Perillyl alcohol

Perillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. Perillyl alcohol is active in inducing apoptosis in tumor cells without affecting normal cells[1].

Solid|Colourless to pale-yellow, dense, oily liquid; characteristic odour similar to linalool and terpineol

Perillyl alcohol is a limonene monoterpenoid consists of a cyclohexene ring substituted by a hydroxymethyl and a prop-1-en-2-yl group at positions 1 and 4 respectively. It is a constituent of a variety of essential oils including lavender. It has a role as a plant metabolite and a volatile oil component.

Hydrogenation Reaction of Perillaldehyde (S/C=500)Into a stainless steel autoclave equipped with a glass inner tube, [Cu(NO(Example 13) Hydrogenation Reaction of Perillaldehyde (S/C=500) Into a stainless steel autoclave equipped with a glass inner tube, [Cu(NOGeneral procedure: Degassed CH2Cl2 (0.25 mL) was added to a microwave tube containing the ligand dppf (8.3 mg, 0.015 mmol) and AgPF6 (2.5 mg, 0.01 mmol) under argon. The resulting suspension was stirred at r.t., until a clear, colorless solution was obtained; then the solvent was removed under high vacuum. Benzaldehyde (1a; 20.3 μL, 0.2 mmol), tripropylsilane (2a;125 μL, 0.6 mmol), DIPEA (6.9 μL, 0.04 mmol), and H2O(0.5 mL) were subsequently added. The reaction mixture was stirred for 24 h at 100 °C, then cooled to r.t. and extracted with CH2Cl2 (3 × 10 mL). The combined organicphase was concentrated and purified by flash column chromatography on silica gel (hexane–EtOAc, 20:1) to give the desired product 3a as a colorless oil (19.5 mg, 90percent).Example 13Hydrogenation Reaction of Perillaldehyde (S/C=500)Into a stainless steel autoclave equipped with a glass inner tube, [Cu(NO(Example 13) Hydrogenation Reaction of Perillaldehyde (S/C=500) Into a stainless steel autoclave equipped with a glass inner tube, [Cu(NOGeneral procedure: Degassed CH2Cl2 (0.25 mL) was added to a microwave tube containing the ligand dppf (8.3 mg, 0.015 mmol) and AgPF6 (2.5 mg, 0.01 mmol) under argon. The resulting suspension was stirred at r.t., until a clear, colorless solution was obtained; then the solvent was removed under high vacuum. Benzaldehyde (1a; 20.3 μL, 0.2 mmol), tripropylsilane (2a;125 μL, 0.6 mmol), DIPEA (6.9 μL, 0.04 mmol), and H2O(0.5 mL) were subsequently added. The reaction mixture was stirred for 24 h at 100 °C, then cooled to r.t. and extracted with CH2Cl2 (3 × 10 mL). The combined organicphase was concentrated and purified by flash column chromatography on silica gel (hexane–EtOAc, 20:1) to give the desired product 3a as a colorless oil (19.5 mg, 90percent).

antineoplastic, apoptosis inducer; skin irritant, LD50(rat) 2100 mg/kg po

Molecular Weight:152.23
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:152.120115130
Monoisotopic Mass:152.120115130
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:179
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes