S-(+)-Carvone

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

What is the S-(+)-Carvone?

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

Carvone is a natural organic compound that gives many plants their characteristic odor. Carvone is a member of the class of compounds known as terpenes. It is the main flavor component of spearmint (Mentha spicata) and also gives caraway (Carum carvi), dill (Anethum graveolens) and anise (Pimpinella anisum) their characteristic flavors. Carvone can be found in the essential oils of many other plants such as ginger (Zingiber officinale), lemongrass (Cymbopogon citratus), and eucalyptus (Eucalyptus globulus)..

Carvone is a chiral molecule. This means that it has two mirror image forms that are non-superimposable. The two forms of carvone are called enantiomers. The most common form of carvone found in nature is (R)-carvone. This form of carvone is also known as levocarvone. The other form of carvone is (S)-carvone. This form of carvone is also known as dextrocarvone. Carvone can be produced synthetically from (R)-limonene..

The two enantiomers of carvone have very different smells. (R)-Carvone smells like spearmint while (S)-carvone smells like caraway. The two enantiomers of carvone also have different tastes. (R)-Carvone tastes sweet while (S)-carvone tastes bitter..

Carvone can be used as a food flavoring. It is also used in the production of certain fragrances. Carvone is sometimes used as a moth repellent..

3D structure

Cartesian coordinates

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

2D drawing

 

S-(+)-Carvone ULDHMXUKGWMISQ-VIFPVBQESA-N chemical compound 2D structure molecule svg
S-(+)-Carvone

 

Molecule descriptors

 
IUPAC name(5S)-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-/m0/s1
InChI KeyULDHMXUKGWMISQ-VIFPVBQESA-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(5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
Molecular formulaC10H14O
Molecular weight150.22
Melting point (ºC) -
Boiling point (ºC)96-98
Density (g/cm3)0.960
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.