4-(2-Dimethylaminoethyl)phenol

Bezeichnung:4-(2-Dimethylaminoethyl)phenol

CAS-Nr539-15-1

Englisch Name:Hordenine

CBNumberCB4747471

SummenformelC10H15NO

Molgewicht165.23

MOL-Datei539-15-1.mol

Synonyma

4-(2-Dimethylaminoethyl)phenol

4-(2-Dimethylaminoethyl)phenol physikalisch-chemischer Eigenschaften

Schmelzpunkt	117-118°
Siedepunkt	bp11 173°
Dichte	1.0203 (rough estimate)
Brechungsindex	1.4820 (estimate)
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	10.05±0.26(Predicted)
Farbe	Pale Yellow to Dark Beige
Merck	14,4746
BRN	2207615
LogP	1.400 (est)
CAS Datenbank	539-15-1(CAS DataBase Reference)
NIST chemische Informationen	Phenol, 4-[2-(dimethylamino)ethyl]-(539-15-1)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36-43
S-Sätze:	26-36/37
WGK Germany	3
HS Code	29222990

Gefahreninformationscode (GHS)

Hordenine Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Hordenine (Item No. 21626) is a naturally occurring alkaloid found in a variety of plants, most commonly germinated barley (Hordeum species) from which the name is derived, and is structurally classified as a phenethylamine. It is biosynthesized by the step-wise double methylation of tyramine . Hordenine binds to and activates the dopamine D₂ receptor (K_i = 13 μM) but antagonizes D₂ receptor β-arrestin recruitment. It inhibits tyrosinase activity and expression at concentrations ≥ 50 μM resulting in reduced melanin accumulation in human melanocytes. Hordenine is present in significant amounts in beer and can be measured in serum in the free form, for up to 2 hours, and the glucuronidated form, for up to 6 hours, after beer consumption. This product is intended for research and forensic applications.
Chemische Eigenschaften
Light yellow solid
Verwenden
Hordenine is suitable to study the effect of reed canary grass alkoloids on in vito digestibility. It is also suitable for use as a standard to identify endogenous hordenine in ungerminated and germinated barley by HPLC/diode array detection analysis. Hordenine may be used as an analytical reference material and in research on the activities of phenethylamine type alkaloids.
Verwenden
A phenethylamine alkaloid with antibacterial and antibiotic properties found mainly in plants from the cactaceae family. It showed effects similar to Cytosine (C998950) and acted as a depressant on the central nervous system (CNS) during animal testing.
Definition
ChEBI: Hordenine is a phenethylamine alkaloid. It has a role as a human metabolite and a mouse metabolite.
Biochem/physiol Actions
Hordenine is an alkaloid found in plants, e.g. the roots of germinating barley and marine algae. It is a metabolite in tyrosine metabolism, biosynthesized from tyramine by two subsequent N-methylations, it is metabolized by monoamine oxidase. Hordenine is a sympathomimetic and its pharmacological actions are of interest, as it is occasionally found in post race urine samples. Hordenine inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production. cAMP is involved in the expression of melanogenesis-related proteins. Hordenine may be used in the inhibition of hyperpigmentation. It is present in barley roots from the first day of seed germination, but is not present in seeds.
läuterung methode
Crystallise Hordenine from EtOH or H2O and sublime it at 105o/5mm. The 4,4’-dichlorodiphenyl disulfimide salt has m 145-146o (from Me2CO/H2O) [Runge et al. Chem Ber 88 50 1955]. [Beilstein 13 H 626, 13 I 236, 13 II 356, 13 III 1640, 13 IV 1790.]

Hordenine Upstream-Materialien And Downstream Produkte

4-(2-Dimethylaminoethyl)phenol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

539-15-1, Hordenine Verwandte Suche:

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