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2-Nonenal
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changed 477215034 2-Nonenal.png 240 Skeletal formula of 2-nonenal 2-Nonenal-3D-balls.png 230 Ball-and-stick model of the 2-nonenal molecule Non-2-enal correct CAS 18829-56-6 (trans) correct ?? 60784-31-8 (cis) correct ?? 2463-53-8 (cis/trans mixture) 142592 5283335 correct EBI 450072 correct chemspider 4446456 242-609-6 (trans) 219-562-5 correct FDA 8VEO649985 (trans) correct FDA ARM1W3309Z (cis) correct FDA 93C6BZW2TV (cis/trans mixture) 1/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7+ BSAIUMLZVGUGKX-BQYQJAHWBS correct chemspider 1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7+ correct chemspider BSAIUMLZVGUGKX-BQYQJAHWSA-N O=C/C=C/CCCCCC (E)O=C/C=\/CCCCCC (Z)O=CC=CCCCCCC (unspecified)
9 16 1 Colorless liquid 188.00 to 190.00 at 760.00 mmHg
External MSDS 1 2 0 79 2-Nonenal https://pubchem.ncbi.nlm.nih.gov/compound/5283335#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov en 07 Warning 315 264 280 302+352 321 332+313 362
2-Nonenal is an unsaturated aldehyde. The colorless liquid is an important aroma component of aged beer Santos J. R. Carneiro J. R. Guido L. F. Almeida P. J. Rodrigues J. A. Barros A. A. Determination of E-2-nonenal by high-performance liquid chromatography with UV detection - Assay for the evaluation of beer ageing Journal of Chromatography A 2008 985 1–2 395–402 10.1016/S0021-9673(02)01396-1 12580508 and buckwheat, and is insoluble in water.Janeš, D. Kantar, D. Kreft, S. Prosen, H. Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS Food Chemistry 2008 112 1 120–4 10.1016/j.foodchem.2008.05.048
2-Nonenal reacts with the Wittig reagent methylenetriphenylphosphorane to give hexyl-1,3-butadiene.Stereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes Organic Syntheses 2011 88 342 10.15227/orgsyn.088.0342 free Robert J. Ely James P. Morken
Odor characteristics
The odour of the mixed isomers is perceived as "fatty, green, waxy, cucumber, melon".2-nonenal https://scentsandflavors.com/database/9dbb5655-bde8-469c-8a0c-fc2cf2b3f1bd scentsandflavors.com 2 August 2026 The odour of the (Z)-isomer is "orris, fatty, waxy, cucumber"(Z)-2-nonenal https://scentsandflavors.com/database/9dbb5677-5897-448b-9474-df3b52e6b237 scentsandflavors.com 2 August 2026 whilst that of the (E)-isomer is "fatty, green, cucumber, aldehydic".(E)-2-nonenal https://scentsandflavors.com/database/9dbb50fd-0a69-4cae-91f4-7f37a0f5c8c9 scentsandflavors.com 2 August 2026 Its odor has been associated with human body odor alterations during aging.Haze, S. Gozu, Y. Nakamura, S. Kohno, Y. Sawano, K. Ohta, H. Yamazaki, K. 2-Nonenal Newly Found in Human Body Odor Tends to Increase with Aging Journal of Investigative Dermatology 2001 116 4 520–4 10.1046/j.0022-202x.2001.01287.x 11286617 free
See also
trans,cis-2,6-Nonadienal - Structurally related, aroma of cucumber
6-Nonenal - Structurally related, aroma of cantaloupe
References
Further reading
Morrison G. C. Nazaroff W. W. Ozone interactions with carpet: secondary emissions of aldehydes Environmental Science & Technology 2002 36 10 2185–92 12038828 10.1021/es0113089 2002EnST...36.2185M
Category:Fatty aldehydes
Category:Flavors
Category:Alkenals