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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:12:42 UTC
Update Date2021-10-13 05:38:04 UTC
HMDB IDHMDB0013070
Secondary Accession Numbers
  • HMDB13070
Metabolite Identification
Common NameSinapyl alcohol
DescriptionSinapyl alcohol belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Sinapyl alcohol has been detected, but not quantified in, several different foods, such as french plantains (Musa X paradisiaca), mamey sapotes (Pouteria sapota), green onion, oil palms (Elaeis), and lotus (Nelumbo). This could make sinapyl alcohol a potential biomarker for the consumption of these foods. Sinapyl alcohol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Sinapyl alcohol.
Structure
Data?1586961983
Synonyms
ValueSource
(e)-Sinapoyl alcoholChEBI
Sinapoyl alcoholChEBI
(e)-Sinapyl alcoholChEBI, HMDB
(e)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propen-1-olHMDB
4-(3-Hydroxy-1-propenyl)-2,6-dimethoxy-phenolHMDB
4-(3-Hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenolHMDB
4-Hydroxy-3,5-dimethoxycinnamyl alcoholHMDB
Sinapic alcoholHMDB
Sinapyl alcohol(e)HMDB
Sinapyl-alcoholHMDB
Sinapyl alcoholMeSH
trans-Sinapoyl alcoholChEBI
Chemical FormulaC11H14O4
Average Molecular Weight210.2265
Monoisotopic Molecular Weight210.089208936
IUPAC Name4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenol
Traditional Namesinapyl alcohol
CAS Registry Number537-33-7
SMILES
COC1=CC(\C=C\CO)=CC(OC)=C1O
InChI Identifier
InChI=1S/C11H14O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-4,6-7,12-13H,5H2,1-2H3/b4-3+
InChI KeyLZFOPEXOUVTGJS-ONEGZZNKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Cinnamyl alcohol
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point61 - 65 °CNot Available
Boiling Point384.00 to 385.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility17130 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.361 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg146.84330932474
[M-H]-Not Available146.843http://allccs.zhulab.cn/database/detail?ID=AllCCS00000310
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP1.36ALOGPS
logP1.2ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.1 m³·mol⁻¹ChemAxon
Polarizability22.26 ųChemAxon
Number of Rings1ChemAxon
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]+150.92231661259
DarkChem[M-H]-150.45231661259
DeepCCS[M+H]+147.50330932474
DeepCCS[M-H]-145.14530932474
DeepCCS[M-2H]-179.63930932474
DeepCCS[M+Na]+155.06530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Sinapyl alcoholCOC1=CC(\C=C\CO)=CC(OC)=C1O3224.7Standard polar33892256
Sinapyl alcoholCOC1=CC(\C=C\CO)=CC(OC)=C1O1877.0Standard non polar33892256
Sinapyl alcoholCOC1=CC(\C=C\CO)=CC(OC)=C1O1981.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sinapyl alcohol,1TMS,isomer #1COC1=CC(/C=C/CO[Si](C)(C)C)=CC(OC)=C1O2047.2Semi standard non polar33892256
Sinapyl alcohol,1TMS,isomer #2COC1=CC(/C=C/CO)=CC(OC)=C1O[Si](C)(C)C1967.4Semi standard non polar33892256
Sinapyl alcohol,2TMS,isomer #1COC1=CC(/C=C/CO[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C2053.8Semi standard non polar33892256
Sinapyl alcohol,1TBDMS,isomer #1COC1=CC(/C=C/CO[Si](C)(C)C(C)(C)C)=CC(OC)=C1O2288.7Semi standard non polar33892256
Sinapyl alcohol,1TBDMS,isomer #2COC1=CC(/C=C/CO)=CC(OC)=C1O[Si](C)(C)C(C)(C)C2238.6Semi standard non polar33892256
