AFCDB: (S)-Limonene (FDB013861)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:57 UTC

Update date

2019-11-26 03:09:11 UTC

Primary ID

FDB013861

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(S)-Limonene

Description

d-Limonene, also known as 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 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

CAS Number

5989-54-8

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

(4R)-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/t10-/m0/s1

InChI Key

XMGQYMWWDOXHJM-JTQLQIEISA-N

Isomeric SMILES

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

Average Molecular Weight

136.234

Monoisotopic Molecular Weight

136.125200512

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

limonene (CHEBI:15382 )
Menthane monoterpenoids (C06099 )
Cyclic monoterpenes (C06099 )
Menthane monoterpenoids (LMPR0102090013 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 88.16%; H 11.84%	DFC
Melting Point	-90 oC
Boiling Point	Bp 177.6-177.8°	DFC
Experimental Water Solubility	Not Available
Experimental logP	4.38	GRIFFIN,S ET AL. (1999)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -122.6	DFC
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-fbf154446f93ee5019c0	2015-03-01	View Spectrum
GC-MS	(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrum	splash10-0173-9100000000-239928f205c8242a700a	Spectrum
GC-MS	(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-507f7afbc17b7c2556e2	Spectrum
GC-MS	(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-1a0c62c6971532ab6782	Spectrum
GC-MS	(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrum	splash10-0173-9100000000-239928f205c8242a700a	Spectrum
GC-MS	(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-507f7afbc17b7c2556e2	Spectrum
GC-MS	(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-1a0c62c6971532ab6782	Spectrum
GC-MS	(+)-Mentha-1,8-diene, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-0b286d388287bcc487f2	Spectrum
Predicted GC-MS	(+)-Mentha-1,8-diene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-df40612bbf371089d7ac	Spectrum
Predicted GC-MS	(+)-Mentha-1,8-diene, 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)	splash10-000i-6900000000-f7ee4bad43b6ccae0ccb	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ou-9000000000-51a52c25a98124e179e9	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-9655665d3d36755028cc	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0173-9100000000-239928f205c8242a700a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-014l-9100000000-bc8708fdb2d1955dce92	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-014l-9100000000-1a0c62c6971532ab6782	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-bce8f8616cfd3b16cac9	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9600000000-583a2621a826cedbca61	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1000-9100000000-d78cd6fbdd7a13fe9dfa	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-2950ad058f77d7bc9f76	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-6f48f3b0b500d4f25ec9	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-5900000000-1c30c00bfa4058f5e22b	2017-07-26	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
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

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15383

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03375

CRC / DFC (Dictionary of Food Compounds) ID

JFH51-A:JJF05-H

EAFUS ID

2035

Dr. Duke ID

L-LIMONENE|DELTA-LIMONENE|(-)-LIMONENE

BIGG ID

47361

KNApSAcK ID

C00000803

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1007831

SuperScent ID

439250

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
anti acetylcholinesterase	38462	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
camphoraceous	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
terpene	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pine	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.
peppery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

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.

(S)-Limonene (FDB013861)

Structure for FDB013861 ((S)-Limonene)