51513-58-7

Usage

Uses

Used in Perfumery and Flavoring Industry:
(6E)-3,7,11-trimethyldodeca-6,10-dienal is used as a key ingredient in the production of perfumes and flavorings due to its strong, sweet, and floral scent. Its unique aroma adds depth and complexity to fragrances, while also enhancing the taste and aroma of various food products.
Used in Insecticides and Repellents:
(6E)-3,7,11-trimethyldodeca-6,10-dienal is used as an active component in some insecticides and repellents, thanks to its natural insect-repelling properties. Its incorporation into these products helps to deter and control various insect species, making it a valuable tool in pest management and control.
Used in Pharmaceutical Research:
(6E)-3,7,11-trimethyldodeca-6,10-dienal is used as a subject of research in the pharmaceutical industry for its potential as an anti-cancer agent. Studies are being conducted to explore its effectiveness in targeting and treating various types of cancer, as well as its potential as a natural remedy for other health conditions.
Used in Cosmetics Industry:
(6E)-3,7,11-trimethyldodeca-6,10-dienal is used as a fragrance component in the cosmetics industry, adding a pleasant and appealing scent to various cosmetic products such as lotions, creams, and shampoos. Its strong, sweet, and floral aroma enhances the sensory experience of using these products, making them more enjoyable for consumers.

Upstream product

• 502-67-0 Farnesal 
• 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 
• 22339-13-5 (E)-9-iodo-2,6-dimethylnona-2,6-diene 
• 459-88-1 (E)-4,8-dimethylnona-3,7-dien-1-ol 
• 106-28-5 Farnesol 
• 76190-00-6 (+/-)-3,7,11-trimethyl-6Z,10-dien-1-ol 
• 72019-02-4 (6E)-3,7,11-trimethyldodeca-2,6,10-trienal 
• 82528-61-8 (1EZ,6E)-3,7,11-trimethyl-1-triethylsiloxydodeca-1,6,10-triene 

Downstream Products

• 108860-89-5 (2E,8E)-5,9,13-Trimethyl-tetradeca-2,8,12-trienoic acid (S)-2-ethoxy-2-phenyl-ethyl ester 

Relevant academic research and scientific papers

Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation

A synthetic route to liphagal, a natural PI3Kα inhibitor isolated from Aka coralliphaga, was established. The present route features an organic redox process where an alkynylquinone undergoes reductive cyclization in the presence of a hydroquinone derivative such as hydroxyquinol (1,2,4-benzenetriol) and catalytic PdCl2 to provide a substituted benzofuran suitable for accessing the natural product. The benzofuran formation takes place via the redox transformation between the alkynylquinone and the electron-rich hydroquinones followed by the concomitant Pd(II)-catalyzed oxycyclization of the resultant alkynylhydroquinone.

FRAGRANCE COMPOSITION

The present invention relates to: a fragrance composition containing (3S)-(6E)-2,3-dihydrofarnesal having a chemical purity of 90 mass% or more and an optical purity of 50% e.e. or more; a cosmetic product containing the fragrance composition; and a method for improving an aroma using the fragrance composition.

Conjugated nitro alkene anticancer agents based on isoprenoid metabolism

Conjugated nitro alkene compounds hamper or prevent proliferation of cancer cells in cell culture and in cancer patients, which can result in a decrease in tumor size and/or disappearance of the cancer. The compounds may act by interference with cancer cell biochemistry, in which isoprenoid groups such as farnesyl and geranylgeranyl become bonded to various oncogenic proteins such as Ras, RhoA, RhoB, or some other growth-related cellular protein(s).

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.

Phosphorus-containing squalene synthetase inhibitors

Compounds which are inhibitors of cholesterol biosynthesis (by inhibiting de novo squalene biosynthesis), and thus are useful as hypocholesterolemic agents and antiatherosclerotic agents are provided which have the structure STR1 wherein m is 0, 1, 2 or 3; n is 0, 1, 2, 3 or 4; Y1 and Y2 are H or halogen; R2, R3 and R4 may be the same or different and are independently H, metal ion, C1 to C8 alkyl or C3 to C12 alkenyl; X is O, S, NH or NCH2 R15 wherein R15 is H or C1 to C5 alkyl; and R1 is R5 --Q1 --Q2 --Q3 -- wherein R5, Q1, Q2 and Q3 are as defined herein; and when m is o, X is other than S; and if m is o and X is 0, then n is 1, 2, 3 or 4; including all stereoisomers thereof.

Mechanism of Formation of Natural Cyclopropanes: Synthesis of Postulated Intermediates in Presqualene and Chrysanthemyl Alcohol Biosynthesis

The α-unsaturated esters (15), (28), and (33) have been used in deconjugative additions to ketones, to provide the β,γ-hydroxy esters (17), (18), (29), (30), and (37) and hence the unsaturated diols (22), (23), and (38).These diols have been postulated as precursors to the natural cyclopropanes chrysanthemyl alcohol and presqualene, through homoallylic participation.Experiments with cell-free extract of Artemisia annua foliage show that neither diol (22) nor (23) is converted to chrysanthemyl alcohol.Limited experiments with an homogenate of Rhizopus arrhizus provide little support for the intervention of the diol (38) in squalene biosynthesis.

SYNTHESIS OF "PRE-PRESQUALENE", A PREDICATED INTERMEDIATE IN PRESQUALENE BIOSYNTHESIS, AND OF PRENYLOGUES.

The synthesis is reported, using deconjugative addition, of the E- and Z- diols (15g) and (16g), postulated intermediates in presqualene biosynthesis.