ipsdienol
2,7-octadien-4-ol, 2-methyl-6-methylene-, (S)-
Identification
| Name | ipsdienol |
| IUPAC | (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol |
| CAS Number | 35628-00-3 |
| FDA UNII | I0CK35047X |
| Molecular Formula | C10 H16 O |
| Molecular Weight | 152.23672000 |
| MDL Number | MFCD00065437 |
| Nikkaji Number | J19.909E |
Regulatory
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 96.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.89000 to 0.91000 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.406 to 7.572 |
| Refractive Index | 1.48000 to 1.50000 @ 20.00 °C. |
| Boiling Point | 49.00 °C. @ 0.50 mm Hg, 233.00 to 235.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.010000 mmHg @ 25.00 °C. (est) |
| Flash Point | 190.00 °F. TCC ( 87.78 °C. ) |
| logP (o/w) | 2.482 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Odor Description | at 100.00 %. |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for ipsdienol usage levels up to | not for fragrance use. |
| Recommendation for ipsdienol flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(4S)-
methyl-6-methylene-2,7-octadien-4-ol
(S)-2-
methyl-6-methylene-2,7-octadien-4-ol
(4S)-2-
methyl-6-methyleneocta-2,7-dien-4-ol
(4S)-2-
methyl-6-methylenocta-2,7-dien-4-ol
(4S)-2-
methyl-6-methylideneocta-2,7-dien-4-ol
2,7-
octadien-4-ol, 2-methyl-6-methylene-, (4S)-
2,7-
octadien-4-ol, 2-methyl-6-methylene-, (S)-
PubMed:
Comparative proteomics and expression analysis of five genes in Epicauta chinensis larvae from the first to fifth instar.
PubMed:
Trap lure blend of pine volatiles and bark beetle pheromones for Monochamus spp. (Coleoptera: Cerambycidae) in pine forests of Canada and the United States.
PubMed:
Saproxylic community, guild and species responses to varying pheromone components of a pine bark beetle.
PubMed:
Attaching lures to multiple-funnel traps targeting saproxylic beetles (Coleoptera) in pine stands: inside or outside funnels?
PubMed:
Functional characterization of myrcene hydroxylases from two geographically distinct Ips pini populations.
PubMed:
Role of ipsdienol, ipsenol, and cis-verbenol in chemical ecology of Ips avulsus, Ips calligraphus, and Ips grandicollis (Coleoptera: Curculionidae: Scolytinae).
PubMed:
Disruptive selection maintains variable pheromone blends in the bark beetle Ips pini.
PubMed:
Ipsdienol dehydrogenase (IDOLDH): a novel oxidoreductase important for Ips pini pheromone production.
PubMed:
Olfactory experience modifies semiochemical responses in a bark beetle predator.
PubMed:
Bark beetle pheromones and pine volatiles: attractant kairomone lure blend for longhorn beetles (Cerambycidae) in pine stands of the southeastern United States.
PubMed:
Enantioselective preference and high antennal sensitivity for (-)-Ipsdienol in scent-collecting male orchid bees, Euglossa cyanura.
PubMed:
Variation in enantiospecific attraction of Ips avulsus (Coleoptera: Curculionidae) to the pheromone ipsdienol in Georgia.
PubMed:
Effects of habitat type and trap placement on captures of bark (Coleoptera: Scolytidae) and longhorned (Coleoptera: Cerambycidae) beetles in semiochemical-baited traps.
PubMed:
Impacts of silvicultural thinning treatments on beetle trap captures and tree attacks during low bark beetle populations in ponderosa pine forests of northern Arizona.
PubMed:
Pheromone production in bark beetles.
PubMed:
Variation in complex semiochemical signals arising from insects and host plants.
PubMed:
Inhibition of predator attraction to kairomones by non-host plant volatiles for herbivores: a bypass-trophic signal.
PubMed:
Aggregation pheromone of the Qinghai spruce bark beetle, Ips nitidus eggers.
PubMed:
Unique animal prenyltransferase with monoterpene synthase activity.
PubMed:
Specificity and redundancy in the olfactory system of the bark beetle Ips typographus: single-cell responses to ecologically relevant odors.
PubMed:
Myrcene hydroxylases do not determine enantiomeric composition of pheromonal ipsdienol in Ips spp.
PubMed:
Traps and attractants for wood-boring insects in ponderosa pine stands in the Black Hills, South Dakota.
