D(+)-Carvone

Description

The nose knows. (S)-(+)-carvone (shown here), a naturally occurring compound found in caraway seeds and mandarin orange peel oil, smells like caraway. Its mirror image, (R)-(–)-carvone, is extracted from spearmint and kuromoji oils and smells like spearmint. Gingergrass oil contains a mixture of both enantiomers.

Description

Carvone is a pale yellow to white clear liquid.Molecular weight=150.22; Boiling point=230℃; Flashpoint=93℃. Hazard Identification (based on NFPA 704 MRating System): Health 2, Flammability 2, Reactivity 0.

Chemical properties

D(+)-Carvone is a clear colorless or pale yellow liquid. Darkens upon exposure to air and daylight. Sp.Gr. 0.97. BP. 230℃. Insoluble in water, soluble in alcohol and oils. Warm-herbaceous, breadlike, spicy and slightly floral odor, reminiscent of Caraway seed or Dill seed. Warm, sweet, spicy - herbaceous, breadlike taste.

Chemical properties

Caravone occurs in different forms. l-Carvone exhibits odor of spearmint, while d-carvone exhibits odor reminiscent of caraway.

Occurrence

The optically active and inactive forms have been reported among the constituents of about 70 essential oils. The dextro form is present in carvi, Antheum graveolens, Antheum sowa, Lippia carviodora, Mentha arvensis, etc. The levo form is present in Metha vifidis var. crispa, Mentha longifolia from South Africa, Eucalyptus globules and several mint species. The racemic form is present in ginger grass, Litsea gutalemaleusis, lavender and Artemisia ferganensis. Reported found in citrus oil and juice (lemon, lime, orange), celery seed, anise, clove, coriander seed, calamus, caraway herb and dill seed.

The Uses of D(+)-Carvone

(S)-(+)-Carvone can be used as a starting material to synthesize:

• (-)-Samaderine Y, a pentacyclic quassinoid.
• (-)-Ambrox, a terpenoid responsible for the odor of ambergris.
• 3β-Acetoxydrimenin (a sesquiterpene) via conjugated addition of potassium cyanide followed by base catalyzed Robinson annulation reaction.
• Thapsigargin family members such as trilobolide, nortrilobolide, and thapsivillosin F.

The Uses of D(+)-Carvone

D(+)-Carvone is occasionally used in perfumes, but the lacvo-Carvone is often preferred here. It is used in flavor compositions as a fortifier for Caraway seed oil or Dill oil seed (in which oils this ketone is a major component). Since this isomer is rarely offered in the synthetic form, it has not become as popular as the laevo-Carvone. The use of Caraway-Dill flavor is confined to a few, although by volume very large, commercial products (Bread, Pickles. Spices, etc.).

What are the applications of Application

(+)-Carvone is a terpene standard for gas chromatography

Definition

ChEBI: A carvone having (S) configuration.

Aroma threshold values

Detection: d-Carvone: 6.7 to 820 ppb; l-carvone: 2.7 to 600 ppb

General Description

Pale yellow or colorless liquid.

Air & Water Reactions

May be sensitive to prolonged exposure to light and air. Insoluble in water.

Reactivity Profile

D(+)-Carvone may be sensitive to prolonged exposure to light and air. Incompatible with strong oxidizing agents and strong reducing agents

Fire Hazard

D(+)-Carvone is combustible.

Flammability and Explosibility

Not classified

Safety Profile

Poison by ingestion and skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

Carvone occurs in the dextro, levo and racemic form; l-carvone can be isolated from the essential oil of spearmint or is commercially synthesized from d-limonene; d-carvone is usually prepared by fractional distillation of oil of caraway, also from dillseed and dillweed oils, but this type differs in odor and flavors.

Potential Exposure

Carvone is found in various natural oils, including caraway and dillseed; mandarin peel and spearmint oils. A food additive, it is used in flavoring liqueurs; in perfumes and soaps.

First aid

Skin Contact: Flood all areas of body that have contacted the substance with water. Do not wait to remove contaminated clothing; do it under the water stream. Use soap tohelp assure removal. Isolate contaminated clothing whenremoved to prevent contact by others. Eye Contact: Removeany contact lenses at once. Flush eyes well with copious quantities of water or normal saline for at least 20-30 min. Seekmedical attention. Inhalation: Leave contaminated area immediately; breathe fresh air. Proper respiratory protection must besupplied to all rescuers. If coughing, difficult breathing, or anyother symptoms develop, seek medical attention at once, evenif symptoms develop many hours after exposure. Ingestion: Ifconvulsions are not present, give a glass or two of water ormilk to dilute the substance. Assure that the person’s airway isunobstructed and contact a hospital or poison center immediately for advice on whether or not to induce vomiting.

storage

Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Store in a cool, dry place or in a refrigerator

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.