Methyl menthyl acetate

SYNS FEMA No. 2668 1-2-ISOPROPYL-5-METHYL-CYCLOHEXAN-l-OL ACETATE (-)-MENTHYL ACETATE 1-MENTHYL ACETATE (FCC) 1-p-MENTH-3-YL ACETATE (R-(la,2P,5a))-5-METHYL-2-(l-METHYLETHYL)-CYCLOHEXANOL ACETATE (9CI)... 

Acetic acid, 5-methyl-2-(1-methylethyl)-cyclohexanyl ester menthyl acetate 172a, 174b, 1053, 3266 ... 

Cyclohexanol, 5-methyl-2-(l-methylethyl)-, acetate menthyl acetate 172a 174a, 174b... 

Acetic acid 2-isopropyl-5-methyl cyclohexyl ester. See Menthyl acetate Acetic acid, lead salt. See Lead acetate Acetic acid, lead(4+) salt. See Lead tetraacetate Acetic acid, lead (+2) salt trihydrate. See Lead acetate tri hydrate... 

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1S-(o,2a,5P)]-. See d-Neomenthol Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate. See l-Menthyl acetate Menthyl acetate dl-Menthyl acetate Cyclohexanol, 3,3,5-trimethyl-. See Trimethylcyclohexanol Cyclohexanone... 

Methyl-2-(1-methylethyl) cyclohexanol acetate dl-5-Methyl-2-(1 -methylethyl) cyclohexanol acetate. See dl-Menthyl acetate (R-(1a,2p,5a))-5-Methyl-2-(1-methylethyl) cyclohexanol acetate. See l-Menthyl acetate 5-Methyl-2(1-methylethyl) cyclohexanol-2-aminobenzoate. See Menthyl anthranilate (1 R,2S,5R)-5-Methyl-2-(1 -methylethyl)... 

Menthyl acetate 1-(p-Methoxyphenyl)-1-penten-3-one 4 -Methyl acetophenone ... 

Hydroxycitronellal methyl anthranilate 201-909-7 Menthyl salicylate 201-911-8 Menthyl acetate 201-924-9... 

Homolinalool C12H22O2 Allyl nonanoate Allyl trimethylhexanoate 2-t-Butylcyclohexyl acetate (exo)-2-Camphanyl-p-hydroxyethyl ether Citral dimethyl acetal Citronelloxyacetaldehyde Citronellyl acetate Citronellyloxy acetaldehyde 9-Decenyl acetate 4,4-Dibutyl-y-butyrolactone Dihydromyrcenyl acetate Dihydroterpinyl acetate 5-Dodecalactone y-Dodecalactone 2-Ethyl hexyl methacrylate cis-3-Hexenyl hexanoate p-Menthanyl acetate Menthyl acetate ( )-Menthyl acetate dl-Menthyl acetate l-Menthyl acetate Methyl 9-undecenoate Methyl 10-undecenoate... 

Steric effects on the substrate also appeared to play a role in the oxidation reactions. An interesting example is 1,1-DMCH, where oxidation at adjacent position to the methyl groups was disfavored because of steric encumbrance, and the other two methylenic sites were thus favored. The enhanced selectivity for secondary sites was best illustrated in the oxidation of (—)-menthyl acetate, which furnished a -2 1 mixture of tertiary alcohol ket(Mie after selective oxidation at the methylenic site. This behavior was in stark contrast with that offered by [Fe(pdp)... 

Metabolic pathways of menthol (137), menthone (149), thymol (179), and carvacrol methyl ether (202) are summarized in Figure 19.201. Menthol (137) is generally hydroxylated to give 1-hydroxy-(138), 2-hydroxy- (140), 4-hydroxy- (141), 6-hydroxy- (139), 7-hydroxy- (143), 8-hydroxy- (142), and 9-hydroxymenthol (144) and 1,8-dihydroxy- (146) and 7,8-dihydroxymenthol (148) (Asakawa et al., 1991 Takahashi et al., 1994 Van der Werf et al., 1997). Racemic menthyl acetate and menthyl chloroacetate are hydrolyzed asymmetrically by an esterase of microorganisms (Brit Patent, 1970 Moroe et al., 1971 Watanabe and Inagaki, 1977a,b). Menthone (149) is reductively metabolized to 137 and oxidatively metabolized to 3,7-dimethyl-6-hydroxyoctanoic acid (152), 3,7-dimethyl-... 

Molecular weights of common esters are bomyl acetate, geranyl acetate, linalyl acetate, 196 3 menthyl acetate, 198 3 menthyl valerianate, 240-3 geranyl tiglate, 236 4 santalyl acetate, 262 4 methyl salicylate, 152 2. 

Figure 13 SPME profile of flavor volatiles sampled from the mouth at 5 and 30 minutes following brushing with a dentifrice. Peaks are identified as Menthone (1), Isomenthone (2), Menthyl acetate (3), Isomenthol (4), Menthol (5), Methyl sahcylate (6), and Anethole (7).

Preparative Methods conveniently prepared - by reaction of the magnesium enolate of r-butyl acetate (readily made with Bromomagnesium Diisopropylamide) with (-)-(lR,2S,5R)-Menthyl (S)-p-Toluenesulfinate (eq 1). It was also made in 91% yield by reacting a solution of Lithium Diisopropylamide with (R)-(+)-methyl p-tolyl sulfoxide and 7-butyl carbonate (eq 2). It should be noted that asymmetric oxidation of 7-butyl 2- p-tolylsulfinyl)acetate with a modified Sharpless reagent gave a... 

Preparative Methods the synthesis of this compound was first reported by methylation of (R)-(+)-t-Butyl 2-(p-Tolylsulfinyl)acetate via enolate generation with lithium bases such as n-Butyllithium or t-Butyllithium at 0 °C and with only lodomethane as the alkylating agent (eq 1). The diastereomeric ratio was shown by H NMR to be 50 50 with BuLi and 42 58 with t-BuLi. The title compound was also prepared from (-)-(1R,2S,5R)-Menthyl (S)-p-Toluenesulfinate and the magnesium enolate of t-butyl propionate in 68% yield as a 1 1 ratio of the two possible diastereomers (eq 2). ... 

Enantioselective Intermolecular Cyclopropenation Reactions. The use of Rh2(MEPY)4 catalysts for intermolecular cyclopropenation of 1-alkynes results in moderate to high selectivity. With propargyl methyl ether (or acetate), for example, reactions with (—)-menthyl [(+)-(l/ ,25,5/ )-2-isopropyT5-methyl-1-cyclohexyl] diazoacetate catalyzed by Rh2(55 -MEPY)4 produces the corresponding cyclopropene product (eq 3) with 98% diastere-omeric excess (de). ... 

The synthesis of L-methyl DOPA 80 by the Strecker reaction was straightforward and of course produced racemic material. A conventional resolution by crystallising the menthyl ester 83 from hexane and hydrolysis of acetal, ester and amide in 48% HBr (note that no racemisation by enolisation can occur) gives good yields.19... 

Further n.m.r. data have been published on isomeric menthyl cf. Vol. 7, pp. 5, 29) and carvomenthyl alcohols and some derivatives.N.m.r. data include [Eu(dpm)3] methyl shift assignments in the menthols, the menthones, two carvomenthols, the isopulegols, the carveols, carvone, carvotanacetol, and carvotanacetone, together with the relevant acetates, and an analysis of... 

Methyl-l-phenylisoquinoline (380) is obtained when the oxazoline (379) is heated with phosphorus pentoxide. An efficient synthesis of alkylated and dialkylated acetic acids consists in the alkylation of 4,5-dihydro-oxazoline bound to polystyrene, followed by hydrolysis." The asymmetric synthesis of a series of a-alkylphenylacetic acids C H2 +i CHPhC02H ( = 1-5) from the chiral oxazoline (381) has been described. Another example of the use of oxazolines for asymmetric synthesis is the preparation of the optically active binaphthyl (383) from 1-lithionaphthalene and compound [382 R = (—)-menthyl]. The stereoselective formation of threo-dXdoX products (385 = Et, Pr, n-pentyl, etc from the chiral boron compound... 

Decanediol 2-Ethylhexyl acetate 12-Hydroxystearyl alcohol Menthyl lactate Methyl acetoacetate Pyrocatechol... 

Ester Methyl salicylate, menthyl lactate, terpineol acetate... 

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