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ipsdienol

Chemical Structure

General Material Information

Preferred name ipsdienol
Trivial Name Ipsdienol
Short Description 2,7-octadien-4-ol, 2-methyl-6-methylene-, (S)-
Formula C10 H16 O
CAS Number 35628-00-3
FDA UNII I0CK35047X
Nikkaji Number J19.909E
MDL MFCD00065437
xLogP3-AA 3.20 (est)
NMR Predictor External link
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)-
  • (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)-
  • (4S)-2-Methyl-6-methylene-2,7-octadien-4-ol
  • 2-Methyl-6-methylene-2,7-octadien-4-ol
  • (+)-2-Methyl-6-methylene-2,7-octadien-4-ol
  • S-Ipsdienol
  • (+)-Ipsdienol
  • (S)-(+)-Ipsdienol
  • (4S)-(+)-Ipsdienol
  • (4S)-2-Methyl-6-methylene-octa-2,7-dien-4-ol

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Literature & References

(4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):92301
Pubchem (sid):135048820
Pherobase:View
Publications by PubMed
Comparative proteomics and expression analysis of five genes in Epicauta chinensis larvae from the first to fifth instar.
Trap lure blend of pine volatiles and bark beetle pheromones for Monochamus spp. (Coleoptera: Cerambycidae) in pine forests of Canada and the United States.
Saproxylic community, guild and species responses to varying pheromone components of a pine bark beetle.
Attaching lures to multiple-funnel traps targeting saproxylic beetles (Coleoptera) in pine stands: inside or outside funnels?
Functional characterization of myrcene hydroxylases from two geographically distinct Ips pini populations.
Role of ipsdienol, ipsenol, and cis-verbenol in chemical ecology of Ips avulsus, Ips calligraphus, and Ips grandicollis (Coleoptera: Curculionidae: Scolytinae).
Disruptive selection maintains variable pheromone blends in the bark beetle Ips pini.
Ipsdienol dehydrogenase (IDOLDH): a novel oxidoreductase important for Ips pini pheromone production.
Olfactory experience modifies semiochemical responses in a bark beetle predator.
Bark beetle pheromones and pine volatiles: attractant kairomone lure blend for longhorn beetles (Cerambycidae) in pine stands of the southeastern United States.
Enantioselective preference and high antennal sensitivity for (-)-Ipsdienol in scent-collecting male orchid bees, Euglossa cyanura.
Variation in enantiospecific attraction of Ips avulsus (Coleoptera: Curculionidae) to the pheromone ipsdienol in Georgia.
Effects of habitat type and trap placement on captures of bark (Coleoptera: Scolytidae) and longhorned (Coleoptera: Cerambycidae) beetles in semiochemical-baited traps.
Impacts of silvicultural thinning treatments on beetle trap captures and tree attacks during low bark beetle populations in ponderosa pine forests of northern Arizona.
Pheromone production in bark beetles.
Variation in complex semiochemical signals arising from insects and host plants.
Inhibition of predator attraction to kairomones by non-host plant volatiles for herbivores: a bypass-trophic signal.
Aggregation pheromone of the Qinghai spruce bark beetle, Ips nitidus eggers.
Unique animal prenyltransferase with monoterpene synthase activity.
Specificity and redundancy in the olfactory system of the bark beetle Ips typographus: single-cell responses to ecologically relevant odors.
Myrcene hydroxylases do not determine enantiomeric composition of pheromonal ipsdienol in Ips spp.
Traps and attractants for wood-boring insects in ponderosa pine stands in the Black Hills, South Dakota.
Comparison of arboreal beetle catches in wet and dry collection cups with Lindgren multiple funnel traps.
Can chemical communication be cryptic? Adaptations by herbivores to natural enemies exploiting prey semiochemistry.
Electrophysiological and behavioral responses of Ips duplicatus to aggregation pheromone in Inner Mongolia, China: amitinol as a potential pheromone component.
Electrophysiological and behavioral responses of Ips subelongatus to semiochemicals from its hosts, non-hosts, and conspecifics in China.
Functional expression of a bark beetle cytochrome P450 that hydroxylates myrcene to ipsdienol.
Genetic control of the enantiomeric composition of ipsdienol in the pine engraver, Ips pini.
Effects of juvenile hormone on gene expression in the pheromone-producing midgut of the pine engraver beetle, Ips pini.
Attraction of southern pine engravers and associated bark beetles (Coleoptera: Scolytidae) to ipsenol, ipsdienol, and lanierone in southeastern United States.
Ipsenol and ipsdienol attract Monochamus titillator (Coleoptera: Cerambycidae) and associated large pine woodborers in southeastern United States.
Electrophysiological and olfactometer responses of two histerid predators to three pine bark beetle pheromones.
Coordinated gene expression for pheromone biosynthesis in the pine engraver beetle, Ips pini (Coleoptera: Scolytidae).
Disruption by conophthorin of the kairomonal response of sawyer beetles to bark beetle pheromones.
Comparison of gene representation in midguts from two phytophagous insects, Bombyx mori and Ips pini, using expressed sequence tags.
Biochemistry and molecular biology of de novo isoprenoid pheromone production in the Scolytidae.
Midgut tissue of male pine engraver, Ips pini, synthesizes monoterpenoid pheromone component ipsdienol de novo.
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?
Kairomonal response by four Monochamus species (Coleoptera: Cerambycidae) to bark beetle pheromones.
Enantiospecific pheromone production and response profiles for populations of pine engraver,Ips pini (Say) (Coleoptera: Scolytidae), in British Columbia.
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).
Enantiomeric composition of ipsdienol: A chemotaxonomic character for north American populations ofIps spp. in thepini subgeneric group (coleoptera: Scolytidae).
Response ofDendroctonus brevicomis Le Conte (Coleoptera: Scolytidae) to different release rates and ratios of aggregation semiochemicals and the inhibitors verbenone and ipsdienol.
Repeatability of female response to ipsdienol enantiomeric mixtures by pine engraver,Ips pini (Coleoptera: Scolytidae).
Influence of aggregation inhibitors (verbenone and ipsidenol) on landing and attack behavior ofDendroctonus brevicomis (Coleoptera: Scolytidae).
Role of chirality in olfactory-directed behavior: Aggregation of pine engraver beetles in the genusIps (Coleoptera: Scolytidae).
Interactions between components of the aggregation pheromone during chemotaxis by the bark beetleIps paraconfusus.
Olfactory receptor cell responses ofIps grandicollis (eichhoff) (Coleoptera: Scolytidae) to intra- and interspecific behavioral chemicals.
The role of lanierone in the chemical ecology ofIps pini (Coleoptera: Scolytidae) in California.
(S)-(+)-Ipsdienol: Interspecific inhibition ofIps latidens (leconte) byIps pini (Say) (Coleoptera: Scolytidae).
Response ofDendroctonus brevicomis andIps paraconfusus (Coleoptera: Scolytidae) to combinations of synthetic pheromone attractants and inhibitors verbenone and ipsdienol.
Variation in semiochemical-mediated prey-predator interaction:Ips pini (Scolytidae) andThanasimus dubius (Cleridae).
Lanierone: A new pheromone component fromIps pini (Coleoptera: Scolytidae) in New York.
Seasonal variability in response ofIps pini (Coleoptera: Scolytidae) to ipsdienol in New York.
Variation in semiochemical-mediated prey-predator interaction:Ips pini (Scolytidae) andThanasimus dubius (Cleridae).
β-Phellandrene: kairomone for pine engraver,Ips pini (Say) (Coleoptera: Scolytidae).
Antennal olfactory responses of black turpentine beetle,Dendroctonus terebrans (Olivier), to bark beetle pheromones and host terpenes.
Inhibition of attraction to aggregation pheromone by verbenone and ipsenol : Density regulation mechanisms in bark beetleIps typographus.
