Dolichodial

Dolichodial
Names
	IUPAC name 2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
Identifiers
CAS Number	60478-52-6 (A) ; 3671-76-9 (B) ; 1127-67-9 (C) ; 5951-57-5 (A') ; 1127-66-8 (B') ; 864826-30-2 (B, B', C or C');
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:4685 ;
ChemSpider	390862;
PubChem CID	534263;
UNII	1KLH0PK5RS (A) ; 48D28040JM (B) ; D08WL9YC5Q (A') ;
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,2R,5R)-(+)-Dolichodial (A')
(1S,2S,5S)-(+)-Anisomorphal (B)
(1R,2R,5R)-(–)-Anisomorphal (B')
(1R,2S,5R)-Peruphasmal (C)
(1S,2R,5S)-Peruphasmal (C')
(1S,2S,5R)-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.^[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. hdl:2013/ULB-DIPOT:oai:dipot.ulb.ac.be:2013/81443. 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.

[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. hdl:2013/ULB-DIPOT:oai:dipot.ulb.ac.be:2013/81443. 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.

[1]

[2]

[3]