EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

carvone
DL-carvone

Sponsors

Name:2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
CAS Number: 99-49-0Picture of molecule3D/inchi
Other:22327-39-5
ECHA EINECS - REACH Pre-Reg:202-759-5
FDA UNII:75GK9XIA8I
Nikkaji Web:J4.522E
Beilstein Number:1364206
CoE Number:146
XlogP3-AA:2.40 (est)
Molecular Weight:150.22078000
Formula:C10 H14 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:2245 carvone
FLAVIS Number:07.012 (Old)
DG SANTE Food Flavourings:07.012 carvone
FEMA Number:2249 carvone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: CARVONE
FDA Regulation:
FDA PART 182 -- SUBSTANCES GENERALLY RECOGNIZED AS SAFE
Subpart A--General Provisions
Sec. 182.60 Synthetic flavoring substances and adjuvants.
 
Physical Properties:
Appearance:colorless to pale yellow clear liquid (est)
Assay: 97.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 231.00 °C. @ 760.00 mm Hg
Boiling Point: 137.00 to 138.00 °C. @ 50.00 mm Hg
Vapor Pressure:0.160000 mm/Hg @ 25.00 °C.
Flash Point: 192.00 °F. TCC ( 88.89 °C. )
logP (o/w): 3.070
Soluble in:
 alcohol
 water, 1300 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor Type: minty
Odor Strength:medium
minty licorice
Odor Description:at 100.00 %. minty licorice
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: masking agents
 
Suppliers:
Aromiens International
Carvone
Axxence Aromatic
D-CARVONE Natural
Sustainability
BOC Sciences
For experimental / research use only.
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one
Indenta Group
Carvone
Jiangyin Healthway
Carvone
New functional food ingredients
Lluch Essence
laevo-CARVONE NATURAL
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 1640 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

oral-guinea pig LD50 766 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

Dermal Toxicity:
subcutaneous-mouse LD50 2675 mg/kg
BEHAVIORAL: ANTICONVULSANT BEHAVIORAL: SLEEP
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 46, Pg. 77, 1957.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor and fragrance agents
IFRA Critical Effect: Sensitization
IFRA: View Standard
Fragrance usage is IFRA RESTRICTED. View Standard for complete information.
Please review all IFRA documents for complete information.
IFRA categories: limits in the finished product: (For a description of the categories, refer to the IFRA QRA Information Booklet.)
Category 1:
See Note (1)
0.08 % (1)
Category 2:  0.10 %
Category 3:  0.40 %
Category 4:  1.20 %
Category 5:  0.60 %
Category 6:  1.90 % (1)
Category 7:  0.20 %
Category 8:  2.00 %
Category 9:  5.00 %
Category 10:  2.50 %
Category 11: See Note (2)
 Notes:
 

(1) IFRA would recommend that any material used to impart perfume or flavour in products intended for human ingestion should consist of ingredients that are in compliance with appropriate regulations for foods and food flavourings in the countries of planned distribution and, where these are lacking, with the recommendations laid down in the Code of Practice of IOFI (International Organisation of the Flavor Industry). Further information about IOFI can be found on its website (www.iofi.org).

 

(2) Category 11 includes all non-skin contact or incidental skin contact products. Due to the negligible skin contact from these types of products there is no justification for a restriction of the concentration of this fragrance ingredient in the finished product.

 
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3. Update in publication number(s): 26
 average usual ppmaverage maximum ppm
baked goods: 94.00000116.00000
beverages(nonalcoholic): 34.00000850.00000
beverages(alcoholic): 126.00000145.00000
breakfast cereal: --
cheese: 0.200000.20000
chewing gum: 10000.0000020000.00000
condiments / relishes: 50.0000060.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 150.00000197.00000
fruit ices: --
gelatins / puddings: 87.0000090.00000
granulated sugar: --
gravies: --
hard candy: 5000.0000010000.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 0.100000.10000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 5000.0000010000.00000
soups: --
sugar substitutes: --
sweet sauces: --
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Scientific Opinion on the safety assessment of carvone, considering all sources of exposure
View page or View pdf

