Pheromone • ChemWhat中文网 | 凯望化学与生物数据库

Z-8-Dodecenyl acetate/E-8-Dodecenyl acetate/Z-8-Dodecenol

By Janice Zhang, 29th July 2020

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

Identification

Patent Information

No data available

Physical Data

Appearance

Colorless or light yellow oil

Spectra

GC of Z-8-Dodecenyl acetateE-8-Dodecenyl acetateZ-8-Dodecenol CAS WPNA-0001

Route of Synthesis (ROS)

No data available

Safety and Hazards

GHS Hazard Statements	Not Classified
	For more detailed information, please visit ECHA C&L website

Source: European Chemicals Agency (ECHA)
License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
License URL: https://echa.europa.eu/web/guest/legal-notice
Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate
URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446
Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database

Other Data

Transportation	Not dangerous goods
	Under the room temperature and away from light
Storage	Under the room temperature and away from light
Market Price	USD

Use Pattern

Z-8-Dodecenyl acetate/E-8-Dodecenyl acetate/Z-8-Dodecenol is used as a pheromone, used in Oriental fruit moth, Carambola fruit borer, Macadamia borer, False codling moth, Plum fruit moth, Small fruit tortrix, as well as other lepidoptera…

Peachflure CAS#: 63408-44-6

By great_watson-int, 11th April 2018

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

Identification

Patent Information

No data available

Physical Data

Appearance	Colorless or light yellow oil
Boiling Point	172 °C(Press: 1 Torr)

Melting Point, °C

21~22

Boiling Point, °C	Pressure (Boiling Point), Torr
155 – 158	4-5
159	0.7
160	0.7
161	0.7
172	1
135-140	0.4

Refractive Index	Wavelength (Refractive Index), nm	Temperature (Refractive Index), °C
1.4545	589	20
1.4544	589	20
1.4546	589	20
1.4608	589	20
1.4542	589	20

Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Solvents (NMR Spectroscopy)	Frequency (NMR Spectroscopy), MHz
Chemical shifts, Spectrum	1H	chloroform-d1	400
Chemical shifts, Spectrum	13C	chloroform-d1	100
Chemical shifts	1H	chloroform-d1	300
Chemical shifts	13C	chloroform-d1	75
Chemical shifts	1H	CDCl3
Chemical shifts	13C	CDCl3
Chemical shifts	1H	CCl4
Chemical shifts	13C	CCl4
Spin-spin coupling constants		CCl4
Spin-spin coupling constants		CDCl3
NMR

Description (IR Spectroscopy)	Solvent (IR Spectroscopy)	Comment (IR Spectroscopy)
Bands	CHCl3	3020 – 720 cm**(-1)
Bands	neat (no solvent)	1725 cm**(-1)
Bands	CCl4	3015 – 1725 cm**(-1)
Bands	neat (no solvent)	1720 – 730 cm**(-1)
IR

Description (Mass Spectrometry)

spectrum

gas chromatography mass spectrometry (GCMS), spectrum

spectrum, electron impact (EI)

Route of Synthesis (ROS)

Conditions

Yield

With hydrogen In hexane; ethyl acetate at 20℃;

Experimental Procedure
General procedure: To a solution of 20a-b (0.2 mmol) and quinolone (0.4 mmol) in ethyl acetate/hexane (5 mL/5 mL) atroom temperature was added 5% Pd/CaCO3 (0.02 mmol), and this was stirred under a H2 atmosphere.The reaction was monitored by 1H NMR, and when it was completed, the mixture was filtered andconcentrated under reduced pressure to afford 16a-b.

97%

Safety and Hazards

GHS Hazard Statements	Not Classified
	For more detailed information, please visit ECHA C&L website

Other Data

Transportation	No data available
	Under the room temperature and away from light
Storage	Under the room temperature and away from light
Market Price	USD

Druglikeness
Lipinski rules component
分子量	294.521
logP	8.71
HBA	1
HBD	0
Matching Lipinski Rules	3
Veber rules component
Polar Surface Area (PSA)	17.07
Rotatable Bond (RotB)	16
Matching Veber Rules	1

Bioactivity

In vitro: Efficacy

Quantitative Results

1 of 1

Results

component of sex pheromone of peach moth Carposina niponensis W.

Use Pattern

Often used as a pheromone

used in Peach Fruit Moth.

used in Carposina niponensis.

TRANS-7, CIS-9-DODECADIENYL ACETATE CAS#: 55774-32-8

By great_watson-int, 22nd March 2018

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

Identification

Patent Information

No data available

Physical Data

Appearance	Colorless or light yellow oil
Solubility	2.0 mg l-1(20 °C, est.)
Flash Point	61ºC
Boiling Point	309.6±21.0 °C(Predicted)

Spectra

HNMR of TRANS-7, CIS-9-DODECADIENYL ACETATE CAS# 55774-32-8

CNMR of 7E, 9Z-TRANS-7, CIS-9-DODECADIENYL ACETATE CAS# 55774-32-8

Description (Mass Spectrometry)

high resolution mass spectrometry (HRMS), spectrum

Spectrum

electron impact (EI), spectrum

Route of Synthesis (ROS)

Conditions

Yield

With dmap; triethylamine at 20℃; for 3h; Overall yield = 43 %; Overall yield = 0.95 g;

Experimental Procedure
1.5 Step 5
In a flask, (7E, 9Z) -dodeca-7,9-dien-1-ol (1.60 g) obtained in Step 4 was added.Acetic anhydride (0.99 g),Triethylamine (0.98 g),4-Dimethylaminopyridine (1.1 mg) was added and stirred at room temperature for 3 hours. After adding water and stirring for 30 minutes, t-butyl methyl ether (ml) was added to separate the solution, and the organic layer was washed with water, dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure using an evaporator. Obtained (GC purity 67%, yield 58%). Subsequently, the mixture was purified by silica gel column chromatography (silica gel 60 (68 ml), heptane / ethyl acetate = 10/1), and an isomer mixture containing (7E, 9Z) -dodec-7,9-dien-1-yl acetate (0. 95 g, GC purity 90%) was obtained with a yield of 43%.Isomer ratio is 7Z9E: 7E9Z: 7Z9Z: 7E9E = 12: 36: 41: 11It was.

99%

Safety and Hazards

Pictogram(s)
Signal	Warning
GHS Hazard Statements	H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (50.56%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H411 (96.11%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard] Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement Codes	P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) For more detailed information, please visit ECHA C&L website

Other Data

Transportation	No data available
	Under the room temperature and away from light
HS Code	No data available
Storage	Under the room temperature and away from light
Shelf Life	1 year
Market Price	USD

Druglikeness
Lipinski rules component
分子量	224.343
logP	5.183
HBA	2
HBD	0
Matching Lipinski Rules	3
Veber rules component
Polar Surface Area (PSA)	26.3
Rotatable Bond (RotB)	10
Matching Veber Rules	2

Bioactivity

In vitro: Efficacy

Quantitative Results

1 of 1	Assay Description	Effect : pheromone activity Target : Idaea biselata, geometrid moth Bioassay : delta traps hung ca. 1 m above the ground and set at least 2 m apart; traps hung on the tree twigs or placed in low bushes and checked once a week; red rubber septa as dispensers field trapping tests; in hexane; in the Hagadal and Nasten regions of Uppsala in south-central Sweden from July 4 to August 21, 1993
	Results	I. biselata captured: 5

Use Pattern

Insect attractant

pheromone

chemical attractant

E3,Z8,Z11-Tetradecatriene acetate CAS#: 163041-94-9

By great_watson-int, 6th February 2018

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

Identification

Patent Information

No data available

Physical Data

Appearance	Pale yellow liquid
Density	0.903±0.06 g/cm3
Boiling point	333.6±31.0 °C

Spectra

HNMR of E3,Z8,Z11-Tetradecatriene acetate CAS 163041-94-9

CNMR of E3,Z8,Z11-Tetradecatriene acetate CAS 163041-94-9

Route of Synthesis (ROS)

No data available

Safety and Hazards

Pictogram(s)
Signal	Warning
GHS Hazard Statements	H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement Codes	P264, P280, P302+P352, P321, P332+P313, and P362 (The corresponding statement to each P-code can be found at the GHS Classification page.) For more detailed information, please visit ECHA C&L website

Other Data

Transportation	Not dangerous goods
	Under the room temperature and away from light
Storage	Store in a cold place for long time, sealed and protected from light.
Market Price	USD 15000/kg

Use Pattern

E3,Z8,Z11-Tetradecatriene acetate CAS#: 163041-94-9 used as insect pheromone and sex attractant.

8,10-DODECADIEN-1-OL CAS#: 33956-49-9

By great_watson-int, 30th November 2017

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

Identification

Structure of 8E, 10E-dodecadien-1-ol CAS 33956-49-9

Patent Information
Patent ID	Title	Publication Date
US2010/113837	Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates	2010
US2006/88563	Use of spray adjuvant to enhance the movement of pesticides through plant canopies to the target	2006
US6838576	Process for preparing functional group-containing olefinic compounds	2005

Physical Data

Appearance	Colorless or light yellow crystalline
Refractive index	1.5050 (estimate)

Melting Point, °C	Solvent (Melting Point)
29 – 30
27 – 28.5
31 – 32	pentane
28 – 29	petroleum ether

Boiling Point, °C	Pressure (Boiling Point), Torr
98 – 101	0.5
90 – 92	0.001
120 – 122	0.5
120 – 121	1
122	0.5
105	0.1
80 – 90	0.01

Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Solvents (NMR Spectroscopy)
Spectrum	13C
Spectrum	1H
Chemical shifts	1H	CDCl3
Chemical shifts	13C	CDCl3
Chemical shifts	1H	CCl4
Chemical shifts	1H	benzene-d6
Chemical shifts	13C	benzene-d6
Spin-spin coupling constants		CDCl3
Spin-spin coupling constants		benzene-d6

HNMR of 8E, 10E-dodecadien-1-ol CAS 33956-49-9

CNMR of 8E, 10E-dodecadien-1-ol CAS 33956-49-9

Description (IR Spectroscopy)	Solvent (IR Spectroscopy)	Comment (IR Spectroscopy)
Bands	neat (no solvent)	3320 – 920 cm**(-1)
Bands	CHCl3	2930 – 990 cm**(-1)
Bands	neat (no solvent)	3350 – 990 cm**(-1)
Bands	KBr	3350 cm**(-1)
Bands		3340 – 985 cm**(-1)
IR

Description (Mass Spectrometry)

spectrum

spectrum, electron impact (EI)

spectrum, chemical ionization (CI)

fragmentation pattern, spectrum

electron impact (EI), spectrum

Description (UV/VIS Spectroscopy)	Solvent (UV/VIS Spectroscopy)	Comment (UV/VIS Spectroscopy)	Absorption Maxima (UV/VIS), nm	Ext./Abs. Coefficient, l·mol^-1cm^-1
Spectrum		205 – 300 nm
Absorption maxima	aq. ethanol		229.9	28000
Absorption maxima	hexane		229	22800
UV/VIS

Route of Synthesis (ROS)

Conditions

Yield

Stage #1: (E,E)-sorbyl acetate; trimethylsilyl 6-chloro-1-hexyl ether With sodium In toluene at 0 – 80℃; for 12h; Inert atmosphere; Green chemistry;
Stage #2: With sulfuric acid In water; toluene at 0 – 20℃; for 1h; Temperature; Green chemistry;

Experimental Procedure
1.C; 2.C Target product synthesis Example 1: E8, E10-dodecadien-1-ol
In a 1500L dry clean enamel reactor, enter 400kg of metered toluene, replace with nitrogen, put 46kg of chopped clean metal sodium, heat up to 80 ° C, cool under stirring, cool with ice water, cool to 10 ° C, drop by A mixture of intermediate B137 kg and intermediate C208.5 kg.Control 0-10 ° C drop, add dropwise, warm to 60 ° C, heat preservation reaction for 12 hours,Cool to 0 ° C, add 300 kg of water, 98 kg of sulfuric acid, control hydrolysis temperature 20 ° C, hydrolysis and stirring for 1 hour, check the water layer pH 3-4, layering, 200 kg of organic layer washed once, separate the water layer, organic layer negative pressure Concentrated to the solvent without, the remaining liquid enters the rectification column rectification, collecting 10mmHg, 118-120 ° C fraction, as shown in Figure 1,Detecting the E, E-isomer content of 99.5%,The quantity is: 141kg. The yield was 77.47%.The total yield was: 68%.

77.47%

Safety and Hazards

Pictogram(s)
Signal	Danger
GHS Hazard Statements	H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H317 (64.62%): May cause an allergic skin reaction [Warning Sensitization, Skin] H334 (29.23%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory] H400 (99.23%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard] H410 (63.85%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard] Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement Codes	P261, P264, P272, P273, P280, P285, P302+P352, P304+P341, P321, P332+P313, P333+P313, P342+P311, P362, P363, P391, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

Transportation	Class 8; Packaging Group: III; UN Number: 3082
	Under the room temperature and away from light
Storage	Under the room temperature and away from light
Market Price	USD

Druglikeness
Lipinski rules component
分子量	182.306
logP	4.548
HBA	1
HBD	1
Matching Lipinski Rules	4
Veber rules component
Polar Surface Area (PSA)	20.23
Rotatable Bond (RotB)	8
Matching Veber Rules	2

