Dolichodial

Dolichodial

Names
IUPAC name 2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
Identifiers
CAS Number	5951-57-5 (A or A') 864826-30-2 (B, B', C or C') 913835-24-3 (C) 60478-52-6 (A) 3671-76-9 (B) 1198-22-7 (A') 1127-66-8 (B') 1127-67-9 (C) (or C'?)
ChEBI	CHEBI:4685 Y
ChemSpider	390862
Jmol 3D model	Interactive image
PubChem	534263
SMILES CC1CCC(C1C=O)C(=C)C=O
Properties
Chemical formula	C10H14O2
Molar mass	166.22 g·mol−1
Vapor pressure	{{{value}}}
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.

Stereoisomers of dolichodial

• (1R,2S,5S) = (−)-Dolichodial (A)
• (1S,2S,5S) = (+)-Anisomorphal (B)
• (1S,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.