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Merck

04476

Hordenin

≥97.0% (HPLC)

Synonym(e):

4-(2-Dimethylaminoethyl)-phenol, N,N-Dimethyl-tyramin, p-Hydroxy-N,N-dimethyl-phenethylamin, Anhalin, Cactin, Eremursine, Peyocactin

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Über diesen Artikel

Empirische Formel (Hill-System):
C10H15NO
CAS-Nummer:
539-15-1
Molekulargewicht:
165.23
NACRES:
NA.25
PubChem Substance ID:
329747931
UNSPSC Code:
41116107
EC Number:
208-710-4
MDL number:
MFCD00051462
Beilstein/REAXYS Number:
2207615

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InChI key

KUBCEEMXQZUPDQ-UHFFFAOYSA-N

InChI

1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3

assay

≥97.0% (HPLC)

form

powder or crystals

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

100

SMILES string

CN(C)CCc1ccc(O)cc1

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Application

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.[1] Hordenine may be used as an analytical reference material and in research on the activities of phenethylamine type alkaloids.

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,[2] it is metabolized by monoamine oxidase.[3] Hordenine is a sympathomimetic and its pharmacological actions are of interest, as it is occasionally found in post race urine samples.[4] 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.[1] It is present in barley roots from the first day of seed germination, but is not present in seeds.[5]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Lagerklasse

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
BCCN3484
BCCK4548
BCCC8693
BCBX1761
BCBB8693V

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M F Goelz et al.
Toxicology, 18(2), 125-131 (1980-01-01)
Meadow voles (Microtus pennsylvanicus) were used to evaluate the relative toxicity of the alkaloids, gramine and hordenine, which are present in reed canarygrass (Phalaris arundinacea) and to assess their effects on the quality of this grass as a forage. One
D L Liu et al.
Journal of chemical ecology, 19(10), 2231-2244 (1993-10-01)
The release of alkaloids by barley was quantified by HPLC. Hordenine was released from the roots of barley in a hydroponic system for up to 60 days. The amount reached a maximum, 2μg/plant/day, at 36 days, then declined. Effects on
M M Mangino et al.
IARC scientific publications, (57)(57), 337-346 (1984-01-01)
The two tertiary amine alkaloids, hordenine and gramine, which are biosynthesized in malt during germination, were subjected to nitrosation under conditions typical for the study of tertiary amine nitrosation. At 65 degrees C in dilute aqueous acid (pH 4.4 or
Alkaloids and plant metabolism. V. The distribution and formation of tyramine methylpherase during germination of barley.
Mann, J.D., et al.
A Practical Guide to Protein and Peptide Purification for Microsequencing (2nd Edition), 238, 676-681 (1963)
Marwan Shabana et al.
Natural product research, 20(8), 710-714 (2006-06-07)
Four alkaloids of the phenethylamine derivatives have been isolated from the n-butanol fraction of the aerial parts of Stapelia hirsuta L. The structures of the isolated alkaloids were determined as N-acetyl hordenine (a new natural compound), hordenine, candicine and hordenine-1-O-beta-D-glucoside
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