172376-82-8

Basic information

• Product Name: (6Z)-3,7,11-trimethyldodeca-6,10-dienal
• Synonyms: (6Z)-3,7,11-Trimethyldodeca-6,10-dienal; 6,10-dodecadienal, 3,7,11-trimethyl-, (6Z)-
• CAS NO: 172376-82-8
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.37
• Mol File: 172376-82-8.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 309.5°C at 760 mmHg
• Flash Point: 146.4°C
• Density: 0.853g/cm³
• Vapor Pressure: 0.000639mmHg at 25°C
• Refractive Index: 1.46
• CAS DataBase Reference: (6Z)-3,7,11-trimethyldodeca-6,10-dienal(CAS DataBase Reference)
• NIST Chemistry Reference: (6Z)-3,7,11-trimethyldodeca-6,10-dienal(172376-82-8)
• EPA Substance Registry System: (6Z)-3,7,11-trimethyldodeca-6,10-dienal(172376-82-8)

Safety Data

• Hazardous Substances Data: 172376-82-8(Hazardous Substances Data)

Usage

General Description

(6Z)-3,7,11-trimethyldodeca-6,10-dienal, also known as 6,10-dimethyl-3,7-undecadienal, is a natural compound commonly found in the essential oils of various plants, including citrus fruits. It is used in the fragrance industry as a component in perfumes and other scented products due to its pleasant and citrusy odor. Additionally, it has been reported to have antimicrobial and antioxidant properties, making it a potential candidate for use in personal care and cosmetic products. The compound is also known for its role as a pheromone in some insects and is being studied for its potential application as an insect repellent. Overall, (6Z)-3,7,11-trimethyldodeca-6,10-dienal has a variety of industrial and scientific applications due to its unique properties and natural occurrence in many plant species.

Upstream product

• 502-67-0 Farnesal 
• 20576-54-9 (3R)-(6E)-2,3-dihydrofarnesol 
• 106-28-5 Farnesol 
• 3899-18-1 (6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene 
• 3482-62-0 N,N-diethyl-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]amine 
• 37519-97-4 1-hydroxy-3,7,11-trimethyl-6,10-dodecadiene 
• 18794-84-8 (E)-β-farnesene 
• 40716-66-3 (E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol 
• 1574173-72-0 (1E,3R,6E)-N,N-diethyl-3,7,11-trimethyldodeca-1,6,10-trien-1-amine 
• 20576-54-9 (3S)-(6E)-2,3-dihydrofarnesol 
• 24405-96-7 diethyl (E)-2-(4,8-dimethylnona-3,7-dien-1-yl)-2-methylmalonate 
• 79-37-8 oxalyl dichloride 
• 58001-88-0 (E)-2,6,10-trimethylundeca-5,9-dien-1-ol 
• 24405-98-9 (E)-5-2,6,10-trimethyl-5,9-undecadienoic acid 

Downstream Products

• 20576-54-9 (3R)-(6E)-2,3-dihydrofarnesol 
• 34114-96-0 methyl (S,E)-2,3-dihydrofarnesenoate 

Relevant articles and documents

Synthesis, characterization and transfection activity of new saturated and unsaturated cationic lipids

We synthesized new cationic lipids, analogue to N-[1-(2,3-dioleoyloxy) propyl]-N,N,N-trimethylammonium chloride (DOTMA) and 1,2-dimyristyloxypropyl-3- dimethyl-hydroxyethylammonium bromide (DMRIE), in order to compare those containing a dodecyl chain with those having a relatively long chain with two or five double bonds, such as squalenyl and dihydrofarnesyl derivatives, or complex saturated structures, such as squalane derivatives. The fusogenic helper lipid dioleoylphosphatidylethanolamine (DOPE) was added to cationic lipids to form a stable complex. Liposomes composed of 50:50 w/w cationic lipid/DOPE were prepared and incubated with plasmidic DNA at various charge ratios and the diameter and zeta potential of the complexes were measured. The surface charge of the DNA/lipid complexes can be controlled by adjusting the cationic lipid/DNA ratio. Finally, we tested the in vitro transfection efficiency of the cationic lipid/DNA complexes using different cell lines. The transfection efficiency was highest for the dodecyloxy derivative containing a single hydroxyethyl group in the head, followed by the dodecyloxy and the farnesyloxy trimethylammonium derivatives. Instead the C27 squalenyl and C27 squalanyl derivatives resulted inactive.

Sex pheromone of Ascogaster quadridentata, a parasitoid of Cydia pomonella

Porapak Q volatile extracts of female Ascogaster quadridentata, an egg- larval endoparasitoid of codling moth, Cydia pomonella, bioassayed in Y-tube olfactometers attracted male, but not female, A. quadridentata. Coupled gas chromatographic-electroantennographic detection (GC-EAD) analysis of bioactive extracts revealed three compounds that elicited responses by male A. quadridentata antennae. GC-mass spectra (MS) indicated, and comparative analyses of authentic standards confirmed, that these compounds were (Z,Z)9.12-octadecadienal, (Z)-9-hexadecenal, and 3,7,11-trimethyl-6E, 10- dodecadienal. (Z,Z)-9,12-Octadecadienal alone attracted laboratory-reared male A. quadridentata in Y-tube olfactometer and field-cage bioassays, and attracted feral A. quadridentata in a field experiment. This sex pheromone could be used to help detect populations of A. quadridentata, delineate their distributions, and determine potential sources of parasitoids for capture and release in integrated programs for control of C. pomonella.

Frogolide – An Unprecedented Sesquiterpene Macrolactone from Scent Glands of African Frogs

Some amphibians use chemical signals in addition to optical and acoustical signals to transmit information. Males of mantellid frogs from Madagascar and hyperoliid frogs from Africa emit complex, species- and sex-specific bouquets of volatiles from their femoral or gular glands. We report here on the identification, synthesis, and determination of the absolute configuration of a macrocyclic lactone occurring in several species of both families, (S)-3,7,11-dodec-6,10-dien-12-olide (S-14, frogolide). Macrolides are a preferred compound class of frog volatiles. Nevertheless, frogolide is the first macrocyclic lactone obviously derived from the terpene pathway, in contrast to known frog macrolides that are usually formed via the fatty acid biosynthetic pathway.

METHOD FOR PRODUCING OPTICALLY ACTIVE 2,3-DIHYDROFARNESAL

A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed. The method includes subjecting β-farnesene f formula (2) to amination in the presence of a lithium salt of an amine to obtain (2E)-farnesyl allylamine of general formula (3); subjecting the (2E)-farnesyl allylamine to asymmetric isomerization to obtain an optically active farnesyl enamine of general formula (4); and subjecting the optically active farnesyl enamine to solvolysis: