Record Information
Version1.0
Creation date2010-04-08 22:04:41 UTC
Update date2019-11-26 02:55:16 UTC
Primary IDFDB000709
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(R)-Synephrine
Description(R)-Synephrine belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position (R)-Synephrine is a very strong basic compound (based on its pKa) (R)-Synephrine has been detected, but not quantified in, several different foods, such as citrus, fruits, lemons, mandarin orange (clementine, tangerine), and sweet oranges. This could make (R)-synephrine a potential biomarker for the consumption of these foods.
CAS Number94-07-5
Structure
Thumb
Synonyms
SynonymSource
(+)-[(Methylamino)methyl]-benzenemethanoHMDB
(+)-P-SynephrineHMDB
(+)-SynephrineHMDB
(+/-)-synephrineChEBI
1-(4-Hydroxyphenyl)-2-(methylamino)ethanolChEBI
1-(4-Hydroxyphenyl)-2-methylaminoethanolChEBI
4-Hydroxy-a-[(methylamino)methyl]benzenemethanolGenerator
4-Hydroxy-alpha-[(methylamino)methyl]benzenemethanolChEBI
4-Hydroxy-α-[(methylamino)methyl]benzenemethanolGenerator
b-Methylamino-a-(4-hydroxyphenyl)ethyl alcoholGenerator
beta-Methylamino-alpha-(4-hydroxyphenyl)ethyl alcoholChEBI
L-Synephrinemanual
OxedrineChEBI
P-Hydroxy-a-[(methylamino)methyl]benzyl alcoholGenerator
P-Hydroxy-alpha-[(methylamino)methyl]benzyl alcoholChEBI
P-Hydroxy-α-[(methylamino)methyl]benzyl alcoholGenerator
p-Synephrinemanual
ParasympatolHMDB
R-(-)-Synephrinemanual
SimpatolHMDB
SympaethaminHMDB
SympaethamineHMDB
SympatolChEBI
Synephrinebiospider
β-methylamino-α-(4-hydroxyphenyl)ethyl alcoholGenerator
Predicted Properties
PropertyValueSource
Water Solubility46.9 g/LALOGPS
logP-0.73ALOGPS
logP0.74ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)8.13ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.17 m³·mol⁻¹ChemAxon
Polarizability19.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H13NO3
IUPAC name4-[(R)-hydroxy[(methylamino)methoxy]methyl]phenol
InChI IdentifierInChI=1S/C9H13NO3/c1-10-6-13-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m1/s1
InChI KeyGBBBJHCSNNEWLH-SECBINFHSA-N
Isomeric SMILESCNCO[C@@H](O)C1=CC=C(O)C=C1
Average Molecular Weight183.2044
Monoisotopic Molecular Weight183.089543287
Classification
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Hemiaminal
  • Hemiacetal
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 64.65%; H 7.84%; N 8.38%; O 19.14%DFC
Melting PointMp 162-164° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-0.45HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -55.6 (c, 0.5 in M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID6904
ChEMBL IDCHEMBL33720
KEGG Compound IDC04548
Pubchem Compound ID7172
Pubchem Substance IDNot Available
ChEBI ID119
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04826
CRC / DFC (Dictionary of Food Compounds) IDBZZ90-X:BFT10-L
EAFUS IDNot Available
Dr. Duke IDSYNEPHRINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSynephrine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiovascular38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
hypertensiveDUKE
oxytocic36063 A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).DUKE
vasoconstrictor50514 Drug used to cause constriction of the blood vessels.DUKE
Enzymes
NameGene NameUniProt ID
Alpha-2A adrenergic receptorADRA2AP08913
Alpha-2B adrenergic receptorADRA2BP18089
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).