AFCDB: (S)-Carvone (FDB014599)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:22 UTC

Update date

2019-11-26 03:10:24 UTC

Primary ID

FDB014599

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(S)-Carvone

Description

Constituent of dill (Anethum graveolens) and caraway (Carum carvi) oils. Flavouring ingredient Carvone is a volatile terpenoid. Carvone is found in many essential oils and is very abundant in the seeds of caraway (Carum carvi). Carvone is occasionally found as a component of biological fluids in normal individuals. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in1841. (PMID: 5556886, 2477620, Wikipedia)

CAS Number

2244-16-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.16 g/L	ALOGPS
logP	2.77	ALOGPS
logP	2.55	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.17 m³·mol⁻¹	ChemAxon
Polarizability	17.65 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H14O

IUPAC name

(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one

InChI Identifier

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

InChI Key

ULDHMXUKGWMISQ-SECBINFHSA-N

Isomeric SMILES

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

Average Molecular Weight

150.2176

Monoisotopic Molecular Weight

150.10446507

Classification

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carvone (CHEBI:15400 )
Menthane monoterpenoids (C01767 )
Cyclic monoterpenes (C01767 )
Menthane monoterpenoids (LMPR0102090007 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 79.96%; H 9.39%; O 10.65%	DFC
Melting Point	<15 oC
Boiling Point	Bp 230°	DFC
Experimental Water Solubility	1.3 mg/mL at 18 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	1.267
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D +61.2	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0f8c-9200000000-88f46d943b306bc533db	2015-03-01	View Spectrum
GC-MS	(R)-Carvone, non-derivatized, GC-MS Spectrum	splash10-0a59-9300000000-0663a3956cbefc28418a	Spectrum
GC-MS	(R)-Carvone, non-derivatized, GC-MS Spectrum	splash10-0a59-9300000000-0663a3956cbefc28418a	Spectrum
GC-MS	(R)-Carvone, non-derivatized, GC-MS Spectrum	splash10-0a59-9300000000-0663a3956cbefc28418a	Spectrum
GC-MS	(R)-Carvone, non-derivatized, GC-MS Spectrum	splash10-0a59-9300000000-0663a3956cbefc28418a	Spectrum
Predicted GC-MS	(R)-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f83-9200000000-e9569993e9ab3a8d9c56	Spectrum
Predicted GC-MS	(R)-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)-Carvone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ , positive (Annotated)	splash10-052f-9600000000-9902205f6d338c08818d	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0udi-0900000000-52f6355f33c4b2243d8a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0udi-0900000000-cb6bd893e3059c4e749a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0udi-0900000000-12445f07d9581bb79ba9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0zfr-0900000000-f9115bab64084ca3e9c6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0zfr-0900000000-c2cc2f68aa635d48f7d2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0pb9-0900000000-34673104b5cbea631cca	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0a4i-0900000000-3c5bc016004147d81ac1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0a4i-0900000000-805c8d6f02a70e4d8ced	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0a4i-1900000000-90f1a3149285030d18d3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-0a4i-4900000000-c900c93dbadd576b2e03	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0a4l-9700000000-ccd0df21a8aba540288c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-052f-9400000000-b05876718fef3d10e1e6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-00kf-9200000000-97e06bb63f72b6a871e6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0a4i-0900000000-62d73cc97ac426baf5d8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-004l-9000000000-672e06fb3b7870b5e066	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-001i-9000000000-a5c95a778293e816e298	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-000t-9100000000-c3c9a32c71b3929313eb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-9000000000-fb41d95361a6747c1394	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-62861ac4cbf0b95e5069	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-5900000000-b282dcb5d4a98c3f852f	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9100000000-0fd631d26260645c64ae	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-97d37f99bcaf0ed7d108	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-1817a8dceee7a31df4e0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-6900000000-581a45ee1ec95e201138	2016-08-03	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15399

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04487

CRC / DFC (Dictionary of Food Compounds) ID

JSX52-Q:JSW31-E

EAFUS ID

Not Available

Dr. Duke ID

D-CARVONE|(+)-CARVONE|D-(+)-CARVONE

BIGG ID

Not Available

KNApSAcK ID

C00010891

HET ID

0WU

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
acetylcholinesterase inhibitor	38462	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.	DUKE
anti acetylcholinesterase	38462	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.	DUKE
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cholinesterase	37733	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).	DUKE
insecticide	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
caraway	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bread	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

(S)-Carvone (FDB014599)

Structure for FDB014599 ((S)-Carvone)