Verbenol, alpha-pinene, and verbenone enantiomers
(1S,4S,5S)-cis-verbenol

Bark beetle, Ips paraconfusus pheromone component produced from (S)-(-)-alpha-pinene (below).

CAS: 1845-30-3
(S)-(-)-alpha-pinene
(1S,5S)-(-)-alpha-pinene

Monoterpene in many conifers. Minus enantiomer.

CAS: 7785-26-4
(-)-trans-verbenol
(1S,4R,5S)-(-)-trans-verbenol

Pheromone component of bark beetle Dendroctonus brevicomis produced from (S)-alpha-pinene (above). Minus enantiomer.

CAS: 19890-02-9
(+)-trans-verbenol
(1R,4S,5R)-(+)-trans-verbenol

Not a pheromone component but small amounts of (1R,4S,5R)-(+)-trans-verbenol converted from (R)-(+)-alpha-pinene (below) by bark beetles Dendroctonus brevicomis and Ips paraconfusus. Plus enantiomer.

CAS: ?
(R)-(+)-alpha-pinene
(1R,5R)-(+)-alpha-pinene

Monoterpene in many conifers. Plus enantiomer.

CAS: 7785-70-8
(S)-(-)-verbenone
(1S,5S)-(-)-verbenone

Repellent pheromone of Dendroctonus brevicomis, produced by males. Minus enantiomer.

CAS: 7785-70-8