PubMed:
Comparison of arboreal beetle catches in wet and dry collection cups with Lindgren multiple funnel traps.
PubMed:
Can chemical communication be cryptic? Adaptations by herbivores to natural enemies exploiting prey semiochemistry.
PubMed:
Electrophysiological and behavioral responses of Ips duplicatus to aggregation pheromone in Inner Mongolia, China: amitinol as a potential pheromone component.
PubMed:
Electrophysiological and behavioral responses of Ips subelongatus to semiochemicals from its hosts, non-hosts, and conspecifics in China.
PubMed:
Functional expression of a bark beetle cytochrome P450 that hydroxylates myrcene to ipsdienol.
PubMed:
Genetic control of the enantiomeric composition of ipsdienol in the pine engraver, Ips pini.
PubMed:
Effects of juvenile hormone on gene expression in the pheromone-producing midgut of the pine engraver beetle, Ips pini.
PubMed:
Attraction of southern pine engravers and associated bark beetles (Coleoptera: Scolytidae) to ipsenol, ipsdienol, and lanierone in southeastern United States.
PubMed:
Ipsenol and ipsdienol attract Monochamus titillator (Coleoptera: Cerambycidae) and associated large pine woodborers in southeastern United States.
PubMed:
Electrophysiological and olfactometer responses of two histerid predators to three pine bark beetle pheromones.
PubMed:
Coordinated gene expression for pheromone biosynthesis in the pine engraver beetle, Ips pini (Coleoptera: Scolytidae).
PubMed:
Disruption by conophthorin of the kairomonal response of sawyer beetles to bark beetle pheromones.
PubMed:
Comparison of gene representation in midguts from two phytophagous insects, Bombyx mori and Ips pini, using expressed sequence tags.
PubMed:
Biochemistry and molecular biology of de novo isoprenoid pheromone production in the Scolytidae.
PubMed:
Midgut tissue of male pine engraver, Ips pini, synthesizes monoterpenoid pheromone component ipsdienol de novo.
PubMed:
A model for peak and width of signaling windows: Ips duplicatus and Chilo partellus pheromone component proportions--does response have a wider window than production?
PubMed:
Kairomonal response by four Monochamus species (Coleoptera: Cerambycidae) to bark beetle pheromones.
PubMed:
Enantiospecific pheromone production and response profiles for populations of pine engraver,Ips pini (Say) (Coleoptera: Scolytidae), in British Columbia.
PubMed:
De novo biosynthesis of the aggregation pheromone components ipsenol and ipsdienol by the pine bark beetles Ips paraconfusus Lanier and Ips pini (Say) (Coleoptera: Scolytidae).
PubMed:
Enantiomeric composition of ipsdienol: A chemotaxonomic character for north American populations ofIps spp. in thepini subgeneric group (coleoptera: Scolytidae).
PubMed:
Response ofDendroctonus brevicomis Le Conte (Coleoptera: Scolytidae) to different release rates and ratios of aggregation semiochemicals and the inhibitors verbenone and ipsdienol.
PubMed:
Repeatability of female response to ipsdienol enantiomeric mixtures by pine engraver,Ips pini (Coleoptera: Scolytidae).
PubMed:
Influence of aggregation inhibitors (verbenone and ipsidenol) on landing and attack behavior ofDendroctonus brevicomis (Coleoptera: Scolytidae).
PubMed:
Role of chirality in olfactory-directed behavior: Aggregation of pine engraver beetles in the genusIps (Coleoptera: Scolytidae).
PubMed:
Interactions between components of the aggregation pheromone during chemotaxis by the bark beetleIps paraconfusus.
PubMed:
Olfactory receptor cell responses ofIps grandicollis (eichhoff) (Coleoptera: Scolytidae) to intra- and interspecific behavioral chemicals.
PubMed:
The role of lanierone in the chemical ecology ofIps pini (Coleoptera: Scolytidae) in California.
PubMed:
(S)-(+)-Ipsdienol: Interspecific inhibition ofIps latidens (leconte) byIps pini (Say) (Coleoptera: Scolytidae).
PubMed:
Response ofDendroctonus brevicomis andIps paraconfusus (Coleoptera: Scolytidae) to combinations of synthetic pheromone attractants and inhibitors verbenone and ipsdienol.
PubMed:
Variation in semiochemical-mediated prey-predator interaction:Ips pini (Scolytidae) andThanasimus dubius (Cleridae).
