Chemistry:Dolichodial
From HandWiki
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| Names | |
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| IUPAC name
2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
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| Identifiers | |
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3D model (JSmol)
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PubChem CID
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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). | |
| Infobox references | |
Tracking categories (test):
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')
-(%E2%80%93)-Dolichodial_Stereoisomer_A_V.1.svg)
-(%2B)-Dolichodial_Stereoisomer_A_V.1.svg)
-(%2B)-Anisomorphal_Stereoisomer_B_V.1.svg)
-(%E2%80%93)-Anisomorphal_Stereoisomer_B_V.1.svg)
-Peruphasmal_Stereoisomer_C_V.1.svg)
-Peruphasmal_Stereoisomer_C_V.1.svg)
-Stereoisomer_D_V.1.svg)
-Stereoisomer_D_V.1.svg)
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
- ↑ "An unexpected mixture of substances in the defensive secretion of the Tubuliferan thrips, Callococcus fuscipennis". Journal of Chemical Ecology 34 (6): 742–747. 2008. doi:10.1007/s10886-008-9494-3. PMID 18506530.
- ↑ "Defensive secretions of Nematinae larvae (Symphyta - Tenthredinidae)". Cellular and Molecular Life Sciences 40 (6): 546–547. 1984. doi:10.1007/BF01982322.
- ↑ "Developmental and geographical variation in the chemical defense of the walkingstick insect Anisomorpha buprestoides". Journal of Chemical Ecology 34 (5): 584–590. 2008. doi:10.1007/s10886-008-9457-8. PMID 18401661. https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=21467&content=PDF.
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