18031-40-8

Usage

Uses

Used in Flavor and Fragrance Industry:
(-)-Perillaldehyde is used as a flavoring agent for its characteristic aroma, adding a pleasant scent to food products and beverages. Its natural occurrence in orange juice and mandarin peel oil makes it a popular choice for enhancing the flavor profile of these products.
Used in Analytical Chemistry:
(-)-Perillaldehyde serves as an analytical reference standard for the determination of perillaldehyde content in laboratory animal diets through high-performance liquid chromatography (HPLC) technique. This application is crucial for ensuring the accuracy and reliability of experimental results in research settings.

InChI:InChI=1/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3/t10-/m1/s1

Upstream product

• 536-59-4 (-)-perillyl alcohol 
• 5989-54-8 (-)-(S)-limonene 
• 18172-67-3 beta-pinene 
• 7785-70-8 (+)-α-pinene 
• 1361023-90-6 C₁₇H₂₁N 
• 56246-58-3 β-pinene oxide 
• 15111-96-3 (S)-(4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl acetate 
• 72506-01-5 perillyl formate 
• 6931-54-0 trans-2,10-epoxypinane 
• 852920-51-5 β-pinene α-oxide 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 161115-51-1 (S)-1-(chloromethyl)-4-(prop-1-en-2-yl)cyclohex-1-ene 
• 90831-19-9 (4S)-7-nitromentha-1,8-diene 
• 875-08-1 (-)-β-Pinenoxid 

Downstream Products

• 536-59-4 (-)-perillyl alcohol 
• 14917-83-0 (1R,6S)-7,7-dimethylbicyclo[4.1.0]hept-2-ene-3-carboxaldehyde 
• 142089-04-1 (1S,3R)-1-Isopropenyl-3-methoxy-cyclohexane 
• 142089-02-9 (1R,2S,4S)-4-Isopropenyl-2-methoxy-cyclohexanecarbaldehyde 
• 142089-03-0 (1S,2S,4S)-4-Isopropenyl-2-methoxy-cyclohexanecarbaldehyde 
• 142089-05-2 4-isopropenyl-2-methoxycyclohexanone 
• 142418-08-4 perillaldehyde dimethyl acetal 
• 68480-28-4 formiate de methyl-3 butene-2 ol-1 
• 95603-65-9 hydroxydihydrolavandulol 
• 76675-48-4 (S)-4-((R)-1-Hydroxy-1,5-dimethyl-hex-4-enyl)-cyclohex-1-enecarbaldehyde 
• 76675-46-2 (S)-4-((S)-1-Hydroxy-1,5-dimethyl-hex-4-enyl)-cyclohex-1-enecarbaldehyde 
• 758714-73-7 (SR)-2-((S)-4-(prop-1-en-2-yl)cyclohex-1-enyl)-2-(trimethylsilyloxy)acetonitrile 
• 26607-23-8 (S)-2-(4-(prop-1-en-2-yl)cyclohex-1-enyl)-1,3-dioxolane 
• 99583-47-8 2-<4(S)-Isopropenylcyclohex-1-enyl>-4-methylenetetrahydrofuran 

Relevant academic research and scientific papers

The identification of perillyl alcohol glycosides with improved antiproliferative activity

A facile route to perillyl alcohol (POH) differential glycosylation and the corresponding synthesis of a set of 34 POH glycosides is reported. Subsequent in vitro studies revealed a sugar dependent antiproliferative activity and the inhibition of S6 ribos

Oxidation of alcohols by TBHP in the presence of sub-stoichiometric amounts of MnO2

Commercially available activated MnO2 has been investigated as a catalyst for the oxidation of alcohols (phenylethanol, 4-methyl- and 4-methoxybenzyl alcohol, trans-cinnamyl alcohol, cyclohexanol, menthol, perillyl alcohol and myrtenol) by TBHP/decane or TBHP/water in MeCN. The activity is highest for benzylic and allylic alcohols. Secondary alcohols yield ketones with good selectivities, while the aldehydes generated from primary alcohols are further oxidized. The process competes with the TBHP catalyzed decomposition. It thus requires the use of excess TBHP and high catalyst loadings to achieve high conversions. However, the low cost of the reagents makes this new protocol convenient for the oxidation of reactive secondary alcohols. The study also suggests that MnO2 should be proscribed as a reagent to quench excess TBHP in oxidative processes when the synthetic target contains easily oxidizable alcohol functions and when carrying our detailed kinetic monitoring of oxidation processes.

A new catalytic approach for aerobic oxidation of primary alcohols based on a Copper(I)-thiophene carbaldimines

We report here novel Cu(I) thiophene carbaldimine catalysts for the selective aerobic oxidation of primary alcohols to their corresponding aldehydes and various diols to lactones or lactols. In the presence of the in situ generated Cu(I) species, a persistent radical (2,2,6,6-tetramethylpiperdine-N-oxyl (TEMPO)) and N-methylimidazole (NMI) as an auxiliary ligand, the reaction proceeds under aerobic conditions and at ambient temperature. Especially the catalytic system of 1-(thiophen-2-yl)-N-(4-(trifluoromethoxy)phenyl)methanimine (ligand L2) with copper(I)-iodide showed high reactivity for all kind of alcohols (benzylic, allylic and aliphatic). In the case of benzyl alcohol even 2.5 mol% of copper loading gave quantitative yield. Beside high activity under aerobic conditions, the catalysts ability to oxidize 1,5-pentadiol to the corresponding lactol (86% in 4 h) and N-phenyldiethanolamine to the corresponding morpholine derivate lactol (86% in 24 h) is particularly noteworthy.

