68330-68-7

Upstream product

• 10458-14-7 (2R,5S)-menthone 
• 491-07-6 isomenthone 
• 491-07-6 (+/-)-menthone 
• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 34048-68-5 isomenthol methyl ether 
• 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

• 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 

Relevant academic research and scientific papers

The synthesis of menthone by ozonization of menthol

A selective method of oxidation of menthol to menthone by Co(OAc)2-catalyzed ozonization in ethyl acetate or Freon-113 was developed.

Oxidative Cleavage of Methyl Ethers Using the HOF*CH3CN Complex

HOF*CH3CN complex, made easily by bubbling fluorine diluted with nitrogen through aqueous acetonitrile, proved to be a suitable oxidizer for various methyl ethers.Secondary ethers are oxidized to ketones and even to lactones via Baeyer-Villiger type of oxidation.The reaction is ionic, and the reagent's electrophilic oxygen attacks the relatively electron rich C-H bond α to the ether moiety.It was found that the more sterically hindered is the C-H bond in question, the slower the reaction.In cases where this bond is an electron poor one as in benzoin methyl ether (9), no reaction takes place.When labeled H(18)OF*CH3CN is used on a (16)O methyl ether, the resulting ketone possesses only the heavier oxygen isotope.Primary methyl ethers are somewhat slower to react, but they too were oxidized in very good yields to acids via the corresponding aldehydes.

Stereoselective syntheses of isomers of 3,7-dimethylnonadecane, a sex pheromone of the alfalfa blotch leafminer (Agromyza frontella (Rondani))

Two related stereoselective syntheses of 3,7-dimethylnonadecane, a sex pheromone of the alfalfa leafminer, are described to show that pulegone can serve as a useful starting material for the preparation of chiral aliphatic isoprenoid compounds.The schemes are designed to place the stereogenic center of pulegone at C.3 in one synthesis and at C.7 in the other so that the optical properties of the products can be compared with one another and with the values calculated using Brewster's rules. Key Words: chiral hydrocarbons, stereoselective synthesis, pheromone, Agromyza frontella.

Structure-Odor Relationships in Monoterpenolactones

Twelve γ-, δ- and ε-monoterpenelactones were synthesized, with seven compounds (5, 6, 7, 8, 13, 13', and 15) being newly formed.The odor of the monoterpenolactones was found to be dependent on the size of their rings and their conformation.Substitution of the equatorial methyl group at C(3) in the δ- and ε-monoterpenolactones with a planar molecular shape was necessary for the monoterpenolactones to produce a pronounced maple-like odor.

PREPARATION OF BIOLOGICALLY ACTIVE SUBSTANCES AND ANIMAL AND MICROBIAL METABOLITES FROM MENTHOLS, CINEOLES AND KAURANES

Six monoterpenoids, l-menthol, l-menthyl acetate, iso-menthol, neo-menthol, 1,4-cineole and 1,8-cineole and one diterpene hydrocarbon, ent-kaurene were oxidized by meta-chloroperbenzoic acid or dry ozone to give various hydroxylated products and their structures elucidated by NMR spectroscopy.Some hydroxylated menthols showed plant growth inhibitory and strong mosquito repellent activity.Among the hydroxylated cineoles, microbial and animal metabolites of cineoles were included.From ent-kauranes, a plant growth inhibitory diterpene alcohol, (-)-16α-hydroxy kaurane was obtained along with 16α-kauran-13α-ol.