Cannabis Compound Database: Showing Compound Card for Limonene (CDB000069)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References Show 2 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:23:38 UTC

Updated at

2020-12-07 19:07:02 UTC

CannabisDB ID

CDB000069

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Limonene

Description

Limonene or dipentene, belongs to the class of organic compounds known as menthane monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. Para-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. Limonene exists as a clear colourless liquid at room temperature. Industrially limonene is used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. Limonene is often marketed as a botanical (plant-derived) solvent of low toxicity. It is a chiral molecule, and biological sources produce only one enantiomer, the D-isomer. Limonene is one of the monoterpenes identified in Cannabis sativa (PMID: 6991645 ). It is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). D-Limonene is a major component of the aromatic scents and resins characteristic of numerous coniferous and broadleaved trees including red and silver maple, cottonwoods, aspens, spruce, various pines, Douglas fir, larches and cedars. D-Limonene is the major component in oil of oranges. Because of its pleasant odor, limonene is widely used as a flavour and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). As the main fragrance of citrus peels, D-limonene is used in food manufacturing and some medicines, such as a flavoring to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products. Limonene is also used as a botanical insecticide. Mild skin irritation may occur from exposure to limonene and oxidation products of limonene may produce dermal sensitization and may have irritative and bronchoconstrictive airway effects. Limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Limonene is one of the active components of dietary phytochemicals that appears to be protective against cancer (PMID: 16563357 , 15499193 , 15325315 , 2024047 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-(S)-Limonene	ChEBI
(-)-(4S)-Limonene	ChEBI
(4S)-1-Methyl-4-isopropenylcyclohex-1-ene	ChEBI
(4S)-4-Isopropenyl-1-methylcyclohexene	ChEBI
(S)-(-)-p-Mentha-1,8-diene	ChEBI
(S)-1-Methyl-4-(1-methylethenyl)cyclohexene	ChEBI
(S)-p-Mentha-1,8-diene	ChEBI
4AlphaH-p-mentha-1,8-diene	ChEBI
L-Limonen	ChEBI
L-Limonene	ChEBI
4-Isopropenyl-1-methyl-1-cyclohexene	HMDB
Limonene	HMDB
(+)-Limonene	HMDB
AISA 5203-L (+)limonene	HMDB
Dipentene	HMDB
1-Methyl-4-(1-methylethenyl)cyclohexene	HMDB
Limonene, (+-)-isomer	HMDB
(D)-Limonene	HMDB
4-Mentha-1,8-diene	HMDB
Limonene, (S)-isomer	HMDB
Limonene, (R)-isomer	HMDB
(R)-(+)-Limonene	HMDB
(R)-4-Isopropenyl-1-methylcyclohexene	HMDB
(+)-(R)-4-Isopropenyl-1-methylcyclohexene	HMDB
(4R)-1-Methyl-4-(1-methylethenyl)cyclohexene	HMDB
D-Limonene	HMDB
4 Mentha 1,8 diene	HMDB
D Limonene	HMDB
(-)-alpha-Limonene	HMDB
(-)-Α-limonene	HMDB
(4S)-1-Methyl-4-(1-methylethenyl)cyclohexene	HMDB
(4S)-Limonene	HMDB
(S)-(-)-Limonene	HMDB
(S)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene	HMDB
(S)-4-Isopropenyl-1-methyl-1-cyclohexene	HMDB
(S)-Limonene	HMDB
beta-Limonene	HMDB
L-Carvene	HMDB
Β-limonene	HMDB
(-)-Limonene	ChEBI

Chemical Formula

C₁₀H₁₆

Average Molecular Weight

136.23

Monoisotopic Molecular Weight

136.1252

IUPAC Name

(4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene

Traditional Name

(-)-limonene

CAS Registry Number

5989-54-8

SMILES

CC(=C)[C@H]1CCC(C)=CC1

InChI Identifier

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1

InChI Key

XMGQYMWWDOXHJM-SNVBAGLBSA-N

Chemical Taxonomy

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
Branched unsaturated hydrocarbon
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

limonene (CHEBI:15383 )
Menthane monoterpenoids (C00521 )
Cyclic monoterpenes (C00521 )
Menthane monoterpenoids (LMPR0102090002 )

