23727-15-3

Usage

Uses

Used in Flavor and Fragrance Industry:
(S)-2,2,3-trimethylcyclopent-3-ene-1-acetaldehyde is utilized as a flavor and fragrance ingredient in a range of products, including perfumes, soaps, and cosmetics. Its strong, fruity scent makes it a valuable addition to these products, enhancing their appeal to consumers.
Used in Food Industry:
In the food industry, (S)-2,2,3-trimethylcyclopent-3-ene-1-acetaldehyde serves as a flavoring agent. Its ability to impart a fruity aroma and taste to food products makes it a popular choice for enhancing the sensory experience of eating.
Used in Pharmaceutical Research:
(S)-2,2,3-trimethylcyclopent-3-ene-1-acetaldehyde has been studied for its potential pharmacological properties, such as its ability to act as an anti-inflammatory and anti-cancer agent. While further research is necessary to fully explore its potential applications in the pharmaceutical industry, its current findings suggest it may offer promising therapeutic benefits in the future.

InChI:InChI=1/C10H16O/c1-8-4-5-9(6-7-11)10(8,2)3/h4,7,9H,5-6H2,1-3H3/t9-/m0/s1

Upstream product

• 64-17-5 ethanol 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 76-22-2 Camphor 
• 1686-14-2 α-pinene epoxide 
• 508-32-7 1,7,7-trimethyltricyclo[2.2.1.02,6]heptane 
• 1901-38-8 (RS)-(+/-)-2-(2,2,3-trimethyl-cyclopent-3-en-1-yl)ethanol 
• 217320-94-0 2-Pinene oxide 
• 80-56-8 Pinene 
• 79-15-2 N-bromoacetamide 
• 14575-92-9 2,3-epoxy-cis-pinane 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 18172-67-3 beta-pinene 
• 15719-64-9 methylammonium carbonate 
• 7785-26-4 (-)-α-pinene 

Downstream Products

• 85187-14-0 1-phenyl-4-(2,2,3-trimethyl-cyclopent-3-enyl)-but-2-en-1-one 
• 20145-44-2 α-Campholenaldehyd-dimethylacetal 
• 25570-84-7 (2,2,3-trimethylcyclopent-3-enyl)ethanamimde 
• 1901-38-8 (RS)-(+/-)-2-(2,2,3-trimethyl-cyclopent-3-en-1-yl)ethanol 
• 25435-53-4 (2,2,3-Trimethyl-cyclopent-3-enyl)-acetic acid 
• 65114-01-4 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-al 
• 65113-95-3 (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-3-penten-2-one 
• 67801-15-4 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-one 
• 68480-24-0 6-(2,2,3-trimethyl-3-cyclopenten-1-yl)-5-hexen-3-one 
• 65113-96-4 6-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-hexen-3-one 
• 947313-99-7 5-hydroxy-6-(2,2,3-trimethyl-3-cyclopenten-1-yl)hexan-3-one 
• 686776-52-3 4-hydroxy-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)pentan-2-one 
• 15373-31-6 α-campholenonitrile 
• 65114-02-5 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-butenal 

Relevant academic research and scientific papers

A chiral two-dimensional coordination polymer based on CuII and (S)-4,4′-bis(4-carboxyphenyl)-2,2′-bis(diphenylphosphinoyl)-1, 1′-binaphthyl: Synthesis, structure, and magnetic and optical properties

The functionalized binaphthyl derivative (S)-4,4′-bis(4- carboxyphenyl)-2,2′-bis(diphenylphosphinoyl)-1,1′-binaphthyl (H 2L) was employed as linker in the synthesis of the chiral Cu II-based two-dimensional network {[Cu2(L) 2(dmf)2]·H2O·9 dmf}n (1). Single-crystal X-ray analysis showed a two-dimensional structure with a copper paddle wheel as secondary building unit. One dmf molecule is additionally axially coordinated to each Cu cation. A lamellar structure results consisting of alternating [Cu2(L)2(dmf)2]n and solvent (dmf, H2O) layers. According to DTA/TG measurements the coordinated dmf molecules are released at about 320 °C, followed by decomposition around 460 °C. Magnetic susceptibility measurements on 1 indicate strong antiferromagnetic coupling between the two metal centers in Cu2(L)2(dmf)2. Compound 1 exhibits ligand-based luminescence, assigned to the S1 → S0 transition of the aromatic units. Moreover, the emission spectrum of 1 is blueshifted in comparison to H2L, due to different dihedral angles within the respective structures. Activated 1 (heating to 300 °C under vacuum for 3 h) showed low activity in the catalytic cyanosilylation of benzaldehyde (up to 27.1% conversion) and the isomerization of α-pinene oxide to campholenic aldehyde (up to 15.5% conversion).

