1731-81-3

Usage

Uses

Used in Perfumery and Flavoring Industry:
Undecanyl acetate is used as a fragrance ingredient for its sweet, fruity scent, ideal for incorporation into soaps, shampoos, and cosmetics. It enhances the sensory experience of these products by providing a pleasant and distinctive aroma.
Used in Food and Beverage Industry:
In the food and beverage sector, undecanyl acetate is used as a flavoring agent to impart a subtle fruity note to various products, thereby enriching their taste profiles and consumer appeal.
Used in Insect Repellent Industry:
Undecanyl acetate is also utilized in the formulation of insect repellents due to its natural insect-repellent properties. It serves as an effective component in products designed to deter insects, offering a dual benefit of scent enhancement and pest control.
Overall, undecanyl acetate is a multifunctional compound with applications in the fragrance, flavor, and insect repellent industries, making it a valuable asset in product development and innovation.

InChI:InChI=1/C13H26O2/c1-3-4-5-6-7-8-9-10-11-12-15-13(2)14/h3-12H2,1-2H3

Upstream product

• 112-19-6 10-undecenyl acetate 
• 26932-87-6 acetyl dodecanoyl peroxide 
• 112-42-5 undecyl alcohol 
• 108-24-7 acetic anhydride 
• 84115-19-5 1-acetoxy-10,11-epoxyundecane 
• 64-19-7 acetic acid 
• 4163-60-4 β-D-galactose peracetate 
• 2754-27-0 trimethylsilyl acetate 
• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 
• 148773-60-8 11-(phenylthio)-1-undecanol 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 604-69-3 β-D-glucose pentaacetate 
• 79128-66-8 1-Methoxymethoxy-undecane 
• 148773-58-4 11-(phenylthio)undecyl acetate 

Downstream Products

• 821-95-4 1-undecene 
• 17322-97-3 1,2-epoxyundecane 

Relevant academic research and scientific papers

Application of glucose derived magnetic solid acid for etherification of 5-HMF to 5-EMF, dehydration of sorbitol to isosorbide, and esterification of fatty acids

In this study, the catalytic activity of Glu-Fe3O4-SO3H was evaluated for three acid catalyzed reactions: etherification of 5-hydroxymethylfurfural (5-HMF) to 5-ethoxymethylfurfural (5-EMF) in ethanol, dehydration of sorbitol to isosorbide, and esterification of fatty acids with good yields and selectivity. Moreover, the catalyst can be easily separated from the reaction with an external magnetic force and reused at least five times without a significant decrease in catalytic activity.

Trimethylsilyl Esters as Novel Dual-Purpose Protecting Reagents

Trimethylsilyl esters, AcOTMS, BzOTMS, TCAOTMS, etc., are inexpensive and chemically stable reagents that pose a negligible environmental hazard. Such compounds prove to serve as efficient dualpurpose reagents to respectively achieve acylation and trimethylsilylation of alcohols under acidic or basic conditions. Herein, a detailed study on protection of various substrates and new methodological investigations is described.

Transfer Hydrogenation of Alkenes Using Ethanol Catalyzed by a NCP Pincer Iridium Complex: Scope and Mechanism

The first general catalytic approach to effecting transfer hydrogenation (TH) of unactivated alkenes using ethanol as the hydrogen source is described. A new NCP-type pincer iridium complex (BQ-NCOP)IrHCl containing a rigid benzoquinoline backbone has been developed for efficient, mild TH of unactivated C-C multiple bonds with ethanol, forming ethyl acetate as the sole byproduct. A wide variety of alkenes, including multisubstituted alkyl alkenes, aryl alkenes, and heteroatom-substituted alkenes, as well as O- or N-containing heteroarenes and internal alkynes, are suitable substrates. Importantly, the (BQ-NCOP)Ir/EtOH system exhibits high chemoselectivity for alkene hydrogenation in the presence of reactive functional groups, such as ketones and carboxylic acids. Furthermore, the reaction with C2D5OD provides a convenient route to deuterium-labeled compounds. Detailed kinetic and mechanistic studies have revealed that monosubstituted alkenes (e.g., 1-octene, styrene) and multisubstituted alkenes (e.g., cyclooctene (COE)) exhibit fundamental mechanistic difference. The OH group of ethanol displays a normal kinetic isotope effect (KIE) in the reaction of styrene, but a substantial inverse KIE in the case of COE. The catalysis of styrene or 1-octene with relatively strong binding affinity to the Ir(I) center has (BQ-NCOP)IrI(alkene) adduct as an off-cycle catalyst resting state, and the rate law shows a positive order in EtOH, inverse first-order in styrene, and first-order in the catalyst. In contrast, the catalysis of COE has an off-cycle catalyst resting state of (BQ-NCOP)IrIII(H)[O(Et)···HO(Et)···HOEt] that features a six-membered iridacycle consisting of two hydrogen-bonds between one EtO ligand and two EtOH molecules, one of which is coordinated to the Ir(III) center. The rate law shows a negative order in EtOH, zeroth-order in COE, and first-order in the catalyst. The observed inverse KIE corresponds to an inverse equilibrium isotope effect for the pre-equilibrium formation of (BQ-NCOP)IrIII(H)(OEt) from the catalyst resting state via ethanol dissociation. Regardless of the substrate, ethanol dehydrogenation is the slow segment of the catalytic cycle, while alkene hydrogenation occurs readily following the rate-determining step, that is, β-hydride elimination of (BQ-NCOP)Ir(H)(OEt) to form (BQ-NCOP)Ir(H)2 and acetaldehyde. The latter is effectively converted to innocent ethyl acetate under the catalytic conditions, thus avoiding the catalyst poisoning via iridium-mediated decarbonylation of acetaldehyde.

