Identification	Physical Data	Spectra
Route of Synthesis (ROS)	Safety and Hazards	Other Data

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Identification

Product Name	cis-9-Tricosene
IUPAC Name	(Z)-tricos-9-ene
Molecular Structure
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 Formula	C23H46
Molecular Weight	322.611
InChI	InChI=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 Key	IGOWHGRNPLFNDJ-ZPHPHTNESA-N
Canonical SMILES	CCCCCCCCCCCCC/C=C\CCCCCCCC

Patent Information
Patent ID	Title	Publication Date
US4670250	Durable controlled release microcapsules	1987
US5888930	Asymmetric microporous beads for controlled release	1999
US5399344	Synergistic fly attractant composition	1995

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Physical Data

Appearance	Colorless or light yellow oil
Solubility	Miscible with water and hexane. Immiscible with alcohol.
Refractive index	n20/D 1.453(lit.)

Melting Point, °C

4

27 – 28

-1

Boiling Point, °C	Pressure (Boiling Point), Torr
156 – 157	0.1
70 – 90	0.1
170	0.1
180	1
140 – 142	0.01
148 – 150	0.04
136 – 140	0.1

Refractive Index	Wavelength (Refractive Index), nm	Temperature (Refractive Index), °C
1.4515	589	26
1.4543	589	20
1.4559	589	20
1.4522	589	20
1.4488	589	20
1.4545	589	20
1.4532	589	23

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Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Solvents (NMR Spectroscopy)	Frequency (NMR Spectroscopy), MHz
Chemical shifts	1H	chloroform-d1	300
Chemical shifts	13C	chloroform-d1	75
Spin-spin coupling constants		CDCl3
Chemical shifts	1H	CDCl3	200
Chemical shifts	13C	CDCl3	22.5
Chemical shifts	1H	CCl4
Spectrum	1H	CDCl3
NMR

Description (IR Spectroscopy)	Solvent (IR Spectroscopy)	Comment (IR Spectroscopy)
Bands	film
Spectrum	KBr	diagram
Bands	neat (no solvent)	3006 – 721 cm**(-1)
Bands	neat (no solvent)	735 cm**(-1)
Bands	neat (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 GCMS
cis-9-Tricosene CAS#: 27519-02-4 GC MS

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Route of Synthesis (ROS)

Conditions	Yield
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

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Safety and Hazards

Pictogram(s)
Signal	Warning
GHS Hazard Statements	H317: May cause an allergic skin reaction [Warning Sensitization, Skin] Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement Codes	P261, 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.)

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Other Data

Transportation	NONH for all modes of transport
	Under the room temperature and away from light
HS Code	290129
Storage	Under the room temperature and away from light
Shelf Life	1 year
Market Price	USD

Druglikeness
Lipinski rules component
Molecular Weight	322.618
logP	12.911
HBA	0
HBD	0
Matching Lipinski Rules	3
Veber rules component
Polar Surface Area (PSA)	0
Rotatable Bond (RotB)	19
Matching Veber Rules	1

Bioactivity

In vitro: Efficacy

Quantitative Results

Quantitative Results
1?of?6	Assay Description	Effect : 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
	Results	relative response: ca. 30 percent at 0.1 μg, ca. 35 percent at 1.0 μg
2?of?6	Assay Description	Effect : 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
	Results	relative response: ca. 35 percent at 0.1 μg, ca. 42 percent at 1.0 μg
3?of?6	Effect	pheromone
	Assay Description	Target : 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?6	Effect	Reproductive Effect
	Assay Description	Target : 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?6	Effect	repellent agent
	Assay Description	Target : 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
	Results	rejection of flowers by B. lapidarius (diagram)
6?of?6	Results	sex pheromone of Musca domestica

In vivo: Animal Model

Quantitative Results

pX	Parameter	Value (qual)	Biological Species
1	Percentage change(of % courtship and amount of courtship behaviour)	Not active	Drosophila suzukii
1	percentage decrease(of copulation)	Active	Drosophila 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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