Ontology

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Role

Biological role:

Industrial application:

Personal care products:

Perfuming agent

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Pharmaceutical

Antineoplastic agent:

Anticancer agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-74.3 °C	Not Available
Boiling Point	176 °C	Wikipedia
Water Solubility	0.014 mg/mL at 25 °C	Not Available
logP	4.57	LI,J & PURDUE,EM (1995)

Predicted Properties

Property	Value	Source
logP	4.5	ALOGPS
logP	3.22	ChemAxon
logS	-2.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.48 m³·mol⁻¹	ChemAxon
Polarizability	17.23 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-014l-9100000000-7e8881e736cecb723a2b	2015-03-01	View Spectrum
GC-MS	Limonene, non-derivatized, GC-MS Spectrum	splash10-0173-9100000000-239928f205c8242a700a	Spectrum
GC-MS	Limonene, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-507f7afbc17b7c2556e2	Spectrum
GC-MS	Limonene, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-1a0c62c6971532ab6782	Spectrum
GC-MS	Limonene, non-derivatized, GC-MS Spectrum	splash10-0173-9100000000-239928f205c8242a700a	Spectrum
GC-MS	Limonene, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-507f7afbc17b7c2556e2	Spectrum
GC-MS	Limonene, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-1a0c62c6971532ab6782	Spectrum
Predicted GC-MS	Limonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fgo-9200000000-a79c6ccef83c7113ab9f	Spectrum
Predicted GC-MS	Limonene, 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 10V, Positive (Annotated)	splash10-001c-8900000000-dfd6c14e6a4e49bfc6dc	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-002f-9000000000-06c43b864c090aaae8ae	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01t9-9000000000-e5ee54500bc5feda4631	2012-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1900000000-5567709cc9ec1c9909db	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9600000000-4570df18c5140586d0bf	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9100000000-61312f12f069cd9de75c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-88ada45edfe65d9e7f3a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-1192305465e6c746cfa9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-4900000000-199ee0c6ed49a35bcff4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001a-9400000000-fb09a1cdd4bc09480281	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0564-9000000000-dc5effa7f00987fc8567	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mo-9000000000-40d99aa482e2ce5a66f1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-8900000000-d835e92fba2c2a238797	2021-09-23	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cytochrome P450 2C9	CYP2C9	10q24	P11712	details
Cytochrome P450 2C19	CYP2C19	10q24	P33261	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.86 mg/g dry wt	David S. Wishart,...	details
Alien Dawg (Indica dominant)	Detected and Quantified	1.44 +/- 0.27 mg/g dry wt	David S. Wishart,...	details
Animal Cookies	Detected and Quantified	3.8 +/- 0.9 mg/g dry wt	PMID: 28861503	details
Blue Cookies	Detected and Quantified	2.5 +/- 0.9 mg/g dry wt	PMID: 28861503	details
Blue Dream	Detected and Quantified	1.1 +/- 0.8 mg/g dry wt	PMID: 28861503	details
Bubba Kush	Detected and Quantified	3 +/- 1.1 mg/g dry wt	PMID: 28861503	details
Chemdog	Detected and Quantified	4.2 +/- 1.1 mg/g dry wt	PMID: 28861503	details
