AFCDB: (±)-Limonene (FDB014115)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:05 UTC

Update date

2019-11-26 03:09:32 UTC

Primary ID

FDB014115

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(±)-Limonene

Description

Polylimonene, also known as (+/-)-limonene or cajeputene, 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. Based on a literature review a significant number of articles have been published on Polylimonene.

CAS Number

9003-73-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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	17.55 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

Chemical Formula

C10H16

IUPAC name

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

InChI Identifier

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

InChI Key

XMGQYMWWDOXHJM-UHFFFAOYSA-N

Isomeric SMILES

CC(=C)C1CCC(C)=CC1

Average Molecular Weight

136.238

Monoisotopic Molecular Weight

136.125200515

Classification

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

monoterpene (CHEBI:15384 )
Menthane monoterpenoids (C06078 )
Terpenoids (C06078 )
a limonene (CPD-8785 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 88.16%; H 11.84%	DFC
Melting Point	< 25 oC
Boiling Point	Bp 178°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-014l-9100000000-498293086493b60c2094	2015-03-01	View Spectrum
GC-MS	Polylimonene, non-derivatized, GC-MS Spectrum	splash10-0006-9300000000-132287e3db63dda49102	Spectrum
GC-MS	Polylimonene, non-derivatized, GC-MS Spectrum	splash10-00kf-9300000000-d7348db845e3e79845dd	Spectrum
Predicted GC-MS	Polylimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-df40612bbf371089d7ac	Spectrum
Predicted GC-MS	Polylimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4o-9000000000-893d8151186383a89b6a	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-bce8f8616cfd3b16cac9	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9600000000-583a2621a826cedbca61	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9100000000-d78cd6fbdd7a13fe9dfa	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-2950ad058f77d7bc9f76	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-6f48f3b0b500d4f25ec9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-5900000000-1c30c00bfa4058f5e22b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001a-9400000000-fb09a1cdd4bc09480281	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0564-9000000000-dc5effa7f00987fc8567	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mo-9000000000-40d99aa482e2ce5a66f1	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-8900000000-d835e92fba2c2a238797	2021-09-25	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

20939

ChEMBL ID

Not Available

KEGG Compound ID

C06078

Pubchem Compound ID

22311

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB32473

CRC / DFC (Dictionary of Food Compounds) ID

JFH51-A:JNZ87-F

EAFUS ID

2036

Dr. Duke ID

DL-LIMONENE|DIPENTENE

BIGG ID

Not Available

KNApSAcK ID

C00003043

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1240221

SuperScent ID

Not Available

Wikipedia ID

Limonene

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
expectorant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
irritant			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
citrus	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
terpene	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

(±)-Limonene (FDB014115)

Structure for FDB014115 ((±)-Limonene)