Peer review of the pesticide risk assessment of the active substance carvone (substance evaluated d-carvone)
View page or View pdf

EPI System: View
NLM Hazardous Substances Data Bank:Search
Cancer Citations:Search
Toxicology Citations:Search
Env. Mutagen Info. Center:Search
EPA Substance Registry Services (TSCA):99-49-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7439
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
Chemidplus:0000099490
 
References:
Leffingwell:Chirality or Article
 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:99-49-0
Pubchem (cid):7439
Pubchem (sid):134971746
Flavornet:99-49-0
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB35824
FooDB:FDB014614
Haz-Map:View
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
Formulations/Preparations:
•assay: 97% min (as ketone content) l-form; 95% min d-form •grades: fcc (both d- & l-forms); technical d- & l-form •the proportion of carvone in herb oil has been reported to vary from 6 to 44%, depending on the geographical origin while the amount of carvone in the oil of dill seeds is more constant, 40-55% •the main constituentof caraway oilis d-carvone (60-70%) •the main constituentof spearmint oilis 1-carvone (ca 50-70%)
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 agathosma crenulata oil @ 0.22%
Data GC Search Trop Picture
 ajowan seed oil turkey @ trace%
Data GC Search Trop Picture
 anise seed oil
Search Trop Picture
 anise star anise fruit
Search Trop Picture
 basil plant
Search Trop Picture
 basil shoot oil
Search Trop Picture
 bay laurel leaf
Search Trop Picture
 bergamot oil @ 0.000-trace%
Data GC Search Trop Picture
 bergamot oil @ 0.09%
Data GC Search Trop Picture
 buchu leaf oil @ trace%
Data GC Search Trop Picture
 cabbage leaf
Search Trop Picture
 caraway oil
Search Trop Picture
 caraway plant
Search Trop Picture
 caraway seed
Search Trop Picture
 caraway seed oil
Search Trop Picture
 caraway seed oil @ 52.30-54.40%
Data GC Search Trop Picture
 cardamom fruit oil
Search Trop Picture
 carrot seed
Search Trop Picture
 carrot weed oil @ 8.77%
Data GC Search Trop Picture
 cascarilla bark oil @ 0.03%
Data GC Search Trop Picture
 cayenne fruit
Search Trop Picture
 celery leaf
Search Trop Picture
 celery seed
Search Trop Picture
 celery seed oil
Search Trop Picture
 celery seed oil CO2 extract india @ 0.02%
Data GC Search Trop Picture
 celery seed oil egypt @ 0.40%
Data GC Search Trop Picture
 celery seed oil india @ 0.06%
Data GC Search Trop Picture
 celery shoot
Search Trop Picture
 cistus oil @ 0.5%
Data GC Search Trop Picture
 clove plant
Search Trop Picture
 coriander fruit
Search Trop Picture
 cornmint leaf
Search Trop Picture
 cornmint oil india @ 0.05%
Data GC Search Trop Picture
 costmary oil @ 51.51%
Data GC Search Trop Picture
 cubeb oil @ trace%
Data GC Search Trop Picture
 cypress cone oil egypt @ trace%
Data GC Search Trop Picture
 dill leaf
Search Trop Picture
 dill leaf oil
Search Trop Picture
 dill oil
Search Trop Picture
 dill root
Search Trop Picture
 dill seed
Search Trop Picture
 dill seed oil
Search Trop Picture
 dill shoot oil
Search Trop Picture
 dill weed oil cuba @ 14.50%
Data GC Search Trop Picture
 dill weed oil reunion @ 0.40%
Data GC Search Trop Picture
 eucalyptus globulus bicostata oil @ 0.16%
Data GC Search Trop Picture
 eucalyptus globulus maidenii f. muell oil @ 0.15%
Data GC Search Trop Picture
 eucalyptus globulus pseudoglobulus oil @ 0.31%
Data GC Search Trop Picture
 fennel seed oil
Search Trop Picture
 fleabane oil @ 1.10%
Data GC Search Trop Picture
 gingergrass oil @ 3.20%
Data GC Search Trop Picture
 helichrysum arenarium (l.) moench oil hungary @ 1.10%
Data GC Search Trop Picture