Crown Og	Detected and Quantified	5.1 +/- 1.6 mg/g dry wt	PMID: 28861503	details
Fortune Cookies	Detected and Quantified	3.6 +/- 1 mg/g dry wt	PMID: 28861503	details
Gabriola	Detected and Quantified	2.48 mg/g dry wt	David S. Wishart,...	details
Gas	Detected and Quantified	5.9 +/- 1.7 mg/g dry wt	PMID: 28861503	details
Gelato	Detected and Quantified	9.1 +/- 1.6 mg/g dry wt	PMID: 28861503	details
Girl Scout Cookies	Detected and Quantified	3.4 +/- 1 mg/g dry wt	PMID: 28861503	details
Godfather	Detected and Quantified	1.9 +/- 0.6 mg/g dry wt	PMID: 28861503	details
Gorilla Glue #4	Detected and Quantified	4.2 +/- 1.1 mg/g dry wt	PMID: 28861503	details
Island Honey	Detected and Quantified	0.12 mg/g dry wt	David S. Wishart,...	details
Jack Herer	Detected and Quantified	0.9 +/- 0.4 mg/g dry wt	PMID: 28861503	details
Master Kush	Detected and Quantified	3.2 +/- 1.3 mg/g dry wt	PMID: 28861503	details
Miami White Kush	Detected and Quantified	8.3 +/- 1.3 mg/g dry wt	PMID: 28861503	details
Mr. Nice	Detected and Quantified	3.4 +/- 1.2 mg/g dry wt	PMID: 28861503	details
Og Kush	Detected and Quantified	5.4 +/- 2.5 mg/g dry wt	PMID: 28861503	details
Quadra	Detected and Quantified	1.38 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.18 mg/g dry wt	David S. Wishart,...	details
Sensi Star (Pure Indica)	Detected and Quantified	0.27 +/- 0.02 mg/g dry wt	David S. Wishart,...	details
Sherbert	Detected and Quantified	5.2 +/- 0.9 mg/g dry wt	PMID: 28861503	details
Skywalker Og Kush	Detected and Quantified	5.1 +/- 1.5 mg/g dry wt	PMID: 28861503	details
Sour Diesel	Detected and Quantified	4.4 +/- 1.1 mg/g dry wt	PMID: 28861503	details
Strawberry Haze	Detected and Quantified	2.4 +/- 0.5 mg/g dry wt	PMID: 28861503	details
Superman Og Kush	Detected and Quantified	6.3 +/- 1.7 mg/g dry wt	PMID: 28861503	details
Tahoe Og Kush	Detected and Quantified	6.8 +/- 1.3 mg/g dry wt	PMID: 28861503	details
Tangerine Dream	Detected and Quantified	0.26 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream (Sativa dominant)	Detected and Quantified	0.19 +/- 0.02 mg/g dry wt	David S. Wishart,...	details
Thin Mints	Detected and Quantified	3.3 +/- 0.9 mg/g dry wt	PMID: 28861503	details
Trainwreck	Detected and Quantified	3.4 +/- 1.9 mg/g dry wt	PMID: 28861503	details
Triple O	Detected and Quantified	6.7 +/- 1.4 mg/g dry wt	PMID: 28861503	details

External Links

HMDB ID

HMDB0004321

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15383

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Flamm WG, Lehman-McKeeman LD: The human relevance of the renal tumor-inducing potential of d-limonene in male rats: implications for risk assessment. Regul Toxicol Pharmacol. 1991 Feb;13(1):70-86. doi: 10.1016/0273-2300(91)90042-t. [PubMed:2024047 ]
Aggarwal BB, Shishodia S: Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol. 2006 May 14;71(10):1397-421. doi: 10.1016/j.bcp.2006.02.009. Epub 2006 Feb 23. [PubMed:16563357 ]
Tsuda H, Ohshima Y, Nomoto H, Fujita K, Matsuda E, Iigo M, Takasuka N, Moore MA: Cancer prevention by natural compounds. Drug Metab Pharmacokinet. 2004 Aug;19(4):245-63. doi: 10.2133/dmpk.19.245. [PubMed:15499193 ]
McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
DeWitt C, Bebarta V: Botanical solvents. Clin Occup Environ Med. 2004 Aug;4(3):445-54, v-vi. doi: 10.1016/j.coem.2004.03.003. [PubMed:15325315 ]

Showing Compound Card for Limonene (CDB000069)

Structure for CDB000069 (Limonene)