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Details

Stereochemistry RACEMIC
Molecular Formula C10H14O
Molecular Weight 150.2179
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARVONE, (+/-)-

SMILES

C=C(C)C1CC=C(C)C(=O)C1

InChI

InChIKey=ULDHMXUKGWMISQ-UHFFFAOYSA-N
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3

HIDE SMILES / InChI

Molecular Formula C10H14O
Molecular Weight 150.2179
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Carvone is a monoterpene ketone that is found in several essential oils and used in the flavor industry, alternative medicine and as starting material for the asymmetric total synthesis of natural products. Carvone is produced in two enantiomeric forms: (R)-(-)-carvone, is found in mint leaves, and it is a principal contributor to the distinctive odor of mint. The other form, (S)-(+)-carvone, is found in caraway seeds. This form has a very different smell and is typically used to flavor rye bread and other Eastern European foods. S-(+)-Carvone is also used to prevent premature sprouting of potatoes during storage, being marketed in the Netherlands for this purpose under the name Talent. In the body, in vivo studies indicate that both enantiomers of carvone are mainly metabolized into dihydrocarvonic acid, carvonic acid and uroterpenolone.

Originator

Sources: Journal fuer Praktische Chemie (Leipzig) (1841), 24, 257-274.

Approval Year

PubMed

PubMed

TitleDatePubMed
Carvone as a versatile chiral building block for total syntheses of heterocyclic sesquiterpenoids.
2013 Jul
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Jun 26 02:23:08 UTC 2021
Edited
by admin
on Sat Jun 26 02:23:08 UTC 2021
Record UNII
75GK9XIA8I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARVONE, (+/-)-
Common Name English
CARVONE, (+-)-
Common Name English
5-ISOPROPYL-2-METHYL-2-CYCLOHEXEN-1-ONE
Systematic Name English
CARVONE [ISO]
Common Name English
CARVONE [HSDB]
Common Name English
NSC-6275
Code English
CARVONE
HSDB   ISO   MI  
Common Name English
2-METHYL-5-ISOPROPENYL-2-CYCLOHEXENONE
Systematic Name English
CARVONE, DL-
Common Name English
P-MENTHA-1(6),8-DIEN-2-ONE
Systematic Name English
DL-CARVONE
Common Name English
CARVONE [MI]
Common Name English
LIMONEN-6-ONE
Common Name English
CARVONE DL-FORM [MI]
Common Name English
CARVONE [INCI]
Common Name English
(+/-)-CARVONE
Common Name English
P-MENTHA-6,8-DIEN-2-ONE
Common Name English
(RS)-5-ISOPROPENYL-2-METHYLCYCLOHEX-2-EN-1-ONE
Systematic Name English
2-METHYL-5-(1-METHYLETHENYL)-2-CYCLOHEXENE-1-ONE
Systematic Name English
2-METHYL-5-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-ONE
Systematic Name English
FEMA NO. 2249, (+/-)-
Code English
KARVON
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
202-759-5
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY
MERCK INDEX
M3144
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY Merck Index
MERCK INDEX
M3144
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY Merck Index
EPA CompTox
99-49-0
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY
CAS
99-49-0
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY
PUBCHEM
7439
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY
HSDB
707
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY
RXCUI
1427075
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
ALTERNATIVE
EVMPD
SUB127035
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY
RXCUI
1427074
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY
FDA UNII
75GK9XIA8I
Created by admin on Sat Jun 26 02:23:08 UTC 2021 , Edited by admin on Sat Jun 26 02:23:08 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Compound measured as 5.50% of the composition of the steam distillate of Elymus repens rhizome as per R Boesel in Planta Medica iss:4 pg:399-400, 1989.