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.
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(1R,2S,5S)-(–)-Dolichodial (A)
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(1S,2R,5R)-(+)-Dolichodial (A')
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(1S,2S,5S)-(+)-Anisomorphal (B)
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(1R,2R,5R)-(–)-Anisomorphal (B')
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(1R,2S,5R)-Peruphasmal (C)
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(1S,2R,5S)-Peruphasmal (C')
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(1S,2S,5R)-Stereoisomer (D)
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(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.[1][2][3]
References
- ^ 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.
- ^ 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.
- ^ 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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