Tyramine (YMDB01797)

Identification

YMDB ID

YMDB01797

Name

Tyramine

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Tyramine (p-hydroxyphenethylamine) is a biogenic amine. Biogenic amines (e.g. histamine, tyramine, phenylethylamine) are produced in fermented foods and beverages as a consequence of decarboxylation of amino acids by lactic acid bacteria (LAB). Biogenic amines in foods and beverages are undesirable because they may induce food-borne intoxications if consumed at too high concentration. [Landete 2007]

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-(4-Hydroxyphenyl)ethylamine
2-(4'-Hydroxyphenyl)ethylamine
2-(P-Hydroxyphenyl)ethylamine
4- (2-Aminoethyl)-phenol
4-(2-Aminoethyl)-phenol
4-(2-Aminoethyl)-phenol(thyramin)
4-(2-Aminoethyl)phenol
4-Hydroxy-b-phenylethylamine
4-Hydroxy-benzeneethanamine
4-Hydroxy-beta-phenylethylamine
4-Hydroxyphenethylamine
4-Hydroxyphenylethylamine
a-(4-Hydroxyphenyl)-b-aminoethane
alpha-(4-Hydroxyphenyl)-beta-aminoethane
Alpha.-(4-hydroxyphenyl)-beta-aminoethane
b-(4-Hydroxyphenyl)ethylamine
beta-(4-Hydroxyphenyl)ethylamine
P-(2-Aminoethyl)-phenol
P-(2-Aminoethyl)phenol
P-beta-Aminoethylphenol
P-Hydroxy-b-phenethylamine
P-Hydroxy-b-phenylethylamine
P-Hydroxy-beta-phenethylamine
P-Hydroxy-beta-phenylethylamine
P-Hydroxyphenethylamine
P-Hydroxyphenylethylamine
P-Tyramine
Para-tyramine
Systogene
Tenosin-wirkstoff
Tocosine
Tyramin
Tyramine base
Tyrosamine
Uteramine
4-Hydroxy-β-phenylethylamine
Β-(4-hydroxyphenyl)ethylamine
4 Hydroxyphenethylamine
2-(4-Hydroxyphenyl)ethanamine
2-(4’-hydroxyphenyl)ethylamine
p-Hydroxy-β-phenylethylamine
p-Β-aminoethylphenol
Α-(4-hydroxyphenyl)-β-aminoethane

CAS number

51-67-2

Weight

Average: 137.179
Monoisotopic: 137.084063979

InChI Key

DZGWFCGJZKJUFP-UHFFFAOYSA-N

InChI

InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2

IUPAC Name

4-(2-aminoethyl)phenol

Traditional IUPAC Name

tyramine

Chemical Formula

C₈H₁₁NO

SMILES

NCCC1=CC=C(O)C=C1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Phenethylamine
2-arylethylamine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monoamine molecular messenger (CHEBI:15760 )
primary amino compound (CHEBI:15760 )
tyramines (CHEBI:15760 )
Biogenic amines (C00483 )
Tyramine derivatives (C00483 )

Physical Properties

State

Solid

Charge

Melting point

164-165 °C

Experimental Properties

Property	Value	Reference
Water Solubility	10.4 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	5.72 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	0.68	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.41	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.27 m³·mol⁻¹	ChemAxon
Polarizability	15.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Cooked	FDB000433
Dirty	FDB000433
Meaty	FDB000433
Mild	FDB000433
Phenolic	FDB000433
Rubbery	FDB000433

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-2900000000-273503edc6a220e152b6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-2900000000-80980d19fa83d4b86f91	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9700000000-78d2ae48da1eee18358e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9200000000-50c21473a7d48011358c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-1900000000-9b1000a8978b57919c35	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-273503edc6a220e152b6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-80980d19fa83d4b86f91	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9700000000-78d2ae48da1eee18358e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-69892c95ab2778a208b3	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9600000000-1d5276a762318a00832d	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-7900000000-8f3b164f36bc5a4df4d7	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-0900000000-066947a256844eb6cbdc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-0900000000-4b0f190d7304f2cec82d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-2feedb2abf4fe5413452	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-052r-0900000000-e67940e0a4f0f1b565c4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00lr-9400000000-47a2e802a22167ed8a63	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0900000000-3229081a448a277191a2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004l-9300000000-e2fc12d41e4c40a9a296	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-92f0b12d0a64443cede8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-001i-9200000000-50c21473a7d48011358c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-d7e9a8705227b4504c5c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-3f02b334907c40a8315c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-e98b3afc6fad78d45d38	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-54239e66d89de3096ca8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0079-0902000000-f09759fc06ef461f3aa5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-9000000000-9ffe6ee0ce68182216f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-020a5decfb44fc4f97df	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0930000000-32ccc375e75dbab3195c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-51c6cc08017f1672b791	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-1900000000-55c25dd64462c06c5316	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0f96-9500000000-83a70aec6da00b51a6df	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-004i-9100000000-5f044e831c0d2db255fa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-99edae3913507430bf9f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4900000000-8944003750ac547c2024	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-00e85becc8cfc59bdb10	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-58e8539844dcdbc977cc	JSpectraViewer \| MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-053r-9500000000-6deb2b5d214f768ca448	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	15760
HMDB ID	HMDB00306
Pubchem Compound ID	5610
Kegg ID	C00483
ChemSpider ID	5408
FOODB ID	FDB000433
Wikipedia ID	Tyramine
BioCyc ID	Not Available

Structure for #<Compound:0xb2e1dab8>