(3Z)-Nonenal Explained

Imagefile:Z3_nonenal.svg
Imagecaption:Structural formula of (3Z)-nonenal
(3Z)-Nonenal

(3Z)-Nonenal is an unsaturated aldehyde that occurs naturally in various plants.

Occurrence

(3Z)-Nonenal is a flavor component in various plants, such as cucumber, honeydew melon, and soy.[1] [2] [3] It is the biosynthetic precursor to (2E)-nonenal, formed by isomerases.[4] It also occurs in the brown algae Laminaria angustata.[5] [6] In the oysterplant, it contributes to its oyster-like taste.[7]

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. In Laminaria angustata, formation also occurs via arachidonic acid and its 12-hydroperoxide.

Synthesis

(3Z)-Nonenal can be synthesized by oxidation of (3Z)-nonen-1-ol with pyridinium chlorochromate.[8] The compound can also be obtained through a multi-step reaction starting from 1,4-butanediol.

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

  1. 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 .
  2. 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 .
  3. 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 .
  4. 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 .
  5. 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 .
  6. 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 .
  7. 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 .
  8. 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.

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