66007-19-0

Basic information

• Product Name: (S,E)-(+)-14-methyl-8-hexadecenal (trogodermal)
• CAS NO: 66007-19-0
• Molecular Weight: 252.44
• Mol File: 66007-19-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S,E)-(+)-14-methyl-8-hexadecenal (trogodermal)(CAS DataBase Reference)
• NIST Chemistry Reference: (S,E)-(+)-14-methyl-8-hexadecenal (trogodermal)(66007-19-0)
• EPA Substance Registry System: (S,E)-(+)-14-methyl-8-hexadecenal (trogodermal)(66007-19-0)

Safety Data

• Hazardous Substances Data: 66007-19-0(Hazardous Substances Data)

Upstream product

• 66007-18-9 (S,E)-(+)-14-methyl-8-hexadecen-1-ol 
• 1448019-31-5 (3R)-3-methyl-16-(tetrahydro-2H-pyran-2-yloxy)hexadec-8-yn-1-ol 
• 1448019-30-4 2-[(R)-16-(benzyloxy)-14-methylhexadec-8-ynyloxy]tetrahydro-2H-pyran 
• 1448019-24-6 (R)-[(3-methylnon-8-ynyloxy)methyl]benzene 
• 1448019-23-5 (R)-[(9,9-dibromo-3-methylnon-8-enyloxy)methyl]benzene 
• 1448019-22-4 (R)-8-(benzyloxy)-6-methyloctanal 
• 83541-13-3 (R)-(+)-6-(benzyloxy)-4-methylhexanal 
• 1448019-20-2 ethyl (R,E)-8-(benzyloxy)-6-methyloct-2-enoate 
• 10160-25-5 7-bromo-1-(2-tetrahydropyranyloxy)heptane 
• 10160-24-4 7-bromoheptyl alcohol 
• 629-30-1 1,7-heptandiol 
• 50837-13-3 (S)-(+)-14-methyl-8-hexadecyn-1-ol 
• 533-87-9 DL-erythro-aleuritic acid 
• 127060-16-6 (S)-14-methylhexadec-8-yn-1-al dimethylacetal 

Downstream Products

• 66007-17-8 (S)-14-Methyl-(Z)-8-hexadecenal 

Relevant articles and documents

Synthesis of chiral sex pheromone components of several species of Trogoderma (Coleoptera: Dermestidae)

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Pheromone synthesis. Part 240: Cross-metathesis with Grubbs I (but not Grubbs II) catalyst for the synthesis of (R)-trogodermal (14-methyl-8-hexadecenal) to study the optical rotatory powers of compounds with a terminal sec-butyl group

(R)-Trogodermal (14-methyl-8-hexadecenal), the sex pheromone of Trogoderma species of pest insects against stored products, and its (S)-isomer were synthesized by using olefin cross-metathesis between (R)- or (S)-7-methyl-1-nonene and 8-nonenyl acetate as the key step. This step was successful with Grubbs I but not with Grubbs II catalyst. The latter caused randomization of the carbon skeleton to give a mixture of abnormal products with both longer or shorter carbon chains than the desired product. The specific rotations of 18 newly and 6 previously synthesized compounds with a terminal sec-butyl group were measured to conclude them to be [α]D +3.5 to +6.5 or -3.6 to -6.4.

PHEROMONES OF COLEOPTERA. COMMUNICATION 5. SYNTHESIS OF R,E-14-METHYL-8-HEXADECENAL (trans-TROGODERMAL)

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