Description
p-Mentha-1,8-dien-7-ol has a characteristic odor similar to linalool
and terpineol. The L-form is obtained starting from (3-pinene or by
reducing perillic aldehyde with zinc dust and acetic acid, followed
by saponification of the acetate.
Chemical Properties
clear colorless to light yellow liquid
Chemical Properties
p-Mentha-1,8-dien-7-ol has a characteristic odor similar to linalool and terpineol.
Occurrence
The d- and l-forms occur naturally in gingergrass essential oil; the l-form is found in lavandin and bergamot,
while the d-form is found in caraway; also reported found in the essential oils of Juniperus sabina L. and East Indian geranium. Also
reported found in citrus peel oils, berries, peppermint oil, Scotch peppermint oil, hop oil, cardamom, laurel, lemon balm, lamb’s let tuce, mastic gum oil and bullock’s head (Annona reticulata).
Uses
(4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol is used in preparation of perilla alcohol leaf alcohol carbonate as perfume.
Uses
antineoplastic, apoptosis inducer; skin irritant, LD50(rat) 2100 mg/kg po
Preparation
The l-form is obtained starting from β-pinene or by reducing perillic aldehyde with zinc dust and acetic acid, followed
by saponification of the acetate.
Definition
ChEBI: 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.
Aroma threshold values
Detection: 7 ppm
Safety Profile
Moderately toxic by ingestion. A severe skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
Synthesis
GENERAL STEPS: Example 13: The hydrogenation reaction for the synthesis of (4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol from 4-(prop-1-en-2-yl)cyclohex-1-enecyclohexene carboxaldehyde was carried out in a stainless steel autoclave equipped with a glass inner tube. The autoclave was pre-charged with [Cu(NO3)(PPh3)2] (11.7 mg, 0.018 mmol) and DPPB (7.7 mg, 0.018 mmol). Subsequently, the atmosphere inside the autoclave was replaced with nitrogen. An ethanol solution of sodium hydroxide (0.03 M, 6.0 mL, 0.18 mmol) and 4-(prop-1-en-2-yl)cyclohex-1-enecarboxaldehyde (2.02 mL, 9 mmol) was added to the autoclave. The reaction was stirred at hydrogen pressure of 5 MPa and 50 °C for 16 hours. Upon completion of the reaction, hydrogen was carefully released and the reaction conversion (>99%) was analyzed by gas chromatography (GC). The reaction mixture was concentrated and purified by silica gel column chromatography to give 1.26 g of the target product (4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanol.
References
[1] Tetrahedron Letters, 1993, vol. 34, # 2, p. 257 - 260
[2] Chemistry - A European Journal, 2017, vol. 23, # 35, p. 8473 - 8481
[3] Synlett, 2009, # 8, p. 1295 - 1298
[4] Patent: US2011/201819, 2011, A1. Location in patent: Page/Page column 10
[5] Patent: EP2377841, 2011, A1. Location in patent: Page/Page column 13-14
