20056-92-2

Basic information

• Product Name: CIS-7-DODECEN-1-OL
• Synonyms: (7Z)-7-Dodecen-1-ol;(z)-7-dodecen-1-o;(Z)-7-Dodecen-1-ol;(Z)-7-Dodecenyl alcohol;7-Dodecen-1-ol, (Z)-;Looplure inhibitor;looplureinhibitor;CIS-7-DODECEN-1-OL
• CAS NO: 20056-92-2
• Molecular Formula: C₁₂H₂₄O
• Molecular Weight: 184.32
• EINECS: 243-488-2
• Product Categories: insect pheromone
• Mol File: 20056-92-2.mol

Chemical Properties

• Melting Point: 77.27°C (estimate)
• Boiling Point: 283.3°C (estimate)
• Flash Point: 61 °C
• Appearance: /
• Density: 0.8597 (estimate)
• Vapor Pressure: 0.000919mmHg at 25°C
• Refractive Index: 1.4531 (estimate)
• Storage Temp.: −20°C
• CAS DataBase Reference: CIS-7-DODECEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-7-DODECEN-1-OL(20056-92-2)
• EPA Substance Registry System: CIS-7-DODECEN-1-OL(20056-92-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: JR5255000
• Hazardous Substances Data: 20056-92-2(Hazardous Substances Data)

Usage

Uses

Used in Pheromone Applications:
CIS-7-DODECEN-1-OL is used as a sex pheromone for the cabbage looper, Trichoplusia ni Hubner, to attract and facilitate mating between individuals of the species. This pheromone plays a crucial role in the reproductive process and can be utilized in pest management strategies to control the population of this agricultural pest.
Used in Chemical Synthesis:
CIS-7-DODECEN-1-OL is used as an intermediate in the synthesis of (7Z)-Dodecenyl Acetate, which is an important compound in the chemical industry. The synthesis of (7Z)-Dodecenyl Acetate involves a nucleophilic substitution reaction between the Grignard reagent of the protected bromohydrin and (Z)-2-hepten-1-yl acetate in the presence of a CuI catalyst. CIS-7-DODECEN-1-OL has various applications in the fragrance, flavor, and pharmaceutical industries.
Used in Pest Management:
CIS-7-DODECEN-1-OL can be employed in pest management strategies, particularly for the control of the cabbage looper, Trichoplusia ni Hubner. By using this pheromone as a lure, it is possible to trap and monitor the population of this pest, allowing for more targeted and effective pest control measures. This approach can reduce the reliance on chemical pesticides and promote more sustainable agricultural practices.
Used in Research and Development:
CIS-7-DODECEN-1-OL is also used in research and development for various applications, including the study of insect behavior, chemical ecology, and the development of new pheromone-based pest control strategies. Understanding the role of this pheromone in the reproductive process of the cabbage looper can lead to the discovery of novel methods for controlling this and other pests, ultimately benefiting agriculture and the environment.

InChI:InChI=1/C12H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h5-6,13H,2-4,7-12H2,1H3/b6-5-

Upstream product

• 52956-99-7 cis-9-tetradecanoic acid 
• 70680-13-6 ethyl (Z)-dodec-7-enoate 
• 110-62-3 pentanal 
• 76771-95-4 7-hydroxy-heptyl-triphenyl-phosphonium bromide 
• 22054-13-3 7-hydroxyheptanal 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 59499-29-5 (Z)-4-nonenyl bromide 
• 34399-67-2 1-bromo-3-(1-ethoxyethoxy)propane 
• 41862-94-6 dodec-7-yn-1-ol 
• 629-03-8 1 ,6-dibromohexane 
• 693-02-7 hex-1-yne 
• 53963-10-3 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran 
• 821-41-0 5-Hexen-1-ol 
• 16504-87-3 Dodec-7-in-1-yl acetat 

Downstream Products

• 63851-40-1 (Z)-7-dodecenal 
• 14959-86-5 (Z)-7-dodecenyl acetate 
• 72530-36-0 (Z)-7-Dodecen-1-ol tosylat 
• 205523-92-8 1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-((Z)-tridec-8-enyl)-benzene 
• 62897-10-3 ardisinol II 
• 426820-02-2 1-(4-Methoxy-benzenesulfonyl)-2-((Z)-tridec-8-enyl)-4-trityl-piperazine 
• 426819-90-1 3-((Z)-Tridec-8-enyl)-1-trityl-piperazine 

Relevant articles and documents

Synthesis of Z-alkenes from alkenylcatecholboranes through reaction with RMgX and I2 induced rearrangement

Addition of RMgX and BrMg(CH2)nMgBr reagents to alkenylcatecholborane followed by iodine induced rearrangement and oxidation provided Z-olefins and Z-olefinic alcohols in moderate to good yields. This procedure is advantageous over the previous methods of synthesis of Z-olefins from alkenylboranes since the alkyl groups which are not available through hydroborations can also be utilized.