 horsemint shoot
Search Trop Picture
 kewda oil @ trace%
Data GC Search Trop Picture
 labdanum leaf oil @ 0.30%
Data GC Search Trop Picture
 labdanum oil @ 0.31%
Data GC Search Trop Picture
 laurel leaf oil turkey @ 0.10%
Data GC Search Trop Picture
 lavandin oil china @ 0.12%
Data GC Search Trop Picture
 lavandin oil grosso @ trace%
Data GC Search Trop Picture
 lemon oil
Search Trop Picture
 lemon verbena oil morocco @ 0.8%
Data GC Search Trop Picture
 lemon verbena oil turkey @ 0.50%
Data GC Search Trop Picture
 levisticum officinale flower oil @ 0.27%
Data GC Search Trop Picture
 levisticum officinale seed oil @ 0.10%
Data GC Search Trop Picture
 lime oil distilled mexico @ 0.01%
Data GC Search Trop Picture
 lime oil distilled peru @ trace%
Data GC Search Trop Picture
 lovage root
Search Trop Picture
 mandarin fruit
Search Trop Picture
 mandarin oil @ 0.20%
Data GC Search Trop Picture
 mandarin oil uruguay @ 0.02-0.07%
Data GC Search Trop Picture
 marjoram oil
Search Trop Picture
 marjoram oil sweet cyprus @ 0.00-0.70%
Data GC Search Trop Picture
 marjoram oil sweet turkey @ 0.15-0.17%
Data GC Search Trop Picture
 marjoram plant
Search Trop Picture
 mastic fruit oil @ 1.32%
Data GC Search Trop Picture
 mikan peel oil @ trace%
Data GC Search Trop Picture
 myrtle oil @ 0.08%
Data GC Search Trop Picture
 nepeta denudata benth. oil iran @ 0.40%
Data GC Search Trop Picture
 orange fruit
Search Trop Picture
 orange peel oil bitter china @ 0.03%
Data GC Search Trop Picture
 oregano plant
Search Trop Picture
 oregano plant
Search Trop Picture
 oregano shoot
Search Trop Picture
 osmanthus absolute @ trace%
Data GC Search Trop Picture
 pennyroyal oil uruguay @ 0.20-2.20%
Data GC Search Trop Picture
 pepper black pepper fruit
Search Trop Picture
 pepper black pepper fruit oil
Search Trop Picture
 peppermint leaf
Search Trop Picture
 peppermint oil mongolia @ 0.16%
Data GC Search Trop Picture
 pimenta leaf oil @ 0.10%
Data GC Search Trop Picture
 plum fruit
Search Trop Picture
 rosemary leaf
Search Trop Picture
 rosemary oil CO2 extract @ 0.26%
Data GC Search Trop Picture
 rosemary oil egypt @ 1.67%
Data GC Search Trop Picture
 rosemary plant
Search Trop Picture
 rugula herb
Search Trop Picture
 sage oil cuba @ 0.21%
Data GC Search Trop Picture
 sage oil spain @ 0.0-0.3%
Data GC Search Trop Picture
 salvia officinalis oil cuba @ 0.21%
Data GC Search Trop Picture
 savory winter savory plant
Search Trop Picture
 spearmint oil america @ 65.79-71.62%
Data GC Search Trop Picture
 spearmint plant
Search Trop Picture
 tansy flower oil canada @ 0.84%
Data GC Search Trop Picture
 tansy oil canada @ 6.60%
Data GC Search Trop Picture
 tansy oil marocco @ 0.30%
Data GC Search Trop Picture
 tarragon plant
Search Trop Picture
 thyme absolute @ trace%
Data GC Search Trop Picture
 thyme plant
Search Trop Picture
 thymus richardii pers. subsp. nitidus (guss.) jalas oil italy @ 0.70%
Data GC Search Trop Picture
 trachyspermum roxburghianum benth. ex. kurz. seed oil india @ trace%
Data GC Search Trop Picture
 tsauri grass oil @ 4.10%
Data GC Search Trop Picture
 turmeric root oil CO2 extract @ 2.12%
Data GC Search Trop Picture
 water mint leaf
Search Trop Picture
 wormseed oil america @ 2.28%
Data GC Search Trop Picture
 wormseed oil spain @ 0.2%
Data GC Search Trop Picture
 wormseed oil spain @ 2.07%
Data GC Search Trop Picture
 wormwood oil italy @ trace%
Data GC Search Trop Picture
 yarrow leaf oil @ trace%
Data GC Search Trop Picture
 yuzu peel oil c.p. @ 0.01-0.02%
Data GC Search Trop Picture
 yuzu peel oil CO2 extract @ 0.01%
Data GC Search Trop Picture
 zingiber officinale root oil china @ 0.26%
Data GC Search Trop Picture
 
Synonyms:
DL-carvone
D-carvone natural
2-cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-
delta-p-mentha-1(6),8-dien-2-one
delta-para-mentha-1(6),8-dien-2-one
p-mentha-6,8-dien-2-one
para-mentha-6,8-dien-2-one
6,8(9)-p-menthadien-2-one
delta-1-methyl-4-isopropenyl-6-cyclohexen-2-one
2-methyl-5-(1-methyl ethenyl)-2-cyclohexen-1-one
2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
2-methyl-5-isopropenyl-2-cyclohexenone
2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
5-isopropenyl-2-methyl-2-cyclohexen-1-one
delta(sup 6,8)-(9)-terpadienone-2
 

Articles:

PubMed:Transfer of terpenes from essential oils into cow milk.
PubMed:(-)-Carvone: antispasmodic effect and mode of action.
PubMed:Chemical composition and biological activities of Calamintha officinalis Moench essential oil.
PubMed:Allergic contact dermatitis from carvone in hair conditioners.
PubMed:Chitosan coating improves retention and redispersibility of freeze-dried flavor oil emulsions.
PubMed:Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
PubMed:Enhanced bioproduction of carvone in a two-liquid-phase partitioning bioreactor with a highly hydrophobic biocatalyst.
PubMed:Chemical and physical stability of protein and gum arabic-stabilized oil-in-water emulsions containing limonene.
PubMed:Inhibitory effects of substrate and product on the carvone biotransformation activity of Rhodococcus erythropolis.
PubMed:Chemical and physical stability of citral and limonene in sodium dodecyl sulfate-chitosan and gum arabic-stabilized oil-in-water emulsions.
PubMed:Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: a comparative study.
PubMed:Character impact odorants of fennel fruits and fennel tea.
PubMed:Changes of the volatile profile and artifact formation in Daidai (Citrus aurantium) cold-pressed peel oil on storage.
PubMed:Influence of drying on the flavor quality of spearmint (Mentha spicata L.).
PubMed:Biotransformation of D-limonene to (+) trans-carveol by toluene-grown Rhodococcus opacus PWD4 cells.
PubMed:Volatile flavor components of ripe and overripe ki-mikans (Citrus flaviculpus Hort. ex Tanaka) in comparison with Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
PubMed:Cinnamaldehyde content in foods determined by gas chromatography-mass spectrometry.
PubMed:Aroma-active compounds of miniature beefsteakplant (Mosla dianthera Maxim).
PubMed:Applications of High-Temperature Aqueous Media for Synthetic Organic Reactions.
PubMed:Variation in odor thresholds for l-carvone and cineole and correlations with suprathreshold intensity ratings.
PubMed:Conductive olfactory losses in chronic rhinosinusitis? A computational fluid dynamics study of 29 patients.
PubMed:Perceptual and processing differences between physical and dichorhinic odor mixtures.
PubMed:Rapid odor perception in rat olfactory bulb by microelectrode array.
PubMed:Stress-related activities induced by predator odor may become indistinguishable by hinokitiol odor.
PubMed:(-)-Carvone: antispasmodic effect and mode of action.
PubMed:Olfactory discrimination ability of South African fur seals (Arctocephalus pusillus) for enantiomers.
PubMed:Odor detection and odor discrimination in subadult and adult rats for two enantiomeric odorants supported by c-fos data.
PubMed:[Characterization of aroma active compounds in blood orange juice by solid phase microextraction and gas chromatography-mass spectrometry-olfactometry].
PubMed:Performance of mice in discrimination of liquor odors: behavioral evidence for olfactory attention.
PubMed:Response accuracy and odor sampling time in mice trained to discriminate between enantiomers of carvone and those of terpinen-4-ol.
PubMed:Character impact odorants of fennel fruits and fennel tea.
PubMed:The number of functional olfactory receptor genes and the relative size of olfactory brain structures are poor predictors of olfactory discrimination performance with enantiomers.
PubMed:Composition and aroma compounds of Ragusano cheese: native pasture and total mixed rations.
PubMed:Olfactory discrimination ability of human subjects for enantiomers with an isopropenyl group at the chiral center.
PubMed:OMP gene deletion results in an alteration in odorant-induced mucosal activity patterns.
PubMed:Olfactory discrimination of short chain fatty acids in rats with large bilateral lesions of the olfactory bulbs.
PubMed:Influence of drying on the flavor quality of spearmint (Mentha spicata L.).
PubMed:Sensitivity-dependent hierarchical receptor codes for odors.
PubMed:Concanavalin A application to the olfactory epithelium reveals different sensory neuron populations for the odour pair D- and L-carvone.
PubMed:Spontaneous versus reinforced olfactory discriminations.
PubMed:A psychophysical study of the relationship between temporal processing in odor mixtures and transduction pathways.
PubMed:Enantioselectivity of odor perception in honeybees (Apis mellifera carnica).
PubMed:Effects of chiral fragrances on human autonomic nervous system parameters and self-evaluation.
PubMed:Relationships between odor-elicited oscillations in the salamander olfactory epithelium and olfactory bulb.
PubMed:Enantioselectivity of odor perception in squirrel monkeys and humans.
PubMed:Olfactory discrimination ability of human subjects for ten pairs of enantiomers.
PubMed:Temporal processing of odor mixtures reveals that identification of components takes precedence over temporal information in olfactory memory.
PubMed:Identification of ligands for olfactory receptors by functional expression of a receptor library.
PubMed:Spatially organized response zones in rat olfactory epithelium.
PubMed:Ca2+ and Cl(-)-dependence of the turtle olfactory response to odorants and forskolin.
PubMed:Variation in odor thresholds for l-carvone and cineole and correlations with suprathreshold intensity ratings.
PubMed:Temperature increase abolishes ability of turtle olfactory receptors to discriminate similar odorant.
PubMed:A mass transport model of olfaction.
PubMed:Differential olfactory perception of enantiomeric compounds by blind subterranean mole rats (Spalax ehrenbergi).
PubMed:Quantitative analysis on odor intensity and quality of optical isomers in turtle olfactory system.
PubMed:Olfactory bulb size, odor discrimination and magnetic insensitivity in hummingbirds.
PubMed:Odor masking in the rat.
PubMed:Sensory evidence for olfactory receptors with opposite chiral selectivity.
PubMed:Quality and intensity of binary odor mixtures.
PubMed:Odor incongruity and chirality.
PubMed:Odor differences between enantiomeric isomers.
PubMed:Study of chemical stability of lemon oil components in sodium caseinate-lactose glycoconjugate-stabilized oil-in-water emulsions using solid-phase microextraction-gas chromatography.
 
Notes:
an oxidized derivative of limonene; l-carvone has spearmint flavor, d-carvone has dill/caraway flavor. Flavouring ingredient
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