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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 02:18:13 UTC
Update Date2023-02-21 17:28:26 UTC
HMDB IDHMDB0040726
Secondary Accession Numbers
  • HMDB40726
Metabolite Identification
Common Name(±)-cis-Linalyl oxide
Description(±)-cis-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 (±)-cis-Linalyl oxide is a sweet, earthy, and floral tasting compound (±)-cis-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 and black tea (±)-cis-Linalyl oxide has also been detected, but not quantified in, several different foods, such as blackberries (Rubus), black elderberries (Sambucus nigra), common oreganos (Origanum vulgare), garden tomato (var.), and tarragons (Artemisia dracunculus). This could make (±)-cis-linalyl oxide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (±)-cis-Linalyl oxide.
Structure
Data?1677000506
Synonyms
ValueSource
cis-Linalyl oxideChEBI
(Z)-Furanoid linalool oxideHMDB
5-ethenyltetrahydro-a,a,5-Trimethyl-(2R,5S)-rel-2-furanmethanolHMDB
5-ethenyltetrahydro-a,a,5-Trimethyl-cis-2-furanmethanolHMDB
cis-Furanoid linalool oxideHMDB
cis-Linalool 3,6-oxideHMDB
Linalool oxide bHMDB
Linalool oxide IHMDB
Chemical FormulaC10H18O2
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
IUPAC Name2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
Traditional Name2-[(2R,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
CAS Registry Number5989-33-3
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-/m1/s1
InChI KeyBRHDDEIRQPDPMG-PSASIEDQSA-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 Point188.00 to 192.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1669 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.764 (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
Polarizability19.43 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]+140.51431661259
DarkChem[M-H]-138.80431661259
DeepCCS[M+H]+140.98430932474
DeepCCS[M-H]-138.58930932474
DeepCCS[M-2H]-171.7930932474
DeepCCS[M+Na]+146.89730932474
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
(??)-cis-Linalyl oxideCC(C)(O)[C@H]1CC[C@](C)(O1)C=C1446.9Standard polar33892256
(??)-cis-Linalyl oxideCC(C)(O)[C@H]1CC[C@](C)(O1)C=C1079.7Standard non polar33892256
(??)-cis-Linalyl oxideCC(C)(O)[C@H]1CC[C@](C)(O1)C=C1073.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)-cis-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
(??)-cis-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
Predicted GC-MSPredicted GC-MS Spectrum - (±)-cis-Linalyl oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-d76b0d8bd5839f5bad932016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-cis-Linalyl oxide GC-MS (1 TMS) - 70eV, Positivesplash10-003r-9720000000-d7880141bef77c136d152017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-cis-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 - (±)-cis-Linalyl oxide 10V, Positive-QTOFsplash10-00di-1900000000-3717374e13c0e4e46e012016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 20V, Positive-QTOFsplash10-0fl0-7900000000-1a57b949dcbd663fc1eb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 40V, Positive-QTOFsplash10-0pbi-9000000000-29f24016ec67ee4e749b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 10V, Negative-QTOFsplash10-014i-0900000000-92d23807ba882368b9c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 20V, Negative-QTOFsplash10-014i-1900000000-9591ca26dd3aa91ec77b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 40V, Negative-QTOFsplash10-00m0-9400000000-adb5d889f7dfc0e0d5582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 10V, Positive-QTOFsplash10-00di-8900000000-a536912550058a32831e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 20V, Positive-QTOFsplash10-0f7p-9100000000-b3759eefd18d5faed1022021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 40V, Positive-QTOFsplash10-0kc6-9000000000-369ce7815f6cf7814da32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 10V, Negative-QTOFsplash10-014i-0900000000-efbd93a1a83feefc94df2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 20V, Negative-QTOFsplash10-0aor-3900000000-6b8e798821e4115bf1d02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-cis-Linalyl oxide 40V, Negative-QTOFsplash10-0a4i-9100000000-ace0a44f890d3bb407342021-09-25Wishart 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 Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020534
KNApSAcK IDC00034746
Chemspider ID4933975
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6428573
PDB IDNot Available
ChEBI ID132839
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1432371
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.. .