CARVONE, (-)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H14O
Molecular Weight	150.2176
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=C)[C@@H]1CC=C(C)C(=O)C1

InChI

InChIKey=ULDHMXUKGWMISQ-SECBINFHSA-N

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C10H14O
Molecular Weight	150.2176
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.hmdb.ca/metabolites/HMDB0035089 | https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=6ac755f6-f615-6c44-e053-2991aa0ade6c&type=display

CARVONE, (-)-, a volatile terpenoid, is found mostly in the seeds of caraway (Carum carvi) and spearmint (Mentha crispa) leaves. It is a constituent of costmary, kuromoji, and other oils. CARVONE, (-)- is a flavoring ingredient. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Franz Varrentrapp obtained it in 1841.

Approval Year

PubMed

Title	Date	PubMed
Insecticidal activity of essential oil of Carum Carvi fruits from China and its main components against two grain storage insects.	2010-12-20	21173724
Anti-inflammatory activity of hydroxydihydrocarvone.	2010-12-09	21138054
Acaricidal and quantitative structure activity relationship of monoterpenes against the two-spotted spider mite, Tetranychus urticae.	2010-11	20431924
Distinct effects of carvone analogues on the isolated nerve of rats.	2010-10-25	20670618
Mint essential oil can induce or inhibit potato sprouting by differential alteration of apical meristem.	2010-06	20390295
Chitosan coating improves retention and redispersibility of freeze-dried flavor oil emulsions.	2010-02-24	20099885
Total synthesis of (+)-chinensiolide B via tandem allylboration/lactonization.	2010-02-10	20067261
Disruption of Adult Neurogenesis in the Olfactory Bulb Affects Social Interaction but not Maternal Behavior.	2010	21160552
Bioassay-guided evaluation of antinociceptive effect of N-salicyloyltryptamine: a behavioral and electrophysiological approach.	2010	20976310
Enhanced biotransformation of TCE using plant terpenoids in contaminated groundwater.	2009-12	19843209
Regioselective biooxidation of (+)-valencene by recombinant E. coli expressing CYP109B1 from Bacillus subtilis in a two-liquid-phase system.	2009-07-10	19591681
Fumigant and contact toxicities of monoterpenes to Sitophilus oryzae (L.) and Tribolium castaneum (Herbst) and their inhibitory effects on acetylcholinesterase activity.	2009-05	19412756
Syntheses of bioactive bisabolane-type Cryptomeria japonica sesquiterpenes.	2009-03-23	19270377
Structure and spasmolytic activity relationships of monoterpene analogues found in many aromatic plants.	2009-02-21	19227827
Use of human senses as sensors.	2009	22412305
Spearmint plantlet culture system as a means to study secondary metabolism.	2009	19521855
Improved reactor performance and operability in the biotransformation of carveol to carvone using a solid-liquid two-phase partitioning bioreactor.	2008-12-01	18546419
Microbial transformation of (-)-carvone.	2008-11-13	18998407
Enhanced bioproduction of carvone in a two-liquid-phase partitioning bioreactor with a highly hydrophobic biocatalyst.	2008-11-01	18478563
Reproducibility of a microbial river water community to self-organize upon perturbation with the natural chemical enantiomers, R- and S-carvone.	2008-11	18680487
Activity of essential oils and individual components against acetyl- and butyrylcholinesterase.	2008-09-25	18810999
An improved asymmetric synthesis of malyngamide U and its 2'-epimer.	2008-09-05	18656980
[Characterization of aroma active compounds in blood orange juice by solid phase microextraction and gas chromatography-mass spectrometry-olfactometry].	2008-07	18959252
Inhibitory effects of substrate and product on the carvone biotransformation activity of Rhodococcus erythropolis.	2008-07	18327538
Stereocontrolled synthesis of the sterically encumbered F ring of lancifodilactone G.	2008-06-05	18454538
Antinociceptive activity of (-)-carvone: evidence of association with decreased peripheral nerve excitability.	2008-05	18451538