Terpene alcohol pheromone production byDendroctonus ponderosae andIps paraconfusus (Coleoptera: Scolytidae) in the absence of readily culturable microorganisms.
Inter- and intrapopulation variation of the pheromone, ipsdienol produced by male pine engravers,Ips pini (Say) (Coleoptera: Scolytidae).
Olfactory orientation responses by walking femaleIps paraconfusus bark beetles I. Chemotaxis assay.
Individual variation in aggregation pheromone content of the bark beetle,Ips typographus.
Antennal olfactory responsiveness of three sympatricIps species [Ips avulsus (Eichhoff),Ips calligraphus (Germar),Ips grandicollis (Eichhoff)], to intra- and interspecific behavioral chemicals.
Effect of juvenile hormone analog, fenoxycarb, on pheromone production byIps paraconfusus (Coleoptera: Scolytidae).
Partial inhibition of pheromone production inDendroctonus ponderosae (Coleoptera: Scolytidae) by polysubstrate monooxygenase inhibitors.
Response of mountain pine beetle,Dendroctonus ponderosae Hopkins, and pine engraver,Ips pint (SAY), to ipsdienol in southwestern British Columbia.
Attraction to pheromone sources of different quantity, quality, and spacing: Density-regulation mechanisms in bark beetleIps typographus.
Field response of spruce bark beetle,Ips typographus, to aggregation pheromone candidates.
Sex-specific production of ipsdienol and myrcenol byDendroctonus ponderosae (Coleoptera: Scolytidae) exposed to myrcene vapors.
Pheromone receptor cell specificity in interpopulational hybrids ofIps pini (Coleoptera: Scolytidae).
Pheromone biosynthetic pathways: Conversion of ipsdienone to (-)-ipsdienol, a mechanism for enantioselective reduction in the male bark beetle,Ips paraconfusus.
Quantitative variation of pheromone components in the spruce bark beetleIps typographus from different attack phases.
Attractive and inhibitory pheromones produced in the bark beetle,Dendroctonus brevicomis, during host colonization: Regulation of inter- and intraspecific competition.
Receptor cells inIps typographus andDendroctonus micans specific to pheromones of the reciprocal genus.
Pheromone production by axenically rearedDendroctonus ponderosae andIps paraconfusus (Coleoptera: Scolytidae).
Response of the clerid predatorThanasimus dubius (F.) to bark beetle pheromones and tree volatiles in a wind tunnel.
Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to its pheromone and other behavior-modifying chemicals.
Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to their natural aggregation pheromone and its enantiomeric components.
Sex-specific responses to aggregation pheromone Regulation of colonization density in the bark beetleIps paraconfusus.
Male-specific conversion of the host plant compound, myrcene, to the pheromone, (+)-ipsdienol, in the bark beetle,Dendroctonus brevicomis.
Effect of mating on terminating aggregation during host colonization in the bark beetle,Ips paraconfusus.
Antibiotic-induced inhibition of pheromone synthesis in a bark beetle.
Kairomone response inThanasimus predators to pheromone components ofIps typographus.
Interspecific effects of pheromones on the attraction of the bark beetles,Dendroctonus brevicomis andIps paraconfusus in the laboratory.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2905.22.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Specific gravity @ 25 °C
Pounds per Gallon 7.406 to 7.572
Refractive Index 1.48 to 1.5 @ 20 °C
Boiling Point 233 to 235°C @ 760 mm Hg
Vapor Pressure 0.01 mmHg @ 25 °C
Flash Point TCC Value 87.78 °C TCC
logP (o/w) 2.482 est
Solubility
alcohol Yes
water, 338 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Balsamic
pine, balsamic
General comment At 100.00 %. pine balsamic

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

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.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):35628-00-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :92301
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol
Chemidplus:0035628003