Chemical characterization of α-pinene secondary organic aerosol constituents using gas chromatography, liquid chromatography, and paper spray-based mass spectrometry techniques

Rationale: Despite ample research into the atmospheric oxidation of α-pinene, an important precursor to biogenic secondary organic aerosol formation, the identification of its reaction products, specifically organic nitrates, which impact atmospheric NOx concentrations, is still incomplete. This negatively impacts our understanding of α-pinene oxidation chemistry and its relation to air quality. Methods: Photochemical chamber experiments were conducted in conjunction with mass spectrometric techniques, including gas chromatography/mass spectrometry (GC/MS), high-performance liquid chromatography/time-of-flight (HPLC/TOF), and paper spray ionization MS, to investigate products from the OH radical initiated oxidation of α-pinene under high NOx conditions. Results: Over 30 compounds were tentatively identified, including those newly detected from photochemical chamber studies of α-pinene oxidation, pinocamphenol, fencholenic aldehyde, and α-pinene-derived nitrate isomers. α-Pinene-derived hydroxynitrate isomers were successfully detected using chromatographic methods, demonstrating, for the first time, the identification of individual first-generation organic nitrate products derived from α-pinene. The application of paper spray ionization to particle-phase compounds collected on filters represents a novel method for the direct analysis of filter samples at ambient pressure and temperature. Conclusions: The use of HPLC/TOF and paper spray ionization methods to identify previously unobserved α-pinene-derived products helps lower the uncertainty in α-pinene oxidation chemistry and provides new platforms that can be used to identify and quantify important atmospheric compounds that relate to air quality in a complex sample matrix, such as ambient aerosol particles. Additionally, the use of paper spray ionization for direct filter analysis is a fast, relatively inexpensive sample preparation technique that can be used to reduce sample manipulation from solvent-induced reactions. Copyright

Alkoxy radical accelerated β-fragmentation of alcohols and lactols

Treatment of alcohols and lactols with Pb(OAc)4/Cu(OAc)2 in refluxing benzene provides the corresponding δ-unsaturated carbonyl products.

Synthesis and analgesic activity of new compounds combining azaadamantane and monoterpene moieties

Synthesis of new compounds that combine the diazaadamantane and monoterpenoid moieties was carried out based on the reaction between dimethylbispidinone and monoterpene-derived aldehydes. Investigation of the analgesic activity of the obtained products revealed that compound 5a synthesized from (-)-myrtenal had a higher efficacy compared with the reference drug, diclofenac sodium, in the acetic acid-induced writhing and hot plate tests. Compound 5a exhibits a low acute toxicity and does not cause damage to the gastric mucosa, and its analgesic effect is, at least partially, mediated by the cannabinoid system involving CB1 receptors.

Organocatalytic epoxidation and allylic oxidation of alkenes by molecular oxygen

Pyrrole-proline diketopiperazine (DKP) acts as an efficient mediator for the reduction of dioxygen by Hantzsch ester under mild conditions to allow the aerobic metal-free epoxidation of electron-rich alkenes. Mechanistic crossovers are underlined, explaining the dual role of Hantzsch ester as a reductant/promoter of the DKP catalyst and a simultaneous competitor for the epoxidation of alkenes when HFIP is used as a solvent. Expansion of this protocol to the synthesis of allylic alcohols was achieved by adding a catalytic amount of selenium dioxide as an additive, revealing a superior method to the classical application of t-BuOOH as a selenium dioxide oxidant.

A recyclable cobalt(iii)-ammonia complex catalyst for catalytic epoxidation of olefins with air as the oxidant

[Co(NH3)6]Cl3and other ammonia complexes with different external anions or metal ions were synthesized to catalyze the epoxidation of α-pinene. The synthesized complexes were characterized using XRD, SEM, TGA, FTIR and UV spectra. With air as the oxidant, [Co(NH3)6]Cl3exhibited excellent catalytic activity for the epoxidation of α-pinene among the prepared complexes. The conversion of α-pinene reached 97.4%, with 98.3% selectivity of epoxide when using a small amount of cumene hydroperoxide (CHP) as the initiator. The results revealed that a single Co(iii) system can also catalyze the epoxidation process in the absence of Co(ii), even showing better catalytic performance than single Co(ii). Recycling experiments showed that there was no significant drop in activity after 10 cycles, demonstrating that it is a stable and efficient heterogeneous catalyst for the epoxidation of α-pinene. The excellent recycling performance may be attributed to the stability of the coordination complex itself.

