2438-12-2

Usage

Uses

Used in Flavoring Agents:
(±)-α,α,4-trimethylcyclohex-3-ene-1-methanol is used as a flavoring agent in the food industry for its pleasant aroma and flavor profile. It adds a minty taste and scent to various food products, enhancing their overall appeal to consumers.
Used in Personal Care Products:
(±)-α,α,4-trimethylcyclohex-3-ene-1-methanol is used in personal care products such as perfumes, soaps, and lotions due to its strong, minty odor. It provides a refreshing scent and can be used to mask unpleasant odors in these products.
Used in Perfumes:
(±)-α,α,4-trimethylcyclohex-3-ene-1-methanol is used in perfumes as a fragrance ingredient for its strong, minty scent. It can be blended with other fragrances to create unique and appealing scents for perfumes and colognes.
Used in the Food Industry:
(±)-α,α,4-trimethylcyclohex-3-ene-1-methanol is used in the food industry as a flavoring agent to impart a minty taste and aroma to various food products. This enhances the overall flavor profile and consumer appeal of these products.
Used in the Perfume Industry:
(±)-α,α,4-trimethylcyclohex-3-ene-1-methanol is used in the perfume industry as a fragrance ingredient for its strong, minty scent. It can be combined with other fragrances to create unique and refreshing scents for perfumes and colognes.

Upstream product

• 123-91-1 1,4-dioxane 
• 80-56-8 rac-α-pinene 
• 98-11-3 benzenesulfonic acid 
• 917-64-6 methyl magnesium iodide 
• 6090-09-1 (+-)-4-acetyl-1-methylcyclohexene 
• 126-90-9 (S)-(+)-linalool 
• 126-91-0 linalool 
• 106-24-1 Geraniol 
• 18172-67-3 beta-pinene 
• 7785-70-8 (+)-α-pinene 
• 5989-27-5 D-limonene 
• 138-86-3 limonene. 
• 2451-01-6 cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate 
• 25570-96-1 1,4-dibromo-p-menthane 

Downstream Products

• 110202-13-6 1,2-dibromo-p-menthan-8-ol 
• 87791-00-2 6-(1-hydroxy-1-methylethyl)-3-methyl-2-cyclohexen-1-one 
• 133371-99-0 (4-phenylazo-phenyl)-carbamic acid-((S)-p-menth-1-en-8-yl ester) 
• 94931-94-9 2,2,6-trimethyl-4-phenyl-3-oxabicyclo<3.3.1>non-6-ene 
• 80731-54-0 [1]naphthyl-carbamic acid p-menth-1-en-8-yl ester 
• 38428-41-0 Heptadecyl-carbamic acid 1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethyl ester 
• 38428-60-3 Octadecyl-carbamic acid 1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethyl ester 
• 65580-47-4 C₁₄H₂₉N₂O₂P 
• 35812-24-9 Dithiocarbonic acid S-methyl ester O-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethyl] ester 
• 119728-77-7 1-Methyl-4-(1-methyl-1-prop-1-ynyloxy-ethyl)-cyclohexene 

Relevant academic research and scientific papers

Preparation of α-terpineol and perillyl alcohol using zeolites beta

The preparation of α-terpineol by direct hydration of limonene catalyzed by zeolites beta was studied. The same catalyst was used to prepare perillyl alcohol by isomerization of β-pinene oxide in the presence of water. The aim was to optimize the reaction conditions to achieve high conversions of starting material and high selectivity to the desired products. In the case of limonene, it was found that the highest selectivity to α-terpineol was 88% with conversion of 36% under the conditions: 50?wt% of catalyst beta 25, 10% aqueous acetic acid (10?mL) (volume ratio limonene:H2O = 1:4.5), temperature 50?°C, after 24?h. In the case of β-pinene oxide, it was found that the highest selectivity to perillyl alcohol, which was 36% at total conversion, was obtained in the reaction under the following conditions: dimethyl?sulfoxide as solvent (volume ratio β-pinene oxide:DMSO = 1:5), catalyst beta 25 without calcination (15?wt%), demineralized water (molar ratio β-pinene oxide:H2O = 1:8), temperature 70?°C, 3?h. The present study shows that the studied reactions are suitable for the selective preparation of chosen compounds.

Study of solid acid catalysis for the hydration of α-pinene

The hydration of α-pinene using solid acid catalysts was studied. The catalysts were prepared by impregnating trichloroacetic acid (TCA) on different supports such as silica, titania and zirconia (TCA/SiO2, TCA/TiO2 and TCA/ZrO2·nH2O, respectively). The TCA/TiO2 catalyst converted α-pinene into hydrocarbons, while the TCA/ZrO2·nH2O catalyst was active and selective for producing alcohols, with a conversion of 57% and a selectivity of 75% of total alcohols, and showed 57% selectivity for α-terpineol. The TCA/SiO2 sample did not show catalytic activity due to the elimination of the trichloroacetic acid during the preparation step of the catalyst. An additional stability study was performed with the TCA/ZrO2·nH2O sample. The presence of TCA in the different impregnated samples was studied using FT-IR, and the TCA content was determined by thermogravimetric analysis. The surface content of TCA in fresh and used catalysts was studied with XPS, and the textural properties and crystalline structures were analysed by BET and XRD, respectively. Additionally, the nature of the acid centres was characterised by pyridine adsorption coupled with FT-IR, and the acidity was determined by potentiometric titration.

