Tyramine

Tyramine Basic information
Product Name:Tyramine
Synonyms:4-(2-aminoethyl)-pheno;4-(2-Aminoethyl)-phenol (thyramin);4-hydroxy-benzeneethanamin;4-Hydroxy-beta-phenylethylamine;TYRAMINE;TYROSAMINE;L-TYRAMINE;AKOS NCG-0021
CAS:51-67-2
MF:C8H11NO
MW:137.18
EINECS:200-115-8
Product Categories:Anilines, Aromatic Amines and Nitro Compounds;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;51-67-2
Mol File:51-67-2.mol
Tyramine Structure
Tyramine Chemical Properties
Melting point 160-162 °C(lit.)
Boiling point 175-181 °C8 mm Hg(lit.)
density 1.0630 (rough estimate)
FEMA 4215 | TYRAMINE
refractive index 1.5849 (estimate)
Fp 165°C
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
pka9.74(at 25℃)
form Liquid
color Clear yellow to orange to slightly brown, may darken on storage
Odorat 100.00 %. mild meaty dirty cooked phenolic rubbery
Odor Typemeaty
Water Solubility 1g/95mL (15 ºC)
Merck 14,9835
JECFA Number1590
BRN 1099914
Stability:Stable. Incompatible with strong acids, strong oxidizing agents.
LogP1.38
CAS DataBase Reference51-67-2(CAS DataBase Reference)
NIST Chemistry ReferencePhenol, 4-(2-aminoethyl)-(51-67-2)
EPA Substance Registry SystemTyramine (51-67-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
WGK Germany 3
RTECS SJ5950000
10-23
HS Code 29214990
Hazardous Substances Data51-67-2(Hazardous Substances Data)
ToxicityLD50 intracervical in mouse: 30mg/kg
MSDS Information
ProviderLanguage
4-(2-Aminoethyl)phenol English
ACROS English
SigmaAldrich English
Tyramine Usage And Synthesis
DescriptionA decarboxylation product of tyrosine found in various fermentation products, including cheeses and some wines. It causes sympathomimetic effects by acting as an indirect agonist, causing the release of endogenous catecholamines. Because it is metabolized principally by monoamine oxidase, patients taking monoamine oxidase inhibitors may have a hypertensive crisis if they ingest foods containing significant amounts of tyramine.
Chemical Propertieswhite to light beige solid
Chemical PropertiesColorless to yellow solid; sweet meaty aroma.
OccurrenceReported found in sauerkraut and soy sauce.
Usesadrenergic agonist, vasoconstrictor
Usestyramine is uses as pharmaceutical intermediates.
UsesClinical studies indicate that tyramine has skin-lightening capacities.
DefinitionChEBI: A primary amino compound obtained by formal decarboxylation of the amino acid tyrosine.
Aroma threshold valuesMedium strength odor, meaty type; recommend smelling in a 5.00% solution or less.
Taste threshold valuesMild, sweet, vegetative phenolic taste at 100 ppm in water.
SynthesisTyramine, 4-(2-aminoethyl)phenol (11.2.1), can be synthesized in various ways, in particular by the decarboxylation of tyrosine [46¨C48]. It is also isolated from the tissues of livestock.

Synthesis_51-67-2

Purification MethodsCrystallise tyramine from *benzene or EtOH. [Beilstein 13 IV 1788.]
Tyramine Preparation Products And Raw materials
Preparation Products5-Aminosalicylic acid-->Roxatidine acetate-->Tetrahydropapaveroline-->N-Trans-Feruloyltyramine-->Termitomycamide E-->[2-(4-HYDROXY-PHENYL)-ETHYL]-CARBAMIC ACID ETHYL ESTER-->N-[(3,4-Dimethoxyphenyl)methyl]-4-methoxy-N-methylbenzeneethanamine-->N-guanyltyramine-->Benzyl N-[2-(4-hydroxyphenyl)ethyl]carbamate
N-ACETYL-L-PHENYLALANYL-3,5-DIIODO-L-TYROSINE 2-PhenylethylaMine DL-Adrenalin Liothyronine sodium Phenol 10-Hydroxycamptothecin D/L-AMPHETAMINE HYDROCHLORIDE N-Methyltyramine Methyl L-tyrosinate L-1-Phenylethylamine 4-Cyanophenol DL-ALPHA-METHYLBENZYLAMINE Levisoprenaline SYNEPHRINE Ethylamine AC-TYR-NH2 3-Aminophenol CHLOROACETYL-L-TYROSINE

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