Chemoselective hydrogen peroxide oxidation of primary alcohols to aldehydes by a water-soluble and reusable iron(iii) catalyst in pure water at room temperature

Hydrogen peroxide oxidation of primary alcohols to aldehydes is described, which is catalyzed by a novel, reusable and water-soluble FeCl3 complex in situ-formed with quaternary ammonium salt-functionalized 8-aminoquinoline. This reaction exhibits unique chemoselectivity and broad functional-group tolerance, and it can operate efficiently in pure water at room temperature.

Evaluation of antiparasitic activity of mentha crispa essential oil, its major constituent rotundifolone and analogues against trypanosoma brucei

Considering the pressing need for new drugs to treat sleeping sickness and Nagana disease, Mentha crispa essential oil, its principal constituent rotundifolone, and four related p-menthane-Type monoterpenes (two stereoisomers of limonene epoxide, perillyl alcohol, and perillyl aldehyde) were investigated for their activity against bloodstream forms of Trypanosoma brucei. The general cytotoxicity of the compounds was determined with human myeloid HL-60 cells. The effect of the M. crispa essential oil and the monoterpenes on the growth of parasite and human cells was evaluated in cell cultures with the resazurin viability assay. Of all of the compounds tested, M. crispa essential oil, rotundifolone, and perillyl aldehyde showed the highest trypanocidal activities with 50% growth inhibition (GI50) and minimum inhibitory concentration values of 0.3 μg/ mL and 1 μg/mL, respectively. In contrast, HL-60 cells were considerably less sensitive to the compounds with minimum inhibitory concentration values of 100 μg/mL and GI50 values ranging between 3.4 to 13.8 μg/mL. As a consequence of this, GI50 and minimum inhibitory concentration ratios of cytotoxic to trypanocidal activity (selectivity index) of these three compounds were promising with values of 11-45 and 100, respectively. These results indicate that the p-menthane-Type monoterpenes rotundifolone and perillyl aldehyde are interesting lead candidates for further rational antitrypanosomal drug development.

Enzyme-inspired functional surfactant for aerobic oxidation of activated alcohols to aldehydes in water

We describe an enzyme-inspired catalytic system based on a rationally designed multifunctional amphiphile. The resulting micelles feature metal-binding sites and stable free radical moieties as well as fluorous pockets that attract and preconcentrate molecular oxygen. In the presence of copper ions, the micelles effect chemoselective aerobic alcohol oxidation under ambient conditions in water, a transformation that is challenging to achieve nonenzymatically.

Solar photochemical oxidations of benzylic and allylic alcohols using catalytic organo-oxidation with DDQ: Application to lignin models

Visible light has a dramatic effect on the oxidation of benzylic and allylic alcohols, including those deactivated by electron-withdrawing groups, and β-O-4 lignin models, using catalytic amounts of the organo-oxidant 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Sodium nitrite or tert-butyl nitrite is used as cocatalyst, and oxygen is employed as the terminal oxidant.

Solar photochemical oxidation of alcohols using catalytic hydroquinone and copper nanoparticles under oxygen: Oxidative cleavage of lignin models

Alcohols are converted into to their corresponding carbonyl compounds using catalytic amounts of 1,4-hydroquinone with a copper nanoparticle electron transfer mediator with oxygen as the terminal oxidant in acetone as solvent under visible light irradiation. These conditions employing biorenewable hydroquinone as reagent were developed from initial experiments using stoichiometric amounts of 1,4-benzoquinone as oxidant. A range of benzylic and aliphatic primary and secondary alcohols are oxidized, affording the corresponding aldehydes or ketones in moderate to excellent yields. The methodology is also applicable to the oxidative degradation of lignin model compounds that undergo C-C bond cleavage to give simple aromatic compounds.

α,β-Unsaturated imines via Ru-catalyzed coupling of allylic alcohols and amines

A convenient synthesis of α,β-unsaturated imines requiring only an allylic alcohol, an amine and a Ru catalyst has been developed. The use of large excesses of oxidant and the purification of sensitive intermediates can be avoided.

Selective aerobic oxidation of allylic and benzylic alcohols catalyzed by N-hydroxyindole and copper(I) chloride

In the presence of copper(I) chloride, tert-butyl 1-hydroxy-2-methyl-6- trifluoromethyl-1H-indole-3-carboxylate acted as a catalyst for the chemoselective aerobic oxidation of allylic and benzylic alcohols. A variety of primary and secondary allylic and benzylic alcohols were oxidized into the corresponding α,β-unsaturated carbonyl compounds in good yields without affecting non-allylic alcohols.