Synthesis of (Z)-7-dodecylene-1-alcohol and acetic ester thereof

The invention belongs to the technical field of insect pheromone synthesis, and discloses a novel method for synthesizing (Z)-7-dodecylene-1-alcohol and acetic ester thereof. The method comprises thefollowing steps: taking n-valeraldehyde as a starting material and reacting with a Wittig reagent to obtain (Z)-7-dodecenoic acid ethyl ester; then performing reduction with lithium aluminum hydroxideto obtain (Z)-dodeca-carbon-7-alkene-1-alcohol; finally taking (Z)-dodeca-carbon-7-alkene-1-alcohol to react with acetyl chloride to obtain (Z)-7-dodecylene-1-farnesyl acetate. By adopting the method, Z-shaped double bonds are directly constructed through a coupling reaction of the Wittig reagent carrying an ester group at the tail end with aldehyde. The method is simple in synthesis route, and is environmentally friendly.

A Facile Synthesis of the Sex Pheromone of the Cabbage Looper Trichoplusia ni

The sex pheromone of the cabbage looper Trichoplusia ni Hubner, (Z)-7-dodecen-1-yl acetate, was synthesized via a bimolecular nucleophilic substitution reaction between the Grignard reagent of the protected bromohydrin with (Z)-2-hepten-1-yl acetate in the presence of CuI catalyst as a key step. An efficient synthetic method of preparation of the pheromone was achieved from (Z)-2-butene-1,4-diol in four steps with an overall yield of 22.1%.

Simple syntheses of (Z)-7-dodecen-1-ol, (Z)-7-tetradecen-1-yl acetate, (Z)-9-tetradecenal and (Z)-9-hexadecen-1-yl acetate from aleuritic acid

Insect sex pheromones are used for monitoring and management of crop pests. Four compounds (Z)-7-dodecen-1-ol, (Z)-7-tetradecen-1-yl acetate, (Z)-9-tetradecenal and (Z)-9-hexadecen-1-yl acetate reported as components of some important agricultural insect pests have been synthesized from theo-aleuritic acid (9,10,16-trihydroxyhexadecanoic acid) involving simplified Wittig reactions with improved yield.

Structure-activity relationships in platelet-activating factor (PAF). 11-From PAF-antagonism to phospholipase A2 inhibition: Syntheses and structure-activity relationships in 1-arylsulfamido-2-alkylpiperazines

1-Benzoyl-2-alkyl piperazines are strong inhibitors of Group I and II secreted PLA2s. An improvement of their activity was obtained by replacing the amide function by a sulfamide and by introduction of electrodonor substituents on the para position of the benzenesulfonyl moiety. Neither the position on one of the carbon of the piperazine ring nor the absolute configuration of this carbon have an effect on the affinity for one or the other group of PLA2, but the lipophilicity remains for these series an essential parameter. In addition structure-activity relationships allow new hypothesis on interaction of these piperazine derivatives with the catalytic site of PLA2s.

New synthesis of (Z)-5- and (Z)-7-monoene components of insect sex pheromones of the Lepidoptera order

A new procedure was developed for the synthesis of (Z)-5- and (Z)-7-monoene components of sex pheromones of Lepidoptera insects based on cometathesis of readily accessible cycloocta-1,5-diene and ethylene.

Synthesis of sub-units of marine polycyclic ethers by ring-closing metathesis and hydroboration of enol ethers

A novel syntheses of Z-5-dezenol, Z-5-decenyl acetate, Z-7-dodecenol, Z- 7-dodecenyl acetate, Z-9-tricosene, Z-7,8-epoxy-methyloctadecane which are sex pheromone components of Lepidoptera and Diptera orders, have been realized via stereoselective cometathesis of 1,5-cyclooctadiene with ethylene in the presence of MoCls/SiO2-SnMe4 as a key reaction. The male cometathesis product, 1,Z-5,9-decatriene, has been converted into pheromone components monocloned above by regioselective partial hydroboration or hydrozirconation with help of 9-BBN and Cp2ZrHCl, correspondingly. The protonolysis of the obtained zirconosene derivative gave 1,Z-5-decadiene. Hydroboration-oxidation or hydroboration-C2-homologation of the latter but to Z-5- or Z-7 monoene pheromone components. Hydroboration-iodination of terminal double bond in 1,Z-5,9-decatriene, and further cross-coupling of the obtained iodine derivative with convenient lithium cuprates resulted in Z-9- tricosene, the main sex pheromone component of House Fly (Musca Domestica), or in 2-methyl-Z-7-octadecene, the presence of Gypsy Moth (Lymantria Dispar) sex attractant.

Synthesis of ardisinol II

The first and also a concise synthesis of ardisinol II by two routes in excellent yields are described.

Pheromone Evaluation of Four Geometric Isomers of 4,11-Hexadecadienal toward Male Eri-Silk Moths

Four geometric isomers of 4,11-hexadecadienal were prepared and their pheromone activities to male eri-silk moths were evaluated by using the fluttering test and electro-antennography.None of these compounds showed any activity in spite of their similar structure to other pheromone mimics and to the natural pheromone.These results suggest that the presence of 6,11-double bonds is essential for pheromone activity.