16106-95-9

Usage

Uses

Used in Food Industry:
2Z,6Z-Farnesol is used as a flavoring agent for its aromatic properties, enhancing the taste and smell of various food products.
Used in Cosmetics Industry:
In cosmetics, 2Z,6Z-Farnesol is used as a fragrance to provide pleasant scents to products, contributing to their overall sensory appeal.
Used in Perfumery:
2Z,6Z-Farnesol is utilized as a key ingredient in perfumes for its unique and versatile scent, which can be blended with other compounds to create complex and attractive fragrances.
Used in Pharmaceutical Industry:
2Z,6Z-Farnesol is investigated for its potential as an antimicrobial agent, targeting various pathogens and contributing to the development of new treatments for infectious diseases.
Used in Oncology Research:
2Z,6Z-Farnesol is studied for its anti-cancer properties, with potential applications in the development of new therapeutic agents that could modulate cell signaling pathways and inhibit tumor growth.
Used in Anti-Inflammatory Applications:
2Z,6Z-Farnesol is explored for its potential as an anti-inflammatory agent, which could be used in the treatment of various inflammatory conditions.
Used in Antiparasitic Research:
2Z,6Z-Farnesol is also being investigated for its potential as an antiparasitic agent, with possible applications in the development of treatments for parasitic infections.

InChI:InChI=1/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9-,15-11-

Upstream product

• 80767-64-2 p-nitrobenzoate de trimethyl-3,7,11 dodecatriene-1,6 Z, 10-yl 
• 20085-73-8 ethyl (2Z,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienoate 
• 159826-46-7 6,10-dimethyl-3-phenylthioundeca-5Z,9-dien-2-one 
• 1528749-28-1 (2Z,6Z)-1-(tert-butyldiphenylsilyloxy)-9-benzenesulfonyl-3,7,11-trimethyldodeca-2,6,10-triene 
• 402915-46-2 (Z)-7,11-dimethyl-6,10-dodecadien-2-yn-1-ol 
• 74-88-4 methyl iodide 
• 19954-66-6 ethyl 3,7,11-trimethyl-2ξ,6Z,10-dodecatrienoate 
• 50-00-0 formaldehyd 
• 3879-26-3 (Z)-nerylacetone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 159826-49-0 3,7,11-trimethyl-4-(phenylthio)dodeca-2Z,6Z,10-trien-1-ol 
• 86636-50-2 1-((6Z,10Z)-12-Benzyloxy-2,6,10-trimethyl-dodeca-2,6,10-triene-4-sulfonyl)-4-methyl-benzene 
• 4176-78-7 methyl (2Z,6Z)-farnesenate 
• 19317-11-4 farnesal 

Downstream Products

• 468-68-8 epi-drimenol 
• 103109-25-7 Z,Z-farnesyl phenyl sulfide 
• 103109-26-8 4-phenylthio-6,10,14-trimethylpentadeca-5Z,9Z,13-trien-1-al ethylene acetal 
• 3790-78-1 cis-nerolidol 
• 469-61-4 (+/-)-cedrene 
• 5975-30-4 epizonarene 
• 1226814-93-2 4-(3’,7’,11’-trimethyldodecyloxy)benzyl alcohol 
• 83689-23-0 farnesyl farnesyl carboxylate 
• 107259-72-3 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-5,5-dimethyl-2-(5-methyl-1-methylene-hex-4-enyl)-cyclohexyl ester 
• 107259-72-3 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R)-5,5-dimethyl-2-(5-methyl-1-methylene-hex-4-enyl)-cyclohexyl ester 
• 107259-61-0 catechol (Z,Z)-monofarnesyl ether 
• 107259-73-4 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 2-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-5,5-dimethyl-cyclohexyl ester 
• 104764-30-9 2-((Z)-1,5-Dimethyl-hexa-1,4-dienyl)-5,5-dimethyl-cyclohexanol 
• 104746-49-8 (1S,2R)-5,5-dimethyl-2-(6-methylhepta-1,5-dien-2-yl)cyclohexanol 

Relevant academic research and scientific papers

Stereospecific synthesis and biological evaluation of farnesyl diphosphate isomers

(Matrix presented) A unified, stereospecific synthetic route to the three geometric isomers of (E,E)-farnesyl diphosphate (E,E-FPP) (1,2, and 3) has been developed. The key feature of this synthesis is the ability to control the stereochemistry of triflation of the β-ketoester 10 to give either 11 or 14. Preliminary evaluation of these compounds with protein-farnesyl transferase indicates that 1 and 2 are surprisingly effective substrates; however, Z,Z-FPP (3) is a poor substrate and a sub-micromolar inhibitor.

PRODUCTION OF FARNESOL

The present invention relates to an improved way for the production of farnesol.

