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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:18:16 UTC
Update Date2023-02-21 17:28:27 UTC
HMDB IDHMDB0040727
Secondary Accession Numbers
  • HMDB40727
Metabolite Identification
Common Name(±)-trans-Linalyl oxide
Description(±)-trans-Linalyl oxide 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 (±)-trans-Linalyl oxide is a floral and flower tasting compound (±)-trans-Linalyl oxide is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea, black tea, and ceylon cinnamons (Cinnamomum verum) (±)-trans-Linalyl oxide has also been detected, but not quantified in, several different foods, such as tarragons (Artemisia dracunculus), cherry tomatoes (Solanum lycopersicum var. cerasiforme), papayas (Carica papaya), common oreganos (Origanum vulgare), and blackberries (Rubus). This could make (±)-trans-linalyl oxide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-trans-Linalyl oxide.
Structure
Data?1677000507
Synonyms
ValueSource
(e)-Linalool oxide aHMDB
5-ethenyltetrahydro-a,a,5-Trimethyl-(2R,5R)-rel-2-furanmethanolHMDB
e-Linalool oxide (furanoid)HMDB
Linalool oxide aHMDB
Linalool oxide IIHMDB
trans-Furanoid linalool oxideHMDB
trans-Linalool 3,6-oxideHMDB
trans-Linalool oxide (furanoid)HMDB
Chemical FormulaC10H18O2
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
IUPAC Name2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
Traditional Name2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
CAS Registry Number34995-77-2
SMILES
CC(C)(O)[C@@H]1CC[C@](C)(O1)C=C
InChI Identifier
InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10+/m0/s1
InChI KeyBRHDDEIRQPDPMG-WCBMZHEXSA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydrofurans
Sub ClassNot Available
Direct ParentTetrahydrofurans
Alternative Parents
Substituents
  • Tetrahydrofuran
  • Tertiary alcohol
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point201.00 to 202.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1669 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.557 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.5 g/LALOGPS
logP1.51ALOGPS
logP1.67ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)14.32ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.04 m³·mol⁻¹ChemAxon
Polarizability19.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.0431661259
DarkChem[M-H]-137.64931661259
DeepCCS[M+H]+141.58530932474
DeepCCS[M-H]-139.18930932474
DeepCCS[M-2H]-172.33130932474
DeepCCS[M+Na]+147.49730932474
AllCCS[M+H]+138.132859911
AllCCS[M+H-H2O]+133.932859911
AllCCS[M+NH4]+142.132859911
AllCCS[M+Na]+143.332859911
AllCCS[M-H]-141.732859911
AllCCS[M+Na-2H]-143.132859911
AllCCS[M+HCOO]-144.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-trans-Linalyl oxideCC(C)(O)[C@@H]1CC[C@](C)(O1)C=C1446.9Standard polar33892256
(??)-trans-Linalyl oxideCC(C)(O)[C@@H]1CC[C@](C)(O1)C=C1079.7Standard non polar33892256
(??)-trans-Linalyl oxideCC(C)(O)[C@@H]1CC[C@](C)(O1)C=C1073.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)-trans-Linalyl oxide,1TMS,isomer #1C=C[C@]1(C)CC[C@@H](C(C)(C)O[Si](C)(C)C)O11220.0Semi standard non polar33892256
(??)-trans-Linalyl oxide,1TBDMS,isomer #1C=C[C@]1(C)CC[C@@H](C(C)(C)O[Si](C)(C)C(C)(C)C)O11447.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (±)-trans-Linalyl oxide EI-B (Non-derivatized)splash10-052f-9000000000-e8c8defcb13d413ce23b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (±)-trans-Linalyl oxide EI-B (Non-derivatized)splash10-052f-9000000000-e8c8defcb13d413ce23b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-trans-Linalyl oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-d76b0d8bd5839f5bad932016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-trans-Linalyl oxide GC-MS (1 TMS) - 70eV, Positivesplash10-003r-9720000000-d7880141bef77c136d152017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-trans-Linalyl 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 - (±)-trans-Linalyl oxide 10V, Positive-QTOFsplash10-00di-1900000000-3717374e13c0e4e46e012016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 20V, Positive-QTOFsplash10-0fl0-7900000000-1a57b949dcbd663fc1eb2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 40V, Positive-QTOFsplash10-0pbi-9000000000-29f24016ec67ee4e749b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 10V, Negative-QTOFsplash10-014i-0900000000-92d23807ba882368b9c52016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 20V, Negative-QTOFsplash10-014i-1900000000-9591ca26dd3aa91ec77b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 40V, Negative-QTOFsplash10-00m0-9400000000-adb5d889f7dfc0e0d5582016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 10V, Negative-QTOFsplash10-014i-0900000000-efbd93a1a83feefc94df2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 20V, Negative-QTOFsplash10-0aor-3900000000-6b8e798821e4115bf1d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 40V, Negative-QTOFsplash10-0a4i-9100000000-ace0a44f890d3bb407342021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 10V, Positive-QTOFsplash10-00di-8900000000-a536912550058a32831e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 20V, Positive-QTOFsplash10-0f7p-9100000000-b3759eefd18d5faed1022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-trans-Linalyl oxide 40V, Positive-QTOFsplash10-0kc6-9000000000-369ce7815f6cf7814da32021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB020535
KNApSAcK IDC00034496
Chemspider ID4937513
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6432254
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1384891
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.. .