Biomass derived β-cyclodextrin-SO3H as a solid acid catalyst for esterification of carboxylic acids with alcohols

A novel β-cyclodextrin-SO3H carbon based solid acid catalyst was prepared in a convenient and ecofriendly manner and was characterized using FTIR, PXRD, EDAX and NH3TPD to illustrate that the carbon material has been functionalized with -SO3H, -COOH and -OH groups. The catalyst was studied for esterification of various carboxylic acids and alcohols under solvent free conditions and showed excellent catalytic performance and gave good yields of esters in the range 78-99% at 70°C. No solvent was used either for catalyst preparation nor for esterification reaction. The catalyst can be easily recovered by simple filtration and reused for subsequent three runs without any significant impact on yields of products. The main advantage of this methodology is easy and ecofriendly catalyst preparation, easy catalyst separation, practical simplicity, safe reaction conditions, recyclable catalyst and high product yields.

Exceptionally high decarboxylation rate of a primary aliphatic acyloxy radical determined by radical product yield analysis and quantitative 1H-CIDNP spectroscopy

Symmetrical (RCO2CO2R; R=XCH2CH 2) and asymmetrical (RCO2CO2R′; R=C 9H19CH2CH2, R′=CH3 or m-ClC6H4) primary diacyl peroxides were thermally decomposed under different conditions to analyze the decarboxylation rates of the thermally generated acyloxy radicals. Quantitative models of the geminate product yields, and qualitative and quantitative 1H-CIDNP spectroscopy were used to obtain the decarboxylation rate estimates. Results reported here suggest that, unlike short chain acyloxy radicals such as propanoyloxyl, long chain acyloxy radicals possess the highest decarboxylation rates of all known acyloxy radicals, estimated at (0.5-1.5)× 10 12s-1 between 80 and 140°C. Given the nature of the dissociative state of acyloxy radicals, such rates appear to be the result of destabilization of the former by the steric bulk of the long chain substituents. Additionally, the rate of this order of magnitude suggests a nearly concerted decarboxylation of primary diacyl peroxides. Copyright

Synthesis of C7-C16-Alkyl maltosides in the presence of tin(IV) chloride as a lewis acid catalyst

The synthesis of C7- to C16-alkyl maltosides in the presence of tin(IV) chloride as Lewis acid catalyst was performed. The characterization of the products and theoretical investigation of the crucial step in the synthesis were carried out. The preparation of the β-maltosides required reaction time of 1 h, and that of the α-maltosides was 72 h. The side products were the α-D-maltosidechloride and 2-hydroxy-β-maltoside, respectively. The PM3 calculation confirmed the formation of the kinetically controlled β-product.

Air-stable titanocene bis(perfluorooctanesulfonate) as a new catalyst for acylation of alcohols, phenols, thiols, and amines under solvent-free condition

Air-stable titanocene bis(perfluorooctanesulfonate) [Cp2Ti(OSO2C8F17)2] that shows high Lewis acidity was prepared from Cp2TiCl2 and AgOSO2C8F17. The compound was characterized by different techniques, and examined as a catalyst for acylation reactions. It was found that using equimolar acetic anhydride as acetylating agent and under solvent-free condition, Cp2Ti(OSO2C8F17)2 exhibits high activity and selectivity in the acetylation of various alcohols, phenols, thiols, and amines. Also, good catalytic efficiency is observed in the acylation of 2-phenylethanol across various acylating reagents. The catalyst can be reused without loss of activity in a test of ten cycles. The Cp2Ti(OSO2C8F17)2 catalyst affords a simple, efficient and general method for the acylation of alcohols, phenols, thiols, and amines.

Structure-Activity relationship of aliphatic compounds for nematicidal activity against pine wood nematode (Bursaphelenchus xylophilus)

Nematicidal activity of aliphatic compounds was tested to determine a structure-activity relationship. There was a significant difference in nematicidal activity among functional groups. In a test with alkanols and 2E-alkenols, compounds with C8-C11 chain length showed 100% nematicidal activity against pine wood nematode, Bursaphelenchus xylophilus, at 0.5 mg/mL concentration. C6-C10 2E-alkenals exhibited >95% nematicidal activity, but the other compounds with C 11-C14 chain length showed weak activity. Nematicidal activity of alkyl acetates with C7-C11 chain length was strong. Compounds belonging to hydrocarbons, alkanals, and alkanoic acetates showed weak activity at 0.5 mg/mL concentration. Nematicidal activity of active compounds was determined at lower concentrations. At 0.25 mg/mL concentration, whole compounds except C8 alkanol, C8 2E-alkenol, and C7 alkanoic acid showed >80% nematicidal activity. C 9-C11 alkanols, C10-C11 2E-alkenols, C8-C9 2E-alkenals, and C9-C10 alkanoic acids showed >80% nematicidal activity at 0.125 mg/mL concentration. Only C11 alkanol exhibited strong nematicidal activity at 0.0625 mg/mL concentration, the lowest concentration that was tested. 2010 American Chemical Society.

BF3 etherate-induced formation of C7-C 16-alkyl β-D-glucopyranosides

BF3 etherate-induced formation of C7-C 16-alkyl D-glucopyranosides is used as the key step in their synthesis from glucose and C7-C16-alkanols.

Synthesis of C7-C16-alkyl glycosides: Part III - Synthesis of alkyl D-galactopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst

The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivative (galactose) with fatty alkanols is used in a synthesis of C7-C16-alkyl galactopyranosides. The process occurs under the influence of tin(IV) chloride as a Lewis acid catalyst.