PubMed:
Lanierone: A new pheromone component fromIps pini (Coleoptera: Scolytidae) in New York.
PubMed:
Seasonal variability in response ofIps pini (Coleoptera: Scolytidae) to ipsdienol in New York.
PubMed:
Variation in semiochemical-mediated prey-predator interaction:Ips pini (Scolytidae) andThanasimus dubius (Cleridae).
PubMed:
β-Phellandrene: kairomone for pine engraver,Ips pini (Say) (Coleoptera: Scolytidae).
PubMed:
Antennal olfactory responses of black turpentine beetle,Dendroctonus terebrans (Olivier), to bark beetle pheromones and host terpenes.
PubMed:
Inhibition of attraction to aggregation pheromone by verbenone and ipsenol : Density regulation mechanisms in bark beetleIps typographus.
PubMed:
Terpene alcohol pheromone production byDendroctonus ponderosae andIps paraconfusus (Coleoptera: Scolytidae) in the absence of readily culturable microorganisms.
PubMed:
Inter- and intrapopulation variation of the pheromone, ipsdienol produced by male pine engravers,Ips pini (Say) (Coleoptera: Scolytidae).
PubMed:
Olfactory orientation responses by walking femaleIps paraconfusus bark beetles I. Chemotaxis assay.
PubMed:
Individual variation in aggregation pheromone content of the bark beetle,Ips typographus.
PubMed:
Antennal olfactory responsiveness of three sympatricIps species [Ips avulsus (Eichhoff),Ips calligraphus (Germar),Ips grandicollis (Eichhoff)], to intra- and interspecific behavioral chemicals.
PubMed:
Effect of juvenile hormone analog, fenoxycarb, on pheromone production byIps paraconfusus (Coleoptera: Scolytidae).
PubMed:
Partial inhibition of pheromone production inDendroctonus ponderosae (Coleoptera: Scolytidae) by polysubstrate monooxygenase inhibitors.
PubMed:
Response of mountain pine beetle,Dendroctonus ponderosae Hopkins, and pine engraver,Ips pint (SAY), to ipsdienol in southwestern British Columbia.
PubMed:
Attraction to pheromone sources of different quantity, quality, and spacing: Density-regulation mechanisms in bark beetleIps typographus.
PubMed:
Field response of spruce bark beetle,Ips typographus, to aggregation pheromone candidates.
PubMed:
Sex-specific production of ipsdienol and myrcenol byDendroctonus ponderosae (Coleoptera: Scolytidae) exposed to myrcene vapors.
PubMed:
Pheromone receptor cell specificity in interpopulational hybrids ofIps pini (Coleoptera: Scolytidae).
PubMed:
Pheromone biosynthetic pathways: Conversion of ipsdienone to (-)-ipsdienol, a mechanism for enantioselective reduction in the male bark beetle,Ips paraconfusus.
PubMed:
Quantitative variation of pheromone components in the spruce bark beetleIps typographus from different attack phases.
PubMed:
Attractive and inhibitory pheromones produced in the bark beetle,Dendroctonus brevicomis, during host colonization: Regulation of inter- and intraspecific competition.
PubMed:
Receptor cells inIps typographus andDendroctonus micans specific to pheromones of the reciprocal genus.
PubMed:
Pheromone production by axenically rearedDendroctonus ponderosae andIps paraconfusus (Coleoptera: Scolytidae).
PubMed:
Response of the clerid predatorThanasimus dubius (F.) to bark beetle pheromones and tree volatiles in a wind tunnel.
PubMed:
Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to its pheromone and other behavior-modifying chemicals.
PubMed:
Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to their natural aggregation pheromone and its enantiomeric components.
PubMed:
Sex-specific responses to aggregation pheromone Regulation of colonization density in the bark beetleIps paraconfusus.
PubMed:
Male-specific conversion of the host plant compound, myrcene, to the pheromone, (+)-ipsdienol, in the bark beetle,Dendroctonus brevicomis.
PubMed:
Effect of mating on terminating aggregation during host colonization in the bark beetle,Ips paraconfusus.
PubMed:
Antibiotic-induced inhibition of pheromone synthesis in a bark beetle.
PubMed:
Kairomone response inThanasimus predators to pheromone components ofIps typographus.
PubMed:
Interspecific effects of pheromones on the attraction of the bark beetles,Dendroctonus brevicomis andIps paraconfusus in the laboratory.