ipsenol
7-octen-4-ol, 2-methyl-6-methylene-, (S)-
Identification
| Name | ipsenol |
| IUPAC | (4S)-2-methyl-6-methylideneoct-7-en-4-ol |
| CAS Number | 35628-05-8 |
| FDA UNII | 02H2YW09TH |
| Molecular Formula | C10 H18 O |
| Molecular Weight | 154.25266000 |
| MDL Number | MFCD00151184 |
| Nikkaji Number | J19.908G |
Regulatory
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 222.23 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 0.021000 mmHg @ 25.00 °C. (est) |
| Flash Point | 182.00 °F. TCC ( 83.40 °C. ) (est) |
| logP (o/w) | 2.761 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| 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 ipsenol usage levels up to | not for fragrance use. |
| Recommendation for ipsenol flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(S)-2-
methyl-6-methylene-7-octen-4-ol
(4S)-2-
methyl-6-methylideneoct-7-en-4-ol
7-
octen-4-ol, 2-methyl-6-methylene-, (4S)-
7-
octen-4-ol, 2-methyl-6-methylene-, (S)-
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:
Role of ipsdienol, ipsenol, and cis-verbenol in chemical ecology of Ips avulsus, Ips calligraphus, and Ips grandicollis (Coleoptera: Curculionidae: Scolytinae).
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:
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:
Test of nonhost angiosperm volatiles and verbenone to protect trap trees for Sirex noctilio (Hymenoptera: Siricidae) from attacks by bark beetles (Coleoptera: Scolytidae) in the northeastern United States.
PubMed:
Pheromone production in bark beetles.
PubMed:
Identification and field activity of a male-produced aggregation pheromone in the pine sawyer beetle, Monochamus galloprovincialis.
PubMed:
Aggregation pheromone of the Qinghai spruce bark beetle, Ips nitidus eggers.
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:
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:
Disruption by conophthorin of the kairomonal response of sawyer beetles to bark beetle pheromones.
PubMed:
Biochemistry and molecular biology of de novo isoprenoid pheromone production in the Scolytidae.
PubMed:
Kairomonal response by four Monochamus species (Coleoptera: Cerambycidae) to bark beetle pheromones.
PubMed:
Proline-catalyzed asymmetric aldol reactions between ketones and alpha-unsubstituted aldehydes.
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:
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:
(S)-(+)-Ipsdienol: Interspecific inhibition ofIps latidens (leconte) byIps pini (Say) (Coleoptera: Scolytidae).
PubMed:
Ipsenol: an aggregation pheromone forIps latidens (Leconte) (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:
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:
Attraction to pheromone sources of different quantity, quality, and spacing: Density-regulation mechanisms in bark beetleIps typographus.
PubMed:
Chiral allenylboronic esters as practical reagents for enantioselective carbon-carbon bond formation. Facile synthesis of (-)-ipsenol.
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:
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:
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.