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In 1803 C. Martrès published a manuscript on the oil of bitter almonds: "Recherches sur la nature et le siège de l'amertume et de l'odeur des amandes amères" (Research on the nature and location of the bitterness and the smell of bitter almonds). However, the memoir was largely ignored until an
1474:. This status was reaffirmed after a review in 2005. It is accepted in the European Union as a flavoring agent. Toxicology studies indicate that it is safe and non-carcinogenic in the concentrations used for foods and cosmetics, and may even have
1608:
Loch, Christine; Reusch, Helmut; Ruge, Ingrid; Godelmann, Rolf; Pflaum, Tabea; Kuballa, Thomas; Schumacher, Sandra; Lachenmeier, Dirk W. (2016). "Benzaldehyde in cherry flavour as a precursor of benzene formation in beverages".
1856:
Adams, T. B.; Cohen, S. M.; Doull, J.; Feron, V. J.; Goodman, J. I.; Marnett, L. J.; Munro, I. C.; Portoghese, P. S.; Smith, R. L. (1 August 2005). "The FEMA GRAS assessment of benzyl derivatives used as flavor ingredients".
781:
689:
994:
oil, benzaldehyde can be extracted from a number of other natural sources. Synthetic benzaldehyde is the flavoring agent in imitation almond extract, which is used to flavor cakes and other baked goods.
1206:
661:
1273:
in air at room temperature, causing a common impurity in laboratory samples. Since the boiling point of benzoic acid is much higher than that of benzaldehyde, it may be purified by
1841:
Process for preparing natural benzaldehyde and acetaldehyde, natural benzaldehyde and acetaldehyde compositions, products produced thereby and organoleptic utilities therefor.
1568:
766:
774:
2169:
1431:. A small amount of benzaldehyde solution is placed on a fume board near the honeycombs. The bees then move away from the honey combs to avoid the fumes. The
2225:
1356:
In industrial settings, benzaldehyde is used chiefly as a precursor to other organic compounds, ranging from pharmaceuticals to plastic additives. The
922:
2178:
2115:
1769:
1128:
Benzaldehyde and similar chemicals occur naturally in many foods. Most of the benzaldehyde that people eat is from natural plant foods, such as
788:
1486:
1471:
409:
2173:
1892:
Beltran-Garcia, Miguel J.; Estarron-Espinosa, Mirna; Ogura, Tetsuya (1997). "Volatile
Compounds Secreted by the Oyster Mushroom (
1003:
Benzaldehyde was first extracted in 1803 by the French pharmacist Martrès. His experiments focused on elucidating the nature of
1572:
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flavor to foods and scented products, including e-cigarette liquids. It is sometimes used in cosmetics products.
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731:
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307:
216:
2089:
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178:
1822:
1510:
1306:
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37:
1925:"The benzaldehyde oxidation paradox explained by the interception of peroxy radical by benzyl alcohol"
1571:. Institute for Occupational Safety and Health of the German Social Accident Insurance. Archived from
138:
2220:
1462:
As used in food, cosmetics, pharmaceuticals, and soap, benzaldehyde is "generally regarded as safe" (
228:
27:
1112:) for 5 to 80 hours, followed by distillation of the formed benzaldehyde. This reaction also yields
1507:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1489:. Benzaldehyde does not accumulate in human tissues. It is metabolized and then excreted in urine.
811:
355:
1700:
1482:
1074:
551:
131:
2210:
1669:
2132:
2063:
2036:
1793:. Passos, Maria Laura., Ribeiro, Claudio P. Boca Raton, Florida: CRC Press. 2010. p. 87.
