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