Bioactivity

In vitro: Efficacy

Quantitative Results

Quantitative Results
1 of 10	Biological material	cat SV-CISM-2 cell line
	Assay Description	Increase in cGMP formation in SV-CISM-2 cells relative to control upon treatment with the compound at 10e-4M
	Results	Activity not calculated
	Measurement	Activity
2 of 10	Target	Multidrug resistance protein 1:Wild
	Substance action on target	Inhibitor
	Assay Description	Inhibitory activity against P-glycoprotein mediated compound efflux was determined
3 of 10	Biological material	cat SV-CISM-2 cell line
	Assay Description	Formation of cGMP in SV-CISM-2 cells upon treatment with the compound at 10e-4M
	Results	Activity not calculated
	Measurement	Activity
4 of 10	Biological material	cat SV-CISM-2 cell line
	Assay Description	Formation of cGMP in SV-CISM-2 cells upon treatment with the compound at 10e-6M
	Results	Activity not calculated
	Measurement	Activity
5 of 10	Biological material	cat SV-CISM-2 cell line
	Assay Description	Increase in cGMP formation in SV-CISM-2 cells relative to control upon treatment with the compound at 10e-8M
	Results	Activity not calculated
	Measurement	Activity
6 of 10	Biological material	cat SV-CISM-2 cell line
	Assay Description	Increase in cGMP formation in SV-CISM-2 cells relative to control upon treatment with the compound at 10e-6M
	Results	Activity not calculated
	Measurement	Activity
7 of 10	Biological material	cat SV-CISM-2 cell line
	Assay Description	Formation of cGMP in SV-CISM-2 cells upon treatment with the compound at 10e-8M
	Results	Activity not calculated
	Measurement	Activity
8 of 10	Effect	Behavioural Symptoms
	Assay Description	Target : Ascogaster quadridentata Bioassay : bioassays conducted between hrs 2 and 12 of insects’ photophase (16:8 h light:dark cycle); parasitoids reaching filter paper contain. title comp. within 15 min classed as responders in vivo; vertical Y-shaped Pyrex glass olfactometers; 25-27 deg C; relat. humid. 50-70 percent; fluorescent “daylight”+wide-spectrum grow light; air drawn through apparatus; responses of walking of flying insects to odor sources record.
9 of 10	Biological material	Cydia pomonella
	Assay Description	Effect : pheromone activity Bioassay : dispensers: a piece of cotton dental roll (0.3-300 ng) and gray elastomer septa (0.1-30.0 μg); effect: upwind flights culminating in contact with the dispenser flight tunnel bioassay; males for bioassays were used three days after eclosion and 0.25-2.5 hr after darkening the room; flight tunnel: 210 cm in length, air speed 12 cm/sec, 23 deg C, dimly lighted overhead by red lights controlled by a rheostat
	Results	response: gray elastomer septa: ca. 10 to ca. 85 percent, cotton dental roll: 0 to ca. 70 percent
10 of 10	Biological material	Cydia pomonella
	Assay Description	Effect : pheromone activity Bioassay : effect: the number of males making a circling motion while wing fanning wing-flutter bioassay; pint fruit jar; males for bioassays were used 3 days after eclosion and 0.25-2.5 hr after darkening the room; the test room was dimly lighted by red lights; 3-mm-diameter glass rod with title comp. was inserted into the jar
	Results	response: 20.5-96.5 percent

Use Pattern

General chemicals

guest material for slow-release pheromon composition comprising mesoporous molecular sieve as host material

Chemical processes/laboratory use

synthesizing a sex pheromone of the codling moth

Agricultural use

method of controlling chestnut tortrix (Cydia splendana)

composition for controlling undesired insect infestation

Insect attractant

4-(4-Acetoxyphenyl)-2-butanone CAS#: 3572-06-3

By great_watson-int, 29th November 2017

Structure of 4-[4-(acetyloxy)phenyl]-2-butanone CAS 3572-06-3

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

Identification

Patent Information
Patent ID	Title	Publication Date
CN108191651	Thio carboxylic acid-mediated visible photocatalytic […] reaction synthetic phenol preparation method (by machine translation)	2018

Physical Data

Appearance	Colorless or light yellow oil
Refractive index	n20/D 1.509(lit.)

Boiling Point, °C	Pressure (Boiling Point), Torr
123 – 124	0.2
107.5 – 109

Density, g·cm^-3	Reference Temperature, °C	Measurement Temperature, °C
1.096	4	20

Refractive Index	Wavelength (Refractive Index), nm	Temperature (Refractive Index), °C
1.5061	589	25
1.5059	589	25
1.5078	589	22

Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Solvents (NMR Spectroscopy)	Frequency (NMR Spectroscopy), MHz
Chemical shifts	1H	chloroform-d1	500
Chemical shifts	13C	chloroform-d1	125
Chemical shifts	1H	chloroform-d1	200
Chemical shifts	13C	chloroform-d1	50

GCMS of 4-(4-Acetoxyphenyl)-2-butanone CAS# 3572-06-3

Route of Synthesis (ROS)

Conditions	Yield
With PS-TN lipase; hydrogen; (c-C5Ph4O)2H[Ru(CO)2]2H In toluene at 70℃; under 760.051 Torr; for 72h; Enzymatic reaction;	92%

Safety and Hazards

GHS Hazard Statements

Not Classified

Other Data

Transportation	NONH for all modes of transport
	Under the room temperature and away from light
HS Code	291470
Storage	Under the room temperature and away from light
Shelf Life	1 year
Market Price	USD

Druglikeness
Lipinski rules component
分子量	206.241
logP	1.668
HBA	2
HBD	0
Matching Lipinski Rules	4
Veber rules component
Polar Surface Area (PSA)	43.37
Rotatable Bond (RotB)	5
Matching Veber Rules	2

Bioactivity

In vitro: Efficacy

Quantitative Results

pX	Parameter	Value (quant)	Unit	Target
4.05	activation percentage(relative to standard agonist)	91.8	%	Transient receptor potential cation channel subfamily V member 1 [human]:WildTransient receptor potential cation channel subfamily A member 1 [human]:Wild
3.16	activation percentage(relative to standard agonist)	51.9	%	Transient receptor potential cation channel subfamily V member 1 [human]:Wild

Quantitative Results
1 of 1	Target	Cystic fibrosis transmembrane conductance regulator:Wild
	Assay Description	Ability to modulate the extracellular transport of thiol containing compound by increasing the activity of cystic fibrosis transmembrane conductance regulator
	Measurement	extracellular transport

Use Pattern

male-specific attractant for insecticide formulation

Attractant

Pheromone

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

By great_watson-int, 28th November 2017

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

Identification

Structure of cis-9-Tricosene CAS# 27519-02-4

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

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

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

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

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

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.)

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
分子量	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

(Z,E)-9,12-TETRADECADIENYLACETATE CAS#: 30507-70-1

By great_watson-int, 26th November 2017

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

Identification

Patent Information
Patent ID	Title	Publication Date
US2013/231499	SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES	2013
US4666767	Dispensers for the controlled release of pest controlling agents and method for combatting pest therewith	1987
US6593299	Compositions and methods for controlling pests	2003
US4296042	Preparation of unsaturated aliphatic insect pheromones using cyclic phosphonium ylids	1981

Physical Data

Appearance	Colorless or light yellow oil
Flash Point	102.3±20.4℃
Boiling Point	334.8±21.0℃ (760 Torr)

Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Coupling Nuclei	Solvents (NMR Spectroscopy)	Frequency (NMR Spectroscopy), MHz
Chemical shifts	1H	1H	chloroform-d1	300
Chemical shifts	13C		chloroform-d1	76
Chemical shifts, Spectrum	1H		chloroform-d1	500
Chemical shifts, Spectrum	13C		chloroform-d1	125
Chemical shifts	1H		CDCl3	400
Chemical shifts	13C		CDCl3
Spectrum			CDCl3	400
Chemical shifts	1H		CCl4
Spin-spin coupling constants			CCl4
Spin-spin coupling constants			CDCl3
NMR

HNMR of (Z,E)-9,12-TETRADECADIENYLACETATE CAS# 30507-70-1

CNMR of (Z,E)-9,12-TETRADECADIENYLACETATE CAS# 30507-70-1

Description (IR Spectroscopy)	Solvent (IR Spectroscopy)	Comment (IR Spectroscopy)
Bands	gas	3017 – 964 cm**(-1)
Bands	neat (no solvent)	2960 – 730 cm**(-1)
Bands	CCl4	3010 – 720 cm**(-1)
Bands	neat (no solvent)	2950 – 730 cm**(-1)
Bands	neat (no solvent)	1745 cm**(-1)
Bands	neat (no solvent)	3010 – 720 cm**(-1)
IR

Description (Mass Spectrometry)

gas chromatography mass spectrometry (GCMS), electron impact (EI), spectrum

high resolution mass spectrometry (HRMS), fast atom bombardment (FAB), spectrum

spectrum, chemical ionization (CI)

spectrum

Description (UV/VIS Spectroscopy)

UV/VIS

Route of Synthesis (ROS)

Conditions	Yield
With hydrogen; sodium tetrahydroborate; nickel diacetate; ethylenediamine In ethanol Ambient temperature;	85%
With quinoline; hydrogen; Lindlar’s catalyst In hexane at -10℃;	55.5%
With hydrogen; P-2Ni
With quinoline; hydrogen; Lindlar’s catalyst In hexane at -10℃; Yield given;

Safety and Hazards

Pictogram(s)
Signal	Warning
GHS Hazard Statements	H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (50.56%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement Codes	P264, P280, P302+P352, P321, P332+P313, and P362 (The corresponding statement to each P-code can be found at the GHS Classification page.) For more detailed information, please visit ECHA C&L website

Other Data

Transportation	No data available
	Under the room temperature and away from light
HS Code	No data available
Storage	Under the room temperature and away from light
Shelf Life	1 year
Market Price	USD

Druglikeness
Lipinski rules component
分子量	252.397
logP	6.543
HBA	2
HBD	0
Matching Lipinski Rules	3
Veber rules component
Polar Surface Area (PSA)	26.3
Rotatable Bond (RotB)	12
Matching Veber Rules	1

Bioactivity

In vitro: Efficacy

Quantitative Results

pX	Parameter	Value (quant)	Unit
5.12	Ki (inhibition constant)	7.58	μM
	percentage(Relative fluorescence)	38.09	%

1 of 11	Effect	pheromone
	Assay Description	Effect : EAG response Target : antenna of Lacinipolia renigera, bristly cutworm Bioassay : title comp. isolated from volatile subst. emitted by adult female bolas spiders Mastophora hutchinsoni and collected during the period of mid-August through October, 1998, between 8 and 10 PM; gas chromatography (GC); electroantennography (EAG) proximal end of a male L. renigera antenna was placed into a pool of an insect saline solution; EAG response to title comp. was recorded and compared with simultaneously obtained GC data; effects of title comp. of synthetic and natural origins compared
	Results	GC-EAG peak of title comp. was identified using DB-Wax and DB-5 capillary columns
2 of 11	Biological material	Ephestia kuehniella
	Assay Description	Effect : insect attractant Example 7; Exosex² SPL was formulated from 1% pheromone (Z9E12-14Ac) , 0.5% flow agent, 19.5% paraffin wax and 79% carnauba wax. This powder was compacted into Ig pellets.In a commercial flour mill in Andover, UK the following 2 treatments were compared during the control of theMediterranean
	Results	45.91% mean trap catches at 0 DAT (26.33% in control); 26.55% mean trap catches at 60 DAT (26.0% in control); 4.27% mean trap catches at 136 DAT (54.0% in control)
3 of 11	Biological material	Ephestia kuehniella
	Assay Description	Effect : insect attractant Bioassay : Example 7; Exosex² SPL was formulated from 1% pheromone (Z9E12-14Ac) , 0.5% flow agent, 19.5% paraffin wax and 79% carnauba wax. This powder was compacted into Ig pellets.In a commercial flour mill in Andover, UK the following 2 treatments were compared during the control of theMediterranean
	Results	45.91% mean trap catches at 0 DAT (26.33% in control); 26.55% mean trap catches at 60 DAT (26.0% in control); 4.27% mean trap catches at 136 DAT (54.0% in control) potential area of application: agro
4 of 11	Assay Description	Effect : electrophysiological Target : Spodoptera littoralis, Egyptian armyworm Bioassay : single sensillum recording (SRR); whole insect preparations; standard tip recording technique
	Results	significant response; recording
5 of 11	Effect	Behavioural Symptoms
	Assay Description	Target : Spodoptera littoralis, Egyptian armyworm Bioassay : behavior: close approach to the lure (ca. 10 cm) laboratory colony; insects on first and second scotophase; glass wind tunnel 180 cm long, 55 cm wide, and 50 cm high; 58-W red fluorescence light; light intensity: 3 lux; airspeed 45-55 cm/sec; 22 deg C; 60 percent RH
	Results	response: ca. 5 to 55 percent; max. effect at 1000 μg
6 of 11	Assay Description	Effect : electrophysiological Target : Spodoptera descoinsi Lalanne-Cassou & Silvain, noctuid moth Bioassay : responses of 10 males measured Lepidoptera: Noctuidae; electrophysiological activity of male antenna measured by electroantenographic technique (EAG); pure air as control; experiments were carried out on whole insect preparations
	Results	corrected EAG response: 2.0 (control: ca. 0.8)
7 of 11	Assay Description	Effect : electrophysiological Target : Spodoptera descoinsi Lalanne-Cassou & Silvain, noctuid moth Bioassay : responses of 10 males measured; LM: 11-40 hairs, MH: 2-3 hairs Lepidoptera: Noctuidae; electrophysiological activity of male antenna measured by single sensillum recordings in long lateral – LM (A and B cells) and short medial hairs (MH); air as control; experiments were carried out on whole insect preparations
	Results	response profile; action potentials (mV)/s: LM: <10 (B cells), ca. 37 (A cells), MH: ca. 40 (control: <10)
8 of 11	Assay Description	Effect : electrophysiological Target : Spodoptera latifascia (Walker), noctuid moth Bioassay : responses of 10 males measured Lepidoptera: Noctuidae; electrophysiological activity of male antenna measured by electroantenographic technique (EAG); pure air as control; experiments were carried out on whole insect preparations
	Results	corrected EAG response: 2.5 (control: ca. 0.8)
9 of 11	Assay Description	Effect : electrophysiological Target : Spodoptera latifascia (Walker), noctuid moth Bioassay : responses of 10 males measured; LM: 11-30 hairs, MH: 10-22 hairs Lepidoptera: Noctuidae; electrophysiological activity of male antenna measured by single sensillum recordings in long lateral – LM (A and B cells) and short medial hairs (MH); air as control; experiments were carried out on whole insect preparations
	Results	response profile; action potentials (mV)/s: LM: ca. 37 (A cells), <10 (B cells), MH: 20 (control: <10)
10 of 11	Results	pheromone of Cadra cautella (almond moth) and Plodia interpunctalla (Indian meal moth)
11 of 11	Results	pheromone component of various butterflys, inhibitor effects of various butterflys

