68330-67-6

Basic information

• Product Name: (4R-trans)-7-isopropyl-4-methyloxepan-2-one
• Synonyms: (4R-trans)-7-isopropyl-4-methyloxepan-2-one;(4R)-4α-Methyl-7β-(1-methylethyl)oxepan-2-one;(4R)-4α-Methyl-7β-isopropyloxepan-2-one;4α-Methyl-7β-isopropyl-4,5,6,7-tetrahydrooxepin-2(3H)-one;(4R-trans)-4-Methyl-7-(1-methylethyl)-2-oxepanone;2-Oxepanone, 4-methyl-7-(1-methylethyl)-, (4R,7S)-;Einecs 269-768-4;(4R,7S)-7-isopropyl-4-methyloxepan-2-one
• CAS NO: 68330-67-6
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.24872
• EINECS: 269-768-4
• Mol File: 68330-67-6.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 248.326°C at 760 mmHg
• Flash Point: 96.562°C
• Appearance: /
• Density: 0.926g/cm³
• Vapor Pressure: 0.024mmHg at 25°C
• Refractive Index: 1.435
• Storage Temp.: -20°C
• CAS DataBase Reference: (4R-trans)-7-isopropyl-4-methyloxepan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R-trans)-7-isopropyl-4-methyloxepan-2-one(68330-67-6)
• EPA Substance Registry System: (4R-trans)-7-isopropyl-4-methyloxepan-2-one(68330-67-6)

Safety Data

• Hazardous Substances Data: 68330-67-6(Hazardous Substances Data)

Usage

Description

(4R-trans)-7-isopropyl-4-methyloxepan-2-one, also known as menthide, is a seven-membered, plant-derived lactone monomer that can be readily polymerized via ring-opening polymerization (ROP). It has been used to produce aliphatic polyesters with high molecular weights and narrow molecular weight distributions (PDI) through controlled ROP. Menthide has also been copolymerized with other biologically derived monomers, such as lactide, to create products like thermoplastic elastomers and pressure-sensitive adhesives.

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

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

Downstream Products

• 99493-42-2 (S)-(+)-14-Methyl-1-octadecene 
• 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 
• 136493-73-7 (R)-3,7-Dimethyl-6-(toluene-4-sulfonyloxy)-octanoic acid methyl ester 
• 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 articles and documents

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.

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.

Oxidation of terpenoids with a cyclohexanone fragment by performic acid

-