2188:
1924:
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1763:
1447:
703:
673:
537:
57:
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1939:
316:
67:
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8:
1716:
Nouvelles expériences sur les amandes amères et sur l'huile volatile qu'elles fournissent
1314:
1254:
1097:
1041:
of synthetic and 100 tonnes of natural benzaldehyde were produced annually. Liquid phase
198:
107:
97:
1943:
1022:
866:
359:
220:
158:
2165:
2017:
1816:
1372:
1338:
1310:
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891:
1594:
1245:
2215:
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2009:
1957:
1874:
1804:
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1522:
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are the main routes. Numerous other methods have been developed, such as the partial
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860:
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1999:
1947:
1905:
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1428:
1388:
1290:
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1159:
1117:
1105:
1101:
1021:
and
Antoine Boutron Charlard, two French chemists, produced benzaldehyde. In 1832,
953:
564:
526:
437:
1718:
Robiquet, Boutron-Charlard, Annales de chimie et de physique, 44 (1830), 352–382,
1364:
1360:
1066:
1018:
824:
727:
2038:
Why Do Bees Buzz?: Why Do Bees Buzz? Fascinating
Answers to Questions about Bees
1518:
280:
2065:
Storey's Guide to
Keeping Honey Bees: Honey Production, Pollination, Bee Health
1376:
1318:
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1278:
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883:
2004:
1987:
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848:
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1808:
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991:
515:
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2013:
1961:
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1754:
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1404:
1357:
800:
1727:
773:
1952:
1416:
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462:
229:
189:
1909:
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1302:
1172:
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1151:
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1004:
583:
327:
1891:
899:
Except where otherwise noted, data are given for materials in their
1481:
For a 70 kg human, the lethal dose is estimated at 50 ml. An
1368:
968:
965:
746:
255:
1337:
With diols, including many sugars, benzaldehyde condenses to form
739:
137:
130:
1790:
Innovation in food engineering : new techniques and products
1380:
1235:
1163:
1136:
1129:
1050:
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1080:
A significant quantity of natural benzaldehyde is produced from
1467:
1350:
1223:
1144:
1062:
983:
975:
961:
169:
1648:
Brühne, Friedrich and Wright, Elaine (2002) "Benzaldehyde" in
1485:
of 15 mg/day has been identified for benzaldehyde by the
2113:
1439:
from the bee hive with less risk to both bees and beekeeper.
1140:
1093:
1038:
291:
149:
120:
343:
2133:"Health and Environmental Effects Profile for Benzaldehyde"
1463:
1147:
979:
485:
246:
2062:
Sanford, Malcolm T.; Bonney, Richard E. (1 January 2010).
1732:[Investigations of the radical of benzoic acid].
2114:
Friedrich Brühne; Elaine Wright (2007), "Benzaldehyde",
1988:"Final report on the safety assessment of benzaldehyde"
1607:
1415:. (The scheme above depicts only one of the two formed
1120:
of benzaldehyde obtained in this way is controversial.
2170:
Organisation for
Economic Co-operation and Development
2131:
1855:
1158:
breaks up under enzyme catalysis into benzaldehyde,
2166:
2035:Evans, Elizabeth; Butler, Carol (9 February 2010).
1321:and another molecule is simultaneously oxidized to
1100:solution between 90 °C and 150 °C with a
1541:
1317:): one molecule of the aldehyde is reduced to the
709:
1730:"Untersuchungen über das Radikal der Benzoesäure"
1728:Wöhler, Friedrich and Liebig, Justus von (1832).
2197:
1375:, benzaldehyde is converted into derivatives of
279:
1367:. Benzaldehyde is also a precursor to certain
974:It is a colorless liquid with a characteristic
762:
510:−57.12 °C (−70.82 °F; 216.03 K)
106:
2179:Benzaldehyde description at ChemicalLand21.com
2117:Ullmann's Encyclopedia of Industrial Chemistry
2041:. Rutgers University Press. pp. 177–178.
1650:Ullmann's Encyclopedia of Industrial Chemistry
2061:
1487:United States Environmental Protection Agency
1768:: CS1 maint: multiple names: authors list (
1349:Benzaldehyde is commonly employed to confer
1281:can be formed from benzaldehyde by means of
520:178.1 °C (352.6 °F; 451.2 K)
2034:
1835:Wienes, Charles and Pittet, Alan O. (1985)
1548:(95th ed.), CRC press, pp. 3–34,
1285:. Reaction of benzaldehyde with anhydrous
1898:Journal of Agricultural and Food Chemistry
1885:
735:
358:
219:
197:
2226:Substances discovered in the 19th century
2003:
1951:
1753:
1644:
1642:
1640:
1446:in the presence of a catalyst to produce
1313:upon treatment with concentrated alkali (
1253:Benzaldehyde contributes to the scent of
971:and one of the most industrially useful.
315:
1985:
1695:extract was published in 1819: Martrès
1499:
393:InChI=1/C6H5CHO/c8-6-7-4-2-1-3-5-7/h1-6H
2161:International Chemical Safety Card 0102
1896:) and Their Antibacterial Activities".
383:InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
354:
2198:
2130:
1922:
1637:
1587:
964:substituent. It is among the simplest
819:192 °C (378 °F; 465 K)
210:
1981:
1979:
1977:
1975:
1973:
1971:
1851:
1849:
1847:
1783:
1781:
1779:
1545:CRC Handbook of Chemistry and Physics
1092:: the cinnamaldehyde is heated in an
805:64 °C (147 °F; 337 K)
386:Key: HUMNYLRZRPPJDN-UHFFFAOYSA-N
177:
157:
2090:"Synthesis of Phenyl-2-Nitropropene"
1305:the condensation of benzaldehyde to
1992:International Journal of Toxicology
1269:Benzaldehyde is easily oxidized to
396:Key: HUMNYLRZRPPJDN-UHFFFAOYAE
270:
254:
13:
2068:. Storey Publishing. p. 167.
1968:
1923:Sankar, Meenakshisundaram (2014).
1844:
1776:
1671:The Cook's Illustrated Baking Book
1363:is prepared from benzaldehyde and
1007:, the poisonous compound found in
758:
36:
26:
14:
2237:
2154:
2120:(7th ed.), Wiley, p. 11
1986:Andersen, Alan (1 January 2006).
1674:. America's Test Kitchen. 2013.
1395:
1329:
1244:
1222:
1205:
1178:
1029:first synthesized benzaldehyde.
907:
679:
449:
2189:Carcinogenicity Potency Project
2124:
2107:
2082:
2055:
2028:
1916:
1829:
1721:
1150:contain significant amounts of
903:(at 25 °C , 100 kPa).
1709:
1688:
1662:
1623:10.1016/j.foodchem.2016.03.034
1601:
1561:
1535:
1511:The Royal Society of Chemistry
1017:. Further work on the oil by
455:
443:
1:
2184:ChemSub Online: Benzaldéhyde.
1492:
1422:
1123:
1032:
31:Skeletal (structural) formula
1859:Food and Chemical Toxicology
1387:starts with the addition of
1264:
7:
1569:"GESTIS Substance database"
1542:Haynes, William M. (2014),
1519:10.1039/9781849733069-FP001
837:or concentration (LD, LC):
22:
10:
2242:
1478:(anti-cancer) properties.
1427:Benzaldehyde is used as a
998:
982:, and is commonly used in
2005:10.1080/10915810600716612
1871:10.1016/j.fct.2004.11.014
1701:"Sur les amandes amères,"
1457:
1442:Benzaldehyde reacts with
1309:. Benzaldehyde undergoes
897:
872:
833:
660:
655:
596:
430:
405:
370:
90:
78:
66:
56:
51:
21:
1746:10.1002/jlac.18320030302
1706:, vol. 5, pages 289–296.
1658:10.1002/14356007.a03_463
718:Precautionary statements
1652:. Wiley-VCH, Weinheim.
1483:acceptable daily intake
1344:
1162:and two equivalents of
1075:Gatterman-Koch reaction
855:1300 mg/kg (rat, oral)
552:Magnetic susceptibility
1821:: CS1 maint: others (
769:
532:6.95 g/L (25 °C)
42:
32:
1932:Nature Communications
1838:U.S. patent 4,617,419
1734:Annalen der Pharmacie
1513:. 2014. p. 908.
1454:and other chemicals.
1448:phenyl-2-nitropropene
768:
81:Benzenecarboxaldehyde
40:
30:
1704:Journal de Pharmacie
1435:can then remove the
751:(fire diamond)
480:strongly refractive
68:Preferred IUPAC name
41:Ball-and-stick model
1944:2014NatCo...5.3332S
1894:Pleurotus ostreatus
1595:"Benzaldehyde_msds"
1383:. The synthesis of
1373:aldol condensations
1339:benzylidene acetals
1315:Cannizzaro reaction
1259:Pleurotus ostreatus
527:Solubility in water
500:1.044 g/mL, liquid
470: g·mol
61:Benzenecarbaldehyde
18:
1998:(Suppl 1): 11–27.
1953:10.1038/ncomms4332
1311:disproportionation
1297:, while alcoholic
1243:
1234:
930:Infobox references
892:Benzaldehyde oxime
873:Related compounds
770:
43:
33:
16:
1910:10.1021/jf960876i
1528:978-0-85404-182-4
1476:anti-carcinogenic
1450:, a precursor to
1391:to benzaldehyde:
1299:potassium cyanide
1241:
1232:
1037:As of 1999, 7000
1027:Justus von Liebig
990:. A component of
938:Chemical compound
936:
935:
879:Related compounds
861:Safety data sheet
704:Hazard statements
558:-60.78·10 cm/mol
478:colorless liquid
339:CompTox Dashboard
139:Interactive image
132:Interactive image
47:
46:
2233:
2221:Phenyl compounds
2148:
2147:
2145:
2143:
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2111:
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2102:
2100:
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2079:
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2053:
2052:
2032:
2026:
2025:
2007:
1983:
1966:
1965:
1955:
1929:
1920:
1914:
1913:
1889:
1883:
1882:
1865:(8): 1207–1240.