Use Pattern

(Z,E)-9,12-TETRADECADIENYLACETATE CAS#: 30507-70-1 Controlling Parapediasia teterrella

(Z,E)-9,12-TETRADECADIENYLACETATE CAS#: 30507-70-1 Controlling Spodoptera exempta

英文名	Z-8-Dodecenyl acetate/E-8-Dodecenyl acetate/Z-8-Dodecenol
IUPAC Name	No data available
分子结构
CAS编号	None
MDL Number	No data available
别名	8Z-12Ac/8E-12Ac/8Z-12OH
分子式	C₁₆H₂₆O₂
分子量	250.376
InChI	No data available
InChI Key	No data available
Canonical SMILES	No data available

英文名	Peachflure
IUPAC Name	(Z)-icos-13-en-10-one
分子结构
CAS编号	63408-44-6
别名	(13Z)-eicos-13-en-10-one, (Z)-13-eicosene-10-one, Z-icos-13-en-10-one, eicos-13c-en-10-one, cis-7-eicosen-11-one, Z-13-icosane-10-one
分子式	C₂₀H₃₈O
分子量	294.515
InChI	InChI=1S/C20H38O/c1-3-5-7-9-11-13-15-17-19-20(21)18-16-14-12-10-8-6-4-2/h13,15H,3-12,14,16-19H2,1-2H3/b15-13-
InChI Key	HVUBXNQWXJBVHB-SQFISAMPSA-N
Canonical SMILES	O=C(CCCCCCCCC)CC\C=C/CCCCCC

英文名	TRANS-7, CIS-9-DODECADIENYL ACETATE
IUPAC Name	[(7Z,9E)-dodeca-7,9-dienyl] acetate
分子结构
CAS编号	55774-32-8
EINECS Number	259-812-0
MDL Number	MFCD00009870
别名	(7Z,9E)-7,9-dodecadien-1-yl acetate, (7Z, 9E)-dodecadien-1-yl acetate, (7Z,9E)-7,9-dodecadienyl acetate, (7Z,9E)-7,9-Dodecadienylacetat, (Z,E)-7,9-Dodecadienyl acetate, (7Z,9E)-dodecadienyl acetate, 7,9-dodecadienyl acetate;CAS Number: 55774-32-8
分子式	C₁₄H₂₄O₂
分子量	224.339
InChI	InChI=1S/C14H24O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h4-7H,3,8-13H2,1-2H3/b5-4-,7-6+
InChI Key	LLRZUAWETKPZJO-SCFJQAPRSA-N
Canonical SMILES	CC/C=C\C=C\CCCCCCOC(=O)C

