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Showing Compound (R)-Synephrine (FDB000709)

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
MOLSDFPDBSMILESInChI
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
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 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Cardiovascular38070 A system that transports blood, oxygen, and nutrients throughout the body, playing a crucial role in overall health. Therapeutically, cardiovascular agents manage conditions like hypertension, heart failure, and atherosclerosis, with key medical uses including regulating blood pressure, preventing blood clots, and improving cardiac function.DUKE
HypertensiveAn agent that increases blood pressure, used therapeutically to treat hypotension (low blood pressure) and shock, and medically to manage conditions such as orthostatic hypotension and postural hypotension.DUKE
Oxytocic36063 A hormone that stimulates uterine contractions, playing a key role in childbirth and lactation. Therapeutically, it induces labor, controls postpartum bleeding, and promotes milk letdown. Medical uses include augmenting labor, treating postpartum hemorrhage, and assisting with breastfeeding.DUKE
Vasoconstrictor50514 An agent that narrows blood vessels, reducing blood flow. It plays a biological role in regulating blood pressure and is therapeutically used to treat conditions like hypotension, nasal congestion, and bleeding. Key medical uses include managing shock, reducing bleeding during surgery, and relieving migraine headaches.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).