Milk Composition Database: Showing metabocard for (-)-Limonene (BMDB0003375)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-09-30 23:04:07 UTC

Update Date

2020-05-11 19:57:32 UTC

MCDB ID

BMDB0003375

Secondary Accession Numbers

BMDB03375

Metabolite Identification

Common Name

(-)-Limonene

Description

D-Limonene, also known as L-limonen or dipentene, 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. Thus, D-limonene is considered to be an isoprenoid lipid molecule. D-Limonene exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. D-Limonene exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-(4R)-Limonene	ChEBI
(+)-(R)-Limonene	ChEBI
(+)-4-Isopropenyl-1-methylcyclohexene	ChEBI
(+)-Limonene	ChEBI
(4R)-1-Methyl-4-isopropenylcyclohex-1-ene	ChEBI
(4R)-4-Isopropenyl-1-methylcyclohexene	ChEBI
(R)-(+)-Limonene	ChEBI
(R)-(+)-p-Mentha-1,8-diene	ChEBI
(R)-1-Methyl-4-(1-methylethenyl)cyclohexene	ChEBI
(R)-4-Isopropenyl-1-methyl-1-cyclohexene	ChEBI
(R)-p-Mentha-1,8-diene	ChEBI
4BetaH-p-mentha-1,8-diene	ChEBI
D-(+)-Limonene	ChEBI
D-Limonen	ChEBI
AISA 5203-L (+)limonene	HMDB
Dipentene	HMDB
(-)-Limonene	HMDB
1-Methyl-4-(1-methylethenyl)cyclohexene	HMDB
Limonene	HMDB
Limonene, (+-)-isomer	HMDB
(D)-Limonene	HMDB
4-Mentha-1,8-diene	HMDB
Limonene, (R)-isomer	HMDB
(+)-Dipentene	HMDB
(+)-alpha-Limonene	HMDB
(+)-p-Mentha-1,8-diene	HMDB
(+)-Α-limonene	HMDB
(4R)-(+)-Limonene	HMDB
(4R)-1-Methyl-4-(1-methylethenyl)cyclohexene	HMDB
(4R)-Limonene	HMDB
(R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene	HMDB
(R)-Limonene	HMDB
1-Methyl-4-prop-1-en-2-yl-cyclohexene	HMDB
(+)-(R)-4-Isopropenyl-1-methylcyclohexene	HMDB
D Limonene	HMDB
4 Mentha 1,8 diene	HMDB
(R)-4-Isopropenyl-1-methylcyclohexene	HMDB
D-Limonene	ChEBI
d-Limonene	HMDB
(4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene	HMDB
R-Limonene	HMDB
p-Mentha-1,8-diene	PhytoBank
(±)-Dipentene	PhytoBank
(±)-Limonene	PhytoBank
(±)-alpha-Limonene	PhytoBank
(±)-α-Limonene	PhytoBank
1,8-p-Menthadiene	PhytoBank
1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene	PhytoBank
1-Methyl-4-isopropenyl-1-cyclohexene	PhytoBank
1-Methyl-4-isopropenylcyclohexene	PhytoBank
1-Methyl-p-isopropenyl-1-cyclohexene	PhytoBank
4-Isopropenyl-1-methyl-1-cyclohexene	PhytoBank
4-Isopropenyl-1-methylcyclohexene	PhytoBank
dl-Limonene	PhytoBank
Dipenten	PhytoBank
Limonen	PhytoBank
alpha-Limonene	PhytoBank
α-Limonene	PhytoBank

Chemical Formula

C₁₀H₁₆

Average Molecular Weight

136.234

Monoisotopic Molecular Weight

136.125200512

IUPAC Name

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

Traditional Name

α-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-/m0/s1

InChI Key

XMGQYMWWDOXHJM-JTQLQIEISA-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:15382 )
Menthane monoterpenoids (C06099 )
Cyclic monoterpenes (C06099 )
Menthane monoterpenoids (LMPR0102090013 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

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	17.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0173-9100000000-239928f205c8242a700a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9100000000-507f7afbc17b7c2556e2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9100000000-1a0c62c6971532ab6782	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0173-9100000000-239928f205c8242a700a	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9100000000-507f7afbc17b7c2556e2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9100000000-1a0c62c6971532ab6782	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-Q (Non-derivatized)	splash10-014l-9100000000-0b286d388287bcc487f2	2020-07-08	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-df40612bbf371089d7ac	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-6900000000-f7ee4bad43b6ccae0ccb	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ou-9000000000-51a52c25a98124e179e9	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-9655665d3d36755028cc	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0173-9100000000-239928f205c8242a700a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-014l-9100000000-bc8708fdb2d1955dce92	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-014l-9100000000-1a0c62c6971532ab6782	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-bce8f8616cfd3b16cac9	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9600000000-583a2621a826cedbca61	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9100000000-d78cd6fbdd7a13fe9dfa	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-2950ad058f77d7bc9f76	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-6f48f3b0b500d4f25ec9	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-5900000000-1c30c00bfa4058f5e22b	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-8900000000-d835e92fba2c2a238797	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001a-9400000000-fb09a1cdd4bc09480281	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0564-9000000000-dc5effa7f00987fc8567	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mo-9000000000-40d99aa482e2ce5a66f1	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014l-9100000000-fbf154446f93ee5019c0	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2015-03-12	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 27236769	details

External Links

HMDB ID

HMDB0003375

DrugBank ID

DB08921

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Limonene

METLIN ID

Not Available

PubChem Compound

440917

PDB ID

Not Available

ChEBI ID

15382

References

Synthesis Reference

v. Braun, Julius; Lemke, Georg. Preparation of pure d- and l-limonene. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1923), 56B 1562-3.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]

Showing metabocard for (-)-Limonene (BMDB0003375)

Structure for BMDB0003375 ((-)-Limonene)