Antinociceptive effect of hydroxydihydrocarvone.	2008-04	18379046
Enantiospecific total synthesis of lairdinol A.	2008-02-01	18179239
Control of asymmetric biaryl conformations with terpenol moieties: syntheses, structures and energetics of new enantiopure C2-symmetric diols.	2008	18941496
Reversible effects of permeation enhancers on human skin.	2007-08	17270406
Influence of the chirality of (R)-(-)- and (S)-(+)-carvone in the central nervous system: a comparative study.	2007-05-05	17299731
Repellence of the red bud borer Resseliella oculiperda from grafted apple trees by impregnation of rubber budding strips with essential oils.	2007-05	17421054
Antinociceptive activity of structural analogues of rotundifolone: structure-activity relationship.	2007-04-12	17425103
TRPV1 receptors and nasal trigeminal chemesthesis.	2006-11	16908491
Rearrangement of 4,5-epoxy-9-trimethylsilyldecalines. Application to the synthesis of the natural eremophilane (-)-aristolochene.	2006-06-23	16776523
Convergent, enantioselective syntheses of guanacastepenes A and E featuring a selective cyclobutane fragmentation.	2006-05-31	16719483
Purinergic receptor antagonists inhibit odorant-induced heat shock protein 25 induction in mouse olfactory epithelium.	2006-01-15	16206165
Synthesis of the zoanthamine ABC ring system: some surprises from intramolecular Diels-Alder reactions.	2006-01-06	16388646
A formal total synthesis of eleutherobin using the ring-closing metathesis (RCM) reaction of a densely functionalized diene as the key step: investigation of the unusual kinetically controlled RCM stereochemistry.	2005-12-16	16173100
Diastereoselective reactions at enantiomerically pure, sterically congested cyclohexanes as an entry to wailupemycins A and B: total synthesis of (+)-wailupemycin B.	2005-11-18	16144024
Adaptation of Rhodococcus erythropolis DCL14 to growth on n-alkanes, alcohols and terpenes.	2005-05	15856218
Monoterpene metabolism. Cloning, expression, and characterization of (-)-isopiperitenol/(-)-carveol dehydrogenase of peppermint and spearmint.	2005-03	15734920
Electroantennogram responses of the three migratory forms of the damson-hop aphid, Phorodon humuli, to aphid pheromones and plant volatiles.	2004-11	15607511
Novel approach for the introduction of a C-1 oxygenated group on the decalin skeleton: first asymmetric total synthesis of 1S,6S-dihydroxy-eudesm-3-ene.	2004-10	15290681
Enantioselective total synthesis of valeriananoids A-C.	2004-07-08	15228273
Synthetic approaches to guanacastepenes. Enantiospecific syntheses of BC and AB ring systems of guanacastepenes and rameswaralide.	2004-01-22	14723519
Monoterpene biosynthesis pathway construction in Escherichia coli.	2003-09	12943759
Sensitivity-dependent hierarchical receptor codes for odors.	2003-02	12588732
Detection and discrimination of carvone enantiomers in rats with olfactory bulb lesions.	2003	14522003
Total synthesis of (+)-ampullicin and (+)-isoampullicin: two fungal metabolites with growth regulatory activity isolated from Ampulliferina sp. 27.	2001-12-14	11735504

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:48:18 GMT 2025` Edited by `admin` on `Mon Mar 31 18:48:18 GMT 2025`
Record UNII	5TO7X34D3D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(-)-CARVONE

Preferred Name

English

CARVONE, (-)-

Common Name

English

R-(-)-CARVONE

Common Name

English

(-)-CARVONE [FCC]

Common Name

English

2-CYCLOHEXEN-1-ONE, 2-METHYL-5-(1-METHYLETHENYL)-, (5R)-

Systematic Name

English

(R)-(-)- P-MENTHA-6,8-DIEN-2-ONE

Common Name

English

(R)-2-METHYL-5-(1- METHYLETHENYL)-2-CYCLOHEXEN-1-ONE

Systematic Name

English

(R)-(-)-CARVONE

Common Name

English

CARVONE, L-

Common Name

English

CARVONE [FHFI]

Common Name

English

L-CARVONE

Common Name

English

(R)-CARVONE (CONSTITUENT OF MYRRH) [DSC]

Common Name

English

CARVONE L-FORM [MI]

Common Name

English

FEMA NO. 2249, (-)-

Code

English

Classification Tree Code System Code

JECFA EVALUATION

(-)-CARVONE