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Dolichodial

From Wikipedia, the free encyclopedia
Dolichodial
Names
IUPAC name
2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • CC1CCC(C1C=O)C(=C)C=O
Properties
C10H14O2
Molar mass 166.220 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Chemistry

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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.

Occurrence

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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

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  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.