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词条 Dolichodial
释义

  1. Chemistry

  2. Occurrence

  3. References

{{Chembox
| ImageFile = Dolichodial.svg
| ImageSize = 150px
| IUPACName = 2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 5951-57-5
| CASNo_Comment = (A or A')
| CASNo1 = 864826-30-2
| CASNo1_Comment = (B, B', C or C')
| CASNo2 = 913835-24-3
| CASNo2_Comment=(C)
| CASNo3 = 60478-52-6
| CASNo3_Comment = (A)
| CASNo4 = 3671-76-9
| CASNo4_Comment = (B)
| CASNo5= 1198-22-7
| CASNo5_Comment = (A')
| CASNoOther = 1127-66-8 (B')
1127-67-9 (C) (or C'?)
| 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.

  • (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

1. ^{{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 | pages = 742–747 | doi=10.1007/s10886-008-9494-3}}
2. ^{{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 | pages = 546–547 | doi =10.1007/BF01982322}}
3. ^{{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| url=https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=21467&content=PDF }}

3 : Aldehydes|Iridoids|Cyclopentanes

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