Canmetcon
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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:12:42 UTC
Update Date2019-01-11 19:32:05 UTC
HMDB IDHMDB0013070
Secondary Accession Numbers
  • HMDB13070
Metabolite Identification
Common NameSinapyl alcohol
DescriptionSinapyl alcohol is an organic compound derived from cinnamic acid. This phytochemical is one of the monolignols. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. Sinapyl alcohol is a precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenes and coumarins.[From Wiki].
Structure
Data?1547235125
Synonyms
ValueSource
(e)-Sinapyl alcoholChEBI
Sinapoyl alcoholChEBI
(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
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
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These 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

Route of exposure:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61 - 65 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0ul0-1498000000-f1ff8135d3d6a46d0d5fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ul0-1498000000-f1ff8135d3d6a46d0d5fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ff0-1963000000-a61969c3a51056cf2757View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-06rl-1591000000-cc313a08a2a4a462462cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02c6-1910000000-483f5859b80c81006212View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0079-9176000000-a74c5b86187073be58d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0960000000-05c3f14530ede23c5f4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-1910000000-e9785ad5d3c4cf38a295View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fri-6900000000-6d2245e76d3fd5d9892aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-5e2811f643e53b1ae5baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0930000000-04bca1d7fd2e630f6476View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-3900000000-fe0913e64f24e42bd773View in MoNA
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
FoodDB IDFDB031178
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
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