1853:
1842:
1840:
1833:
1827:
1826:
1820:
1812:
1785:
1774:
1773:
1767:
1759:
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1713:
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1584:
1582:
1580:
1565:
1559:
1558:
1539:
1533:
1532:
1503:
1399:
1389:hydrocyanic acid
1333:
1291:acetic anhydride
1255:oyster mushrooms
1248:
1226:
1209:
1195:
1182:
1160:hydrogen cyanide
1106:sodium carbonate
1073:of benzene (the
1023:Friedrich Wöhler
956:consisting of a
954:organic compound
920:
914:
911:
910:
825:Explosive limits
790:
783:
776:
761:
741:
737:
733:
729:
725:
711:
683:
647:
620:
597:Thermochemistry
565:Refractive index
469:
457:
451:
445:
438:Chemical formula
363:
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347:
345:
319:
283:
272:
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231:
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141:
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110:
85:Benzoic aldehyde
23:
19:
15:
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2236:
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2230:
2196:
2195:
2157:
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2056:
2049:
2033:
2029:
1984:
1969:
1927:
1921:
1917:
1890:
1886:
1854:
1845:
1836:
1834:
1830:
1814:
1813:
1801:
1787:
1786:
1777:
1761:
1760:
1755:2027/hvd.hxdg3f
1726:
1722:
1714:
1710:
1693:
1689:
1682:
1668:
1667:
1663:
1647:
1638:
1606:
1602:
1593:
1592:
1588:
1578:
1576:
1575:on 3 March 2016
1567:
1566:
1562:
1556:
1540:
1536:
1529:
1505:
1504:
1500:
1495:
1460:
1425:
1365:dimethylaniline
1361:malachite green
1347:
1301:can be used to
1267:
1251:
1250:
1249:
1239:
1228:
1227:
1220:
1212:
1211:
1210:
1202:
1201:
1196:
1193:
1189:
1184:
1183:
1176:
1126:
1104:(most commonly
1067:benzal chloride
1035:
1019:Pierre Robiquet
1011:, the fruit of
1001:
951:
947:
939:
932:
927:
926:
925: ?)
916:
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795:
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706:
692:
676:
651:−3525.1 kJ/mol
648:
645:
639:
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632:
631:Std enthalpy of
621:
618:
612:
608:
605:
604:Std enthalpy of
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2155:External links
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1740:(3): 249–282.
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1611:Food Chemistry
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1497:
1496:
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1424:
1421:
1403:The resulting
1401:
1400:
1377:cinnamaldehyde
1346:
1343:
1335:
1334:
1319:benzyl alcohol
1287:sodium acetate
1279:Benzyl alcohol
1266:
1263:
1242:2 ×
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1187:
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1169:
1168:
1125:
1122:
1118:natural status
1090:aldol reaction
1084:obtained from
1082:cinnamaldehyde
1065:hydrolysis of
1059:benzyl alcohol
1034:
1031:
1009:bitter almonds
1000:
997:
949:
945:
937:
934:
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901:standard state
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884:Benzyl alcohol
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83:Phenylmethanal
80:
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9:
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2238:
2227:
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2219:
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2214:
2212:
2211:Benzaldehydes
2209:
2207:
2204:
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2201:
2194:
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1429:bee repellent
1420:
1418:
1414:
1413:mandelic acid
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1406:
1398:
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1385:mandelic acid
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1016:
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1014:Prunus dulcis
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992:bitter almond
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624:−36.8 kJ/mol
623:
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592:(25 °C)
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39:
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29:
25:
24:
20:
17:Benzaldehyde
2193:
2142:16 September
2140:. Retrieved
2136:
2126:
2116:
2109:
2097:. Retrieved
2093:
2084:
2064:
2057:
2037:
2030:
1995:
1991:
1935:
1931:
1918:
1904:(10): 4049.
1901:
1897:
1893:
1887:
1862:
1858:
1831:
1789:
1764:cite journal
1737:
1733:
1723:
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1711:
1703:
1696:
1690:
1670:
1664:
1649:
1614:
1610:
1603:
1589:
1577:. Retrieved
1573:the original
1563:
1544:
1537:
1506:
1501:
1480:
1461:
1441:
1437:honey frames
1426:
1402:
1355:
1348:
1336:
1323:benzoic acid
1275:distillation
1271:benzoic acid
1268:
1258:
1252:
1231:
1217:benzaldehyde
1216:
1215:
1171:
1134:
1127:
1114:acetaldehyde
1079:
1043:chlorination
1036:
1012:
1002:
973:
960:ring with a
942:Benzaldehyde
941:
940:
888:Benzoic acid
834:
812:Autoignition
747:
695:
662:
640:
613:
568:
539:
490:almond-like
292:RTECS number
91:Identifiers
79:Other names
72:Benzaldehyde
1452:amphetamine
1444:nitroethane
1417:enantiomers
1405:cyanohydrin
1358:aniline dye
1110:bicarbonate
952:CHO) is an
867:J. T. Baker
849:median dose
835:Lethal dose
814:temperature
801:Flash point
690:Signal word
475:Appearance
431:Properties
417:O=Cc1ccccc1
217:100.002.601
179:ChEMBL15972
159:CHEBI:17169
2200:Categories
1493:References
1423:Niche uses
1409:hydrolysed
1371:dyes. Via
1124:Occurrence
1086:cassia oil
1069:, and the
1033:Production
986:-flavored
674:Pictograms
633:combustion
463:Molar mass
317:TA269SD04T
190:ChemSpider
119:3D model (
98:CAS Number
58:IUPAC name
2168:from the
2099:7 October
1817:cite book
1809:500683261
1617:: 74–77.
1579:21 August
1466:) by the
1433:beekeeper
1265:Reactions
1173:Amygdalin
1156:glycoside
1152:amygdalin
1135:Almonds,
1098:alcoholic
1055:oxidation
1047:oxidation
1005:amygdalin
969:aldehydes
829:1.4–8.5%
732:P301+P312
665:labelling
606:formation
584:Viscosity
328:UN number
238:202-860-4
230:EC Number
2216:Solvents
2174:Archived
2022:32177208
2014:16835129
1962:24567108
1938:: 3332.
1879:15950815
1631:27041300
1369:acridine
1303:catalyze
1137:apricots
966:aromatic
748:NFPA 704
656:Hazards
554:(χ)
299:CU437500
108:100-52-7
2206:Flavors
2172:(OECD)
1940:Bibcode
1699:(1819)
1381:styrene
1307:benzoin
1293:yields
1236:glucose
1164:glucose
1154:. This
1130:almonds
1094:aqueous
1051:toluene
999:History
958:benzene
923:what is
921: (
696:Warning
578:1.5456
496:Density
468:106.124
268:PubChem
2094:Erowid
2072:
2045:
2020:
2012:
1960:
1877:
1807:
1797:
1678:
1629:
1552:
1525:
1468:US FDA
1458:Safety
1351:almond
1145:cherry
1143:, and
1141:apples
1116:. The
1063:alkali
1039:tonnes
984:cherry
978:-like
976:almond
962:formyl
918:verify
915:
863:(SDS)
588:1.321
410:SMILES
256:D02314
170:ChEMBL
52:Names
2018:S2CID
1928:(PDF)
988:sodas
545:1.64
375:InChI
332:1990
150:ChEBI
121:JSmol
2144:2017
2101:2023
2070:ISBN
2043:ISBN
2010:PMID
1958:PMID
1875:PMID
1823:link
1805:OCLC
1795:ISBN
1770:link
1697:fils
1676:ISBN
1627:PMID
1581:2012
1550:ISBN
1523:ISBN
1472:FEMA
1470:and
1464:GRAS
1379:and
1345:Uses
1289:and
1233:2 ×
1148:seed
1102:base
1045:and
1025:and
980:odor
740:P501
736:P330
728:P270
724:P264
710:H302
538:log
486:Odor
308:UNII
247:KEGG
2000:doi
1948:doi
1906:doi
1867:doi
1750:hdl
1742:doi
1654:doi
1619:doi
1615:206
1515:doi
1419:).
1411:to
1407:is
1261:).
1199:HCN
1108:or
1077:).
1057:of
1049:of
663:GHS
644:298
617:298
344:EPA
281:240
271:CID
199:235
2202::
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2092:.
2016:.
2008:.
1996:25
1994:.
1990:.
1970:^
1956:.
1946:.
1934:.
1930:.
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726:,
667::
636:(Δ
609:(Δ
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1942::
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611:f
574:)
572:D
569:n
567:(
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456:O
453:6
450:H
447:7
444:C
346:)
342:(
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