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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:09:52 UTC
Update Date2021-10-13 06:53:47 UTC
HMDB IDHMDB0036097
Secondary Accession Numbers
  • HMDB36097
Metabolite Identification
Common NameRose oxide
DescriptionRose oxide belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. Rose oxide is a fresh, geranium, and green tasting compound. Rose oxide is found, on average, in the highest concentration within lemon balms (Melissa officinalis) and peppermints (Mentha X piperita). Rose oxide has also been detected, but not quantified in, a few different foods, such as black elderberries (Sambucus nigra), cucumbers (Cucumis sativus), and gingers (Zingiber officinale). This could make rose oxide a potential biomarker for the consumption of these foods. Rose oxide 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 Rose oxide.
Structure
Data?1563862820
Synonyms
ValueSource
4-Methyl-2-(2-methyl-1-propenyl)tetrahydro-2H-pyranChEBI
Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyranChEBI
Tetrahydro-4-methyl-2-(2-methylprop-1-enyl)pyranChEBI
Rose-oxideMeSH
(Z)-Rose oxideHMDB
2-Isobutenyl-4-methyltetrahydropyranHMDB
cis Rose oxideHMDB
FEMA 3236HMDB
Rose oxide , IHMDB
Rose oxide cisHMDB
Rose oxide levoHMDB
tetrahydro-4-Methyl-2-(2-methyl-1-propenyl)pyran, 9ciHMDB
tetrahydro-4-Methyl-2-[2-methyl-1-propenyl]-2H-pyranHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name4-methyl-2-(2-methylprop-1-en-1-yl)oxane
Traditional Namerose oxide
CAS Registry Number16409-43-1
SMILES
CC1CCOC(C1)C=C(C)C
InChI Identifier
InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3
InChI KeyCZCBTSFUTPZVKJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxanes
Sub ClassNot Available
Direct ParentOxanes
Alternative Parents
Substituents
  • Oxane
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point86.00 °C. @ 20.00 mm HgThe Good Scents Company Information System
Water Solubility764 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP3.186 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP10(3.3) g/LALOGPS
logP10(2.68) g/LChemAxon
logS10(-2.6) g/LALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.49 m³·mol⁻¹ChemAxon
Polarizability19.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.7831661259
DarkChem[M-H]-134.44331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Rose oxideCC1CCOC(C1)C=C(C)C1328.5Standard polar33892256
Rose oxideCC1CCOC(C1)C=C(C)C1094.1Standard non polar33892256
Rose oxideCC1CCOC(C1)C=C(C)C1106.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rose oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aos-9500000000-2daa25f61007ae428cb82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rose oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 10V, Positive-QTOFsplash10-0a4i-1900000000-149372f88fa8074a4bd12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 20V, Positive-QTOFsplash10-0aor-9600000000-f302a974d3f4b7aff64a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 40V, Positive-QTOFsplash10-0ldl-9000000000-3c15002efcc5364698db2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 10V, Positive-QTOFsplash10-0a4i-1900000000-149372f88fa8074a4bd12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 20V, Positive-QTOFsplash10-0aor-9600000000-f302a974d3f4b7aff64a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 40V, Positive-QTOFsplash10-0ldl-9000000000-3c15002efcc5364698db2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 10V, Negative-QTOFsplash10-0udi-1900000000-7b1cc721b7f61d370f4e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 20V, Negative-QTOFsplash10-0udi-4900000000-415021470c7b3b804fbf2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 40V, Negative-QTOFsplash10-0ap0-9100000000-a526a89a3df301bc7f2b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 10V, Negative-QTOFsplash10-0udi-1900000000-7b1cc721b7f61d370f4e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 20V, Negative-QTOFsplash10-0udi-4900000000-415021470c7b3b804fbf2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 40V, Negative-QTOFsplash10-0ap0-9100000000-a526a89a3df301bc7f2b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 10V, Negative-QTOFsplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 20V, Negative-QTOFsplash10-0udi-3900000000-a44a1691a9a96f7a67252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 40V, Negative-QTOFsplash10-0a4i-9000000000-d8ae95f38480653597982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 10V, Positive-QTOFsplash10-03di-5900000000-cf9f07d1c2ded48f26aa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 20V, Positive-QTOFsplash10-0a4i-9000000000-d0a837c1536a267f15ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rose oxide 40V, Positive-QTOFsplash10-0ap3-9000000000-c976c3394c5736040c1e2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014937
KNApSAcK IDC00053057
Chemspider ID25927
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRose_oxide
METLIN IDNot Available
PubChem Compound27866
PDB IDNot Available
ChEBI ID90075
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1035651
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .