Dolichodial

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Dolichodial
Dolichodial.svg
Names
IUPAC name
2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
Properties
C10H14O2
Molar mass 166.22 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dolichodial is a natural chemical compound with two aldehyde groups, which belongs to the group of iridoids.

Chemistry[edit]

It has in its five-membered ring three asymmetric carbon atoms and accordingly exists in four diastereomeric pairs of enantiomers. The pairs with a different stereochemistry of dolichodial are called anisomorphal and peruphasmal.

Stereoisomers of dolichodial

  • (1R,2S,5S) = (−)-Dolichodial (A)
  • (1S,2S,5S) = (+)-Anisomorphal (B)
  • (1S,2S,5R) = Peruphasmal (C)
  • (1S,2S,5R) = D
  • (1S,2R,5R) = (+)-Dolichodial (A’)
  • (1R,2R,5R) = (−)-Anisomorphal (B’)
  • (1S,2R,5S) = Peruphasmal (C’)
  • (1R,2R,5S) = D’

Occurrence[edit]

Dolichodial and its stereoisomers can be found in the essential oils of certain plants, and also in the defensive secretions of some insect species.[1][2][3]

References[edit]

  1. ^ Tschuch G, Lindemann P, Moritz G (2008). "An unexpected mixture of substances in the defensive secretion of the Tubuliferan thrips, Callococcus fuscipennis". Journal of Chemical Ecology. 34: 742–747. doi:10.1007/s10886-008-9494-3. 
  2. ^ Boevé JL, Braekman JC, Daloze D, Houart M, Pasteels JM (1984). "Defensive secretions of Nematinae larvae (Symphyta - Tenthredinidae)". Cellular and Molecular Life Sciences. 40: 546–547. doi:10.1007/BF01982322. 
  3. ^ Dossey AT, Walse S, Edison AS (2008). "Developmental and geographical variation in the chemical defense of the walkingstick insect Anisomorpha buprestoides". Journal of Chemical Ecology. 34 (5): 584–590. doi:10.1007/s10886-008-9457-8. PMID 18401661.