilepsia
1048:anhydride
1034:Reactions
1024:ruthenium
881:with the
795:P304+P340
787:P302+P352
779:P301+P312
691:labelling
341:EC Number
138:1730-91-2
1540:96864200
1279:15509234
1094:See also
1052:chloride
1022:using a
977:rotation
951:valerian
913:)- and (
909:forms, (
682:Hazards
187:1098537
116:116-53-0
1648:Flavors
1138:of the
1134:in the
1132:Record
1086:Biology
1012:brucine
996:Racemic
939:History
640:Density
626:
510::
473::
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382:C18319
310:395556
243:ChEMBL
64:Names
1536:S2CID
1159:(PDF)
1102:, an
1044:ester
1040:amide
1028:BINAP
925:and (
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876:alkyl
677:1.18
527:InChI
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