68330-67-6

Usage

Uses

Used in Polymer Industry:
Menthide is used as a monomer for the production of aliphatic polyesters with high molecular weights and narrow PDI through controlled ring-opening polymerization. This allows for the creation of materials with improved properties and performance.
Used in Copolymerization:
Menthide is used as a comonomer in the copolymerization process with other biologically derived monomers, such as lactide. This results in the formation of products like thermoplastic elastomers and pressure-sensitive adhesives, which have various applications in different industries.
Used in the Production of Thermoplastic Elastomers:
Menthide is used as a key component in the synthesis of thermoplastic elastomers, which are versatile materials with properties similar to vulcanized rubber but with the processing ease of thermoplastics. These elastomers find applications in various industries, including automotive, construction, and consumer goods.
Used in the Synthesis of Pressure-Sensitive Adhesives:
Menthide is utilized in the production of pressure-sensitive adhesives, which are essential in various applications such as tapes, labels, and medical products. These adhesives offer strong adhesion under light pressure and are easily removable without leaving residue.

InChI:InChI=1/C10H18O2/c1-7(2)9-5-4-8(3)6-10(11)12-9/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1

Upstream product

• 491-07-6 isomenthone 
• 491-07-6 (+/-)-menthone 
• 2216-52-6 Neomenthol 
• 10458-14-7 (2R,5S)-menthone 
• 34048-68-5 isomenthol methyl ether 
• 1565-76-0 (-)-<(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl> methyl ether 
• 53067-10-0 3,7-dimethyl-1,6-octanediol 
• 84465-67-8 3R,7-Dimethyl-6S-hydroxy-octanoic acid 
• 2216-51-5 (-)-menthol 
• 15356-70-4 menthol 
• 120324-18-7 (4S,7R)-7-Isopropenyl-4-methyl-oxepan-2-one 
• 120324-18-7 (4R,7R)-7-Isopropenyl-4-methyl-oxepan-2-one 
• 1196-31-2 (1R,4R)-(+)-isomenthone 

Downstream Products

• 136493-73-7 (R)-3,7-Dimethyl-6-(toluene-4-sulfonyloxy)-octanoic acid methyl ester 
• 1237740-96-3 (R)-1-(2-hydroxyphenyl)-3,7-dimethyloctane-1,6-dione 
• 1237740-97-4 (S)-1-(2-hydroxyphenyl)-3,7-dimethyloctane-1,6-dione 
• 99493-42-2 (S)-(+)-14-Methyl-1-octadecene 
• 142746-66-5 (4S,5R,8S)-8-(methoxymethoxy)-5,9-dimethyl-4-<(4-tolylsulfonyloxy)methyl>-1-decene 
• 159107-50-3 (3R,6S)-6-methoxymethoxy-3,7-dimethyl-1-(4-toluenesulfonyloxy)octane 
• 146512-86-9 (R)-6-benzyloxy-4-methylhexyl tosylate 
• 146512-84-7 (7R)-9-benzyloxy-3-oxa-4-oxo-2,7-dimethylnonane 
• 146512-83-6 (6R)-8-benzyloxy-3-oxo-2,6-dimethyloctane 
• 146512-87-0 (3R)-1-benzyloxy-3-methyloctane 
• 146512-85-8 (3R)-1-benzyloxy-3-methyl-6-hexanol 
• 84560-01-0 (6R)-8-hydroxy-2,6-dimethyloctan-3-one 
• 873798-62-0 isopropyl (R)-4-methyl-6-(tosyloxy)hexanoate 
• 873798-61-9 (R)-3,7-dimethyl-1-(tosyloxy)octan-6-one 

Relevant academic research and scientific papers

Pressure-sensitive adhesives from renewable triblock copolymers

ABA triblock copolymers were prepared using the renewable monomers menthide and lactide, by sequential ring-opening polymerizations. Initially, hydroxy telechelic polymenthide was synthesized by the diethylene glycol-initiated and tin(II) ethylhexanoate-catalyzed polymerization of menthide. The resulting 100 kg mol-1 polymer was used as a macroinitiator for the tin(II) ethylhexanoate-catalyzed ring-opening polymerization of d,l-lactide. Two polylactide-polymenthide-polylactide triblock copolymers were prepared with 5 and 10 kg mol-1 polylactide end blocks. Transesterification between the two blocks, and polylactide homopolymer formation were minimized, and triblock copolymers with narrow molecular weight distributions were produced. Microphase separation in these systems was corroborated by differential scanning calorimetry and small-angle X-ray scattering measurements. The triblocks were combined with up to 60 wt % of a renewable tackifier, and the resulting mixtures were evaluated using probe tack, 180° peel adhesion, and shear strength tests. Maximum values of peel adhesion (3.2 N cm-1) and tack (1.1 N) were obtained at 40 wt % of tackifier. These new materials hold promise as renewable and hydrolytically degradable pressure-sensitive adhesives.

Macrocyclic Lactonization of 3R,7-Dimethyl-6S-Hydroxyoctanoic Acid

A mixture of cyclic lactones [7- (mentholactone), 14-, 21-, 28-, and 35-membered polylactones] instead of the expected [2 + 1]-condensation products was obtained from the reaction of 3R,7-dimethyl-6Shydroxyoctanoic acid, which is accessible from l-menthol, and glutaric, adipic, and bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dichlorides in Py in the presence of N,N-dimethylaminopyridine. The structures were confirmed using PMR, 13C NMR, and mass spectra.

