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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:06:17 UTC

Update Date

2022-03-07 02:54:23 UTC

HMDB ID

HMDB0035158

Secondary Accession Numbers

HMDB35158

Metabolite Identification

Common Name

1,2-Epoxy-p-menth-8-ene

Description

1,2-Epoxy-p-menth-8-ene, also known as 1,2-epoxylimonene or limonene 1,2-oxide, 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. 1,2-Epoxy-p-menth-8-ene is a green tasting compound. 1,2-Epoxy-p-menth-8-ene has been detected, but not quantified in, a few different foods, such as celery stalks (Apium graveolens var. dulce), lemons (Citrus limon), and wild celeries (Apium graveolens). This could make 1,2-epoxy-p-menth-8-ene a potential biomarker for the consumption of these foods. 1,2-Epoxy-p-menth-8-ene is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 1,2-Epoxy-p-menth-8-ene.

Structure

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

COMPND    HMDB0035158
HETATM    1  C1  UNL     1      -2.132   1.120  -0.641  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.798   0.121   0.138  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.793  -0.989   0.375  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.475   0.070   0.787  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.352   1.259   0.630  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.280   1.297  -0.558  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.850  -0.042  -0.829  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.738  -0.538   0.307  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.702  -0.910  -1.804  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.574  -0.868  -1.135  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.171  -1.222   0.237  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.136   1.101  -1.089  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.460   1.939  -0.851  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.815  -0.626   0.274  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.623  -1.809  -0.328  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.653  -1.298   1.430  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.676  -0.204   1.867  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.227   2.193   0.647  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.985   1.330   1.579  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.835   1.767  -1.456  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.133   1.968  -0.265  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.751  -0.080   0.098  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.886  -1.623   0.287  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.433  -0.127   1.282  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.249  -0.337  -1.702  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.957  -1.491   0.935  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.610  -2.000   0.262  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9   10
CONECT    8   22   23   24
CONECT    9   10
CONECT   10   11   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Epoxylimonene	ChEBI
4-Isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane	ChEBI
Limonene 1,2-oxide	ChEBI
Limonene-1,2-epoxide, cis-isomer	MeSH
Limonene-1,2-epoxide, (1R-(1alpha,4beta,6alpha))-isomer	MeSH
Limonene-1,2-epoxide, (1S-(1alpha,4alpha,6alpha))-isomer	MeSH
Limonene-1,2-epoxide, cis-(+)-isomer	MeSH
Limonene-1,2-oxide	MeSH
Limoxide	MeSH
Limonene-1,2-epoxide, trans-(+)-isomer	MeSH
Limonene-1,2-epoxide, trans-isomer	MeSH
Limonene-1,2-epoxide	MeSH
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
Limonene 1,2-epoxide	HMDB
Limonene epoxide	HMDB
Limonene monoxide	HMDB
Limonene oxide	HMDB, MeSH

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

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

Traditional Name

limonene 1,2-epoxide

CAS Registry Number

1195-92-2

SMILES

CC(=C)C1CCC2(C)OC2C1

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

Chemical Taxonomy

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

Physiological effect

Organoleptic effect

Odor

Fruit

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035158)
Membrane (HMDB: HMDB0035158)

Source

Exogenous

Exogenous (HMDB: HMDB0035158)

Food

Herb and spice

Herb

Spearmint (FooDB: FOOD00112)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Endogenous (HMDB: HMDB0035158)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	198.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	137.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.200 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.619	31661259
DarkChem	[M-H]-	128.881	31661259
DeepCCS	[M+H]+	136.632	30932474
DeepCCS	[M-H]-	133.828	30932474
DeepCCS	[M-2H]-	170.459	30932474
DeepCCS	[M+Na]+	145.925	30932474
AllCCS	[M+H]+	133.3	32859911
AllCCS	[M+H-H2O]+	128.9	32859911
AllCCS	[M+NH4]+	137.5	32859911
AllCCS	[M+Na]+	138.7	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	138.7	32859911
AllCCS	[M+HCOO]-	140.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	4.99 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4659 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.76 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2113.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	494.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	270.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	156.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	645.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	698.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1129.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	350.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1273.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	446.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	537.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	544.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	40.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Epoxy-p-menth-8-ene	CC(=C)C1CCC2(C)OC2C1	1457.3	Standard polar	33892256
1,2-Epoxy-p-menth-8-ene	CC(=C)C1CCC2(C)OC2C1	1118.3	Standard non polar	33892256
1,2-Epoxy-p-menth-8-ene	CC(=C)C1CCC2(C)OC2C1	1142.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1,2-Epoxy-p-menth-8-ene EI-B (Non-derivatized)	splash10-052f-9200000000-fecff1839cd311e2483c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Epoxy-p-menth-8-ene EI-B (Non-derivatized)	splash10-052f-9200000000-fecff1839cd311e2483c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Epoxy-p-menth-8-ene GC-MS (Non-derivatized) - 70eV, Positive	splash10-003u-9200000000-d81e209c09694ad9f313	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Epoxy-p-menth-8-ene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Epoxy-p-menth-8-ene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 10V, Positive-QTOF	splash10-0udi-0900000000-3c1aa1a5e0f61835962d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 20V, Positive-QTOF	splash10-0udr-3900000000-86882c765e64ddc05192	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 40V, Positive-QTOF	splash10-0ldi-9000000000-a653f610d8c769c8f581	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 10V, Negative-QTOF	splash10-0udi-0900000000-b330335669a8886c1ed3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 20V, Negative-QTOF	splash10-0udi-1900000000-b7f31881782717e4ef0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 40V, Negative-QTOF	splash10-05n0-9600000000-66905c235c49a5386841	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 10V, Positive-QTOF	splash10-0udr-3900000000-fbc31cf20658ca9fcd34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 20V, Positive-QTOF	splash10-05n3-9500000000-edf4637ffc55f65c3f8f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 40V, Positive-QTOF	splash10-0fr6-9100000000-b94cebb6da5a89465afb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 20V, Negative-QTOF	splash10-0udi-0900000000-4c49b375f7aae96ad305	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Epoxy-p-menth-8-ene 40V, Negative-QTOF	splash10-1000-6900000000-ab085761a68f75073256	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91496

PDB ID

Not Available

ChEBI ID

16431

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1124781

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 1,2-Epoxy-p-menth-8-ene (HMDB0035158)

MOL for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

3D MOL for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

3D SDF for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

3D-SDF for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

PDB for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

3D PDB for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

SMILES for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

INCHI for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

Structure for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

3D Structure for HMDB0035158 (1,2-Epoxy-p-menth-8-ene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra