D(+)-Carvone

D(+)-Carvone Basic information
Product Name:D(+)-Carvone
Synonyms:D-6,8(9)-P-MENTHADIEN-2-ONE;d-1-methyl-4-isopropenyl-6-cyclohexen-2-one;D-p-Mentha-6,8,(9)-dien-2-one;(+)-CARVONE;CARVONE, (+)-;ALPHA(+)-CARVONE;D-CARVONE 96+%;(+)-CARVONE, TERPENE STANDARD
CAS:2244-16-8
MF:C10H14O
MW:150.22
EINECS:218-827-2
Product Categories:Biochemistry;Monocyclic Monoterpenes;Terpenes
Mol File:2244-16-8.mol
D(+)-Carvone Structure
D(+)-Carvone Chemical Properties
Melting point 88.9°C
alpha 57 º (c=neat)
Boiling point 96-98 °C/10 mmHg (lit.)
density 0.96 g/mL at 25 °C (lit.)
vapor pressure 20.665hPa at 25℃
FEMA 2249 | CARVONE
refractive index n20/D 1.499
Fp 204 °F
storage temp. Store below +30°C.
solubility 1300mg/l
form Liquid
color Clear colorless to pale yellow
Odorat 100.00 %. spice mint bread caraway
Odor Typeminty
optical activity[α]23/D +55.0±7°, neat
Water Solubility <0.1 g/100 mL at 25 ºC
JECFA Number380
Merck 14,1874
BRN 2042970
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong reducing agents.
LogP3.07 at 25℃
CAS DataBase Reference2244-16-8(CAS DataBase Reference)
NIST Chemistry Reference2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (S)-(2244-16-8)
EPA Substance Registry SystemD-Carvone (2244-16-8)
Safety Information
Hazard Codes Xi
Risk Statements 22
Safety Statements 24/25
RIDADR 2810
WGK Germany 1
RTECS OS8670000
8-9-23
Hazard Note Irritant
TSCA Yes
HazardClass 6.1(a)
PackingGroup II
HS Code 29142900
ToxicityLD50 oral in rat: 3710uL/kg
MSDS Information
ProviderLanguage
D-1-Methyl-4-isopropenyl-6-cyclohexen-2-oneEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
D(+)-Carvone Usage And Synthesis
Chemical PropertiesCaravone occurs in different forms. l-Carvone exhibits odor of spearmint, while d-carvone exhibits odor reminiscent of caraway.
Chemical PropertiesCarvone is a pale yellow to white clear liquid.
Chemical Propertiescolourless or pale yellow liquid
OccurrenceThe 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.
DefinitionChEBI: A carvone having (S) configuration.
Aroma threshold valuesDetection: d-Carvone: 6.7 to 820 ppb; l-carvone: 2.7 to 600 ppb
General DescriptionPale yellow or colorless liquid.
Air & Water ReactionsMay be sensitive to prolonged exposure to light and air. Insoluble in water.
Reactivity ProfileD(+)-Carvone may be sensitive to prolonged exposure to light and air. Incompatible with strong oxidizing agents and strong reducing agents
Fire HazardD(+)-Carvone is combustible.
Flammability and ExplosibilityNotclassified
Safety ProfilePoison by ingestion and skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
SynthesisCarvone 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 ExposureCarvone 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.
ShippingUN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
IncompatibilitiesIncompatible 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.
D(+)-Carvone Preparation Products And Raw materials
Raw materialsHydrogen Sulfide–>Dill Oil
Preparation Products(5R)-2-Methyl-5-(5-methyl-1-methylene-4-hexenyl)-2-cyclohexen-1-one

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