472-20-8

Usage

Uses

Used in Organic Synthesis:
2,6,6-Trimethylcyclohexene-1-methanol is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to serve as a building block for the creation of more complex molecules, which can be utilized in a wide range of applications, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Fragrance Industry:
In the fragrance industry, 2,6,6-Trimethylcyclohexene-1-methanol is used as a component in the formulation of perfumes and scented products. Its distinct aroma profile contributes to the overall scent of the final product, providing a unique and pleasant olfactory experience.
Used in Flavor Industry:
Similarly, in the flavor industry, 2,6,6-Trimethylcyclohexene-1-methanol is employed as an additive to enhance the taste and aroma of various food and beverage products. Its ability to mimic natural flavors makes it a valuable ingredient in the creation of artificial flavors.
Used in Pharmaceutical Industry:
2,6,6-Trimethylcyclohexene-1-methanol may also find applications in the pharmaceutical industry, where it can be used as a starting material for the development of new drugs or as a component in the formulation of existing medications. Its chemical properties make it a versatile candidate for various therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 2,6,6-Trimethylcyclohexene-1-methanol serves as a valuable compound for studying various aspects of organic chemistry, such as reaction mechanisms, stereochemistry, and the development of new synthetic methods. Its unique structure and properties make it an interesting subject for scientific investigation.

InChI:InChI=1/C10H18O/c1-8-5-4-6-10(2,3)9(8)7-11/h11H,4-7H2,1-3H3

Upstream product

• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 79-77-6 (E)-β-ionone 
• 6627-74-3 (+/-)-α-cyclogeraniol 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 15356-72-6 (E)-3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acrylic acid methyl ester 

Downstream Products

• 4481-69-0 15,15'-didehydro-β,β-carotene 
• 79-77-6 (E)-β-ionone 
• 127-41-3 alpha-ionone 
• 3899-20-5 ethyl retinoate 
• 56013-01-5 triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide 
• 35482-74-7 2-Hydroxymethyl-1,3,3-trimethyl-1,2-cyclohexandiol 
• 78996-11-9 (2,2,6-trimethylbicyclo<4.1.0>hept-1-yl)methanol 
• 138801-62-4 1-(1,3,3-Trimethyl-2-methylenecyclohexyl)-propan-2-one 
• 59633-88-4 2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene 
• 68406-89-3 α-cyclogeraniol acetate 
• 128261-29-0 (1,3,3-Trimethyl-2-methylene-cyclohexyl)-acetic acid ethyl ester 
• 51417-30-2 2-(1,3,3-Trimethyl-2-methylenecyclohexyl)acetaldehyde 
• 54345-58-3 acetic acid-(2,6,6-trimethyl-cyclohex-2-enyl ester) 
• 514-95-4 1,5,5-trimethyl-6-methylene-cyclohexene 

Relevant academic research and scientific papers

Ligand-based rational design, synthesis and evaluation of novel potential chemical chaperones for opsin

Inherited blinding diseases retinitis pigmentosa (RP) and a subset of Leber's congenital amaurosis (LCA) are caused by the misfolding and mistrafficking of rhodopsin molecules, which aggregate and accumulate in the endoplasmic reticulum (ER), leading to photoreceptor cell death. One potential therapeutic strategy to prevent the loss of photoreceptors in these conditions is to identify opsin-binding compounds that act as chemical chaperones for opsin, aiding its proper folding and trafficking to the outer cell membrane. Aiming to identify novel compounds with such effect, a rational ligand-based approach was applied to the structure of the visual pigment chromophore, 11-cis-retinal, and its locked analogue 11-cis-6mr-retinal. Following molecular docking studies on the main chromophore binding site of rhodopsin, 49 novel compounds were synthesized according to optimized one-to seven-step synthetic routes. These agents were evaluated for their ability to compete for the chromophore binding site of opsin, and their capacity to increase the trafficking of the P23H opsin mutant from the ER to the cell membrane. Different new molecules displayed an effect in at least one assay, acting either as chemical chaperones or as stabilizers of the 9-cis-retinal-rhodopsin complex. These compounds could provide the basis to develop novel therapeutics for RP and LCA.

BORONIC ESTER PRODRUGS AND USES THEREOF

Disclosed herein are compounds of Formula (I) or (II). The compounds include an agent (e.g., pharmaceutical agent, cosmetic agent, or nutraceutical agent) through a linker that includes a boronic ester moiety in the backbone of the linker. The compounds may be monomers. Also provided are polymers prepared by polymerizing the monomers. The polymers may be useful for delivering the agent to a subject, tissue, biological sample, or a cell. Also provided are methods of preparing the polymers, compositions and kits comprising the polymers, and methods of use (e.g., use in delivering the agent, treating a disease, preventing a disease, diagnosing a disease) involving the polymers or compositions. The structure of the boronic ester moiety may be fine tuned so that the properties related to delivery to a subject, biological sample, tissue, or cell may be fine tuned.

