Verbenol

Last updated
Verbenol
+ cis Verbenol.svg
(+)-cis-verbenol
- cis Verbenol.svg
(-)-cis-verbenol
+ trans Verbenol.svg
(+)-trans-verbenol
- trans Verbenol.svg
(-)-trans-verbenol
Names
Preferred IUPAC name
4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol
Other names
2-Pine-4-ol
Pin-2-en-4-ol
Identifiers
3D model (JSmol)
ECHA InfoCard 100.006.793 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • Key: WONIGEXYPVIKFS-UHFFFAOYSA-N
  • CC1=CC(C2CC1C2(C)C)O
Properties
C10H16O
Molar mass 152.237 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Verbenol (2-pine-4-ol) is a group of stereoisomeric bicyclic monoterpene alcohols. These compounds have been found to be active components of insect pheromones and essential oils.

Contents

Isomers

Four stereoisomers of verbenol are known. For the cis isomer, the two methyl groups (-CH3) are on the same side of the carbon ring as the hydroxy group (-OH), and for the trans isomer, they are on the opposite sides. Again, there are enantiomers of each form that exhibit optical activity, that is, turn the plane of linearly polarized light as it passes through the substance or its solution. trans-Verbenol is a mountain pine beetle pheromone that attracts insects to a tree. [1] cis-Verbenol is an aggregation pheromone of Ipstypographus [2] and Dendroctonus ponderosae Hopkins. [3]

Enantiomeric composition

Typically, verbenol and related cyclic monoterpenes are available as non‐racemic mixtures of their enantiomers. [4] There are methods to increase enantiomeric excess (optical purity) of verbenol and to isolate individual enantiomers. [5] [6]

Related Research Articles

<span class="mw-page-title-main">Stereoisomerism</span> When molecules have the same atoms and bond structure but differ in 3D orientation

In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer.

<span class="mw-page-title-main">Nepetalactone</span> Chemical compound

Nepetalactone is a name for multiple iridoid analog stereoisomers. Nepetalactones are produced by Nepeta cataria (catnip) and many other plants belonging to the genus Nepeta, in which they protect these plants from herbivorous insects by functioning as insect repellents. They are also produced by many aphids, in which they are sex pheromones. Nepetalactones are cat attractants, and cause the behavioral effects that catnip induces in domestic cats. However, they affect visibly only about two thirds of adult cats. They produce similar behavioral effects in many other felids, especially in lions and jaguars. In 1941, the research group of Samuel M. McElvain was the first to determine the structures of nepetalactones and several related compounds.

<span class="mw-page-title-main">Meso compound</span> Optically inactive isomer in a set of stereoisomers

A meso compound or meso isomer is an optically inactive isomer in a set of stereoisomers, at least two of which are optically active. This means that despite containing two or more stereocenters, the molecule is not chiral. A meso compound is superposable on its mirror image. Two objects can be superposed if all aspects of the objects coincide and it does not produce a "(+)" or "(-)" reading when analyzed with a polarimeter. The name is derived from the Greek mésos meaning “middle”.

<span class="mw-page-title-main">Bark beetle</span> Subfamily of beetles

A bark beetle is the common name for the subfamily of beetles Scolytinae. Previously, this was considered a distinct family (Scolytidae), but is now understood to be a specialized clade of the "true weevil" family (Curculionidae). Although the term "bark beetle" refers to the fact that many species feed in the inner bark (phloem) layer of trees, the subfamily also has many species with other lifestyles, including some that bore into wood, feed in fruit and seeds, or tunnel into herbaceous plants. Well-known species are members of the type genus Scolytus, namely the European elm bark beetle S. multistriatus and the large elm bark beetle S. scolytus, which like the American elm bark beetle Hylurgopinus rufipes, transmit Dutch elm disease fungi (Ophiostoma). The mountain pine beetle Dendroctonus ponderosae, southern pine beetle Dendroctonus frontalis, and their near relatives are major pests of conifer forests in North America. A similarly aggressive species in Europe is the spruce ips Ips typographus. A tiny bark beetle, the coffee berry borer, Hypothenemus hampei is a major pest on coffee plantations around the world.

<span class="mw-page-title-main">Mountain pine beetle</span> Species of beetle

The mountain pine beetle is a species of bark beetle native to the forests of western North America from Mexico to central British Columbia. It has a hard black exoskeleton, and measures approximately 5 millimetres, about the size of a grain of rice.

<span class="mw-page-title-main">Verbenone</span> Chemical compound

Verbenone is a natural organic compound classified as a terpene that is found naturally in a variety of plants. The chemical has a pleasant characteristic odor. Besides being a natural constituent of plants, it and its analogs are insect pheromones. In particular, verbenone when formulated in a long-lasting matrix has an important role in the control of bark beetles such as the mountain pine beetle and the Southern pine bark beetle.

<i>Thanasimus formicarius</i> Species of beetle

The ant beetle, also known as the European red-bellied clerid, is a medium size insect, rather soft-bodied, with strong mandibles that can tear between the hard sclerotized integument of bark beetles. Larvae and adults are common predators of bark beetles in Europe.

<i>trans</i>-Cyclooctene Chemical compound

trans-Cyclooctene is a cyclic hydrocarbon with the formula [–(CH2)6CH=CH–], where the two C–C single bonds adjacent to the double bond are on opposite sides of the latter's plane. It is a colorless liquid with a disagreeable odor.

