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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:15:03 UTC

Update Date

2022-03-07 02:55:09 UTC

HMDB ID

HMDB0037008

Secondary Accession Numbers

HMDB37008

Metabolite Identification

Common Name

6,8-Epoxy-p-menth-2-ene

Description

6,8-Epoxy-p-menth-2-ene belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. 6,8-Epoxy-p-menth-2-ene has been detected, but not quantified in, several different foods, such as herbs and spices, green tea, teas (Camellia sinensis), red tea, and herbal tea. This could make 6,8-epoxy-p-menth-2-ene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6,8-Epoxy-p-menth-2-ene.

Structure

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

COMPND    HMDB0037008
HETATM    1  C1  UNL     1      -2.410  -0.945   1.075  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.936   0.086   0.095  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.542  -0.598  -1.156  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.242  -0.620  -1.514  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.683   0.421  -1.058  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.174   1.605  -0.588  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.793   0.929   0.645  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.181   0.133   1.189  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.213  -0.017   0.314  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.726  -1.410   0.157  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.394   0.884   0.608  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.601  -0.528   2.083  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.390  -1.324   0.711  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.737  -1.838   1.132  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.784   0.771  -0.104  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.305  -1.066  -1.759  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.106  -1.415  -2.140  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.465   0.709  -1.745  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.441   2.468  -0.317  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.966   1.828  -1.334  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.155   1.717   1.324  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.642  -1.350  -0.493  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.012  -2.048  -0.362  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.041  -1.813   1.156  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.420   1.779  -0.053  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.350   1.285   1.647  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.361   0.358   0.486  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    7   15
CONECT    3    4    4   16
CONECT    4    5   17
CONECT    5    6    9   18
CONECT    6    7   19   20
CONECT    7    8   21
CONECT    8    9
CONECT    9   10   11
CONECT   10   22   23   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

4,7,7-trimethyl-6-oxabicyclo[3.2.1]oct-2-ene

Traditional Name

4,7,7-trimethyl-6-oxabicyclo[3.2.1]oct-2-ene

CAS Registry Number

52812-45-0

SMILES

CC1C=CC2CC1OC2(C)C

InChI Identifier

InChI=1S/C10H16O/c1-7-4-5-8-6-9(7)11-10(8,2)3/h4-5,7-9H,6H2,1-3H3

InChI Key

OVUFWOJDFGZYRB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037008)

Source

Endogenous

Endogenous (HMDB: HMDB0037008)

Plant

Plant (HMDB: HMDB0037008)

Exogenous

Food

Food (HMDB: HMDB0037008)

Tea

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0037008)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0037008)

Role

Biological role

Energy source (HMDB: HMDB0037008)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037008)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.07	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.81 m³·mol⁻¹	ChemAxon
Polarizability	17.79 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]+	133.724	31661259
DarkChem	[M-H]-	130.59	31661259
DeepCCS	[M+H]+	136.484	30932474
DeepCCS	[M-H]-	133.444	30932474
DeepCCS	[M-2H]-	170.256	30932474
DeepCCS	[M+Na]+	145.794	30932474
AllCCS	[M+H]+	131.4	32859911
AllCCS	[M+H-H2O]+	126.8	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	136.9	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	138.8	32859911
AllCCS	[M+HCOO]-	140.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6,8-Epoxy-p-menth-2-ene	CC1C=CC2CC1OC2(C)C	1277.1	Standard polar	33892256
6,8-Epoxy-p-menth-2-ene	CC1C=CC2CC1OC2(C)C	1059.6	Standard non polar	33892256
6,8-Epoxy-p-menth-2-ene	CC1C=CC2CC1OC2(C)C	1086.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6,8-Epoxy-p-menth-2-ene GC-MS (Non-derivatized) - 70eV, Positive	splash10-01r6-9600000000-e9b45e6098b4a528e8c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6,8-Epoxy-p-menth-2-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 - 6,8-Epoxy-p-menth-2-ene 10V, Positive-QTOF	splash10-0udi-0900000000-450a7457b9acbb7ca07e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 20V, Positive-QTOF	splash10-0w2c-6900000000-e82cf173490a0ed65755	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 40V, Positive-QTOF	splash10-1000-9100000000-75d8d2807d0187539588	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 10V, Negative-QTOF	splash10-0udi-0900000000-e2733f2df14e4efb5524	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 20V, Negative-QTOF	splash10-0udi-0900000000-eac33084e27b4fb7d130	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 40V, Negative-QTOF	splash10-0a5l-9600000000-761ac5369b8375ce55b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 20V, Negative-QTOF	splash10-0udi-0900000000-3f022e72c205286a6ff4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 40V, Negative-QTOF	splash10-0f6t-2900000000-cf0b0ecdf62a9d33127f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 10V, Positive-QTOF	splash10-0uds-5900000000-f661022989349108b094	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 20V, Positive-QTOF	splash10-000e-9300000000-715215506c18f76ba8c6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,8-Epoxy-p-menth-2-ene 40V, Positive-QTOF	splash10-0006-9000000000-f21bcfbc2b2f48521984	2021-09-25	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

FDB015983

KNApSAcK ID

C00010839

Chemspider ID

35014346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72746984

PDB ID

Not Available

ChEBI ID

171974

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 6,8-Epoxy-p-menth-2-ene (HMDB0037008)

MOL for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

3D MOL for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

3D SDF for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

3D-SDF for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

PDB for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

3D PDB for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

SMILES for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

INCHI for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

Structure for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

3D Structure for HMDB0037008 (6,8-Epoxy-p-menth-2-ene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra