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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:03:37 UTC

Update Date

2023-02-21 17:25:29 UTC

HMDB ID

HMDB0036878

Secondary Accession Numbers

HMDB36878

Metabolite Identification

Common Name

1,4-Epidioxy-p-mentha-2,8-diene

Description

1,4-Epidioxy-p-mentha-2,8-diene belongs to the class of organic compounds known as 1,2-dioxanes. These are organic compounds containing 1,2-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 2. 1,4-Epidioxy-p-mentha-2,8-diene has been detected, but not quantified in, herbs and spices and parsleys (Petroselinum crispum). This could make 1,4-epidioxy-p-mentha-2,8-diene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,4-Epidioxy-p-mentha-2,8-diene.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.560   1.561   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.640   0.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.880  -0.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.560  -1.401   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.921  -0.680   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.921   0.840   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.522   1.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.961   1.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.401  -0.440   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.522  -1.561   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.159   0.360   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.960  -0.440   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9   11                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7   12                                             
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    3    8   10                                                  
CONECT   10    9                                                            
CONECT   11    3   12                                                       
CONECT   12    6   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Methyl-4-(1-methylethenyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene	HMDB

Chemical Formula

C₁₀H₁₄O₂

Average Molecular Weight

166.217

Monoisotopic Molecular Weight

166.099379692

IUPAC Name

1-methyl-4-(prop-1-en-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene

Traditional Name

1-methyl-4-(prop-1-en-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene

CAS Registry Number

120749-17-9

SMILES

CC(=C)C12CCC(C)(OO1)C=C2

InChI Identifier

InChI=1S/C10H14O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6H,1,5,7H2,2-3H3

InChI Key

RWPXEQVVWFZXTC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-dioxanes. These are organic compounds containing 1,2-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 2.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxanes

Sub Class

1,2-dioxanes

Direct Parent

1,2-dioxanes

Alternative Parents

Substituents

Ortho-dioxane
Dialkyl peroxide
Oxacycle
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: HMDB0036878)

Source

Endogenous

Endogenous (HMDB: HMDB0036878)

Plant

Plant (HMDB: HMDB0036878)

Exogenous

Food

Food (HMDB: HMDB0036878)

Herb and spice

Herb

Parsley (FooDB: FOOD00131)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036878)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036878)

Role

Biological role

Energy source (HMDB: HMDB0036878)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036878)

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	57.47 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.85 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.37	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.3 m³·mol⁻¹	ChemAxon
Polarizability	18.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	137.161	31661259
DarkChem	[M-H]-	133.837	31661259
DeepCCS	[M-2H]-	172.26	30932474
DeepCCS	[M+Na]+	147.798	30932474
AllCCS	[M+H]+	133.1	32859911
AllCCS	[M+H-H2O]+	128.6	32859911
AllCCS	[M+NH4]+	137.3	32859911
AllCCS	[M+Na]+	138.5	32859911
AllCCS	[M-H]-	136.5	32859911
AllCCS	[M+Na-2H]-	137.1	32859911
AllCCS	[M+HCOO]-	138.0	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.	5.53 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0692 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.96 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1153.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	257.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	117.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	296.2 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	300.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	421.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	687.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	40.9 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	637.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	206.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	423.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	354.5 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	159.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,4-Epidioxy-p-mentha-2,8-diene	CC(=C)C12CCC(C)(OO1)C=C2	1574.3	Standard polar	33892256
1,4-Epidioxy-p-mentha-2,8-diene	CC(=C)C12CCC(C)(OO1)C=C2	1185.7	Standard non polar	33892256
1,4-Epidioxy-p-mentha-2,8-diene	CC(=C)C12CCC(C)(OO1)C=C2	1216.7	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 - 1,4-Epidioxy-p-mentha-2,8-diene GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-3900000000-880014204e6a8f0d01b7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 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 - 1,4-Epidioxy-p-mentha-2,8-diene 10V, Positive-QTOF	splash10-014i-0900000000-86b7eed94b30ab072dbf	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 20V, Positive-QTOF	splash10-014i-0900000000-8c0cb00c2cd2b06a67b5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 40V, Positive-QTOF	splash10-0udi-0900000000-0f11aa2541d25df65f75	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 10V, Negative-QTOF	splash10-014i-0900000000-8f98cff54bce3719c5e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 20V, Negative-QTOF	splash10-014i-0900000000-1ffb0f1e97866bd44686	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 40V, Negative-QTOF	splash10-0aba-0900000000-f237090843faa72e53dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 10V, Negative-QTOF	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 20V, Negative-QTOF	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 40V, Negative-QTOF	splash10-0400-0900000000-8897bd5183183d3324d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 10V, Positive-QTOF	splash10-014i-0900000000-ddb0b4ad317a92ec611b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 20V, Positive-QTOF	splash10-00or-0900000000-296ed38e9985dedae75f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,4-Epidioxy-p-mentha-2,8-diene 40V, Positive-QTOF	splash10-00fr-0900000000-de2871e346d60659f14e	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB015836

KNApSAcK ID

C00010819

Chemspider ID

35014291

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14414153

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1636831

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 1,4-Epidioxy-p-mentha-2,8-diene (HMDB0036878)

MOL for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

3D MOL for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

3D SDF for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

3D-SDF for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

PDB for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

3D PDB for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

SMILES for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

INCHI for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

Structure for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

3D Structure for HMDB0036878 (1,4-Epidioxy-p-mentha-2,8-diene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra