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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:13 UTC
Update Date2023-02-21 17:21:55 UTC
HMDB IDHMDB0032331
Secondary Accession Numbers
  • HMDB32331
Metabolite Identification
Common Name(Z)-4-Hydroxy-6-dodecenoic acid lactone
Description(Z)-4-Hydroxy-6-dodecenoic acid lactone, also known as (Z)-6-dodecen-laquo gammaraquo -lactone or (+,-)-(Z)-6-dodecen-4-olide, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Based on a literature review very few articles have been published on (Z)-4-Hydroxy-6-dodecenoic acid lactone.
Structure
Data?1677000115
Synonyms
ValueSource
(Z)-4-Hydroxy-6-dodecenoate lactoneGenerator
(+,-)-(Z)-6-Dodecen-4-olideHMDB
(Z)-6-Dodecen-4-olideHMDB
(Z)-6-Dodecen-laquo gammaraquo -lactoneHMDB
(Z)-6-Dodeceno-laquo gammaraquo -lactoneHMDB
(Z)-6-Dodecenyl-laquo gammaraquo -lactoneHMDB
(Z)-Dihydro-5-(2-octenyl)-2(3H)-furanoneHMDB
(Z)-Dihydro-5-(2-octenyl)furan-2(3H)-oneHMDB
(Z)-Dodec-6-en-4-olideHMDB
5-[(2Z)-2-Octenyl]dihydro-2(3H)-furanoneHMDB
6-(Z)-Dodecen-laquo gammaraquo -lactoneHMDB
cis-1,4-Dodec-6-enolactoneHMDB
cis-4-Hydroxy-6-dodecenoic acid lactoneHMDB
cis-4-Hydroxydodec-6-enoic acid lactoneHMDB
cis-6-Dodecen-4-olideHMDB
cis-Laquo gammaraquo -dodec-6-enolactoneHMDB
D-Glucono-1,4-lactoneHMDB
Dihydro-5-(2-octenyl)-(Z)-2(3H)-furanoneHMDB
gamma-Dodecen-6-lactoneHMDB
Laquo gammaraquo -6-(Z)-dodecenolactoneHMDB
Laquo gammaraquo -dodec-cis-6-enolactoneHMDB
Chemical FormulaC12H20O2
Average Molecular Weight196.286
Monoisotopic Molecular Weight196.146329884
IUPAC Name5-[(2Z)-oct-2-en-1-yl]oxolan-2-one
Traditional Name5-[(2Z)-oct-2-en-1-yl]oxolan-2-one
CAS Registry Number18679-18-0
SMILES
CCCCC\C=C/CC1CCC(=O)O1
InChI Identifier
InChI=1S/C12H20O2/c1-2-3-4-5-6-7-8-11-9-10-12(13)14-11/h6-7,11H,2-5,8-10H2,1H3/b7-6-
InChI KeyQFXOXDSHNXAFEY-SREVYHEPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point159.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility64.91 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.105 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP4.23ALOGPS
logP3.39ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity57.97 m³·mol⁻¹ChemAxon
Polarizability23.24 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]+150.52231661259
DarkChem[M-H]-147.75831661259
DeepCCS[M+H]+153.6930932474
DeepCCS[M-H]-149.6730932474
DeepCCS[M-2H]-187.20730932474
DeepCCS[M+Na]+162.8730932474
AllCCS[M+H]+149.632859911
AllCCS[M+H-H2O]+145.632859911
AllCCS[M+NH4]+153.332859911
AllCCS[M+Na]+154.432859911
AllCCS[M-H]-153.832859911
AllCCS[M+Na-2H]-154.832859911
AllCCS[M+HCOO]-156.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(Z)-4-Hydroxy-6-dodecenoic acid lactoneCCCCC\C=C/CC1CCC(=O)O12410.2Standard polar33892256
(Z)-4-Hydroxy-6-dodecenoic acid lactoneCCCCC\C=C/CC1CCC(=O)O11588.1Standard non polar33892256
(Z)-4-Hydroxy-6-dodecenoic acid lactoneCCCCC\C=C/CC1CCC(=O)O11681.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bta-9600000000-547eeca455ec1144c7952017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 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 - (Z)-4-Hydroxy-6-dodecenoic acid lactone 10V, Positive-QTOFsplash10-0002-0900000000-8465ed71ed5f16cafe452016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 20V, Positive-QTOFsplash10-000b-8900000000-f1c0db0381f579ec9f3e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 40V, Positive-QTOFsplash10-0006-9000000000-2979bab4efd30bcf59702016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 10V, Negative-QTOFsplash10-0002-0900000000-9bc4df0a3eec1858c2602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 20V, Negative-QTOFsplash10-0f6t-3900000000-43b97b433e9bcb7d0cf22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 40V, Negative-QTOFsplash10-0006-9100000000-77065d8dea101d11acfb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 10V, Positive-QTOFsplash10-0aov-9300000000-71ea87e5047ff086c2472021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 20V, Positive-QTOFsplash10-0aou-9200000000-d6c73a708b7e50f125a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 40V, Positive-QTOFsplash10-0a4l-9100000000-9c8446a594178c3736172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 10V, Negative-QTOFsplash10-0002-0900000000-ef43b29361591e9067152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 20V, Negative-QTOFsplash10-0002-4900000000-a05f06285a08dfbb7f092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-4-Hydroxy-6-dodecenoic acid lactone 40V, Negative-QTOFsplash10-0apm-9200000000-2642e5c1de10a1f217822021-09-22Wishart 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+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB009601
KNApSAcK IDNot Available
Chemspider ID4509320
KEGG Compound IDC03107
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352428
PDB IDNot Available
ChEBI ID16165
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1038301
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .