Dolichodial is a natural
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with two
aldehyde group
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group ...
s, which belongs to the group of
iridoid
Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, mos ...
s.
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.
(1S,2R,3S)-(–)-Dolichodial Stereoisomer A V.1.svg, (1''R'',2''S'',5''S'')-(–)-Dolichodial (A)
(1R,2S,3R)-(+)-Dolichodial Stereoisomer A V.1.svg, (1''S'',2''R'',5''R'')-(+)-Dolichodial (A')
(1S,2S,3S)-(+)-Anisomorphal Stereoisomer B V.1.svg, (1''S'',2''S'',5''S'')-(+)-Anisomorphal (B)
(1R,2R,3R)-(–)-Anisomorphal Stereoisomer B V.1.svg, (1''R'',2''R'',5''R'')-(–)-Anisomorphal (B')
(1R,2R,3S)-Peruphasmal Stereoisomer C V.1.svg, (1''R'',2''S'',5''R'')-Peruphasmal (C)
(1S,2S,3R)-Peruphasmal Stereoisomer C V.1.svg, (1''S'',2''R'',5''S'')-Peruphasmal (C')
(1R,2S,3S)-Stereoisomer D V.1.svg, (1''S'',2''S'',5''R'')-Stereoisomer (D)
(1S,2R,3R)-Stereoisomer D V.1.svg, (1''R'',2''R'',5''S'')-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.
References
{{reflist
Conjugated aldehydes
Iridoids
Cyclopentanes
Vinylidene compounds