Carvone

Carvone
Names
	Preferred IUPAC name 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
	Other names 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone; 2-Methyl-5-(1-methylethenyl)-2-cyclohexenone; Δ6:8(9)-p-Menthadien-2-one; 1-Methyl-4-isopropenyl-Δ6-cyclohexen-2-one; Carvol (obsolete)
Identifiers
CAS Number	99-49-0 (R/S) ; 6485-40-1 (R) ; 2244-16-8 (S) ;
3D model (JSmol)	(R): Interactive image; (S): Interactive image;
ChEBI	CHEBI:38265 ;
ChEMBL	ChEMBL15676 ;
ChemSpider	21106424 (R/S) ; 15855 (S) ; 388655 (R) ;
ECHA InfoCard	100.002.508
KEGG	C01767 ;
PubChem CID	7439;
RTECS number	OS8650000 (R); OS8670000 (S);
UNII	75GK9XIA8I (R/S) ; 5TO7X34D3D (R) ; 4RWC1CMS3X (S) ;
CompTox Dashboard (EPA)	DTXSID8047426 ;
	InChI InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3 Key: ULDHMXUKGWMISQ-UHFFFAOYSA-N ; InChI=1/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3 Key: ULDHMXUKGWMISQ-UHFFFAOYAB;
	SMILES (R): O=C1C[C@@H](C\C=C1\C)C(C)=C; (S): O=C1C[C@H](C\C=C1\C)C(C)=C;
Properties
Chemical formula	C10H14O
Molar mass	150.22 g/mol
Appearance	Clear, colorless liquid
Density	0.96 g/cm3
Melting point	25.2 °C (77.4 °F; 298.3 K)
Boiling point	231 °C (448 °F; 504 K) (91 °C @ 5 mmHg)
Solubility in water	Insoluble (cold); Slightly soluble (hot)/soluble in trace amounts
Solubility in ethanol	Soluble
Solubility in diethyl ether	Soluble
Solubility in chloroform	Soluble
Chiral rotation ([α]D)	−61° (R)-Carvone; 61° (S)-Carvone
Magnetic susceptibility (χ)	−92.2×10−6 cm3/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H304, H315, H317, H411
Precautionary statements	P261, P264, P270, P272, P273, P280, P301+P310, P301+P312, P302+P352, P321, P330, P331, P332+P313, P333+P313, P362, P363, P391, P405, P501
NFPA 704 (fire diamond)	1 2 0
Safety data sheet (SDS)	External MSDS
Related compounds
Related ketone	menthone; dihydrocarvone; carvomenthone
Related compounds	limonene, menthol,; p-cymene, carveol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Carvone is a member of a family of chemicals called terpenoids.^[2] Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (Carum carvi), spearmint (Mentha spicata), and dill.^[3]

^ Vollhardt, K. Peter C.; Schore, Neil E. (2007). Organic Chemistry (5th ed.). New York: W. H. Freeman. p. 173.
^ Simonsen, J. L. (1953). The Terpenes. Vol. 1 (2nd ed.). Cambridge: Cambridge University Press. pp. 394–408.
^ De Carvalho, C. C. C. R.; Da Fonseca, M. M. R. (2006). "Carvone: Why and how should one bother to produce this terpene". Food Chemistry. 95 (3): 413–422. doi:10.1016/j.foodchem.2005.01.003.

[1] Vollhardt, K. Peter C.; Schore, Neil E. (2007). Organic Chemistry (5th ed.). New York: W. H. Freeman. p. 173.

[simonsen-2] Simonsen, J. L. (1953). The Terpenes. Vol. 1 (2nd ed.). Cambridge: Cambridge University Press. pp. 394–408.

[carvalho-3] De Carvalho, C. C. C. R.; Da Fonseca, M. M. R. (2006). "Carvone: Why and how should one bother to produce this terpene". Food Chemistry. 95 (3): 413–422. doi:10.1016/j.foodchem.2005.01.003.

[1]

[2]

[3]