(3Z)-Nonenal is an unsaturated aldehyde that occurs naturally in various plants.
 Structural formula of (3Z)-nonenal
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Other names
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C9H16O | |
| Molar mass | 140.226 g·mol−1 |
| Appearance | Colorless oil[1] |
| Boiling point | 105 °C (221 °F; 378 K) (20 mmHg)[2] |
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| GHS labelling:[1] | |
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| H315, H319, H335 | |
| P261, P305+P351+P338 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence
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(3Z)-Nonenal is a flavor component in various plants, such as cucumber, honeydew melon, and soy.[3][4][5][6] It is the biosynthetic precursor to (2E)-nonenal, formed by isomerases.[6] It also occurs in the brown algae Laminaria angustata.[7][8] In the oysterplant, it contributes to its oyster-like taste.[9]
Biosynthesis
editIn various plants such as cucumbers and melons, (3Z)-nonenal is formed from linoleic acid to 9-hydroperoxy-10,12-octadecadienoic acid and its splitting.[4][6][clarification needed] In Laminaria angustata, formation also occurs via arachidonic acid and its 12-hydroperoxide.[7][8][how?]
Synthesis
edit(3Z)-Nonenal can be synthesized by oxidation of (3Z)-nonen-1-ol with pyridinium chlorochromate.[2] The compound can also be obtained through a multi-step reaction starting from 1,4-butanediol.[2][how?]
Properties
editThe scent is described as fruity, melony, or maritime in low concentrations.[9] In an in vitro study, (3Z)-nonenal acted as a fungicide against various types of fungi.[3]
References
edit- ^ a b "(Z)-3-Nonenal". 2023-08-27.
{{cite web}}: Missing or empty|url=(help) - ^ a b c Tadahiko Kajiwara, Yoshinobu Odake, Akikazu Hatanaka (1975). "Synthesis of 3Z-Nonenal and 3Z,6Z-Nonadienal". Agricultural and Biological Chemistry. 39 (8): 1617–1621. doi:10.1080/00021369.1975.10861815.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ a b S. F. Vaughn, H. W. Gardner (1993-10-01). "Lipoxygenase-derived aldehydes inhibit fungi pathogenic on soybean". Journal of Chemical Ecology. 19 (10): 2337–2345. Bibcode:1993JCEco..19.2337V. doi:10.1007/BF00979668. PMID 24248580.
- ^ a b Nathalie Tijet, Claus Schneider, Bernard L. Muller, Alan R. Brash (2001-02-01). "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): 281–289. doi:10.1006/abbi.2000.2218. PMID 11368353.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Akikazu Hatanaka, Tadahiko Kajiwara, Takahiro Harada (1975-12-01). "Biosynthetic pathway of cucumber alcohol: Trans-2,cis-6-nonadienol via cis-3,cis-6-nonadienal". Phytochemistry. 14 (12): 2589–2592. Bibcode:1975PChem..14.2589H. doi:10.1016/0031-9422(75)85230-7.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ a b c David R. Phillips, Jennifer A. Matthew, John Reynolds, G.Roger Fenwick (1979-01-01). "Partial purification and properties of a cis-3: trans-2-enal isomerase from cucumber fruit". Phytochemistry. 18 (3): 401–404. Bibcode:1979PChem..18..401P. doi:10.1016/S0031-9422(00)81874-9.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ a b Kangsadan Boonprab, Kenji Matsui, Yoshihiko Akakabe, Norishige Yotsukura, Tadahiko Kajiwara (2003-07-01). "Hydroperoxy-arachidonic acid mediated n-hexanal and (Z)-3- and (E)-2-nonenal formation in Laminaria angustata". Phytochemistry. 63 (6): 669–678. Bibcode:2003PChem..63..669B. doi:10.1016/S0031-9422(03)00026-8. PMID 12842139.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ a b Kangsadan Boonprab, Kenji Matsui, Yoshihiko Akakabe, Miyuki Yoshida, Norishige Yotsukura, Anong Chirapart, Tadahiko Kajiwara (2006-11-27). "Formation of Aldehyde Flavor (n-hexanal, 3Z-nonenal and 2E-nonenal) in the Brown Alga, Laminaria Angustata". Journal of Applied Phycology. 18 (3–5): 409–412. Bibcode:2006JAPco..18..409B. doi:10.1007/s10811-006-9038-6.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ a b Estelle Delort, Alain Jaquier, Christian Chapuis, Mark Rubin, Christian Starkenmann (2012-11-28). "Volatile Composition of Oyster Leaf (Mertensia maritima (L.) Gray)". Journal of Agricultural and Food Chemistry. 60 (47): 11681–11690. Bibcode:2012JAFC...6011681D. doi:10.1021/jf303395q. PMID 23140514.
{{cite journal}}: CS1 maint: multiple names: authors list (link)