(3Z)-Nonenal

Organic compound in various plants Z3_nonenal.svg Structural formula of (3Z)-nonenal (3Z)-Nonenal (3Z)-Non-3-enal (Z)-3-Nonenal (Z)-Non-3-enal cis-3-Nonenal 31823-43-5 191226 6431042 4936380 1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h6-7,9H,2-5,8H2,1H3/b7-6- YXEAENVLZOODMT-SREVYHEPSA-N CCCCC/C=C\CC=O 9 16 1 Colorless oil 105 (20 mmHg) (Z)-3-Nonenal 2023-08-27 07 Warning 315 319 335 261 305+351+338 (3Z)-Nonenal is an unsaturated aldehyde that occurs naturally in various plants. Occurrence left|thumb|The oysterplant, also known as sea bluebells, contains (3Z)-nonenal (3Z)-Nonenal is a flavor component in various plants, such as cucumber, honeydew melon, and soy.S. F. Vaughn, H. W. Gardner Lipoxygenase-derived aldehydes inhibit fungi pathogenic on soybean Journal of Chemical Ecology 19 10 1993-10-01 10.1007/BF00979668 2337–2345 24248580 1993JCEco..19.2337V Nathalie Tijet, Claus Schneider, Bernard L. Muller, Alan R. Brash Biogenesis of Volatile Aldehydes from Fatty Acid Hydroperoxides: Molecular Cloning of a Hydroperoxide Lyase (CYP74C) with Specificity for both the 9- and 13-Hydroperoxides of Linoleic and Linolenic Acids Archives of Biochemistry and Biophysics 386 2 2001-02-01 10.1006/abbi.2000.2218 281–289 11368353 Akikazu Hatanaka, Tadahiko Kajiwara, Takahiro Harada Biosynthetic pathway of cucumber alcohol: Trans-2,cis-6-nonadienol via cis-3,cis-6-nonadienal Phytochemistry 14 12 1975-12-01 10.1016/0031-9422(75)85230-7 2589–2592 1975PChem..14.2589H It is the biosynthetic precursor to (2E)-nonenal, formed by isomerases.David R. Phillips, Jennifer A. Matthew, John Reynolds, G.Roger Fenwick Partial purification and properties of a cis-3: trans-2-enal isomerase from cucumber fruit Phytochemistry 18 3 1979-01-01 10.1016/S0031-9422(00)81874-9 401–404 1979PChem..18..401P It also occurs in the brown algae Laminaria angustata.Kangsadan Boonprab, Kenji Matsui, Yoshihiko Akakabe, Norishige Yotsukura, Tadahiko Kajiwara Hydroperoxy-arachidonic acid mediated n-hexanal and (Z)-3- and (E)-2-nonenal formation in Laminaria angustata Phytochemistry 63 6 2003-07-01 10.1016/S0031-9422(03)00026-8 669–678 12842139 2003PChem..63..669B Kangsadan Boonprab, Kenji Matsui, Yoshihiko Akakabe, Miyuki Yoshida, Norishige Yotsukura, Anong Chirapart, Tadahiko Kajiwara Formation of Aldehyde Flavor (n-hexanal, 3Z-nonenal and 2E-nonenal) in the Brown Alga, Laminaria Angustata Journal of Applied Phycology 18 3–5 2006-11-27 10.1007/s10811-006-9038-6 409–412 2006JAPco..18..409B In the oysterplant, it contributes to its oyster-like taste.Estelle Delort, Alain Jaquier, Christian Chapuis, Mark Rubin, Christian Starkenmann Volatile Composition of Oyster Leaf (Mertensia maritima (L.) Gray) Journal of Agricultural and Food Chemistry 60 47 2012-11-28 10.1021/jf303395q 11681–11690 23140514 2012JAFC...6011681D Biosynthesis In various plants such as cucumbers and melons, (3Z)-nonenal is formed from linoleic acid to 9-hydroperoxy-10,12-octadecadienoic acid and its splitting.October 2024 In Laminaria angustata, formation also occurs via arachidonic acid and its 12-hydroperoxide.October 2024 Synthesis (3Z)-Nonenal can be synthesized by oxidation of (3Z)-nonen-1-ol with pyridinium chlorochromate.Tadahiko Kajiwara, Yoshinobu Odake, Akikazu Hatanaka Synthesis of 3Z-Nonenal and 3Z,6Z-Nonadienal Agricultural and Biological Chemistry 39 8 1975 10.1080/00021369.1975.10861815 1617–1621 free The compound can also be obtained through a multi-step reaction starting from 1,4-butanediol.October 2024 Properties The scent is described as fruity, melony, or maritime in low concentrations. In an in vitro study, (3Z)-nonenal acted as a fungicide against various types of fungi. References Category:Alkenals Category:Skin chemical irritants