Rationally designed short polyisoprenol-linked PglB substrates for engineered polypeptide and protein N-glycosylation

The lipid carrier specificity of the protein N-glycosylation enzyme C. jejuni PglB was tested using a logical, synthetic array of natural and unnatural C10, C20, C30, and C40 polyisoprenol sugar pyrophosphates, including those bearing repeating cis-prenyl units. Unusual, short, synthetically accessible C20 prenols (nerylnerol 1d and geranylnerol 1e) were shown to be effective lipid carriers for PglB sugar substrates. Kinetic analyses for PglB revealed clear KM-only modulation with lipid chain length, thereby implicating successful in vitro application at appropriate concentrations. This was confirmed by optimized, efficient in vitro synthesis allowing >90% of Asn-linked β-N-GlcNAc-ylated peptide and proteins. This reveals a simple, flexible biocatalytic method for glycoconjugate synthesis using PglB N-glycosylation machinery and varied chemically synthesized glycosylation donor precursors.

Method for Converting Farnesol to Nerolidol in the Presence of Alpha-Bisabolol

A method for converting farnesol to nerolidol in the presence of alpha-bisabolol including providing or preparing a mixture of alpha-bisabolol, farnesol, and one or more catalysts for selective isomerization of farnesol to nerolidol in the presence of alpha-bisabolol, and converting at least a portion of the farnesol to nerolidol.

UNIQUE HALOGEN-INDUCED CYCLIZATIONS, REAGENTS THEREFOR, AND COMPOUNDS PRODUCED THEREBY

This disclosure is related to halonium compounds useful for cyclization of polyenes, alkenoic acids, and alkenyl alkyl ethers, and halogenation of aromatic compounds. The synthesis of such halonium compounds, compounds made using such halonium compounds, and synthesis of natural compounds, including decalins, using the halonium compounds is also disclosed. A representative halonium compound of the disclosure is: Formula (I).

Simple reagents for direct halonium-induced polyene cyclizations

Although there are many reagent combinations that can initiate polyene cyclizations, simple electrophilic halogen sources have not yet proven broadly effective as promoters of such processes. Herein is described a readily prepared and stable class of reagents capable of effecting such transformations for a wide range of electron-rich and -deficient terpenes derived from geraniol, farnesol, and nerol, thereby enabling the effective synthesis of a diverse array of complex chlorine-, bromine-, and iodine-containing polycyclic frameworks. Efforts to date have led to the first racemic laboratory total synthesis and structural revision of the anti-HIV natural product peyssonol A as well as an efficient and concise inaugural total synthesis of peyssonoic acid A. They have also permitted formal racemic total syntheses of aplysin-20, loliolide, K-76, and stemodin to be achieved through routes that are typically shorter, higher-yielding, and more environmentally conscious than previous efforts. Preliminary attempts to use chiral forms of the reagent class for enantioselective alkene halogenation are also described.

Synthesis of farnesol isomers via a modified wittig procedure

(Chemical Equation Presented) The four olefin stereoisomers of farnesol have been synthesized from readily available nerylacetone or commercial geranylacetone. A new variation on the use of β-oxido ylides favored the (2Z)-stereoisomers, whereas the (2E)-isomers were obtained through a classical Horner-Wadsworth-Emmons condensation with triethyl phosphonoacetate and reduction of the resulting ester.

Composition, method, and apparatus to attract bees

Applicant's invention includes an improved bee attracting composition. Applicant's invention further includes a bee attracting device formed from his improved bee attracting composition. Applicant's bee attracting device can be further coated with a second bee attracting composition. Applicant's invention further includes a method and apparatus for attracting and immobilizing bees using a substrate coated with an adhesive composition upon which Applicant's bee attracting composition is disposed.

A novel, highly selective, and general methodology for the synthesis of 1,5-diene-containing oligoisoprenoids of all possible geometrical combinations exemplified by an iterative and convergent synthesis of coenzyme Q10

Chemical equation presented A truly general, versatile, and highly regio- and stereoselective methodology for the synthesis of terpenoids containing 1,5-diene units of E and/or Z geometry critically involves Pd-catalyzed homoallyl- and homopropargyl-alkenyl coupling and Zr-catalyzed carboalumination of alkynes. By using this methodology, coenzyme Q10, (E,Z,E)-geranylgeranoil, and other natural or unnatural compounds have been synthesized efficiently.

Synthesis and biological evaluation of the geometric farnesylated analogues of the a-factor mating peptide of Saccharomyces cerevisiae

The a-factor of Saccharomyces cerevisiae is a dodecapeptide pheromone (YIIKGVFWDPAC-(Farnesyl)-OCH3, 1), in which post-translational modification with a farnesyl isoprenoid and carboxymethyl group is required for full biological activity. This peptide has been used as a model system to explore the biological function of the farnesylcysteine moiety, which is found on and required for the biological activity of many key mammalian proteins. The objective of this particular study was the determination of the biological effect of double bond isomerization of the natural E,E-farnesyl moiety on the biological activity of the a-factor. A unified, stereoselective synthetic route to the three geometric isomers of E,E-farnesol (12, 13, and 14) has been developed. The key feature of this synthesis is the ability to control the stereochemistry of triflation of the β-ketoester 22 to give either 23 or 25. The three farnesol isomers were converted to the corresponding isomeric a-factors (9, 10 and 11) via a modified version of a previously utilized synthetic route. Biological evaluation of these peptides indicates that, surprisingly, all three possess nearly equivalent activity to the natural a-factor bearing the E,E-farnesyl moiety.