4680-24-4

Usage

Uses

Used in Flavor and Fragrance Industry:
(+)-CIS-LIMONENE 1,2-EPOXIDE is used as a flavor and fragrance ingredient for its natural citrus scent, adding a refreshing aroma to various products such as perfumes, soaps, and cosmetics.
Used in Chemical Synthesis:
(+)-CIS-LIMONENE 1,2-EPOXIDE serves as a precursor in the synthesis of other chemicals, playing a crucial role in the production of various compounds for different applications.
Used in Pharmaceutical and Biotechnology Research:
(+)-CIS-LIMONENE 1,2-EPOXIDE is used in research for its potential biological and pharmacological properties, including its antimicrobial and anti-inflammatory effects, which may contribute to the development of new treatments and therapies.
Used in Antimicrobial Applications:
(+)-CIS-LIMONENE 1,2-EPOXIDE is utilized for its antimicrobial properties, which can help in the development of products that combat harmful microorganisms and contribute to improved hygiene and sanitation.
Used in Anti-Inflammatory Research:
(+)-CIS-LIMONENE 1,2-EPOXIDE is employed in studies exploring its anti-inflammatory effects, which may lead to the creation of new agents for the treatment of inflammation-related conditions.

InChI:InChI=1/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9+,10-/m0/s1

Upstream product

• 5989-27-5 D-limonene 
• 147781-61-1 (1R,2S,4R,8R)-1,2-epoxy-8,9-dibromo-p-menthane 
• 1195-92-2 (4R)-limonene 1,2-epoxide 
• 124-40-3 dimethyl amine 
• 123-75-1 pyrrolidine 
• 110-89-4 piperidine 
• 110-91-8 morpholine 
• 123-90-0 Thiomorpholin 
• 109-01-3 1-methyl-piperazine 
• 626-58-4 4-methylpiperidin 
• 111-49-9 hexamethylene imine 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 120-43-4 4-ethoxycarbonylpiperazine 
• 31252-42-3 4-benzylpyperidine 

Downstream Products

• 96-08-2 (1R,4R,6S)-1-methyl-4-(S)-2-methyloxiran-2-yl-7-oxa-bicyclo[4.1.0]heptane 
• 96-08-2 (1R,4R,6S)-1-methyl-4-((R)-2-methyloxiran-2-yl)-7-oxa-bicyclo[4.1.0]heptane 
• 57072-60-3 (1R,2S,4R)-1-methyl-4-(1-oxoethyl)cyclohexane 1,2-oxide 
• 111613-36-6 (+)-N,N-1-dimethylaminoneodihydrocarveol 
• 78478-86-1 (+)-trans-N,N-2-dimethylamino-8-cis-p-menthene-1-ol 
• 7299-40-3 (r-l,t-4)-p-menth-8-en-1-ol 
• 20549-48-8 (+)-neodihydrocarveol 
• 29431-60-5 (-)-2-Hydroxy-1-ethoxy-trans-p-menth-8-en 
• 4680-28-8 (+)-1-Acetoxy-neo-dihydro-carveol 
• 7070-05-5 (1S,5R)-5-isopropyl-2-methylene cyclohexanol 
• 1946-00-5 (1S,2S,4R)-limonene-1,2-diol 
• 31269-74-6 trans-(1S,5R)-5-isopropyl-2-methyl-2-cyclohexen-1-ol 
• 6090-09-1 methyl-[(1R)-4-methylcyclohex-3-enyl]ketone 
• 66378-56-1 (1S,2S,5R)-2-amino-2-methyl-5-(1-methylethenyl)cyclohexanol 

Relevant academic research and scientific papers

Synthesis and catalytic activity of Mo(II) complexes of α-diimines intercalated in layered double hydroxides

The two layered double hydroxides ZnAl-LDH and MgAl-LDH were functionalized with bis(4-HOOC-phenyl)-acenaphthenequinonediimine) (H2BIAN), leading to the intercalation of its dianion, which in a second step reacted with [Mo(CO)3X2(NCMe)2] (X = I, Br), affording four new materials. These materials and the two complexes [Mo(CO)3X2(H2BIAN)2] (X = I, Br) were tested in the olefin epoxidation reaction with substrates cis-cyclooctene, styrene, 1-octene, trans-hex-3-en-1-ol, and R-(+)-limonene, using tert-butylhydroperoxide (tbhp) as oxidant. The new catalysts were particularly good for cis-cyclooctene and styrene (100% conversions) and at least one heterogeneous catalyst was comparable to the homogeneous ones in the epoxidation of 1-octene and trans-hex-3-en-1-ol. The homogeneous catalysts were the best to oxidize R-(+)-limonene (higher conversions).