英文名	E3,Z8,Z11-Tetradecatriene acetate
IUPAC Name	[(3E,8Z,11Z)-tetradeca-3,8,11-trienyl] acetate
分子结构
CAS编号	163041-94-9
MDL Number	MFCD22581574
别名	[(3E,8Z,11Z)-tetradeca-3,8,11-trienyl] acetate UNII-6CQR9SPA87; (3E,8Z,11Z)-Tetradeca-3,8,11-trienyl acetate; 6CQR9SPA87; (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate; Tetradeca-3,8,11-trienyl acetate, (3E,8Z,11Z)-; 3E,8Z,11Z-Tetradecatrienyl acetate; (3E,8Z,11Z)-Tetradeca-3,8,11-trien-1-yl acetate; 3,8,11-Tetradecatrien-1-ol, 1-acetate, (3E,8Z,11Z)-; (E,Z,Z)-3,8,11-Tetradecatrien-1-ol acetate; SCHEMBL1301147; DTXSID50700624; HWPJPNQEVWTZSJ-XBZOLNABSA-N; LMFA07010306; ZINC59725211; (E,Z,Z)-3,8,11-Tetradecatrienyl acetate; Q27264506; [(3E,8Z,11Z)-tetradeca-3,8,11-trienyl] acetate; acetic acid [(3E,8Z,11Z)-tetradeca-3,8,11-trienyl] ester; [(3E,8Z,11Z)-tetradeca-3,8,11-trienyl] ethanoate
分子式	C₁₆H₂₆O₂
分子量	250.376
InChI	InChI=1S/C16H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16(2)17/h4-5,7-8,12-13H,3,6,9-11,14-15H2,1-2H3/b5-4-,8-7-,13-12+
InChI Key	HWPJPNQEVWTZSJ-XBZOLNABSA-N
Canonical SMILES	CC/C=C\C/C=C\CCC/C=C/CCOC(=O)C

英文名	8,10-DODECADIEN-1-OL
IUPAC Name	(8E,10E)-dodeca-8,10-dien-1-ol
分子结构
CAS编号	33956-49-9
别名	(8E,10E)-dodeca-8,10-dienol;CAS Number: 33956-49-9; CAS NO:.33956-49-9
分子式	C₁₂H₂₂O
分子量	182.30
InChI	InChI=1S/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h2-5,13H,6-12H2,1H3/b3-2+,5-4+
InChI Key	CSWBSLXBXRFNST-MQQKCMAXSA-N
Canonical SMILES	C/C=C/C=C/CCCCCCCO

Peachflure CAS#: 63408-44-6 HNMR
Peachflure CAS#: 63408-44-6 CNMR

8,10-DODECADIEN-1-OL CAS#: 33956-49-9 HNMR
8,10-DODECADIEN-1-OL CAS#: 33956-49-9 CNMR

英文名	4-(4-Acetoxyphenyl)-2-butanone
IUPAC Name	[4-(3-oxobutyl)phenyl] acetate
分子结构
CAS编号	3572-06-3
别名	4-(p-hydroxyphenyl)-2-butanone acetate, 4-(4-acetoxyphenyl)butan-2-one, 4-(p-acetoxyphenyl)-2-butanone, 4-(3-oxobutyl)phenyl acetate, cue lure, 4-(4-acetoxyphenyl)-2-butanone, cuelure
分子式	C₁₂H₁₄O₃
分子量	206.238
InChI	InChI=1S/C12H14O3/c1-9(13)3-4-11-5-7-12(8-6-11)15-10(2)14/h5-8H,3-4H2,1-2H3
InChI Key	UMIKWXDGXDJQJK-UHFFFAOYSA-N
Canonical SMILES	CC(=O)CCc1ccc(cc1)OC(=O)C

英文名	cis-9-Tricosene
IUPAC Name	(Z)-tricos-9-ene
分子结构
CAS编号	27519-02-4
别名	(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
分子式	C₂₃H₄₆
分子量	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

cis-9-Tricosene CAS#: 27519-02-4 GCMS
cis-9-Tricosene CAS#: 27519-02-4 GC MS

英文名	(Z,E)-9,12-TETRADECADIENYLACETATE
IUPAC Name	tetradeca-9,12-dienyl acetate
分子结构
CAS编号	30507-70-1
别名	Tetradec-9Z,12E-dien-1-yl Acetate;CAS Number: 30507-70-1
分子式	C₁₆H₂₈O₂
分子量	252.392
InChI	InChI=1S/C16H28O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16(2)17/h3-4,6-7H,5,8-15H2,1-2H3/b4-3-,7-6+
InChI Key	ZZGJZGSVLNSDPG-WWVFNRLHSA-N
Canonical SMILES	C/C=C\C/C=C/CCCCCCCCOC(=O)C