A practical synthesis of d-α-terpineol via Markovnikov addition of d-limonene using trifluoroacetic acid

d-α-Terpineol (1), which is a useful flavor and fragrance compound, has been synthesized from d-limonene by Markovnikov addition using trifluoroacetic acid, followed by hydrolysis in 76% yield with 98% purity.

Terpene cyclization catalysed inside a self-assembled cavity

In nature, complex terpene natural products are formed by the so-called tail-to-head terpene (THT) cyclization. The cationic reaction cascade is promoted efficiently in complex enzyme pockets, in which cationic intermediates and transition states are stabilized. In solution, the reaction is hard to control and man-made catalysts able to perform selective THT cyclizations are lacking. We herein report the first example of a successful THT cyclization inside a supramolecular structure. The basic mode of operation in cyclase enzymes was mimicked successfully and a catalytic non-stop THT was achieved with geranyl acetate as the substrate. The results presented have implications for the postulated reaction mechanism in cyclase enzymes. Evidence indicates that the direct isomerization of a geranyl cation to the cisoid isomer, which so far was considered unlikely, is feasible.

Preparation of α-Terpineol from Biomass Resource Catalysed by Acid Treated Montmorillonite K10

Abstract: A new type of heterogeneous catalyst for hydration of α-pinene was prepared. Montmorillonite K10 was treated by various acids (H2SO4, HCl, HNO3, and ClCH2COOH) and successfully used for the mentioned reaction. The used characterization techniques showed that the acid treatment improved the properties of K10 important for the catalytic activity (SBET and acidity). On the other hand, the morphology and particle size distribution remained the same. Regarding the selectivity (side and consecutive reactions can proceed), the optimal reaction conditions were found (temperature, type of the catalyst, amount of the catalyst, molar ratio α-pinene:?water, type of water, solvent). Using the optimal reaction conditions, 60% conversion of α-pinene was achieved with 45% selectivity to α-terpineol (80?°C, 25 wt% of K10/HCl, or K10/H2SO4, nα-pinene:nwater 1:7.5, 1,4-dioxane as a solvent, 24?h). Higher conversions of α-pinene, as well as higher selectivity to α-terpineol, were achieved using all acid treated K10 in comparison to raw K10. Considering the heterogeneous form of prepared catalysts, its availability, low price and easy method of preparation, these catalysts dispose of a large potential for application as catalysts for hydration reactions. Graphic Abstract: [Figure not available: see fulltext.].

Selective Deoxygenation of Allylic Alcohols and Acetates by Lithium Perchlorate Promoted Triethylsilane Reduction

A series of cyclic secondary allylic alcohols and acetates was deoxygenated using triethylsilane in the presence of ethereal lithium perchlorate.Under these conditions the allylic oxygen functionality was selectively removed in the presence of esters, isolated olefins, ketals and tertiary alcohols.Primary allylic alcohols were not deoxygenated under these conditions.

Ultrasound in Organic Synthesis. 18. Selective Oxymercuration via Sonochemically in Situ Generated Mercury Salts

Selective mercuration of diolefins is favored by a proper choice of the mercuric salt, which can be generated in situ from mercuric oxide and the corresponding acid under sonochemical activation.

Synthesis of Aristoquinoline Enantiomers and Their Evaluation at the α3β4 Nicotinic Acetylcholine Receptor

The first synthesis of aristoquinoline (1), a naturally occurring nicotinic acetylcholine receptor (nAChR) antagonist, was accomplished using two different approaches. Comparison of the synthetic material's spectroscopic data to that of the isolated alkaloid identified a previously misassigned stereogenic center. An evaluation of each enantiomer's activity at the α3β4 nAChR revealed that (+)-1 is significantly more potent than (-)-1. This unexpected finding suggests that naturally occurring 1 possesses the opposite absolute configuration from indole-containing Aristotelia alkaloids.

Two-step continuous flow synthesis of α-terpineol

α-Terpineol is a naturally occurring monoterpene present in essential oils, of high value on the market as it is widely used as flavoring in the cosmetics and food industry. This study aims to produce α-terpineol by two different synthetic strategies, using both batch and continuous flow systems, focusing on the optimization of the process, improving the reaction conversion and selectivity. The first strategy adopted was a one-stage hydration reaction of (+)-α-pinene by an aqueous solution of chloroacetic acid (molar ratio 1:1 between pinene and the acid) in continuous flow conditions. This reaction was carried out at 80 °C with a residence time of 15 min, obtaining good conversion (72%) and selectivity (76%), and productivity of 0.53 kg.day?1. The second strategy accomplished was a two-step cascade reaction with (+)-limonene as starting material, where the first step is a chemospecific double bond addition using trifluoroacetic acid, and the second step is the basic hydrolysis of the ester promoted by a solution of sodium hydroxide (2.25 M) in methanol (1:1). This reaction was adapted to a continuous flow condition, where all steps involved a residence time of 40 min, at 25 °C, with no quenching between steps required, with 97% conversion, 81% selectivity and up to 0.14 kg.day?1.

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.