cis-9-Tricosene CAS#: 27519-02-4

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Namecis-9-Tricosene
IUPAC Name(Z)-tricos-9-ene
Molecular StructureStructure of cis-9-Tricosene CAS# 27519-02-4
CAS Registry Number 27519-02-4
Synonyms
(Z)-tricos-9-ene, cis-tricos-9-ene, (Z)-9-Tricosene, 9-(Z)-tricosene, cis-9-tricosene, 9-tricosene, muscalure; CAS Number: 27519-02-4
Molecular FormulaC23H46
Molecular Weight322.611
InChIInChI=1S/C23H46/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h17,19H,3-16,18,20-23H2,1-2H3/b19-17-
InChI KeyIGOWHGRNPLFNDJ-ZPHPHTNESA-N
Canonical SMILESCCCCCCCCCCCCC/C=C\CCCCCCCC
Patent Information
Patent IDTitlePublication Date
US4670250Durable controlled release microcapsules1987
US5888930Asymmetric microporous beads for controlled release1999
US5399344Synergistic fly attractant composition1995

Physical Data

AppearanceColorless or light yellow oil
SolubilityMiscible with water and hexane. Immiscible with alcohol.
Refractive indexn20/D 1.453(lit.)
Melting Point, °C
4
27 – 28
-1
Boiling Point, °CPressure (Boiling Point), Torr
156 – 1570.1
70 – 900.1
1700.1
1801
140 – 1420.01
148 – 1500.04
136 – 1400.1
Refractive IndexWavelength (Refractive Index), nmTemperature (Refractive Index), °C
1.451558926
1.454358920
1.455958920
1.452258920
1.448858920
1.454558920
1.453258923

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts1Hchloroform-d1300
Chemical shifts13Cchloroform-d175
Spin-spin coupling constantsCDCl3
Chemical shifts1HCDCl3200
Chemical shifts13CCDCl322.5
Chemical shifts1HCCl4
Spectrum1HCDCl3
NMR
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Comment (IR Spectroscopy)
Bandsfilm
SpectrumKBrdiagram
Bandsneat (no solvent)3006 – 721 cm**(-1)
Bandsneat (no solvent)735 cm**(-1)
Bandsneat (no solvent)1650 – 712 cm**(-1)
IR
Description (Mass Spectrometry)
gas chromatography mass spectrometry (GCMS), electron impact (EI), spectrum
gas chromatography mass spectrometry (GCMS), spectrum
high resolution mass spectrometry (HRMS), electron impact (EI), spectrum
spectrum, electron impact (EI)
spectrum, chemical ionization (CI)
chemical ionization (CI), spectrum
electron impact (EI), spectrum
cis-9-Tricosene CAS#: 27519-02-4 GCMSGCMS of cis-9-Tricosene CAS# 27519-02-4
cis-9-Tricosene CAS#: 27519-02-4 GC MSGC MS of cis-9-Tricosene CAS# 27519-02-4

Route of Synthesis (ROS)

Route of Synthesis (ROS) of cis-9-Tricosene CAS 27519-02-4
Route of Synthesis (ROS) of cis-9-Tricosene CAS 27519-02-4
ConditionsYield
With hydrogen; Pd-Pb-CaCO3 (Lindlar catalyst) In hexane
With 9-borabicyclo[3.3.1]nonane dimer; acetic acid 1) THF, 0 deg C, 24 h, 2) reflux, 5 h; Yield given. Multistep reaction;
With methanol; 9-borabicyclo[3.3.1]nonane dimer; acetic acid 1.) THF, 0 deg C, 48 h, 2.) 25 deg C, 1 h; Yield given. Multistep reaction;
With quinoline; hydrogen; Pd-BaSO4 In Petroleum ether Ambient temperature;
With iron(II) acetylacetonate; hydrogen; diisobutylaluminium hydride In tetrahydrofuran; toluene at 30℃; under 975.098 Torr; for 12h; Sealed tube; stereoselective reaction;n/a

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH317: May cause an allergic skin reaction [Warning Sensitization, Skin]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesP261, P272, P280, P302+P352, P321, P333+P313, P363, and P501
(The corresponding statement to each P-code can be found at the?GHS Classification?page.)

Other Data

TransportationNONH for all modes of transport
Under the room temperature and away from light
HS Code290129
StorageUnder the room temperature and away from light
Shelf Life1 year
Market PriceUSD
Druglikeness
Lipinski rules component
Molecular Weight322.618
logP12.911
HBA0
HBD0
Matching Lipinski Rules3
Veber rules component
Polar Surface Area (PSA)0
Rotatable Bond (RotB)19
Matching Veber Rules1
Bioactivity
In vitro: Efficacy
Quantitative Results
Quantitative Results
1?of?6Assay DescriptionEffect : electrophysiological
Target : Idea leuconoe, giant danaine butterfly
Bioassay : electroantennography; antennae of 10- to 14-day-old adults; 2 ml odor puff; continuous airflow (350 ml/min); 1 cm from the antennal preparation; EAG response relative to 1-hexanol (100 percent); n = 10-11
Resultsrelative response: ca. 30 percent at 0.1 μg, ca. 35 percent at 1.0 μg
2?of?6Assay DescriptionEffect : electrophysiological
Target : Idea leuconoe, giant danaine butterfly
Bioassay : electroantennography; antennae of 10- to 14-day-old adults; 2 ml odor puff; continuous airflow (350 ml/min); 1 cm from the antennal preparation; EAG response relative to 1-hexanol (100 percent); n = 10-14
Resultsrelative response: ca. 35 percent at 0.1 μg, ca. 42 percent at 1.0 μg
3?of?6Effectpheromone
Assay DescriptionTarget : Lygocoris pabulinus (L.), green capsid bug
Bioassay : vibration of abdomen of male bugs observed; controls: extract of legs of male bugs; this extract + 5 μg (Z)-9-heptacosene; positive control: extract of legs of female bugs virgin bug 6-9 days old (N=32); legs of male bugs loaded with 1 μg title comp. and 5 μg (Z)-9-pentacosene placed in Petri dish; one male per dish introduced; 19 – 23 deg C
4?of?6EffectReproductive Effect
Assay DescriptionTarget : Varroa destructor Anderson and Trueman, mite
Bioassay : inhibition of reproduction of Varroa destructor mite reared on Apis mellifera larva in artificial cells studied; control: hexane; RH: relative humidity title comp. applied to interior of 6.5 mm gelatin cells, then 1 mite and bee larva inserted into each cell; incubator, 34.5 deg C, 75 percent RH, 10 days; then cells opened; presence and number of offsprings per mite in each cell noted
5?of?6Effectrepellent agent
Assay DescriptionTarget : Bombus lapidarius (L.), bumblebee
Bioassay : controls: not treated flowers and treated with pentane test comp. dilution 10-12?μg/5 ml pentane; appled to Melitotus officinalis flowers; offered to bumblebees
Resultsrejection of flowers by B. lapidarius (diagram)
6?of?6Resultssex pheromone of Musca domestica
In vivo: Animal Model
Quantitative Results
pXParameterValue (qual)Biological Species
1Percentage change(of % courtship and amount of courtship behaviour)Not activeDrosophila suzukii
1percentage decrease(of copulation)ActiveDrosophila suzukii
Use Pattern
Agricultural use
inhibits mating
pest control agent against Drosophila suzukii
Attractant for fly gel
Attractant for an insect trap functions
arresting effect on insects
Fights against social, sub-social or gregarious insects
pheromone
chemical attractant

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