57491-33-5

Basic information

• Product Name: (E)-hexadec-11-enal
• Synonyms: (E)-hexadec-11-enal;(11E)-11-Hexadecenal;11-Hexadecenal, (E)-;Ai3-36726;Einecs 260-765-3
• CAS NO: 57491-33-5
• Molecular Formula: C₁₆H₃₀O
• Molecular Weight: 238.4088
• EINECS: 260-765-3
• Mol File: 57491-33-5.mol

Chemical Properties

• Boiling Point: 324°Cat760mmHg
• Flash Point: 156.6°C
• Appearance: /
• Density: 0.84g/cm³
• Vapor Pressure: 0.000253mmHg at 25°C
• Refractive Index: 1.451
• CAS DataBase Reference: (E)-hexadec-11-enal(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-hexadec-11-enal(57491-33-5)
• EPA Substance Registry System: (E)-hexadec-11-enal(57491-33-5)

Safety Data

• Hazardous Substances Data: 57491-33-5(Hazardous Substances Data)

Usage

Uses

(11E)-11-Hexadecenal is a monounsaturated 16 carbon aldehyde found in pheromones of insects.

InChI:InChI=1/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h5-6,16H,2-4,7-15H2,1H3/b6-5+

Upstream product

• 86652-97-3 Phenylsulfonyl-8 octanol-1 
• 113789-13-2 11-hexadecene-1-ol 
• 132255-29-9 8-phenylsulfonyl-11E-hexadecen-1-ol 
• 113267-16-6 1-(2-tetrahydropyranyloxy)-11E-hexadecene 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 56218-72-5 (E)-11-hexadecen-1-yl acetate 
• 50816-18-7 9-decen-1-yl acetate 
• 1119-64-8 1-bromohexyne 
• 693-02-7 hex-1-yne 
• 65686-49-9 11-hexadecyn-1-ol 
• 51309-10-5 10-chlorodecanol 
• 61301-56-2 trans-11-hexadecen-1-ol 
• 53155-10-5 (E)-1-oct-3-enyl bromide 

Relevant articles and documents

SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES

The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.

Sex pheromone of tomato fruit borer, Neoleucinodes elegantalis

Five candidate pheromone components were identified by analyzing pheromone gland extracts by gas chromatography (GC), coupled GC-electro-antennographic detection (EAD), and coupled GC-mass spectrometry (MS): (E)-11-hexadecenol(E11-16: OH), (Z)-11-hexadecenol(Z11-16: OH), (E)-11-hexadecenal, (E)-11-hexadecenyl acetate, and (Z)-3,(Z)-6,(Z)-9-tricosatriene (Z3,Z6,Z9-23: Hy). In electroantennogram (EAG) recordings, synthetic E11-16: OH elicited stronger antennal responses at low doses than other candidate pheromone components. Field tests demonstrated that synthetic E11-16: OH as a trap bait was effective in attracting males, whereas addition of Z11-16: OH inhibited the males' response. Z3,Z6,Z9-23 : Hy strongly enhanced attractiveness of E11-16: OH, but was not attractive by itself. A pheromone blend with synergistic behavioral activity of an alcohol (E11- 16: OH) and hydrocarbon (Z3,Z6,Z9-23: Hy) component is most unusual in the Lepidoptera. The synthetic two-component pheromone is approximately 60 times more attractive than the female-produced blend and might facilitate the control of this pest.

SYNTHESIS OF TRANS-2,CIS-13- AND TRANS-3,CIS-13-OCTADECADIEN-1-OL ACETATES, COMPONENTS OF THE SEX PHEROMONE OF SYNANTHEDON TIPULIFORMIS (LEPIDOPTERA, SISIIDAE)

The Wittig-Horner reaction of ethoxycarbonylmethylenetriphenylphosphorane or ethyl diethylphosphonoacetic acid with cis-11-hexadecenal and the modified Knoevenagel reaction of this aldehyde with malonic acid gave the ethyl ester of trans-2,cis-13-octadecadienoic acid and trans,cis-13-octadecadienoic acid, which upon reduction and acetylation were converted into trans-2,cis-13- and trans-3-cis-13-octadecadien-1-yl acetates, which are components of the sex pheromone of Synanthedon tipuliformis (Lepidoptera, Sisiidae).

STEREOSPECIFIC SYNTHESIS OF TRANSOID MONO- AND 1,3-DIENE PHEROMONES OF LEPIDOPTERA FROM SECONDARY CYCLOPROPYLCARBINOLS

The zinc halide-initiated homoallylic rearrangement of saturated or allylic cyclopropylcarbinols in the presence of trimethylsilyl halides has been employed as the key step in the total synthesis of seven behavioral regulators in twenty insects of the Lepidoptera family, namely 9E-tetradecenol and its acetate, 11E-hexadecenol and its acetate, 11E-hexadecenal, 5E,7E-dodecadienol, and 3E,5E-tetradecadienyl acetate.

Pheromones via Organoboranes. 2. Vinylic Organoboranes. 8. Applications of the General Stereoselective Synthesis of (E)-Disubstituted Alkenes via Thexylchloroborane-Dimethyl Sulfide to the Synthesis of Pheromones Containing an (E)-Alkene Moiety

Various (E)-pheromones of the general structure (E)-X-alken-1-yl acetates, (E)-X-alken-1-ols, and (E)-X-alken-1-als have been prepared via thexylchloroborane-dimethyl sulfide (ThxBHCl*SMe2).Hydroboration of acetate-functionalized alkenes with ThxBHCl*SMe2 gives cleanly the corresponding thexylalkylchloroboranes (ThxBRCl, B).Hydridation of B with potassium triisopropoxyhydride (KIPBH) at -78 deg C gives cleanly the corresponding thexylalkylboranes (ThxBRH, C).These are quenched immediately with 1-halo-1-alkynes to give B-(cis-1-halo-1-alkenyl)thexylalkylboranes (D).Treatment of D with sodium methoxide results in the displacement of bromine by the alkyl group on boron to produce B-(trans-1-alkyl-1-alkenyl)thexylborinates (E).Protonolysis of E with acetic acid provides (E)-X-alken-1-yl acetates in high yields and in >99percent isomeric purities.Treatment of (E)-X-alken-1-yl acetates with base affords the corresponding (E)-X-alken-1-ols.Oxidation of (E)-X-alken-1-ols with dimethyl sulfoxide activated by oxalyl chloride or the complex of dimethyl sulfide and chlorine produces (E)-X-alken-1-als quantitatively.By properly choosing the starting functionalized alkenes and 1-halo-1-alkynes, various (E)-pheromones can be prepared easily.The present procedure appears to be general.There does not appear to be any limitation on the length of the carbon chain or the position of the double bond in the target molecules.