Biocatalytic Characterization of Human FMO5: Unearthing Baeyer-Villiger Reactions in Humans

Flavin-containing mono-oxygenases are known as potent drug-metabolizing enzymes, providing complementary functions to the well-investigated cytochrome P450 mono-oxygenases. While human FMO isoforms are typically involved in the oxidation of soft nucleophiles, the biocatalytic activity of human FMO5 (along its physiological role) has long remained unexplored. In this study, we demonstrate the atypical in vitro activity of human FMO5 as a Baeyer-Villiger mono-oxygenase on a broad range of substrates, revealing the first example to date of a human protein catalyzing such reactions. The isolated and purified protein was active on diverse carbonyl compounds, whereas soft nucleophiles were mostly non- or poorly reactive. The absence of the typical characteristic sequence motifs sets human FMO5 apart from all characterized Baeyer-Villiger mono-oxygenases so far. These findings open new perspectives in human oxidative metabolism.

Baeyer-Villiger oxidation under Payne epoxidation conditions

A novel method for the Baeyer-Villiger oxidation of ketones has been developed and optimized. The transformation involves a transition metal-free activation of hydrogen peroxide under Payne epoxidation conditions. Reaction of a ketone with hydrogen peroxide in the presence of a nitrile under mildly basic reaction conditions leads to the corresponding ester. The transformation has been successfully applied to a range of ketones in moderate to excellent yields (30-91%) and good to excellent regioselectivities (7:1 to 20:1).

Epoxidation and Baeyer-Villiger oxidation using hydrogen peroxide and a lipase dissolved in ionic liquids

Epoxidation and Baeyer-Villiger oxidation of olefins and (cyclic) ketones were successfully carried out in hydrogen-bond-donating (HBD) ionic liquids, using a lipase-catalysed cascade and hydrogen peroxide as the terminal oxidant. The effect of the ionic liquids turned out to be twofold. The HBD ionic liquids exhibited a substantial positive solvent effect on the second step of the cascade, namely the oxygen transfer by peracid. In addition, we found that the Candida antarctica B lipase (CaLB) dissolved in 1-(3-hydroxypropyl)-3-methyl imidazolium nitrate 1a and 1-butyl-3-methylimidazolium nitrate 2a. This stable enzyme-ionic liquid solution opens the possibility for continuous chemical processing.

Extensive substrate profiling of cyclopentadecanone monooxygenase as Baeyer-Villiger biocatalyst reveals novel regiodivergent oxidations

Cyclopentadecanone monooxygenase (CPDMO) is one of the latest additions to the established library of Baeyer-Villiger monooxygenases. Desymmetrizations of substituted cyclobutanones and -hexanones as well as kinetic resolutions of racemic cycloketones are efficiently catalyzed by CPDMO. Moreover the enzyme shows unprecedented preference in regiodivergent oxidations of terpenones and the bicyclic Geissman-Waiss lactone precursor giving access to the optical antipode of retronecine and other pyrrolizidine alkaloids.

Lactones 34 [1]. Application of alcohol dehydrogenase from horse liver (HLADH) in enantioselective synthesis of δ- and ε-lactones

The ability of horse liver alcohol dehydrogenase (HLADH) to the enantioselective oxidation of primary-primary, primary-secondary and primary-tertiary aliphatic 1,5- and 1,6-diols 1a-i was studied. No enantioselectivity of the transformations of primary-primary 1,6-diols 1a-d to ε-lactones 4a-d was observed. Regioselective oxidation of primary-secondary 1,6-diols 1e,f and 1,5-diols 1h,i afforded enantiomerically enriched ε-lactones 4e,f and δ-lactones 4h,i. ε-Lactones 4e,f were formed with higher enantiomeric excesses (e.e. = 85-99%). Enzymatic oxidation of primary-tertiary 1,6-diol 1g did not give lactone product.

Baeyer-Villiger oxidations in ionic liquids. A facile conversion of ketones to esters and lactones

A variety of cyclic and acyclic ketones underwent readily oxidation with m-chloroperbenzoic acid (m-CPBA) in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF4 to afford esters/lactones with high selectivity, ease of product separation and in excellent chemical yields. The reaction proceeded smoothly in ionic liquid without the need of any additional acid or base catalyst. The ketones show enhanced reactivity in ionic liquids thereby reducing reaction times and improving the yields significantly.

Tin(IV) bis(perfluoroalkanesulfonyl)amide complex as a highly selective Lewis acid catalyst for Baeyer-Villiger oxidation using hydrogen peroxide in a fluorous recyclable phase

Sn[N(SO2C8F17)2]4 catalyst was shown to give an excellent yield and selectivity in a fluorous biphasic catalytic system for Baeyer-Villiger oxidation of cyclic ketones by 35% aqueous hydrogen peroxide, a green, safe and cheap oxidant. Furthermore, the catalyst was completely recovered and reused in the fluorous immobilized phase without loss of activity.