(''S'')-Ipsdienol is a

terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes ar ...

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

. It is one of the major aggregation pheromones of the

bark beetle 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 ...

. It was first identified from ''

Ips confusus ''Ips confusus'', known generally as the pinyon pine beetle or pinyon ips, is a species of typical bark beetle in the family Curculionidae The Curculionidae are a family of weevils, commonly called snout beetles or true weevils. They are one o ...

'', 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 IPS, ips, or iPS may refer to: Science and technology Biology and medicine * ''Ips'' (genus), a genus of bark beetle * Induced pluripotent stem cell or iPS cells * Intermittent photic stimulation, a neuroimaging technique * Intraparietal sulcus, ...

'' and ''

Ips ini IPS, ips, or iPS may refer to: Science and technology Biology and medicine * ''Ips'' (genus), a genus of bark beetle * Induced pluripotent stem cell or iPS cells * Intermittent photic stimulation, a neuroimaging technique * Intraparietal sulcus, ...

'', facilitating reductions in competition for breeding material and/or mating interference.

Synthesis

The compound has been synthesized from D-mannitol. Alternative syntheses were realized through the asymmetric isoprenylation of correspondent aldehyde (prenal) and alcohol (

prenol Prenol, or 3-methyl-2-buten-1-ol, is a natural alcohol. It is one of the most simple terpenoids. It is a clear colorless oil that is reasonably soluble in water and miscible with most common organic solvents. It has a fruity odor and is used oc ...

Chiral resolution Chiral resolution, or enantiomeric resolution, is a process in stereochemistry for the separation of racemic compounds into their enantiomers. It is an important tool in the production of optically active compounds, including drugs. Another term wi ...

of racemic precursor has been found to provide both

enantiomers In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical anti ...

of ipsdienol in high enantiomeric purity and in preparative scale.

References

{{DEFAULTSORT:Ipsdienol, (S)- Monoterpenes Insect pheromones Secondary alcohols