Dolichodial
Dolichodial
Chemical compound
Dolichodial is a natural chemical compound with two aldehyde groups, which belongs to the group of iridoids.
Quick Facts Names, Identifiers ...
| Names | |
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| IUPAC name
2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde | |
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3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
PubChem CID |
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| UNII |
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CompTox Dashboard (EPA) |
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| 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).
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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.
- (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')
-(–)-Dolichodial_Stereoisomer_A_V.1.svg){kind=link}
-(+)-Dolichodial_Stereoisomer_A_V.1.svg){kind=link}
-(+)-Anisomorphal_Stereoisomer_B_V.1.svg){kind=link}
-(–)-Anisomorphal_Stereoisomer_B_V.1.svg){kind=link}
-Peruphasmal_Stereoisomer_C_V.1.svg){kind=link}
-Peruphasmal_Stereoisomer_C_V.1.svg){kind=link}
-Stereoisomer_D_V.1.svg){kind=link}
-Stereoisomer_D_V.1.svg){kind=link}
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]
- 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.