NP-MRD: Showing NP-Card for (-)-Limonene (NP0000505)

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Record Information

Version

1.0

Created at

2006-08-13 16:44:29 UTC

Updated at

2021-10-07 20:41:32 UTC

NP-MRD ID

NP0000505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Limonene

Description

Limonene is a monoterpene with a clear colourless liquid at room temperature, a naturally occurring chemical which is the major component in oil of oranges. 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.). Limonene is a botanical (plant-derived) solvent of low toxicity. 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; however, data are scant and more studies are required. Limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to limonene causes a significant incidence of renal tubular tumours exclusively in male rats. Limonene is one of the active components of dietary phytochemicals that appears to be protective against cancer (PMID: 16563357 , 15499193 , 15325315 , 2024047 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments

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
(4S)-1-Methyl-4-(prop-1-en-2-yl)cyclohexene	Kegg
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 Mass

136.2340 Da

Monoisotopic Mass

136.12520 Da

IUPAC Name

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

Traditional Name

(-)-limonene

CAS Registry Number

5989-27-5

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies alba	LOTUS Database	35616633
Abies grandis	KNApSAcK Database	22123792
Abies nebrodensis	LOTUS Database	35616633
Andropogon spp.	Plant	KNApSAcK
Anethum graveolens	LOTUS Database	35616633
Angelica archangelica	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Carum carvi	LOTUS Database	35616633
Citrofortunella mitis	KNApSAcK Database	22123792
Citrus aurantium var. bergamia	Plant	KNApSAcK
Citrus limon	LOTUS Database	35616633
Citrus spp.	KNApSAcK Database	22123792
Citrus unshiu	KNApSAcK Database	22123792
Citrus x microcarpa	LOTUS Database	35616633
Conocephalum conicum	LOTUS Database	35616633
Cymbopogon spp.	Plant	KNApSAcK
Foeniculum vulgare	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Kippistia suaedifolia	LOTUS Database	35616633
Melaleuca alternifolia	LOTUS Database	35616633
Mentha longifolia	KNApSAcK Database	22123792
Mentha piperita	KNApSAcK Database	22123792
Mentha spicata	KNApSAcK Database	22123792
Mentha x piperita	Plant	KNApSAcK
Methylosinus trichosporium	LOTUS Database	35616633
Minthostachys mollis	LOTUS Database	35616633
Nicotiana tabacum	KNApSAcK Database	22123792
Pelargonicum graveolens	-	KNApSAcK
Perilla frutescens	KNApSAcK Database	22123792
Picea abies	LOTUS Database	35616633
Picea schrenkiana	Plant	KNApSAcK
Pinus banksiana	KNApSAcK Database	22123792
Pinus contorta var. latifolia	KNApSAcK Database	22123792
Pinus densiflora	LOTUS Database	35616633
Pinus heldreichii	LOTUS Database	35616633
Pinus spp.	Plant	KNApSAcK
Pinus taeda	KNApSAcK Database	22123792
Piper cubeba	Plant	KNApSAcK
Poiretia latifolia	LOTUS Database	35616633
Pseudotsuga menziesii	LOTUS Database	35616633
Psidium guajava	KNApSAcK Database	22123792
Ricciocarpos natans	LOTUS Database	35616633
Salvia officinalis	KNApSAcK Database	22123792
Schizonepeta tenuifolia	LOTUS Database	35616633
Trifolium pratense	Plant	KNApSAcK
Trypanosoma brucei	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633

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 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-74.3 °C	Not Available
Boiling Point	176.00 to 177.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.014 mg/mL at 25 °C	Not Available
LogP	4.57	Li, J., Perdue, E.M. (1995) Physicochemical properties of selected monoterpenes. Pre-print Extended Abstract, Presented Before The Division of Environmental Chemistry, Amer Chem Soc, Anaheim, Ca: April 2-7

Predicted Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
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

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

Good Scents ID

rw1007831

References

General References

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. [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. 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. [PubMed:15499193 ]
DeWitt C, Bebarta V: Botanical solvents. Clin Occup Environ Med. 2004 Aug;4(3):445-54, v-vi. [PubMed:15325315 ]
Liu Y, Ma X, Liang H, Stephanopoulos G, Zhou K: Monoterpenoid biosynthesis by engineered microbes. J Ind Microbiol Biotechnol. 2021 Oct 2. pii: 6380491. doi: 10.1093/jimb/kuab065. [PubMed:34601590 ]

Showing NP-Card for (-)-Limonene (NP0000505)

MOL for NP0000505 ((-)-Limonene)

3D MOL for NP0000505 ((-)-Limonene)

3D SDF for NP0000505 ((-)-Limonene)

3D-SDF for NP0000505 ((-)-Limonene)

PDB for NP0000505 ((-)-Limonene)

3D PDB for NP0000505 ((-)-Limonene)

SMILES for NP0000505 ((-)-Limonene)

INCHI for NP0000505 ((-)-Limonene)

Structure for NP0000505 ((-)-Limonene)

3D Structure for NP0000505 ((-)-Limonene)