D-Limonene

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

What is the D-Limonene?

The molecule D-Limonene presents a molecular formula of C10H16 and its IUPAC name is (4R)-1-methyl-4-prop-1-en-2-ylcyclohexene.

D-Limonene is a naturally occurring molecule that can be found in the peel of citrus fruits. It is a colourless liquid with a strong citrus smell. D-Limonene is used as a flavouring agent and as a fragrance in many products. It is also used in cleaning products and as a solvent for cleaning up oil spills..

D-Limonene is a terpene, which is a type of hydrocarbon. Terpenes are made up of isoprene units, which are five-carbon molecules. D-Limonene is made up of two isoprene units. The structure of D-Limonene is similar to that of other terpenes, such as pinene and limonene..

D-Limonene is produced by the citrus tree when the fruit is peeled. The peel of the fruit contains a high concentration of D-Limonene. The D-Limonene is then extracted from the peel and used in various products..

D-Limonene has a variety of uses. It is used as a flavouring agent in food and beverages. It is also used in cleaning products and as a solvent for cleaning up oil spills..

D-Limonene is a safe and non-toxic molecule. It is not known to cause any adverse effects in humans..

3D structure

Cartesian coordinates

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

2D drawing

 

D-Limonene XMGQYMWWDOXHJM-JTQLQIEISA-N chemical compound 2D structure molecule svg
D-Limonene

 

Molecule descriptors

 
IUPAC name(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene
InChI codeInChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1
InChI KeyXMGQYMWWDOXHJM-JTQLQIEISA-N
SMILESC=C(C)[C@H]1CC=C(C)CC1

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.

  • (+) Limonene
  • (+)-(4R)-Limonene
  • (+)-(R)-4-isopropenyl-1-methylcyclohexene
  • (+)-(R)-Limonene
  • (+)-1,8-para-Menthadiene
  • (+)-4-Isopropenyl-1-methylcyclohexene
  • (+)-Dipentene
  • (+)-Limonene
  • (+)-R-Limonene
  • (+)-alpha-Limonene
  • (+)-carvene
  • (+)-p-Mentha-1,8-diene
  • (4R)-(+)-Limonene
  • (4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohexene
  • (4R)-1-methyl-4-(1-methylethenyl)cyclohexene
  • (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
  • (4R)-1-methyl-4-isopropenylcyclohex-1-ene
  • (4R)-1-methyl-4-prop-1-en-2-ylcyclohexene
  • (4R)-4-isopropenyl-1-methyl-cyclohexene
  • (4R)-4-isopropenyl-1-methylcyclohexene
  • (4R)-Limonene
  • (D)-Limonene
  • (R)-(+)-4-Isopropenyl-1-methylcyclohexene
  • (R)-(+)-Limonene
  • (R)-(+)-p-Mentha-1,8-diene
  • (R)-1-Methyl-4-(1-methylethenyl)cyclohexene
  • (R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
  • (R)-4-Isopropenyl-1-methyl-1-cyclohexene
  • (R)-4-isopropenyl-1-methylcyclohexene
  • (R)-Limonene
  • (R)-p-Mentha-1,8-diene
  • 1-Methyl-4-(1-methylethenyl)cyclohexene, (R)-
  • 4betaH-p-mentha-1,8-diene
  • 5989-27-5
  • 68647-72-3
  • AI3-15191
  • BS-22387
  • Biogenic SE 374
  • C06099
  • CCG-266134
  • CCRIS 671
  • CS-M3273
  • Carvene
  • Citrene
  • Citrus stripper oil
  • Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-
  • Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-
  • Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (theta)-
  • D-(+)-Limonene
  • D-1,8-p-Menthadiene
  • D-Limonen
  • D-Limonene
  • D91245
  • DB08921
  • DSSTox_CID_778
  • DSSTox_GSID_20778
  • DSSTox_RID_75785
  • Dextro-limonene
  • Dipentene no. 122
  • EC 227-813-5
  • EC 7
  • FEMA No. 2633
  • GFD7C86Q1W
  • Glidesafe
  • Glidsafe
  • HSDB 4186
  • Hemo-sol
  • J-502148
  • Kautschiin
  • L0047
  • L0105
  • LMPR0102090013
  • Limonene, (+)-
  • Limonene, D-
  • MFCD00062991
  • NCGC00248591-01
  • NCGC00248591-02
  • NCGC00257954-01
  • NCI-C55572
  • NSC 757069
  • NSC-757069
  • ORANGE OIL DISTILLATE
  • Orange x
  • Q27888324
  • Refchole
  • Sulfate turpentine, distilled
  • W-105295
  • d limonene
  • d-Limoneno
  • d-p-Mentha-1,8-diene
  • p-Mentha-1,8-diene, (R)-(+)-
  • r-(+)-limonene

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC967513
  • CAS-5989-27-5
  • UNII-GFD7C86Q1W
  • AKOS015899935
  • DTXSID1020778
  • CHEMBL449062
  • CHEBI:15382
  • Tox21_200400
  • EINECS 227-813-5
  • EINECS 266-034-5

Physico-Chemical properties

IUPAC name(4R)-1-methyl-4-prop-1-en-2-ylcyclohexene
Molecular formulaC10H16
Molecular weight136.234
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity47.12
LogP3.3
Topological polar surface area0.0

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.