Dolichodial

Dolichodial is a natural chemical compound with two aldehyde groups, which belongs to the group of iridoids.

Dolichodial

Names
IUPAC name 2-Methyl-5-(3-oxo-1-propen-2-yl)cyclopentanecarbaldehyde
Identifiers
CAS Number	60478-52-6 (A) Y 3671-76-9 (B) Y 1127-67-9 (C) N 5951-57-5 (A') Y 1127-66-8 (B') N 864826-30-2 (B, B', C or C')
3D model (JSmol)	Interactive image
ChEBI	CHEBI:4685 Y
ChemSpider	390862
PubChem CID	534263
UNII	1KLH0PK5RS (A) Y 48D28040JM (B) Y D08WL9YC5Q (A') Y
CompTox Dashboard (EPA)	DTXSID00331826
SMILES CC1CCC(C1C=O)C(=C)C=O
Properties
Chemical formula	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

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')

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.