16750-82-6

Basic information

• Product Name: (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one
• Synonyms: (4S)-1,8-p-Menthadiene-3-one;(S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one;[S,(+)]-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-one;[S,(+)]-3-Methyl-6-(1-methylethenyl)-2-cyclohexene-1-one;[S,(+)]-3-Methyl-6β-(1-methylethenyl)-2-cyclohexene-1-one
• CAS NO: 16750-82-6
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• Mol File: 16750-82-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 228.9±40.0 °C(Predicted)
• Appearance: /
• Density: 0.940±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one(16750-82-6)
• EPA Substance Registry System: (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one(16750-82-6)

Safety Data

• Hazardous Substances Data: 16750-82-6(Hazardous Substances Data)

Usage

Description

(S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one, also known as (S)-Isopiperitenone, is an organic compound that serves as a valuable synthetic intermediate in the chemical industry. It is characterized by its unique molecular structure, which includes a cyclohexene ring with a methyl group at position 3 and an isopropenyl group at position 6β. (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one is known for its potential applications in various fields due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
(S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one is used as a synthetic intermediate for the preparation of cis-isopiperitenol. (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one is significant in the investigation of the lipase-catalyzed resolution of p-menthan-3-ol monoterpenes, which are essential components in the development of various pharmaceutical products. The ability to synthesize cis-isopiperitenol from (S)-Isopiperitenone allows for the exploration of new drug candidates and the enhancement of existing medications.
Used in Chemical Synthesis:
In the field of chemical synthesis, (S)-3-Methyl-6β-isopropenyl-2-cyclohexene-1-one is utilized as a key building block for the creation of more complex molecules. Its unique structure allows for further functionalization and modification, making it a versatile compound in the synthesis of various organic compounds. This can lead to the development of new materials, catalysts, and other specialty chemicals with diverse applications.
Used in Flavor and Fragrance Industry:
(S)-Isopiperitenone, due to its distinct chemical structure, can also be used in the flavor and fragrance industry. It can be employed as a starting material for the synthesis of various aroma compounds, which can be used to create unique and appealing scents for perfumes, cosmetics, and other consumer products. The compound's potential in this industry highlights its versatility and the wide range of applications it can be used for.

Upstream product

• 5989-27-5 D-limonene 
• 108-24-7 acetic anhydride 
• 491-05-4 (+)-cis/trans-p-mentha-2,8-dien-1-ol 
• 22972-51-6 (1S,4R)-p-mentha-2,8-dien-1-ol 
• 491-05-4 (+)-p-menthadiene-3-ol 
• 3886-78-0 (+)-2,8-p-menthadien-1-ol 
• 84284-59-3 d-carene nitrosate 
• 52154-82-2 (1R,4R)-p-mentha-2,8-dien-1-ol 

Downstream Products

• 1972-08-3 dronabinol 
• 120467-11-0 (6aR,10aR)-6,6,9-trimethyl-3-phenethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 491-05-4 (+)-p-menthadiene-3-ol 
• 166990-10-9 (-)-murrayamine P 
• 166990-10-9 (+)-murrayamine-O 

Relevant articles and documents

Enantiospecific Total Syntheses of (+)-Hapalindole H and (?)-12-epi-Hapalindole U

Enantiospecific total syntheses of (+)-hapalindole H and (?)-12-epi-hapalindole U as well as the formal syntheses of (+)-hapalindole Q and (+)-12-epi-fischerindole U isothiocyanate have been described. Key steps of our approach feature expedient, highly regio- and diastereoselective Lewis acid catalyzed Friedel–Crafts reaction of indole with cyclic allylic alcohols and intramolecular reductive Heck reaction. Efficiency of the synthetic route also relies on an alkynyl aluminate complex driven regioselective nucleophilic epoxide opening from a sterically hindered site.

Enantiospecific total syntheses and assignment of absolute configuration of cannabinol-skeletal carbazole alkaloids murrayamines-O and -P

First enantiospecific total syntheses of the cannabinol-skeletal carbazole alkaloids murrayamines-O and -P isolated from root barks of Murraya euchrestifoli, have been accomplished by highly diastereoselective, Lewis acid catalyzed coupling reactions of commercially available monoterpenes with carbazole derivative, which in addition to confirming the structure also established the absolute configuration of the natural products. Synthesis of both natural products and their enantiomers was achieved with high atom economy, in a protecting-group free manner and in six steps longest linear sequence from commercially available aniline derivative and verbenol.

Daucus carota and baker's yeast mediated bio-reduction of prochiral ketones

Stereoselective reduction of prochiral ketones to the corresponding alcohols using biocatalysts has attracted much attention, from the viewpoint of green chemistry. Asymmetric reduction of indanone, tetralone and hydroxyl trimonoterpene ketones to the corresponding enantiomerically pure (S)-alcohols, using Daucus carota plant homogenate and fermented baker's yeast cells, is described. The present study illustrates the broad substrate selectivity of the dehydrogenase enzymes present in the D. carota in the synthesis of a wide range of chiral secondary alcohols of biological importance.