376:
233:
595:
34:
674:
43:
3206:
3220:
679:
678:
677:
653:
1758:
McDonald, Julie A.K.; Mullish, Benjamin H.; Pechlivanis, Alexandros; Liu, Zhigang; Brignardello, Jerusa; Kao, Dina; Holmes, Elaine; Li, Jia V.; Clarke, Thomas B.; Thursz, Mark R.; Marchesi, Julian R. (2018).
603:
1546:
Shahidi, Fereidoon; Rubin, Leon J.; d'Souza, Lorraine A.; Teranishi, Roy; Buttery, Ron G. (1986). "Meat flavor volatiles: A review of the composition, techniques of analysis, and sensory evaluation".
2210:
2204:
575:
2150:
2275:
1031:
and can also be produced by metabolism of its esters found in food. The restoration of levels of this acid in the gut has been suggested as the mechanism that results in control of
2263:
2144:
2138:
2174:
2413:
2269:
2132:
1003:
panel, who concluded that there were no safety concerns at the likely levels of intake. The compound is used for the preparation of derivatives, notably its volatile
680:
2466:
2120:
2071:
2065:
1007:
which, unlike the parent acid, have pleasant odors and fruity flavors and hence find applications in perfumes, cosmetics and foodstuffs. Typical examples are the
2126:
2340:
2300:
2294:
2235:
2108:
649:
2529:
2521:
2502:
2483:
2077:
2221:
2541:
2114:
2102:
2096:
1412:
3093:
702:
3024:
1337:
Ni, Ji-Qin; Robarge, Wayne P.; Xiao, Changhe; Heber, Albert J. (2012). "Volatile organic compounds at swine facilities: A critical review".
425:
3061:
1254:
695:
3036:
1486:
Yan, Long; Yao, Qian; Fu, Yao (2017). "Conversion of levulinic acid and alkyl levulinates into biofuels and high-value chemicals".
995:
Valeric acid occurs naturally in some foods but is also used as a food additive. Its safety in this application was reviewed by an
3041:
3066:
3056:
1826:
1530:
270:
2575:
828:. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including
3188:
1429:
1032:
1445:
Lange, Jean-Paul; Price, Richard; Ayoub, Paul M.; Louis, Jurgen; Petrus, Leo; Clarke, Lionel; Gosselink, Hans (2010).
1223:
390:
856:), from which it gets its name. The dried root of this plant has been used medicinally since antiquity. The related
688:
3264:
3183:
3051:
3002:
1171:
753:
3083:
2920:
1161:
1761:"Inhibiting Growth of Clostridioides difficile by Restoring Valerate, Produced by the Intestinal Microbiota"
868:. Valeric acid is one volatile component in swine manure. Other components include other carboxylic acids,
2813:
1380:
Wang, Pao-Shui; Kato, Hiromichi; Fujimaki, Masao (1970). "Studies on Flavor
Components of Roasted Barley".
860:
shares its unpleasant odor and their chemical identity was investigated by oxidation of the components of
635:
331:
228:
3175:
3088:
1039:
353:
181:
645:
3030:
539:
2346:
1676:"The Effect of Probiotics on the Production of Short-Chain Fatty Acids by Human Intestinal Microbiome"
3155:
3071:
3046:
1819:
240:
2915:
1166:
371:
131:
3259:
3249:
2568:
2059:
1149:
558:
3098:
1144:
594:
2835:
2370:
2364:
2192:
2186:
2180:
2053:
1582:
1182:
1124:
857:
804:
617:
587:
55:
2247:
2241:
1248:
210:
3254:
3224:
3170:
3160:
2895:
2767:
2757:
2322:
2198:
2023:
1812:
1346:
341:
106:
1650:
1626:
1602:
202:
8:
3140:
2961:
2860:
2692:
98:
87:
33:
2168:
2156:
1350:
375:
232:
160:
152:
3210:
3150:
2976:
2850:
2752:
2737:
2561:
2448:
2424:
2381:
2286:
2088:
1785:
1760:
1715:
1702:
1675:
1119:
1358:
3114:
3076:
2992:
2946:
2890:
2875:
2865:
2825:
2820:
2535:
2312:
1987:
1963:
1927:
1790:
1719:
1707:
1563:
1526:
1468:
1425:
1362:
1139:
1129:
3119:
2997:
2880:
2747:
2614:
2389:
2358:
2229:
2162:
2047:
2011:
1951:
1780:
1772:
1697:
1687:
1555:
1518:
1495:
1458:
1417:
1393:
1389:
1354:
1319:
1286:
1134:
1091:
1087:
984:
813:
780:
528:
448:
304:
3165:
3145:
3124:
2885:
2855:
2787:
2630:
1999:
1981:
1975:
1915:
1891:
1776:
1099:
1016:
1008:
877:
873:
849:
833:
799:
776:
296:
1522:
2925:
2870:
2845:
2840:
2830:
2782:
2772:
2762:
2677:
2407:
2352:
2334:
2029:
1957:
1903:
1855:
1107:
1083:
1028:
1012:
976:
952:
837:
829:
747:
627:
20:
2803:
1559:
1291:
1270:
3243:
3009:
2951:
2910:
2808:
2777:
2682:
2510:
2491:
2460:
2395:
2328:
2306:
2017:
2005:
1939:
1933:
1921:
1885:
1879:
1847:
1421:
1243:
1188:
1103:
980:
955:
and this alternative has received considerable attention as a way to produce
901:
861:
738:
517:
507:
221:
3014:
2930:
2702:
2624:
2619:
2609:
2438:
2401:
2257:
2035:
1993:
1969:
1945:
1873:
1861:
1794:
1711:
1472:
1463:
1446:
1366:
1176:
865:
734:
72:
1733:
1580:
1567:
808:, from which it gets its name. Its primary use is in the synthesis of its
701:
3019:
2971:
2697:
2667:
2454:
2041:
1909:
1897:
1323:
1208:
889:
714:
1258:. Vol. 27 (11th ed.). Cambridge University Press. p. 859.
