R-(-)-Carvone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for R-(-)-Carvone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the R-(-)-Carvone?

The molecule R-(-)-Carvone presents a molecular formula of C10H14O and its IUPAC name is (5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one.

R-(-)-carvone is a molecule with the formula C10H14O. It is a colorless liquid with a characteristic minty odor. It is the major constituent of the essential oil of caraway (Carum carvi) and of spearmint (Mentha spicata). R-(-)-carvone can be produced synthetically or extracted from natural sources..

R-(-)-carvone has a wide range of applications in food, beverage, and flavor industries. It is used as a flavoring agent in chewing gum, candy, ice cream, and baked goods. It is also used as a fragrance in cosmetics and soaps..

R-(-)-carvone is a naturally occurring compound and is also produced synthetically. It is a chiral molecule, meaning that it has two non-superimposable mirror image forms. The two forms are designated as R-(-)-carvone and S-(+)-carvone. The R-(-)-carvone form is the naturally occurring form and the S-(+)-carvone form is the synthetic form..

R-(-)-carvone is produced commercially by the hydrogenation of (-)-carvone. This process is carried out in the presence of a platinum catalyst. The R-(-)-carvone that is produced is then purified by distillation..

R-(-)-carvone has a minty odor and a characteristic flavor. It is used as a flavoring agent in chewing gum, candy, ice cream, and baked goods. It is also used as a fragrance in cosmetics and soaps..

3D structure

Cartesian coordinates

Geometry of R-(-)-Carvone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

R-(-)-Carvone ULDHMXUKGWMISQ-SECBINFHSA-N chemical compound 2D structure molecule svg
R-(-)-Carvone

 

Molecule descriptors

 
IUPAC name(5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
InChI codeInChI=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 KeyULDHMXUKGWMISQ-SECBINFHSA-N
SMILESCC1=CC[C@H](CC1=O)C(=C)C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:

Physico-Chemical properties

IUPAC name(5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
Molecular formulaC10H14O
Molecular weight150.22
Melting point (ºC) -
Boiling point (ºC)227-230
Density (g/cm3)0.959
Molar refractivity
LogP2.4
Topological polar surface area17.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.