DIHYDRO CUMINYL ALCOHOL Chemical Properties

Melting point:

271-272 °C

Boiling point:

119-121 °C11 mm Hg(lit.)

Density 

0.96 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.501(lit.)

FEMA 

2664 | P-MENTHA-1,8-DIEN-7-OL

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Very slightly soluble in water, soluble in alcohol and oils

form 

Liquid

pka

14.85±0.10(Predicted)

color 

Colorless to light yellow

Odor

at 100.00 %. green cumin spicy aromatic woody cardamom floral waxy violet

Odor Type

green

JECFA Number

974

LogP

3.170

CAS DataBase Reference

536-59-4

EPA Substance Registry System

1-Cyclohexene-1-methanol, 4-(1-methylethenyl)- (536-59-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41-36/37/38

Safety Statements 

26-39-36

WGK Germany 

3

RTECS 

OS8395000

HS Code 

29061990

Toxicity

LD50 orl-rat: 2100 mg/kg FCTXAV 19,253,81

DIHYDRO CUMINYL ALCOHOL Usage And Synthesis

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

p-Mentha-1,8-dien-7-ol has a characteristic odor similar to linalool and terpineol.

Chemical Properties

clear colorless to light yellow liquid

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

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.

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.

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

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