687:
42:
2712:
2707:
2687:
2662:
2657:
2647:
2604:
2594:
2432:
1839:
1692:
1499:
694:
476:
259:
241:
192:
1804:
2584:
2472:
848:
Valeric acid is a minor constituent of the perennial flowering plant
623:
1307:
746:
Except where otherwise noted, data are given for materials in their
409:
Valeric acid: InChI=1/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)
2956:
2722:
2717:
2672:
2652:
1247:
1070:
956:
905:
893:
660:
130:
2966:
2905:
1447:"Valeric Biofuels: A Platform of Cellulosic Transportation Fuels"
1095:
869:
497:
282:
1545:
1410:
Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic".
1086:
of valeric acid. It is the form found in biological systems at
1077:
1064:
1004:
897:
641:
171:
1583:"Safety evaluation of certain food additives and contaminants"
967:
Valeric acid reacts as a typical carboxylic acid: it can form
798:. Like other low-molecular-weight carboxylic acids, it has an
2900:
1835:
1757:
972:
968:
817:
809:
773:
315:
142:
119:
2553:
358:
1513:
Jenkins, P. R. (1985). "Carboxylic acids and derivatives".
987:
is commonly used as the intermediate to obtain the others.
1059:
1000:
996:
1673:
951:
It can also be produced from biomass-derived sugars via
1674:
Markowiak-Kopeć, Paulina; Śliżewska, Katarzyna (2020).
1444:
1581:FAO/WHO Expert Committee on food additives (1998).
269:
1548:CRC Critical Reviews in Food Science and Nutrition
1336:
1027:In humans, valeric acid is a minor product of the
399:InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)
3241:
1379:
1271:"Biomedically relevant chemical constituents of
802:. It is found in the perennial flowering plant
303:
295:
1409:
880:. It is also a flavor component in some foods.
676:
105:
97:
1413:Ullmann's Encyclopedia of Industrial Chemistry
2569:
1820:
1110:, include the steroid as the valerate ester.
888:In industry, valeric acid is produced by the
1045:
512:−34.5 °C (−30.1 °F; 238.7 K)
1268:
1090:. A valerate, or pentanoate, compound is a
2576:
2562:
1827:
1813:
374:
231:
209:
201:
1784:
1701:
1691:
1462:
1405:
1403:
1290:
1221:
340:
1485:
1242:
1834:
1512:
1451:Angewandte Chemie International Edition
1308:"On the isomeric forms of valeric acid"
370:
3242:
3042:European Cocoa and Chocolate Directive
1400:
1305:
522:185 °C (365 °F; 458 K)
222:
3057:International Cocoa Quarantine Centre
2557:
1808:
1382:Agricultural and Biological Chemistry
1236:
719:86 °C (187 °F; 359 K)
402:Key: NQPDZGIKBAWPEJ-UHFFFAOYSA-N
180:
159:
151:
3025:Côte d'Ivoire–Ghana Cocoa Initiative
1215:
3094:Production in São Tomé and Príncipe
412:Key: NQPDZGIKBAWPEJ-UHFFFAOYAU
285:
13:
2211:6,9,12,15,18,21-Tetracosahexaenoic
1269:Patočka, Jiří; Jakl, Jiří (2010).
672:
14:
3276:
2205:9,12,15,18,21-Tetracosapentaenoic
1359:10.1016/j.chemosphere.2012.04.061
864:, which includes the five-carbon
840:because of their fruity flavors.
3218:
3205:
3204:
3052:International Cocoa Organization
3003:Child labour in cocoa production
1517:. Vol. 7. pp. 96–160.
1212:, 13th Edition, 2001, page 1764.
1172:4-Hydroxy-4-methylpentanoic acid
593:
460:
41:
32:
3219:
1751:
1726:
1667:
1643:
1619:
1595:
1574:
1539:
1506:
1479:
1312:Journal of the Chemical Society
1094:or ester of valeric acid. Many
750:(at 25 °C , 100 kPa).
16:Carboxylic acid – CH3(CH2)3COOH
1438:
1394:10.1080/00021369.1970.10859653
1373:
1330:
1299:
1279:Journal of Applied Biomedicine
1262:
1201:
883:
466:
454:
1:
3067:Philippine chocolate industry
2583:
1734:"Metabocard for Valeric acid"
1515:General and Synthetic Methods
1194:
1185:, also called isovaleric acid
1162:List of saturated fatty acids
820:of valeric acid are known as
433:Valeric acid: CCCCC(O)=O
1777:10.1053/j.gastro.2018.07.014
1179:(2,2-dimethylpropanoic acid)
1102:, for example ones based on
962:
323:Valeric acid: YV6100000
250:Valeric acid: 203-677-2
7:
1523:10.1039/9781847556196-00096
1155:
1113:
1040:fecal microbiota transplant
10:
3281:
3031:The Dark Side of Chocolate
1306:Pedler, Alexander (1868).