<i>Dendroctonus</i> Genus of beetles

Dendroctonus is a genus of bark beetles. It includes several species notorious for destroying trees in the forests of North America. The genus has a symbiotic relationship with many different yeasts, particularly those in the genera Candida and Pichia that aid in digestion and pheromone production.

<span class="mw-page-title-main">Isomer</span> Chemical compounds with the same molecular formula but different atomic arrangements

In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Diamond and graphite are a familiar example; they are isomers of carbon. Isomerism refers to the existence or possibility of isomers.

<span class="mw-page-title-main">Lineatin</span> Chemical compound

Lineatin is a pheromone produced by female striped ambrosia beetle, Trypodendron lineatum Olivier. These kinds of beetles are responsible for extensive damage of coniferous forest infestation in Europe and North America. Since lineatin can act as lures used for mass-trapping of T. lineatum, it is being studied to apply as a pest control reagent.

<span class="mw-page-title-main">European spruce bark beetle</span> Species of beetle

The European spruce bark beetle, is a species of beetle in the weevil subfamily Scolytinae, the bark beetles, and is found from Europe to Asia Minor and some parts of Africa.

<i>Dendroctonus frontalis</i> Species of beetle

Dendroctonus frontalis, the southern pine beetle, often shortened to simply SPB, is a species of bark beetle native to the forests of the southern United States, Mexico and Central America. It has recently expanded its range to the northeastern United States, where it is considered an invasive species and has destroyed massive amounts of pine forest.

(<i>S</i>)-Ipsdienol Chemical compound

(S)-Ipsdienol is a terpene alcohol. It is one of the major aggregation pheromones of the bark beetle. It was first identified from Ips confusus, in which it is believed to be a principle sex attractant. It is suggested that the compound plays a role in interspecies communication between Ips latidens and Ips ini, facilitating reductions in competition for breeding material and/or mating interference.

(−)-α-Pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (−)-α-pinene-forming]. This enzyme catalyses the following chemical reaction

<i>Ips</i> (beetle) Genus of beetles

Ips is a genus of beetles in the family Curculionidae, the true weevils. They are bark beetles, members of the subfamily Scolytinae. Species are distributed throughout the Northern Hemisphere. Some are known as introduced species in Australia and Africa. Many species are pests of forest trees, especially pines and spruces. They are known commonly as engraver beetles, ips engraver beetles, and pine engravers.

<span class="mw-page-title-main">Lavandulol</span> Chemical compound

Lavandulol is a monoterpene alcohol found in a variety of essential oils such as lavender oil. The term refers to either of two enantiomers. The (R)-enantiomer is natural and has an aroma described as "weak floral, herbal odor with slightly lemon-like, fresh citrus fruity nuance"; the (S)-enantiomer has only a weak odor.

<i>Dendroctonus valens</i> Species of beetle

Dendroctonus valens, the red turpentine beetle, is a species of bark beetle native to the forests of North America, Mexico, Guatemala and Honduras. It has been introduced to China where it has become invasive. In its native range it causes little damage, but in China it is a destructive pest and has killed more than six million pine trees.

<i>Ips pini</i> Species of beetle

Ips pini, also known as the pine engraver or North American pine engraver, is a species of typical bark beetle in the family Curculionidae that exists primarily in North America. Among the broadly distributed species across the entirety of North America, populations of these beetles are further broken down into distinctive geographical ranges with a distinctive feature of how the groups produce the enantiomeric composition of ipsdienol—the major pheromone component produced by males.

<span class="mw-page-title-main">Insect pheromones</span> Neurotransmitters used by insects

Insect pheromones are neurotransmitters that serve the chemical communication between individuals of an insect species. They thus differ from kairomones, in other words, neurotransmitters that transmit information to non-species organisms. Insects produce pheromones in special glands and release them into the environment. In the pheromone receptors of the sensory cells of the recipient, they produce a nerve stimulus even in very low concentrations, which ultimately leads to a behavioral response. Intraspecific communication of insects via these substances takes place in a variety of ways and serves, among other things, to find sexual partner, to maintain harmony in a colony of socially living insects, to mark territories or to find nest sites and food sources.

References

  1. "New pheromone insight may help predict mountain pine beetle outbreaks" . Retrieved 26 March 2018.
  2. Jakus, R.; Blazenec, M. (2002). "Influence of proportion of (4S)-cis-verbenol in pheromone bait on Ips typographus (Col., Scolytidae) catch in pheromone trap barrier and in single traps". Journal of Applied Entomology. 126 (6): 306–311. doi:10.1046/j.1439-0418.2002.00659.x. S2CID   83484064.
  3. Miller, Daniel R. (1991). "Cis-Verbenol: An aggregation pheromone for the mountain pine beetle, Dendroctonus ponderosae Hopkins (Coleoptera: Scolytidae)". J. Entomol. Soc. Brit. Columbia 88: 34-38.
  4. Gambliel, H.; Croteau, R. (1984). "Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration". Journal of Biological Chemistry. 259 (2): 740–748. doi: 10.1016/S0021-9258(17)43520-4 . PMID   6693393.
  5. Kovalenko, Vitaly et al. Practical method for increasing optical purity of cis‐verbenol. https://doi.org/10.1002/chir.23119
  6. Mori, Kenji et al. Synthesis of Optically Pure (1S, 4S, 5S)-2-Pinen-4-ol (cis-Verbenol) and Its Antipode, the Pheromone of Ips Bark Beetles. https://doi.org/10.1080/00021369.1976.10862248