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Dolichodial

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Dolichodial
Names
IUPAC name 2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • CC1CCC(C1C=O)C(=C)C=O
Properties
Chemical formula C10H14O2
Molar mass 166.220 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

Chemistry

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.

  • (1R,2S,5S)-(–)-Dolichodial (A) (1R,2S,5S)-(–)-Dolichodial (A)
  • (1S,2R,5R)-(+)-Dolichodial (A') (1S,2R,5R)-(+)-Dolichodial (A')
  • (1S,2S,5S)-(+)-Anisomorphal (B) (1S,2S,5S)-(+)-Anisomorphal (B)
  • (1R,2R,5R)-(–)-Anisomorphal (B') (1R,2R,5R)-(–)-Anisomorphal (B')
  • (1R,2S,5R)-Peruphasmal (C) (1R,2S,5R)-Peruphasmal (C)
  • (1S,2R,5S)-Peruphasmal (C') (1S,2R,5S)-Peruphasmal (C')
  • (1S,2S,5R)-Stereoisomer (D) (1S,2S,5R)-Stereoisomer (D)
  • (1R,2R,5S)-Stereoisomer (D') (1R,2R,5S)-Stereoisomer (D')

Occurrence

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

References

  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 (6): 742–747. doi:10.1007/s10886-008-9494-3. PMID 18506530. S2CID 19787509.
  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 (6): 546–547. doi:10.1007/BF01982322. S2CID 28094203.
  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. S2CID 10765114.
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