3391-87-5

Usage

Uses

Used in Flavor Industry:
(+)-Menthone is used as a flavoring agent for its cooling and refreshing taste. It is commonly added to various food products, such as candies, chewing gum, and beverages, to provide a minty flavor and a pleasant sensation on the palate.
Used in Fragrance Industry:
(+)-Menthone is used as a fragrance ingredient for its fresh, minty, and slightly fruity aroma. It is widely utilized in the formulation of perfumes, colognes, and other personal care products to impart a refreshing and invigorating scent.
Used in Biological Studies:
(+)-Menthone is used as an odorant in the characterization of various mouse odorant receptors, such as MOR256-17, MOR256-8, and MOR256-22. These receptors are involved in detecting different odorant molecules, including nitrotoluenes, and play a crucial role in the sense of smell in mice. The use of (+)-menthone in these studies helps researchers understand the molecular mechanisms underlying odor detection and perception.

InChI:InChI=1/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3

Upstream product

• 89-81-6 piperitone 
• 491-09-8 3-terpinolenone 
• 114529-48-5 (7R,10S)-7-Isopropyl-10-methyl-1,5-dithia-spiro[5.5]undecane 
• 127129-06-0 (3S,6R)-3-methyl-6-(prop-2-yl)-1-trimethylsilyloxy-cyclohexene 
• 73808-92-1 C₁₈H₂₉NO₂S 
• 73808-92-1 C₁₈H₂₉NO₂S 
• 204916-68-7 (S)-Methoxy-phenyl-acetic acid 2-((R)-4-methyl-2-oxo-cyclohex-3-enyl)-allyl ester 
• 5949-05-3 (S)-Citronellal 
• 3391-90-0 (S)-(-)-pulegone 
• 20747-49-3 (-)-neomenthol 
• 72311-09-2 3-Methyl-6-(1-methylethyl)-1-trimethylsilyloxy-1-cyclohexen 
• 75-36-5 acetyl chloride 
• 106-95-6 allyl bromide 
• 6485-40-1 (R)-Carvone 

Downstream Products

• 26127-89-9 ((1S,2R,5S)-1-Hydroxy-2-isopropyl-5-methyl-cyclohexyl)-acetic acid tert-butyl ester 
• 50281-16-8 (1R,4S)-1-isopropyl-4-methyl-2-methylenecyclohexane 
• 20747-49-3 (-)-neomenthol 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 1196-31-2 (1R,4R)-(+)-isomenthone 
• 7599-80-6 (1S,4S)-4-hydroxy-p-menthan-3-one 
• 18309-28-9 (1S,4S)-isomenthone 
• 222020-89-5 (1S,2R,5S)-2-Isopropyl-5-methyl-1-((E)-propenyl)-cyclohexanol 
• 222020-96-4 (1R,2R,5S)-2-i-propyl-5-methyl-1-(3-methyl-1-butyn-1-yl)cyclohexan-1-ol 
• 262352-81-8 (1S,2R,4R)-1-Methyl-2-(3-oxobutyl)-3-oxo-4-(1-methylethyl)cyclohexane 
• 412324-05-1 (3R,6S)-6-Isopropyl-3-methyl-cyclohex-1-enol 

Relevant academic research and scientific papers

Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide

Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.

SBA-15 Supported 1-Methyl-2-azaadamanane N-Oxyl (1-Me-AZADO) as Recyclable Catalyst for Oxidation of Alcohol

Herein, we designed and synthesized an SBA-15 supported 1-methyl-2-azaadamanane N-oxyl (1-Me-AZADO) and investigated its catalytic performance for selective oxidation of alcohols under Anelli's conditions. The first example of immobilization of 1-Me-AZADO was very important to advance the oxgenation effectively because this supported N-oxyl has excellent catalytic activity for oxidation of alcohols to carbonyl compounds, and more importantly, it can be conveniently recovered and reused at least 6 times without significant effect on its catalytic efficiency.

Method of preparing L-menthone from R-citronellal

The invention discloses a method of preparing L-menthone from R-citronellal. Under the action of a Pd-Co-MOF-MMT catalyst, R-citronellal carries out heterogeneous catalytic reactions to generate L-menthone, the conversion rate of R-citronellal can reach 90-99.9%, the yield of L-menthone can reach 85-98%, and the ee value of menthone can reach 95-99.99%.

Method for preparation of L-menthone from R-citronellal

The invention discloses a method for preparation of L-menthone from R-citronellal. In the presence of a Ru-Cu-MOF catalyst, R-citronellal is cyclized to prepare L-menthone, the reaction conditions aremild, the reaction enantioselectivity is 90%-99.5%, the conversion rate can reach 95%-99.9%, and the ee value of menthone can reach 90%-99.9%.

Amino-TEMPO Grafted on Magnetic Multi-Walled Nanotubes: An Efficient and Recyclable Heterogeneous Oxidation Catalyst

An efficient and easy recyclable heterogeneous oxidation catalyst was prepared by grafting TEMPO–NH2 moieties on the surface of magnetic multi-walled carbon nanotubes (MWCNT), first by a radical reaction introducing butyric acid moieties on carbon nanotube surface. Subsequently, carboxylic acid moieties were submitted for amidation using TEMPO–NH2. The functionalized nanotubes [MWCNT-{(CH2)3-CO-NH-TEMPO}n] were investigated as a (pre-)catalyst for the oxidation of primary and secondary alcohols for the production of aldehydes and ketones in a Montanari-type catalytic oxidation using the cheap and readily available 1,3-dichloro-5,5-dimethylhydantoin as the terminal oxidant.

Chemoselective Hydrogenation of α,β-Unsaturated Carbonyls Catalyzed by Biomass-Derived Cobalt Nanoparticles in Water

Herein, we report highly chemoselective hydrogenation of α,β-unsaturated carbonyls to saturated carbonyls catalyzed by cobalt nanoparticles supported on the biomass-derived carbon from bamboo shoots with molecular hydrogen in water, which is the first prototype using a heterogeneous non-noble metal catalyst for such organic transformation as far as we know. The optimal cobalt nanocatalyst, CoOx@NC-800, manifested remarkable activity and selectivity for hydrogenation of C=C in α,β-unsaturated carbonyls under mild conditions. A broad set of α,β-aromatic and aliphatic unsaturated carbonyls were selectively reduced to their corresponding saturated carbonyls in up to 99 % yields with good tolerance of various functional groups. Meanwhile, a new straightforward one-pot cascade synthesis of saturated carbonyls was realized with high activity and selectivity via the cross-aldol condensation of ketones with aldehydes followed by selective hydrogenation. More importantly, this one-pot strategy is applicable for the expedient synthesis of Loureirin A, a versatile bioactive and medicinal molecule, from readily available starting materials, further highlighting the practical utility of the catalyst. In addition, the catalyst can be easily separated for successive reuses without significant loss in both activity and selectivity.

Cyclopropenium-Activated DMSO for Swern-Type Oxidation

Swern oxidation is widely used to convert alcohols into their corresponding carbonyl compounds. However, the conventional method with use of the volatile oxalyl chloride as an activator requires the reaction to be conducted below -60 °C. We discovered that 3,3-dichloro-1,2-diphenylcyclopropene (DDC) can be used as a new activator for Swern-type oxidations of alcohols, which can be conducted at -20 °C. This new protocol features mild and fast reactions with easy operation. Furthermore, the activator DDC is easy to handle, and diphenylcyclopropenone can be recovered quantitively. This new type of Swern oxidation shows a broad scope of substrates including benzylic, allylic, aliphatic, and biobased alcohols, and gives high yields of up to 93%.

A rapid and convenient oxidation of secondary alcohols

A rapid (normally 20?min to 2?h) and selective oxidation of secondary alcohols to ketones can be achieved using 0.4?equivalents trichloroisocyanuric acid and 1.2?equivalents pyridine at room temperature in ethyl acetate. A likely mechanism for the reaction is proposed.

Cooperative Electrocatalytic and Chemoselective Alcohol Oxidation by Shvo's Catalyst

A new electrocatalytic conversion of alcohols to ketones and aldehydes was developed based on an electrochemical study of Shvo's complex. The oxidation of secondary alcohols was efficiently performed under mild conditions using a catalytic amount of Shvo's catalyst, in combination with a sub-stoichiometric amount of 2,6-dimethoxy-1,4-benzoquinone in N,N-dimethylformamide at 80 °C. The hydroquinone thus formed is continuously reoxidized with the aid of an electrochemical device. Excellent yields for different ketones, aromatic as well as aliphatic and α,β-unsaturated ketones, are obtained. In addition, chemoselectivity towards oxidation of the secondary alcohol is achieved when converting vicinal diols such as 1,2-octanediol and 1,2-decanediol. (Figure presented.).

Secondary Phosphine Oxides as Multitalented Preligands En Route to the Chemoselective Palladium-Catalyzed Oxidation of Alcohols

Secondary phosphine oxides O=PHR2 (SPOs) were identified as multitalented preligands for the chemoselective Pd-catalyzed oxidation of alcohols by a hydrogen-abstracting methodology. SPOs were found to promote the hydrogen-abstraction step as well as hydrogen transfer to a Michael acceptor by generating a putative active H?Pd species. The catalytic system operates under neutral conditions and was proven to be compatible with various electrophilic and nucleophilic functionalities within the substrates as well as water- and air-sensitive functional groups.