Dolichodial

Dolichodial
Names
	IUPAC name 2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
Identifiers
CAS Number	5951-57-5 (A or A') ; 864826-30-2 (B, B', C or C'); 913835-24-3 (C); 60478-52-6 (A) ; 3671-76-9 (B) ; 1198-22-7 (A') ; 1127-66-8 (B'); 1127-67-9 (C) (or C'?);
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:4685 ;
ChemSpider	390862;
PubChem CID	534263;
UNII	D08WL9YC5Q (A or A') ; 1KLH0PK5RS (A) ; 48D28040JM (B) ;
CompTox Dashboard (EPA)	DTXSID00331826 ;
	SMILES CC1CCC(C1C=O)C(=C)C=O;
Properties
Chemical formula	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).
	Infobox references

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)
(1S,2S,5S) = (+)-Anisomorphal (B)
(1R,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

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: 742–747. doi:10.1007/s10886-008-9494-3.
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.
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.

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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: 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.