Development of rapid and selective epoxidation of α-pinene using single-step addition of H2O2in an organic solvent-free process

This study reports substantial improvement in the process for oxidising α-pinene, using environmentally friendly H2O2 at high atom economy (～93%) and selectivity to α-pinene oxide (100%). The epoxidation of α-pinene with H2O2 was catalysed by tungsten-based polyoxometalates without any solvent. The variables in the screening parameters were temperatures (30-70 °C), oxidant amount (100-200 mol%), acid concentrations (0.02-0.09 M) and solvent types (i.e., 1,2-dichloroethane, toluene, p-cymene and acetonitrile). Screening the process parameters revealed that almost 100% selective epoxidation of α-pinene to α-pinene oxide was possible with negligible side product formation within a short reaction time (～20 min), using process conditions of a 50 °C temperature in the absence of solvent and α-pinene/H2O2/catalyst molar ratio of 5?:?1?:?0.01. A kinetic investigation showed that the reaction was first-order for α-pinene and catalyst concentration, and a fractional order (～0.5) for H2O2 concentration. The activation energy (Ea) for the epoxidation of α-pinene was ～35 kJ mol-1. The advantages of the epoxidation reported here are that the reaction could be performed isothermally in an organic solvent-free environment to enhance the reaction rate, achieving nearly 100% selectivity to α-pinene oxide.

Tailoring Lewis/Br?nsted acid properties of MOF nodesviahydrothermal and solvothermal synthesis: simple approach with exceptional catalytic implications

The Lewis/Br?nsted catalytic properties of the Metal-Organic Framework (MOF) nodes can be tuned by simply controlling the solvent employed in the synthetic procedure. In this work, we demonstrate that Hf-MOF-808 can be prepared from a material with a higher amount of Br?nsted acid sites,viamodulated hydrothermal synthesis, to a material with a higher proportion of unsaturated Hf Lewis acid sites,viamodulated solvothermal synthesis. The Lewis/Br?nsted acid properties of the resultant metallic clusters have been studied by different characterization techniques, including XAS, FTIR and NMR spectroscopies, combined with a DFT study. The different nature of the Hf-MOF-808 materials allows their application as selective catalysts in different target reactions requiring Lewis, Br?nsted or Lewis-Br?nsted acid pairs.

Heteropoly acid catalysts in upgrading of biorenewables: Synthesis of para-menthenic fragrance compounds from α-pinene oxide

The isomerization of α-pinene oxide in the presence of Cs2.5H0.5PW12O40 (CsPW) heteropolysalt as solid acid catalyst is reported. The reactions were performed in various solvents, which allowed to obtain trans-carveol, trans-sobrerol and pinol in 60–80% yield each, which exceed the yields reported so far. The CsPW catalyst could be recovered and reused without loss of its activity and selectivity.

Engineering a Highly Defective Stable UiO-66 with Tunable Lewis-Br?nsted Acidity: The Role of the Hemilabile Linker

The stability of metal-organic frameworks (MOFs) typically decreases with an increasing number of defects, limiting the number of defects that can be created and limiting catalytic and other applications. Herein, we use a hemilabile (Hl) linker to create up to a maximum of six defects per cluster in UiO-66. We synthesized hemilabile UiO-66 (Hl-UiO-66) using benzene dicarboxylate (BDC) as linker and 4-sulfonatobenzoate (PSBA) as the hemilabile linker. The PSBA acts not only as a modulator to create defects but also as a coligand that enhances the stability of the resulting defective framework. Furthermore, upon a postsynthetic treatment in H2SO4, the average number of defects increases to the optimum of six missing BDC linkers per cluster (three per formula unit), leaving the Zr-nodes on average sixfold coordinated. Remarkably, the thermal stability of the materials further increases upon this treatment. Periodic density functional theory calculations confirm that the hemilabile ligands strengthen this highly defective structure by several stabilizing interactions. Finally, the catalytic activity of the obtained materials is evaluated in the acid-catalyzed isomerization of α-pinene oxide. This reaction is particularly sensitive to the Br?nsted or Lewis acid sites in the catalyst. In comparison to the pristine UiO-66, which mainly possesses Br?nsted acid sites, the Hl-UiO-66 and the postsynthetically treated Hl-UiO-66 structures exhibited a higher Lewis acidity and an enhanced activity and selectivity. This is further explored by CD3CN spectroscopic sorption experiments. We have shown that by tuning the number of defects in UiO-66 using PSBA as the hemilabile linker, one can achieve highly defective and stable MOFs and easily control the Br?nsted to Lewis acid ratio in the materials and thus their catalytic activity and selectivity.