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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:44:37 UTC
Update Date2023-02-21 17:27:53 UTC
HMDB IDHMDB0040205
Secondary Accession Numbers
  • HMDB40205
Metabolite Identification
Common Name3-Methylbutyl 3-hydroxy-2-methylidenebutanoate
Description3-Methylbutyl 3-hydroxy-2-methylidenebutanoate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate has been detected, but not quantified in, herbs and spices. This could make 3-methylbutyl 3-hydroxy-2-methylidenebutanoate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate.
Structure
Data?1677000473
Synonyms
ValueSource
3-Methylbutyl 3-hydroxy-2-methylidenebutanoic acidGenerator
Chemical FormulaC10H18O3
Average Molecular Weight186.2481
Monoisotopic Molecular Weight186.125594442
IUPAC Name3-methylbutyl 3-hydroxy-2-methylidenebutanoate
Traditional Name3-methylbutyl 3-hydroxy-2-methylidenebutanoate
CAS Registry Number80758-72-1
SMILES
CC(C)CCOC(=O)C(=C)C(C)O
InChI Identifier
InChI=1S/C10H18O3/c1-7(2)5-6-13-10(12)8(3)9(4)11/h7,9,11H,3,5-6H2,1-2,4H3
InChI KeyURBTVTZTLQVLCO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Fatty acid ester
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2575 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.99 g/LALOGPS
logP2.06ALOGPS
logP2.05ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)14.67ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.03 m³·mol⁻¹ChemAxon
Polarizability21.39 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.03431661259
DarkChem[M-H]-140.36431661259
DeepCCS[M+H]+147.39830932474
DeepCCS[M-H]-144.6730932474
DeepCCS[M-2H]-181.04630932474
DeepCCS[M+Na]+156.57730932474
AllCCS[M+H]+145.032859911
AllCCS[M+H-H2O]+141.432859911
AllCCS[M+NH4]+148.332859911
AllCCS[M+Na]+149.332859911
AllCCS[M-H]-144.732859911
AllCCS[M+Na-2H]-146.332859911
AllCCS[M+HCOO]-148.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methylbutyl 3-hydroxy-2-methylidenebutanoateCC(C)CCOC(=O)C(=C)C(C)O1807.6Standard polar33892256
3-Methylbutyl 3-hydroxy-2-methylidenebutanoateCC(C)CCOC(=O)C(=C)C(C)O1237.5Standard non polar33892256
3-Methylbutyl 3-hydroxy-2-methylidenebutanoateCC(C)CCOC(=O)C(=C)C(C)O1268.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methylbutyl 3-hydroxy-2-methylidenebutanoate,1TMS,isomer #1C=C(C(=O)OCCC(C)C)C(C)O[Si](C)(C)C1360.7Semi standard non polar33892256
3-Methylbutyl 3-hydroxy-2-methylidenebutanoate,1TBDMS,isomer #1C=C(C(=O)OCCC(C)C)C(C)O[Si](C)(C)C(C)(C)C1573.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-9000000000-2d8aa32f0aee738610282017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9310000000-dff46ec742a31ca355e42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 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 - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 10V, Positive-QTOFsplash10-014r-3900000000-46e7503ba08f7efc1a2e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 20V, Positive-QTOFsplash10-00di-9200000000-bd0d433d801577b2f97b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 40V, Positive-QTOFsplash10-0pir-9000000000-036a4301b11aa4a0c3a62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 10V, Negative-QTOFsplash10-000i-2900000000-7d05421ff2a5235e105e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 20V, Negative-QTOFsplash10-01ba-9500000000-7a457f653a43a494bc342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 40V, Negative-QTOFsplash10-00xr-9000000000-f6285fe8154838b4bc922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 10V, Positive-QTOFsplash10-0002-9300000000-67c32606ebfd9d9bf3c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 20V, Positive-QTOFsplash10-007k-9000000000-2ef4574d78a4f7cb2db02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 40V, Positive-QTOFsplash10-0aba-9000000000-a5794991aa881f83c6932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 10V, Negative-QTOFsplash10-00kr-5900000000-d956e6eb789750fc15da2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 20V, Negative-QTOFsplash10-00rl-9200000000-16342c389986d90a412a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylbutyl 3-hydroxy-2-methylidenebutanoate 40V, Negative-QTOFsplash10-00di-9000000000-3149e6ba364d6caea8202021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDFDB019917
KNApSAcK IDNot Available
Chemspider ID479563
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound551273
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1624361
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.. .