Highly pH-Dependent Chemoselective Transfer Hydrogenation of α,β-Unsaturated Aldehydes in Water

The pH-dependent selective Ir-catalyzed hydrogenation of α,β-unsaturated aldehydes was realized in water. Using HCOOH as the hydride donor at low pH, the unsaturated alcohol products were obtained exclusively, while the saturated alcohol products were formed preferentially by employing HCOONa as the hydride donor at high pH. A wide range of functional groups including electron-rich as well as electron-poor substituents on the aryl group of α,β-unsaturated aldehydes can be tolerated, affording the corresponding products in excellent yields with high TOF values. High selectivity and yields were also observed for α,β-unsaturated aldehydes with aliphatic substituents. Our mechanistic investigations indicate that the pH value is critical to the chemoselectivity.

Synthesis of terpenoid oxo derivatives with antiureolytic activity

Urease is an important virulence factor for a variety of pathogenic bacteria strains such as Helicobacter pylori, which colonizes human gastric mucosa, and Proteus sp., responsible for urinary tract infections. Specific inhibition of urease activity could be a promising adjuvant strategy for eradication of these pathogens. Due to the interesting antiureolytic activity of carvone and the scant information regarding the inhibitory properties of corresponding monoterpenes, we decided to study selected monoterpenic ketones and their oxygen derivatives. Several monoterpenes and their terpenoid oxygen derivatives were evaluated in vitro against Sporosarcina pasteurii urease. The most effective inhibitors—derivatives of β-cyclocitral (ester 10 and bromolactone 14)—were described with Ki of 46.7?μM and 45.8?μM, respectively. Active inhibitors of native urease were tested against H. pylori and Proteus mirabilis whole cells. Here, the most active inhibitor, 14, was characterized with IC50 values of 0.32?mM and 0.61?mM for P. mirabilis and H. pylori, respectively. The antibacterial activity of a few tested inhibitors was also observed. Compound 14 limited the growth of E. coli (MIC50= 250?μg/mL). Interestingly, 10 was the only compound that was effective against both Gram-negative and Gram-positive bacteria. It had a MIC50 of 150?μg/mL against E. coli and S. aureus. In the presented study a group of novel antiureolytic compounds was characterised. Besides carvone stereoisomers, these are the only terpenoid urease inhibitors described so far.

A general strategy for the stereoselective synthesis of the furanosesquiterpenes structurally related to pallescensins 1-2

Here, we describe a general stereoselective synthesis of the marine furanosesquiterpenes structurally related to pallescensins 1-2. The stereoisomeric forms of the pallescensin 1, pallescensin 2, and dihydropallescensin 2 were obtained in high chemical and isomeric purity, whereas isomicrocionin-3 was synthesized for the first time. The sesquiterpene framework was built up by means of the coupling of the C10 cyclogeranyl moiety with the C5 3-(methylene)furan moiety. The key steps of our synthetic procedure are the stereoselective synthesis of four cyclogeraniol isomers, their conversion into the corresponding cyclogeranylsulfonylbenzene derivatives, their alkylation with 3-(chloromethyl)furan, and the final reductive cleavage of the phenylsulfonyl functional group to afford the whole sesquiterpene framework. The enantioselective synthesis of the α-, 3,4-dehydro-γ- and γ-cyclogeraniol isomers was performed using both a lipase-mediated resolution procedure and different regioselective chemical transformations.

STABILIZED MUTANT OPSIN PROTEINS

Methods and compositions for stabilizing opsin protein, such as a Pro23His mutant opsin protein, in a vertebrate visual system, by administration of opsin-binding synthetic retinoids, are provided. The mutant opsin protein binds to the synthetic retinoid, which stabilizes the mutant opsin protein and/or ameliorates the effects of the mutant opsin protein on the vertebrate visual system.

SUBSTITUTED QUINOLIZINE DERIVATIVES USEFUL AS HIV INTEGRASE INHIBITORS

The present invention relates to Substituted Quinolizine Derivatives of Formula (I): and pharmaceutically acceptable salts or prodrug thereof, wherein X, Y, R1, R2, R3, R4, R5, R9 and R10 are as defined herein. The present invention also relates to compositions comprising at least one Substituted Quinolizine Derivative, and methods of using the Substituted Quinolizine Derivatives for treating or preventing HIV infection in a subject.

OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE

Compounds and compositions are disclosed that are useful for treating ophthalmic conditions caused by or related to production of toxic visual cycle products that accumulate in the eye, such as dry adult macular degeneration, as well as conditions caused by or related to the misfolding of mutant opsin proteins and/or the mis-localization of opsin proteins. Compositions of these compounds alone or in combination with other therapeutic agents are also described, along with therapeutic methods of using such compounds and/or compositions. Methods of synthesizing such agents are also disclosed.

Discrete iron complexes for the selective catalytic reduction of aromatic, aliphatic, and α,β-unsaturated aldehydes under water-gas shift conditions

Iron-catalyzed reductions: Selective iron-catalyzed reduction of aldehydes with hydrogen generated in situ by the water-gas shift reaction is presented (see scheme). The generality and selectivity of this mild procedure are demonstrated by the efficient reduction of various aromatic, aliphatic and α,β-unsaturated aldehydes.

OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE

Compounds and compositions of said compounds along with methods of use of compounds are disclosed for treating ophthalmic conditions related to mislocalization of opsin proteins, the misfolding of mutant opsin proteins and the production of toxic visual cycle products that accumulate in the eye. Compounds and compositions useful in the these methods, either alone or in combination with other therapeutic agents, are also described.