Myrcene

Description

Myrcene has a pleasant odor. Prepared from linalool.

Description

β-Myrcene is a terpene that has been found in Cannabis and has antioxidative properties. It reduces thiobarbituric acid reactive substance (TBARS) and increases glutathione (GSH), catalase, GSH peroxidase, and CuZn superoxide dismutase levels in a rat model of persistent environmental pollutant-induced oxidative stress when administered at a dose of 200 mg/kg per day.

Chemical properties

colourless viscous liquid

Chemical properties

Myrcene has a pleasant, sweet, balsamic, plastic odor.

Occurrence

Reported found in Mircia acris D.C.; in the distillates from leaves of Rhus cotinus and Barosma venustum (52 and 43%, respectively); in lemongrass, cypress, artemisia; in the fruits of Phellodendron amurense (92%) and Phellodendron japonicum; in the oils of Picea balsamea, Tsuga canadenis, Abies balsamea, clary sage and others. Also reported in over 200 foods and beverages including citrus peel oils and juices, apricot, sweet and sour cherry, berries, guava, pineapple, carrot, celery, potato, bell pepper, black currants, anise, anise seed, cardamom, cinnamon, cassia, clove, capsicum varities, ginger, mentha oils, mace, parsley, thyme, cheeses, cream, pork, hop oil, beer, white wine, rum, cocoa, coffee, tea, mango, tamarind, coriander, gin, sweet bay, prickly pear, calamus, dill, lovage, caraway, buckwheat, corn, basil, fennel, kiwifruit, rosemary, myrtle berry, turmeric, lemon balm, sage, pimento, angelica oil, Roman and German chamomile oil, eucalyptus and mastic gum oil

The Uses of Myrcene

Myrcene is the suitable synthetic standard used in the identification of E-myrcenol (2-methyl-6-methylene-E-2,7-octadien-1-01) as a major hindgut constituent in Eurasian bark beetle Ips duplicatus by GC-MS.

The Uses of Myrcene

Found in oil of bay, verbena, hop, etc. Used as an intermediate in the manufacturing of perfume chemicals.

What are the applications of Application

β-Myrcene is an intermediate in the manufacturing of perfume chemicals

Definition

ChEBI: A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.

Preparation

From linalool

Aroma threshold values

Aroma characteristics at 10%: terpy, herbaceous, woody with a rosy celery and carrot nuance

Taste threshold values

Taste characteristics at 5 to 100 ppm: woody, vegetative, citrus fruity with a tropical mango and slight, leafy, minty nuance

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 3252, 1975 DOI: 10.1021/ja00844a073
The Journal of Organic Chemistry, 47, p. 4161, 1982 DOI: 10.1021/jo00142a031
Tetrahedron Letters, 25, p. 5193, 1984 DOI: 10.1016/S0040-4039(01)81561-6

General Description

A yellow oily liquid with a pleasant odor. Flash point below 200°F. Insoluble in water and less dense than water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

The unsaturated aliphatic hydrocarbons, such as MYRCENE, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions. Many of these compounds undergo autoxidation upon exposure to the air to form explosive peroxides. Violent explosions have occurred at low temperatures in ammonia synthesis gas units. These explosions have been traced to the addition products of dienes and oxides of nitrogen, produced from the interaction of nitrogen oxide and oxygen [Bretherick, 1995].

Health Hazard

May be harmful by inhalation, ingestion or skin absorption.

Fire Hazard

Special Hazards of Combustion Products: Vapor may travel considerable distance to a source of ignition and flashback.

Biochem/physiol Actions

Odor at 1%

Safety Profile

Low toxicity by ingestion and skin contact. Experimental reproductive effects. A moderate skin and eye irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Myrcene occurs naturally in many organisms, but its extraction is uneconomic; it is produced industrially by pyrolysis of b-pinene. The fragmentation of linalool and linalyl acetate and the catalytic dimerization of isoprene have been described as laboratory synthesis methods of myrcene.