dolichodial
{{Chembox
| ImageFile = Dolichodial Structural Formula V.2.svg
| ImageSize = 150px
| IUPACName = 2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 60478-52-6
| CASNo_Comment = (A)
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1 = 3671-76-9
| CASNo1_Comment = (B)
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo2 = 1127-67-9
| CASNo2_Comment=(C)
| CASNo2_Ref = {{cascite|changed|CAS}}
| CASNo3= 5951-57-5
| CASNo3_Comment = (A')
| CASNo3_Ref = {{cascite|correct|CAS}}
| CASNo4= 1127-66-8
| CASNo4_Comment = (B')
| CASNo4_Ref = {{cascite|changed|CAS}}
| CASNo5 = 864826-30-2
| CASNo5_Comment = (B, B', C or C')
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1KLH0PK5RS
| UNII_Comment = (A)
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 48D28040JM
| UNII1_Comment = (B)
| UNII3_Ref = {{fdacite|correct|FDA}}
| UNII3 = D08WL9YC5Q
| UNII3_Comment = (A')
| PubChem = 534263
| ChemSpiderID = 390862
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4685
| SMILES = CC1CCC(C1C=O)C(=C)C=O
}}
|Section2={{Chembox Properties
| C=10 | H=14 | O=2
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
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.
(1S,2R,3S)-(–)-Dolichodial Stereoisomer A V.1.svg|(1R,2S,5S)-(–)-Dolichodial (A)
(1R,2S,3R)-(+)-Dolichodial Stereoisomer A V.1.svg|(1S,2R,5R)-(+)-Dolichodial (A')
(1S,2S,3S)-(+)-Anisomorphal Stereoisomer B V.1.svg|(1S,2S,5S)-(+)-Anisomorphal (B)
(1R,2R,3R)-(–)-Anisomorphal Stereoisomer B V.1.svg|(1R,2R,5R)-(–)-Anisomorphal (B')
(1R,2R,3S)-Peruphasmal Stereoisomer C V.1.svg|(1R,2S,5R)-Peruphasmal (C)
(1S,2S,3R)-Peruphasmal Stereoisomer C V.1.svg|(1S,2R,5S)-Peruphasmal (C')
(1R,2S,3S)-Stereoisomer D V.1.svg|(1S,2S,5R)-Stereoisomer (D)
(1S,2R,3R)-Stereoisomer D V.1.svg|(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.{{cite journal |vauthors=Tschuch G, Lindemann P, Moritz G | date = 2008 | title = An unexpected mixture of substances in the defensive secretion of the Tubuliferan thrips, Callococcus fuscipennis | journal = Journal of Chemical Ecology | volume = 34 | issue = 6 | pages = 742–747 | doi=10.1007/s10886-008-9494-3| pmid = 18506530 | s2cid = 19787509 }}{{cite journal |vauthors=Boevé JL, Braekman JC, Daloze D, Houart M, Pasteels JM | date = 1984 | title = Defensive secretions of Nematinae larvae (Symphyta - Tenthredinidae) | journal = Cellular and Molecular Life Sciences | volume = 40 | issue = 6 | pages = 546–547 | doi =10.1007/BF01982322| s2cid = 28094203 | hdl = 2013/ULB-DIPOT:oai:dipot.ulb.ac.be:2013/81443 | hdl-access = free }}{{cite journal |vauthors=Dossey AT, Walse S, Edison AS | year = 2008 | title = Developmental and geographical variation in the chemical defense of the walkingstick insect Anisomorpha buprestoides | journal = Journal of Chemical Ecology | volume = 34 | pages = 584–590 | doi = 10.1007/s10886-008-9457-8 | pmid=18401661 | issue=5| s2cid = 10765114 | url=https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=21467&content=PDF | url-access = subscription }}