Showing Compound cis-Limonene epoxide (FDB004782)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:23 UTC

Update date

2019-11-26 03:00:13 UTC

Primary ID

FDB004782

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

cis-Limonene epoxide

Description

(1s,2r,4r)-1,2-epoxy-p-menth-8-ene, also known as limonene-1,2-epoxide or 1,2-epoxylimonene, is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms (1s,2r,4r)-1,2-epoxy-p-menth-8-ene is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (1s,2r,4r)-1,2-epoxy-p-menth-8-ene is a green tasting compound found in lemon and wild celery, which makes (1s,2r,4r)-1,2-epoxy-p-menth-8-ene a potential biomarker for the consumption of these food products.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
1,2-Epoxylimonene	ChEBI
1-Methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane, 9ci	HMDB
1-Methyl-4-(1-methylvinyl)-7-oxabicyclo(4.1.0)heptane	HMDB
1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane	HMDB
4-Isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane	ChEBI
Limonene 1,2-epoxide	HMDB
Limonene 1,2-oxide	ChEBI
Limonene epoxide	HMDB
Limonene monoxide	HMDB
Limonene oxide	HMDB, MeSH

Showing 1 to 10 of 19 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	2.81	ALOGPS
logP	2.32	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	45.24 m³·mol⁻¹	ChemAxon
Polarizability	18.2 Å³	ChemAxon
Number of Rings	2	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

C10H16O

IUPAC name

1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

InChI Identifier

InChI=1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3

InChI Key

CCEFMUBVSUDRLG-UHFFFAOYSA-N

Isomeric SMILES

CC(=C)C1CCC2(C)OC2C1

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

Classification

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:16431 )
limonene monoterpenoid (CHEBI:16431 )
a 4S-limonene-1,2-epoxide (CPD-10142 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, GC-MS Spectrum	splash10-052f-9200000000-fecff1839cd311e2483c	Spectrum
GC-MS	(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, GC-MS Spectrum	splash10-052f-9200000000-fecff1839cd311e2483c	Spectrum
Predicted GC-MS	(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-003u-9200000000-d81e209c09694ad9f313	Spectrum
Predicted GC-MS	(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(1S,2R,4R)-1,2-Epoxy-p-menth-8-ene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-3c1aa1a5e0f61835962d	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-3900000000-86882c765e64ddc05192	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ldi-9000000000-a653f610d8c769c8f581	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-b330335669a8886c1ed3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-b7f31881782717e4ef0d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05n0-9600000000-66905c235c49a5386841	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-3900000000-fbc31cf20658ca9fcd34	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n3-9500000000-edf4637ffc55f65c3f8f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr6-9100000000-b94cebb6da5a89465afb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-4c49b375f7aae96ad305	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-1000-6900000000-ab085761a68f75073256	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

CIS-LIMONENE-EPOXIDE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

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).

Showing Compound cis-Limonene epoxide (FDB004782)

Structure for FDB004782 (cis-Limonene epoxide)