Effect of the substrate and catalyst chirality on the diastereoselective epoxidation of limonene using Jacobsen-type catalysts

Chiral and achiral Jacobsen's catalysts in their homogeneous form or immobilized on Al-MCM-41 exhibit similar catalytic activity during diastereoselective epoxidation of limonene when in situ generated dimethyldioxirane is used as oxidizing agent. Experim

New heterogeneous catalysts with Mo(II) intercalated in layered double hydroxides

The Mo(II) complexes [MoX2(CO)3(BDC)] (X?=?I, Br; H2BDC?=?2,2′-bipyridine-5,5′-dicarboxylic acid) were immobilized by intercalation in two layered double hydroxides (LDH), containing Zn/Al (synthesized) and Mg/Al (commercial), as shown by infrared and13C solid state NMR spectroscopies, and X-ray powder diffraction. Their catalytic activity was studied in olefin oxidation, using as oxidant tert-butylhydroperoxide (tbhp), and was compared with the activity of the related [MoX2(CO)3(bpy)] complexes (bpy?=?2,2′-bipyridine). cis-Cyclooctene, styrene, 1-octene, trans-hex-3-en-1-ol, and R-(+)-limonene were the substrates tested. All the catalyst showed in average a high selectivity toward the epoxide of each substrate (above 90%, except for styrene), with variable conversions, but none of the heterogeneous catalysts proved to be more active than the homogeneous ones. The same or higher activity in a second catalytic run, as observed in most reactions, suggests a good recycling capability.

Sustainable catalytic epoxidation of biorenewable terpene feedstocks using H2O2as an oxidant in flow microreactors

Solvent-free continuous flow epoxidation of the alkene bonds of a range of biorenewable terpene substrates have been carried out using a recyclable tungsten-based polyoxometalate phase transfer catalyst and aqueous H2O2 as a benign oxidant. These sustainable flow epoxidation reactions are carried out in commercial microreactors containing static mixing channels that enable common monoterpenes (e.g. untreated crude sulfate turpentine, limonene, etc.) to be safely epoxidized in short reaction times and in good yields. These flow procedures are applicable for the flow epoxidation of trisubstituted and disubstituted alkenes for the safe production of multigram quantities of a wide range of epoxides. This journal is

OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF

The present disclosure provides modified oligonucleotides and compositions and methods thereof. In some embodiments, provided technologies comprise modified sugars and/or modified internucleotidic linkages. In some embodiments, the present disclosure provides technologies for preparing modified oligonucleotides. In some embodiments, the present disclosure provides chirally controlled oligonucleotide compositions and methods for their preparation and uses.

Selective Catalytic Synthesis of 1,2- and 8,9-Cyclic Limonene Carbonates as Versatile Building Blocks for Novel Hydroxyurethanes

The selective catalytic synthesis of limonene-derived monofunctional cyclic carbonates and their subsequent functionalisation via thiol–ene addition and amine ring-opening is reported. A phosphotungstate polyoxometalate catalyst used for limonene epoxidation in the 1,2-position is shown to also be active in cyclic carbonate synthesis, allowing a two-step, one-pot synthesis without intermittent epoxide isolation. When used in conjunction with a classical halide catalyst, the polyoxometalate increased the rate of carbonation in a synergistic double-activation of both substrates. The cis isomer is shown to be responsible for incomplete conversion and by-product formation in commercial mixtures of 1,2-limomene oxide. Carbonation of 8,9-limonene epoxide furnished the 8,9-limonene carbonate for the first time. Both cyclic carbonates underwent thiol–ene addition reactions to yield linked di-monocarbonates, which can be used in linear non-isocyanate polyurethanes synthesis, as shown by their facile ring-opening with N-hexylamine. Thus, the selective catalytic route to monofunctional limonene carbonates gives straightforward access to monomers for novel bio-based polymers.

Biochar as supporting material for heterogeneous Mn(II) catalysts: Efficient olefins epoxidation with H2O2

A novel type of hybrid catalytic materials [MnII-L?BC] has been developed using biochar (BC) as support material for covalent grafting of a MnII Schiff-base catalyst (MnII-L). The hybrid [MnII-L?BC] materials have been evaluated for an important catalytic process, epoxidation of olefins using H2O2 as oxidant. A number of different substrates were used, with cyclohexene achieving the highest yields. When compared to the non-grafted, homogeneous MnII-L, the hybrid catalysts [MnII-L?BC] show a significant enhancement of the catalytic efficiency i.e. as documented by the increase of Turnover Numbers (TONs) (826 for [MnII-L-SS550ox] and 822 for [MnII-L-SW550ox]) and Turnover Frequencies (TOFs) (551 h?1 for [MnII-L-SS550ox] and 411 h?1 for [MnII-L-SW550ox]). The interfacial catalytic mechanism and the role of the BC support have been analyzed by Raman and Electron Paramagnetic Resonance spectroscopies. Based on these data we discuss a mechanism where the high efficiency of the hybrid materials involves the biochar carbon layers acting as promoters of the substrate and products kinetics. To a broader context, this work exemplifies that biochar-based hybrid materials are potent for oxidative catalysis technologies.

Sustainable catalytic protocols for the solvent free epoxidation and: Anti -dihydroxylation of the alkene bonds of biorenewable terpene feedstocks using H2O2 as oxidant

A tungsten-based polyoxometalate catalyst employing aqueous H2O2 as a benign oxidant has been used for the solvent free catalytic epoxidation of the trisubstituted alkene bonds of a wide range of biorenewable terpene substrates. This epoxidation protocol has been scaled up to produce limonene oxide, 3-carene oxide and α-pinene oxide on a multigram scale, with the catalyst being recycled three times to produce 3-carene oxide. Epoxidation of the less reactive disubstituted alkene bonds of terpene substrates could be achieved by carrying out catalytic epoxidation reactions at 50 °C. Methods have been developed that enable direct epoxidation of untreated crude sulfate turpentine to afford 3-carene oxide, α-pinene oxide and β-pinene oxide. Treatment of crude epoxide products (no work-up) with a heterogeneous acid catalyst (Amberlyst-15) results in clean epoxide hydrolysis to afford their corresponding terpene-anti-diols in good yields.

A trans - menthyl - 2, 8 - diene -1 - alcohol synthesis process

The invention belongs to the trans - menthyl - 2, 8 - diene - 1 - ol preparation technology field, in particular to a trans - menthyl - 2, 8 - diene - 1 - ol synthesis process. The synthesizing process comprises the following steps: (1) in order to limonene as raw materials, in order to lipase catalytic oxidation to obtain the 1, 2 - epoxy limonene; (2) the 1, 2 - epoxy limonene in the presence of sodium borohydride and diphenyl [...] open-loop formed limonene selenide; (3) the limonene selenide in under the action of the oxidizing agent forms the selenium oxide then undergo elimination reaction trans - menthyl - 2, 8 - diene - 1 - ol. The invention through the material and a prepared selective lipase catalyzed the situation that the 1, 2 - epoxy limonene, the need for complex purification process can increase the purity of the reaction intermediate, thereby improving the final product trans - menthyl - 2, 8 - diene - 1 - ol of chiral purity.

Exploring the substrate specificity of Cytochrome P450cin

Cytochromes P450 are enzymes that catalyse the oxidation of a wide variety of compounds that range from small volatile compounds, such as monoterpenes to larger compounds like steroids. These enzymes can be modified to selectively oxidise substrates of interest, thereby making them attractive for applications in the biotechnology industry. In this study, we screened a small library of terpenes and terpenoid compounds against P450cin and two P450cin mutants, N242A and N242T, that have previously been shown to affect selectivity. Initial screening indicated that P450cin could catalyse the oxidation of most of the monoterpenes tested; however, sesquiterpenes were not substrates for this enzyme or the N242A mutant. Additionally, both P450cin mutants were found to be able to oxidise other bicyclic monoterpenes. For example, the oxidation of (R)- and (S)-camphor by N242T favoured the production of 5-endo-hydroxycamphor (65–77% of the total products, dependent on the enantiomer), which was similar to that previously observed for (R)-camphor with N242A (73%). Selectivity was also observed for both (R)- and (S)-limonene where N242A predominantly produced the cis-limonene 1,2-epoxide (80% of the products following (R)-limonene oxidation) as compared to P450cin (23% of the total products with (R)-limonene). Of the three enzymes screened, only P450cin was observed to catalyse the oxidation of the aromatic terpene p-cymene. All six possible hydroxylation products were generated from an in vivo expression system catalysing the oxidation of p-cymene and were assigned based on 1H NMR and GC-MS fragmentation patterns. Overall, these results have provided the foundation for pursuing new P450cin mutants that can selectively oxidise various monoterpenes for biocatalytic applications.