Sinapyl alcohol,2TBDMS,isomer #1COC1=CC(/C=C/CO[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C2535.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Sinapyl alcohol GC-MS (2 TMS)splash10-0ul0-1498000000-f1ff8135d3d6a46d0d5f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapyl alcohol GC-MS (Non-derivatized)splash10-0ul0-1498000000-f1ff8135d3d6a46d0d5f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapyl alcohol GC-EI-TOF (Non-derivatized)splash10-0ff0-1963000000-a61969c3a51056cf27572017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sinapyl alcohol GC-EI-TOF (Non-derivatized)splash10-06rl-1591000000-cc313a08a2a4a462462c2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinapyl alcohol GC-MS (Non-derivatized) - 70eV, Positivesplash10-02c6-1910000000-483f5859b80c810062122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinapyl alcohol GC-MS (2 TMS) - 70eV, Positivesplash10-0079-9176000000-a74c5b86187073be58d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sinapyl alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol LC-ESI-QTOF 35V, negative-QTOFsplash10-0a4i-0090000000-602a2e14b33c30c3e91a2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol n/a 14V, negative-QTOFsplash10-00di-0009100000-36f51ff1821919e02dca2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol n/a 14V, negative-QTOFsplash10-0006-0900000000-3a73e5daddcd05b7914d2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol n/a 14V, positive-QTOFsplash10-03di-0900000000-be9c70dc000fe516c98e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol n/a 14V, positive-QTOFsplash10-002b-0900000000-dd341f985c8717688c862020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol n/a 14V, positive-QTOFsplash10-0a4i-0390000000-23fd3e2b83322f5cbdf72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 3V, positive-QTOFsplash10-03dl-0900000000-7590f4f1f32763b2765b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 4V, positive-QTOFsplash10-03dl-0900000000-20d8d646de0bb37740902020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 5V, positive-QTOFsplash10-03di-0900000000-caf158fef19ad3b6bb652020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 7V, positive-QTOFsplash10-03di-0900000000-fb34fca92160edf417372020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 10V, positive-QTOFsplash10-03e9-0900000000-1ab7dc6b13aeb403011b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 15V, positive-QTOFsplash10-0bu0-0900000000-e5d28e66343eef2876db2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 17V, positive-QTOFsplash10-0api-1900000000-a5be2f9ca060395b24fa2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 20V, positive-QTOFsplash10-0api-1900000000-12d11ae51510e9082ac12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 25V, positive-QTOFsplash10-069r-3900000000-b6fa51093a215d65de962020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 27V, positive-QTOFsplash10-0690-3900000000-146837c3a0ceff99347f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 30V, positive-QTOFsplash10-0lfu-6900000000-d563c428d1b44f2113772020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 33V, positive-QTOFsplash10-00ou-9800000000-79fe37355291b2e02ae22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sinapyl alcohol QTOF 35V, positive-QTOFsplash10-0fvl-9700000000-e9c1d0f950c1d92969342020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapyl alcohol 10V, Positive-QTOFsplash10-01ox-0960000000-05c3f14530ede23c5f4c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapyl alcohol 20V, Positive-QTOFsplash10-01ox-1910000000-e9785ad5d3c4cf38a2952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapyl alcohol 40V, Positive-QTOFsplash10-0fri-6900000000-6d2245e76d3fd5d9892a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapyl alcohol 10V, Negative-QTOFsplash10-0a4i-0390000000-5e2811f643e53b1ae5ba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapyl alcohol 20V, Negative-QTOFsplash10-0a4l-0930000000-04bca1d7fd2e630f64762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sinapyl alcohol 40V, Negative-QTOFsplash10-000l-3900000000-fe0913e64f24e42bd7732017-09-01Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB029281
KNApSAcK IDC00002778
Chemspider ID4444145
KEGG Compound IDC02325
BioCyc IDSINAPYL-ALCOHOL
BiGG IDNot Available
Wikipedia LinkSinapyl alcohol
METLIN IDNot Available
PubChem Compound5280507
PDB ID55B
ChEBI ID64557
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1282941
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
Reactions
Sinapyl alcohol → Syringyl lignindetails