1022:
843:
18:
3199:
3133:
3107:
3084:Production in Ivory Coast
2985:
2939:
2796:
2736:
2640:
2593:
2520:
2501:
2482:
2423:
2380:
2285:
2220:
2087:
1846:
1738:Human Metabolome Database
1560:10.1080/10408398609527435
1292:10.2478/v10136-009-0002-z
1046:Valerate salts and esters
983:derivatives. The latter,
744:
723:
574:
569:
441:
421:
386:
80:
64:
54:
49:
40:
31:
3062:Manufacturers (vertical)
2264:7,10,13-Octadecatrienoic
1422:10.1002/14356007.a05_235
1167:List of carboxylic acids
1034:Clostridioides difficile
636:Precautionary statements
19:Not to be confused with
3265:Foul-smelling chemicals
2921:Chocolate-covered foods
1655:The Good Scents Company
1631:The Good Scents Company
1607:The Good Scents Company
1416:. Weinheim: Wiley-VCH.
1255:Encyclopædia Britannica
1150:Hydrocortisone valerate
990:
559:Magnetic susceptibility
67:1-Butanecarboxylic acid
3099:World Cocoa Foundation
2414:7,10,13-Eicosatrienoic
2270:9,12,15-Eicosatrienoic
1464:10.1002/anie.201000655
1145:Betamethasone valerate
908:to the final product.
683:
3089:Production in Nigeria
3047:Harkin–Engel Protocol
2836:Chocolate chip cookie
1273:Valeriana officinalis
1183:3-Methylbutanoic acid
1125:Testosterone valerate
854:Valeriana officinalis
805:Valeriana officinalis
682:
3037:Environmental impact
2896:Cioccolato di Modica
1771:(5): 1495–1507.e15.
1324:10.1039/JS8682100074
1249:"Valeric Acid"
772:is a straight-chain
665:(fire diamond)
3180:Military chocolate
3141:Chocolate addiction
3072:Production in Ghana
2861:Chocolate ice cream
2693:Tetramethylpyrazine
1351:2012Chmsp..89..769N
654:P305+P351+P338+P310
529:Solubility in water
484: g·mol
369:Valeric acid:
339:Valeric acid:
294:Valeric acid:
268:Valeric acid:
200:Valeric acid:
179:Valeric acid:
150:Valeric acid:
129:Valeric acid:
96:Valeric acid:
28:
3151:Chocolate fountain
2851:Chocolate crackles
2467:8,11-Eicosadienoic
2347:Dihomo-γ-linolenic
2276:β-Eicosatetraenoic
2175:Dihomo-α-linolenic
2060:Heptatriacontanoic
1693:10.3390/nu12041107
1500:10.1039/C7GC02503C
1120:Estradiol valerate
754:Infobox references
724:Related compounds
684:
26:
3237:
3236:
3176:In savory cooking
3156:Chocolate museums
3077:Ghana Cocoa Board
2993:Organic chocolate
2947:Aerated chocolate
2891:Chocolate truffle
2876:Chocolate pudding
2866:Chocolate liqueur
2826:Chocolate brownie
2821:Chocolate biscuit
2551:
2550:
2072:Nonatriacontanoic
2066:Octatriacontanoic
1603:"Methyl valerate"
1532:978-0-85186-884-4
1494:(23): 5527–5547.
1457:(26): 4479–4483.
762:Chemical compound
760:
759:
730:Related compounds
618:Hazard statements
565:-66.85·10 cm/mol
492:Colorless liquid
354:CompTox Dashboard
132:Interactive image
69:Propylacetic acid
3272:
3227:
3222:
3221:
3213:
3208:
3207:
2998:Fair trade cocoa
2881:Chocolate spread
2740:
2615:Chocolate liquor
2597:
2587:
2578:
2571:
2564:
2555:
2554:
2522:ω−12 Unsaturated
2503:ω−11 Unsaturated
2484:ω−10 Unsaturated
2187:Eicosapentaenoic
2181:Eicosatetraenoic
2145:Palmitolinolenic
2139:Myristolinolenic
2054:Hexatriacontylic
1829:
1822:
1815:
1806:
1805:
1799:
1798:
1788:
1765:Gastroenterology
1755:
1749:
1748:
1746:
1745:
1730:
1724:
1723:
1705:
1695:
1671:
1665:
1664:
1662:
1661:
1647:
1641:
1640:
1638:
1637:
1627:"Ethyl valerate"
1623:
1617:
1616:
1614:
1613:
1599:
1593:
1592:
1590:
1589:
1578:
1572:
1571:
1543:
1537:
1536:
1510:
1504:
1503:
1483:
1477:
1476:
1466:
1442:
1436:
1435:
1407:
1398:
1397:
1377:
1371:
1370:
1334:
1328:
1327:
1303:
1297:
1296:
1294:
1266:
1260:
1259:
1251:
1240:
1234:
1233:
1231:
1230:
1219:
1213:
1205:
1092:carboxylate salt
1088:physiological pH
1081:
1017:pentyl valerates
1009:methyl valerates
985:valeryl chloride
946:
797:
781:chemical formula
704:
697:
690:
675:
655:
651:
647:
643:
629:
625:
597:
483:
468:
462:
456:
449:Chemical formula
379:
378:
362:
360:
344:
307:
299:
287:
273:
243:
235:
224:
213:
205:
184:
163:
155:
134:
109:
101:
45:
36:
29:
25:
3280:
3279:
3275:
3274:
3273:
3271:
3270:
3269:
3240:
3239:
3238:
3233:
3232:
3225:
3211:
3195:
3166:Cocoa smuggling
3146:Chocolate bloom
3129:
3103:
2981:
2935:
2886:Chocolate syrup
2856:Chocolate gravy
2846:Chocolate coins
2792:
2738:
2732:
2636:
2631:Theobroma cacao
2595:
2589:
2585:
2582:
2552:
2547:
2516:
2497:
2478:
2425:ω−9 Unsaturated
2419:
2382:ω−7 Unsaturated
2376:
2341:Dihomo-linoleic
2301:12-Octadecenoic
2295:8-Tetradecenoic
2287:ω−6 Unsaturated
2281:
2236:Palmitovaccenic
2222:ω−5 Unsaturated
2216:
2199:Docosahexaenoic
2133:Myristolinoleic
2127:Myristovaccenic
2089:ω−3 Unsaturated
2083:
2024:Hentriacontylic
1842:
1833:
1803:
1802:
1756:
1752:
1743:
1741:
1732:
1731:
1727:
1672:
1668:
1659:
1657:
1651:"Amyl valerate"
1649:
1648:
1644:
1635:
1633:
1625:
1624:
1620:
1611:
1609:
1601:
1600:
1596:
1587:
1585:
1579:
1575:
1544:
1540:
1533:
1511:
1507:
1488:Green Chemistry
1484:
1480:
1443:
1439:
1432:
1408:
1401:
1378:
1374:
1335:
1331:
1304:
1300:
1267:
1263:
1241:
1237:
1228:
1226:
1222:Sigma-Aldrich.
1220:
1216:
1206:
1202:
1197:
1158:
1140:Pentyl valerate
1130:Methyl valerate
1116:
1100:pharmaceuticals
1075:
1069:
1063:
1048:
1025:
1013:ethyl valerates
993:
965:
944:
940:
936:
932:
928:
924:
920:
916:
912:
886:
878:isovaleric acid
874:trimethyl amine
858:isovaleric acid
846:
834:pentyl valerate
800:unpleasant odor
795:
791:
787:
783:
777:carboxylic acid
763:
756:
751:
731:
709:
708:
707:
706:
699:
692:
685:
681:
673:
638:
620:
606:
590:
562:
548:
531:
481:
471:
465:
459:
451:
437:
434:
429:
428:
417:
414:
413:
410:
404:
403:
400:
394:
393:
382:
363:
356:
347:
326:
310:
302:Valerate:
288:
276:
262:
253:
216:
208:Valerate:
187:
166:
158:Valerate:
137:
123:
112:
104:Valerate:
90:
76:
70:
68:
60:
24:
17:
12:
11:
5:
3278:
3268:
3267:
3262:
3260:Alkanoic acids
3257:
3252:
3250:GABA analogues
3235:
3234:
3231:
3230:
3216:
3201:
3200:
3197:
3196:
3194:
3193:
3192:
3191:
3186:
3178:
3173:
3168:
3163:
3158:
3153:
3148:
3143:
3137:
3135:
3131:
3130:
3128:
3127:
3122:
3117:
3111:
3109:
3105:
3104:
3102:
3101:
3096:
3091:
3086:
3081:
3080:
3079:
3069:
3064:
3059:
3054:
3049:
3044:
3039:
3034:
3027:
3022:
3017:
3012:
3007:
3006:
3005:
2995:
2989:
2987:
2983:
2982:
2980:
2979:
2974:
2969:
2964:
2959:
2954:
2949:
2943:
2941:
2937:
2936:
2934:
2933:
2928:
2926:Mint chocolate
2923:
2918:
2913:
2908:
2903:
2898:
2893:
2888:
2883:
2878:
2873:
2871:Chocolate milk
2868:
2863:
2858:
2853:
2848:
2843:
2841:Chocolate chip
2838:
2833:
2831:Chocolate cake
2828:
2823:
2818:
2817:
2816:
2806:
2800:
2798:
2794:
2793:
2791:
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2744:
2742:
2734:
2733:
2731:
2730:
2725:
2720:
2715:
2710:
2705:
2700:
2695:
2690:
2685:
2680:
2678:Phenethylamine
2675:
2670:
2665:
2660:
2655:
2650:
2644:
2642:
2638:
2637:
2635:
2634:
2627:
2622:
2617:
2612:
2607:
2601:
2599:
2591:
2590:
2581:
2580:
2573:
2566:
2558:
2549:
2548:
2546:
2545:
2539:
2533:
2530:4-Hexadecenoic
2526:
2524:
2518:
2517:
2515:
2514:
2507:
2505:
2499:
2498:
2496:
2495:
2488:
2486:
2480:
2479:
2477:
2476:
2470:
2464:
2458:
2452:
2446:
2436:
2429:
2427:
2421:
2420:
2418:
2417:
2411:
2405:
2399:
2393:
2386:
2384:
2378:
2377:
2375:
2374:
2368:
2362:
2356:
2350:
2344:
2338:
2332:
2326:
2320:
2310:
2304:
2298:
2291:
2289:
2283:
2282:
2280:
2279:
2273:
2267:
2261:
2255:
2245:
2239:
2233:
2226:
2224:
2218:
2217:
2215:
2214:
2208:
2202:
2196:
2190:
2184:
2178:
2172:
2166:
2160:
2154:
2148:
2142:
2136:
2130:
2124:
2118:
2112:
2106:
2100:
2093:
2091:
2085:
2084:
2082:
2081:
2078:Tetracontanoic
2075:
2069:
2063:
2057:
2051:
2045:
2039:
2033:
2027:
2021:
2015:
2009:
2003:
1997:
1991:
1985:
1979:
1973:
1967:
1961:
1955:
1949:
1943:
1937:
1931:
1925:
1919:
1913:
1907:
1901:
1895:
1889:
1883:
1877:
1871:
1865:
1859:
1852:
1850:
1844:
1843:
1832:
1831:
1824:
1817:
1809:
1801:
1800:
1750:
1725:
1666:
1642:
1618:
1594:
1573:
1554:(2): 141–243.
1538:
1531:
1505:
1478:
1437:
1431:978-3527306732
1430:
1399:
1388:(4): 561–567.
1372:
1345:(7): 769–788.
1329:
1298:
1261:
1246:, ed. (1911).
1244:Chisholm, Hugh
1235:
1224:"Valeric acid"
1214:
1199:
1198:
1196:
1193:
1192:
1191:
1186:
1180:
1174:
1169:
1164:
1157:
1154:
1153:
1152:
1147:
1142:
1137:
1135:Ethyl valerate
1132:
1127:
1122:
1115:
1112:
1108:hydrocortisone
1084:conjugate base
1073:
1067:
1047:
1044:
1029:gut microbiome
1024:
1021:
992:
989:
964:
961:
953:levulinic acid
949:
948:
942:
938:
934:
930:
926:
922:
918:
914:
885:
882:
845:
842:
838:food additives
830:ethyl valerate
793:
789:
785:
770:pentanoic acid
761:
758:
757:
752:
748:standard state
745:
742:
741:
732:
729:
726:
725:
721:
720:
717:
711:
710:
700:
693:
686:
671:
670:
669:
668:
666:
657:
656:
650:P303+P361+P353
639:
634:
631:
630:
621:
616:
613:
612:
607:
602:
599:
598:
591:
586:
583:
582:
572:
571:
567:
566:
563:
557:
554:
553:
550:
546:
536:
535:
534:4.97 g/100 mL
532:
527:
524:
523:
520:
514:
513:
510:
504:
503:
500:
494:
493:
490:
486:
485:
479:
473:
472:
469:
463:
457:
452:
447:
444:
443:
439:
438:
436:
435:
432:
424:
423:
422:
419:
418:
416:
415:
411:
408:
407:
405:
401:
398:
397:
389:
388:
387:
384:
383:
381:
380:
366:
364:
352:
349:
348:
346:
345:
336:
334:
328:
327:
325:
324:
320:
318:
312:
311:
309:
308:
300:
291:
289:
281:
278:
277:
275:
274:
265:
263:
258:
255:
254:
252:
251:
247:
245:
237:
236:
226:
218:
217:
215:
214:
206:
197:
195:
189:
188:
186:
185:
176:
174:
168:
167:
165:
164:
156:
147:
145:
139:
138:
136:
135:
126:
124:
117:
114:
113:
111:
110:
102:
93:
91:
86:
83:
82:
78:
77:
66:
62:
61:
59:Pentanoic acid
58:
52:
51:
47:
46:
38:
37:
21:Valerenic acid
15:
9:
6:
4:
3:
2:
3277:
3266:
3263:
3261:
3258:
3256:
3253:
3251:
3248:
3247:
3245:
3229:
3228:
3217:
3215:
3214:
3203:
3202:
3198:
3190:
3189:United States
3187:
3185:
3182:
3181:
3179:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3138:
3136:
3132:
3126:
3123:
3121:
3118:
3116:
3113:
3112:
3110:
3106:
3100:
3097:
3095:
3092:
3090:
3087:
3085:
3082:
3078:
3075:
3074:
3073:
3070:
3068:
3065:
3063:
3060:
3058:
3055:
3053:
3050:
3048:
3045:
3043:
3040:
3038:
3035:
3033:
3032:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3010:Big Chocolate
3008:
3004:
3001:
3000:
2999:
2996:
2994:
2991:
2990:
2988:
2984:
2978:
2975:
2973:
2970:
2968:
2965:
2963:
2962:Dutch process
2960:
2958:
2955:
2953:
2952:Broma process
2950:
2948:
2945:
2944:
2942:
2938:
2932:
2929:
2927:
2924:
2922:
2919:
2917:
2914:
2912:
2911:Hot chocolate
2909:
2907:
2904:
2902:
2899:
2897:
2894:
2892:
2889:
2887:
2884:
2882:
2879:
2877:
2874:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2854:
2852:
2849:
2847:
2844:
2842:
2839:
2837:
2834:
2832:
2829:
2827:
2824:
2822:
2819:
2815:
2812:
2811:
2810:
2809:Chocolate bar
2807:
2805:
2802:
2801:
2799:
2795:
2789:
2786:
2784:
2781:
2779:
2778:Raw chocolate
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
2746:
2745:
2743:
2741:
2735:
2729:
2726:
2724:
2721:
2719:
2716:
2714:
2711:
2709:
2706:
2704:
2701:
2699:
2696:
2694:
2691:
2689:
2686:
2684:
2683:Phenylalanine
2681:
2679:
2676:
2674:
2671:
2669:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2645:
2643:
2639:
2633:
2632:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2611:
2608:
2606:
2603:
2602:
2600:
2598:
2592:
2588:
2579:
2574:
2572:
2567:
2565:
2560:
2559:
2556:
2543:
2540:
2537:
2534:
2531:
2528:
2527:
2525:
2523:
2519:
2512:
2509:
2508:
2506:
2504:
2500:
2493:
2490:
2489:
2487:
2485:
2481:
2474:
2471:
2468:
2465:
2462:
2459:
2456:
2453:
2450:
2447:
2444:
2440:
2437:
2434:
2431:
2430:
2428:
2426:
2422:
2415:
2412:
2409:
2406:
2403:
2400:
2397:
2394:
2391:
2388:
2387:
2385:
2383:
2379:
2372:
2369:
2366:
2363:
2360:
2357:
2354:
2351:
2348:
2345:
2342:
2339:
2336:
2333:
2330:
2327:
2324:
2321:
2318:
2314:
2311:
2308:
2305:
2302:
2299:
2296:
2293:
2292:
2290:
2288:
2284:
2277:
2274:
2271:
2268:
2265:
2262:
2259:
2256:
2253:
2249:
2248:β-Eleostearic
2246:
2243:
2242:α-Eleostearic
2240:
2237:
2234:
2231:
2228:
2227:
2225:
2223:
2219:
2212:
2209:
2206:
2203:
2200:
2197:
2194:
2191:
2188:
2185:
2182:
2179:
2176:
2173:
2170:
2167:
2164:
2161:
2158:
2155:
2152:
2149:
2146:
2143:
2140:
2137:
2134:
2131:
2128:
2125:
2122:
2121:Laurolinoleic
2119:
2116:
2113:
2110:
2107:
2104:
2101:
2098:
2095:
2094:
2092:
2090:
2086:
2079:
2076:
2073:
2070:
2067:
2064:
2061:
2058:
2055:
2052:
2049:
2046:
2043:
2040:
2037:
2034:
2031:
2028:
2025:
2022:
2019:
2016:
2013:
2010:
2007:
2004:
2001:
1998:
1995:
1992:
1989:
1986:
1983:
1980:
1977:
1974:
1971:
1968:
1965:
1962:
1959:
1956:
1953:
1950:
1947:
1944:
1941:
1938:
1935:
1932:
1929:
1926:
1923:
1920:
1917:
1914:
1911:
1908:
1905:
1902:
1899:
1896:
1893:
1890:
1887:
1884:
1881:
1878:
1875:
1872:
1869:
1866:
1863:
1860:
1857:
1854:
1853:
1851:
1849:
1845:
1841:
1837:
1830:
1825:
1823:
1818:
1816:
1811:
1810:
1807:
1796:
1792:
1787:
1782:
1778:
1774:
1770:
1766:
1762:
1754:
1739:
1735:
1729:
1721:
1717:
1713:
1709:
1704:
1699:
1694:
1689:
1685:
1681:
1677:
1670:
1656:
1652:
1646:
1632:
1628:
1622:
1608:
1604:
1598:
1584:
1577:
1569:
1565:
1561:
1557:
1553:
1549:
1542:
1534:
1528:
1524:
1520:
1516:
1509:
1501:
1497:
1493:
1489:
1482:
1474:
1470:
1465:
1460:
1456:
1452:
1448:
1441:
1433:
1427:
1423:
1419:
1415:
1414:
1406:
1404:
1395:
1391:
1387:
1383:
1376:
1368:
1364:
1360:
1356:
1352:
1348:
1344:
1340:
1333:
1325:
1321:
1317:
1313:
1309:
1302:
1293:
1288:
1284:
1280:
1276:
1274:
1265:
1257:
1256:
1250:
1245:
1239:
1225:
1218:
1211:
1210:
1204:
1200:
1190:
1189:Valproic acid
1187:
1184:
1181:
1178:
1175:
1173:
1170:
1168:
1165:
1163:
1160:
1159:
1151:
1148:
1146:
1143:
1141:
1138:
1136:
1133:
1131:
1128:
1126:
1123:
1121:
1118:
1117:
1111:
1109:
1105:
1104:betamethasone
1101:
1097:
1093:
1089:
1085:
1079:
1072:
1066:
1061:
1057:
1053:
1043:
1041:
1037:
1035:
1030:
1020:
1018:
1014:
1010:
1006:
1002:
998:
988:
986:
982:
978:
974:
970:
960:
958:
954:
911:
910:
909:
907:
903:
902:valeraldehyde
899:
895:
891:
881:
879:
875:
871:
867:
866:amyl alcohols
863:
862:fusel alcohol
859:
855:
851:
841:
839:
835:
831:
827:
823:
819:
815:
811:
807:
806:
801:
782:
778:
775:
771:
767:
755:
749:
743:
740:
739:Hexanoic acid
736:
733:
728:
727:
722:
718:
716:
713:
712:
705:
698:
691:
667:
664:
663:
659:
658:
640:
637:
633:
632:
622:
619:
615:
614:
611:
608:
605:
601:
600:
596:
592:
589:
585:
584:
580:
578:
573:
568:
564:
560:
556:
555:
551:
545:
541:
538:
537:
533:
530:
526:
525:
521:
519:
518:Boiling point
516:
515:
511:
509:
508:Melting point
506:
505:
501:
499:
496:
495:
491:
488:
487:
480:
478:
475:
474:
453:
450:
446:
445:
440:
431:
430:
427:
420:
406:
396:
395:
392:
385:
377:
373:
372:DTXSID7021655
368:
367:
365:
355:
351:
350:
343:
338:
337:
335:
333:
330:
329:
322:
321:
319:
317:
314:
313:
306:
301:
298:
293:
292:
290:
284:
280:
279:
272:
267:
266:
264:
261:
257:
256:
249:
248:
246:
244:
239:
238:
234:
230:
227:
225:
223:ECHA InfoCard
220:
219:
212:
207:
204:
199:
198:
196:
194:
191:
190:
183:
178:
177:
175:
173:
170:
169:
162:
157:
154:
149:
148:
146:
144:
141:
140:
133:
128:
127:
125:
121:
116:
115:
108:
103:
100:
95:
94:
92:
89:
85:
84:
79:
74:
73:Lipid numbers
63:
57:
53:
48:
44:
39:
35:
30:
27:Valeric acid
22:
3223:
3209:
3161:Chocolatiers
3134:Other topics
3029:
3015:Chocolaterie
2728:Valeric acid
2727:
2703:Theophylline
2629:
2625:Cocoa solids
2620:Cocoa butter
2610:Flavor cocoa
2542:8-Eicosenoic
2536:Petroselinic
2442:
2316:
2313:Linolelaidic
2251:
2193:Clupanodonic
2151:Palmitidonic
1988:Pentacosylic
1964:Heneicosylic
1928:Pentadecylic
1867:
1768:
1764:
1753:
1742:. Retrieved
1740:. 2020-04-23
1737:
1728:
1683:
1679:
1669:
1658:. Retrieved
1654:
1645:
1634:. Retrieved
1630:
1621:
1610:. Retrieved
1606:
1597:
1586:. Retrieved
1576:
1551:
1547:
1541:
1514:
1508:
1491:
1487:
1481:
1454:
1450:
1440:
1411:
1385:
1381:
1375:
1342:
1338:
1332:
1315:
1311:
1301:
1282:
1278:
1272:
1264:
1253:
1238:
1227:. Retrieved
1217:
1207:
1203:
1177:Pivalic acid
1055:
1051:
1049:
1033:
1026:
994:
966:
950:
947:valeric acid
887:
853:
847:
836:are used as
825:
821:
803:
769:
766:Valeric acid
765:
764:
735:Butyric acid
661:
609:
576:
543:
316:RTECS number
182:ChEMBL268736
81:Identifiers
65:Other names
3255:Fatty acids
3184:Switzerland
3125:Switzerland
3020:Chocolatier
2972:Sugar crust
2804:Caffè mocha
2698:Theobromine
2668:Flavan-3-ol
2390:Palmitoleic
2359:Arachidonic
2323:γ-Linolenic
2230:Myristoleic
2169:α-Parinaric
2163:Stearidonic
2157:α-Linolenic
2109:Decadienoic
2048:Ceroplastic
2012:Nonacosylic
1952:Nonadecylic
1840:fatty acids
1686:(4): 1107.
1339:Chemosphere
1209:Merck Index
904:, which is
890:oxo process
884:Manufacture
826:pentanoates
715:Flash point
604:Signal word
502:0.930 g/cm
489:Appearance
442:Properties
229:100.003.344
161:CHEBI:31011
153:CHEBI:17418
3244:Categories
3108:By country
2758:Couverture
2713:Tryptophan
2708:Tryptamine
2688:Salsolinol
2663:Enkephalin
2658:Endorphins
2648:Anandamide
2641:Components
2605:Bulk cocoa
2596:Cocoa bean
2000:Carboceric
1982:Lignoceric
1976:Tricosylic
1916:Tridecylic
1892:Pelargonic
1744:2020-09-30
1660:2020-09-30
1636:2020-09-30
1612:2020-09-30
1588:2020-09-30
1229:2020-09-29
1195:References
1056:pentanoate
900:, forming
588:Pictograms
477:Molar mass
342:GZK92PJM7B
260:IUPHAR/BPS
193:ChemSpider
118:3D model (
107:10023-74-2
88:CAS Number
56:IUPAC name
2977:Tempering
2940:Processes
2916:beverages
2586:Chocolate
2408:Paullinic
2353:Sciadonic
2335:Pinolenic
2115:Lauroleic
2030:Lacceroic
1958:Arachidic
1904:Undecylic
1856:Propionic
1848:Saturated
1720:216075062
1680:Nutrients
1318:: 74–76.
1285:: 11–18.
1036:infection
977:anhydride
963:Reactions
917:+ CO + CH
822:valerates
779:with the
579:labelling
242:EC Number
3212:Category
2986:Industry
2957:Conching
2797:Products
2768:Gianduja
2753:Compound
2723:Tyrosine
2718:Tyramine
2673:Lecithin
2653:Caffeine
2511:Gadoleic
2492:Sapienic
2461:Nervonic
2396:Vaccenic
2329:Calendic
2307:Linoleic
2103:Decenoic
2097:Octenoic
2018:Melissic
2006:Montanic
1940:Margaric
1934:Palmitic
1922:Myristic
1886:Caprylic
1880:Enanthic
1795:30025704
1712:32316181
1473:20446282
1367:22682363
1156:See also
1114:Examples
1052:valerate
981:chloride
957:biofuels
906:oxidised
894:1-butene
850:valerian
662:NFPA 704
570:Hazards
561:(χ)
99:109-52-4
3226:Outline
3171:History
3115:Belgium
2967:Enrober
2906:Ganache
2449:Gondoic
2439:Elaidic
2402:Rumenic
2365:Adrenic
2258:Punicic
2036:Psyllic
1994:Cerotic
1970:Behenic
1946:Stearic
1874:Caproic
1868:Valeric
1862:Butyric
1786:6347096
1703:7230973
1568:3527563
1347:Bibcode
1098:-based
1096:steroid
1023:Biology
870:skatole
844:History
540:Acidity
498:Density
482:102.133
283:PubChem
3120:France
2814:brands
2748:Baking
2544:(20:1)
2538:(18:1)
2532:(16:1)
2513:(20:1)
2494:(16:1)
2475:(20:3)
2469:(20:2)
2463:(24:1)
2457:(22:1)
2455:Erucic
2451:(20:1)
2445:-18:1)
2435:(18:1)
2416:(20:3)
2410:(20:1)
2404:(18:2)
2398:(18:1)
2392:(16:1)
2373:(22:5)
2371:Osbond
2367:(22:4)
2361:(20:4)
2355:(20:3)
2349:(20:3)
2343:(20:2)
2337:(18:3)
2331:(18:3)
2325:(18:3)
2319:-18:2)
2309:(18:2)
2303:(18:1)
2297:(14:1)
2278:(20:4)
2272:(20:3)
2266:(18:3)
2260:(18:3)
2254:-18:3)
2244:(18:3)
2238:(16:1)
2232:(14:1)
2213:(24:6)
2207:(24:5)
2201:(22:6)
2195:(22:5)
2189:(20:5)
2183:(20:4)
2177:(20:3)
2171:(18:4)
2165:(18:4)
2159:(18:3)
2153:(16:4)
2147:(16:3)
2141:(14:3)
2135:(14:2)
2129:(14:1)
2123:(12:2)
2117:(12:1)
2111:(10:2)
2105:(10:1)
2042:Geddic
1910:Lauric
1898:Capric
1836:Lipids
1793:
1783:
1718:
1710:
1700:
1566:
1529:
1471:
1428:
1365:
1082:, the
1038:after
1015:, and
1005:esters
979:, and
898:syngas
876:, and
818:esters
810:esters
610:Danger
426:SMILES
305:114781
211:102757
172:ChEMBL
71:C5:0 (
50:Names
2901:Fudge
2788:White
2739:Types
2443:trans
2433:Oleic
2317:trans
2252:trans
2099:(8:1)
2080:(C40)
2074:(C39)
2068:(C38)
2062:(C37)
2056:(C36)
2050:(C35)
2044:(C34)
2038:(C33)
2032:(C32)
2026:(C31)
2020:(C30)
2014:(C29)
2008:(C28)
2002:(C27)
1996:(C26)
1990:(C25)
1984:(C24)
1978:(C23)
1972:(C22)
1966:(C21)
1960:(C20)
1954:(C19)
1948:(C18)
1942:(C17)
1936:(C16)
1930:(C15)
1924:(C14)
1918:(C13)
1912:(C12)
1906:(C11)
1900:(C10)
1716:S2CID
1054:, or
973:ester
969:amide
945:CHO →
925:CH=CH
892:from
814:Salts
774:alkyl
552:4.82
391:InChI
143:ChEBI
120:JSmol
2931:Mole
2783:Ruby
2773:Milk
2763:Dark
2473:Mead
1894:(C9)
1888:(C8)
1882:(C7)
1876:(C6)
1870:(C5)
1864:(C4)
1858:(C3)
1791:PMID
1708:PMID
1564:PMID
1527:ISBN
1469:PMID
1426:ISBN
1363:PMID
1050:The
999:and
991:Uses
929:→ CH
896:and
832:and
816:and
796:COOH
768:or
646:P280
642:P273
628:H412
624:H314
332:UNII
297:7991
271:1061
203:7701
1781:PMC
1773:doi
1769:155
1698:PMC
1688:doi
1556:doi
1519:doi
1496:doi
1459:doi
1418:doi
1390:doi
1355:doi
1320:doi
1287:doi
1106:or
1062:is
1060:ion
1058:,
1001:WHO
997:FAO
824:or
788:(CH
577:GHS
359:EPA
286:CID
3246::
1838::
1789:.
1779:.
1767:.
1763:.
1736:.
1714:.
1706:.
1696:.
1684:12
1682:.
1678:.
1653:.
1629:.
1605:.
1562:.
1552:24
1550:.
1525:.
1492:19
1490:.
1467:.
1455:49
1453:.
1449:.
1424:.
1402:^
1386:34
1384:.
1361:.
1353:.
1343:89
1341:.
1316:21
1314:.
1310:.
1281:.
1277:.
1252:.
1042:.
1019:.
1011:,
975:,
971:,
959:.
941:CH
937:CH
933:CH
921:CH
872:,
812:.
784:CH
737:,
652:,
648:,
644:,
626:,
581::
549:)
542:(p
464:10
2577:e
2570:t
2563:v
2441:(
2315:(
2250:(
1828:e
1821:t
1814:v
1797:.
1775::
1747:.
1722:.
1690::
1663:.
1639:.
1615:.
1591:.
1570:.
1558::
1535:.
1521::
1502:.
1498::
1475:.
1461::
1434:.
1420::
1396:.
1392::
1369:.
1357::
1349::
1326:.
1322::
1295:.
1289::
1283:8
1275:"
1232:.
1080:O
1078:O
1076:C
1074:9
1071:H
1068:4
1065:C
943:2
939:2
935:2
931:3
927:2
923:2
919:3
915:2
913:H
852:(
794:3
792:)
790:2
786:3
703:0
696:1
689:3
547:a
544:K
470:2
467:O
461:H
458:5
455:C
361:)
357:(
122:)
75:)
23:.
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