04476
Hordenine
≥97.0% (HPLC)
Synonym(s):
2-(4-Hydroxyphenyl)-N,N-dimethylethylamine, 4-(2-Dimethylaminoethyl)phenol, N,N-Dimethyltyramine, p-Hydroxy-N,N-dimethylphenethylamine, Anhaline, Cactine, Eremursin, Peyocactine
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About This Item
Empirical Formula (Hill Notation):
C10H15NO
CAS Number:
Molecular Weight:
165.23
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
41116107
EC Number:
208-710-4
MDL number:
Beilstein/REAXYS Number:
2207615
Quality Level
assay
≥97.0% (HPLC)
form
powder or crystals
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
SMILES string
CN(C)CCc1ccc(O)cc1
InChI
1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3
InChI key
KUBCEEMXQZUPDQ-UHFFFAOYSA-N
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. 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, 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.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
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signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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E Meyer
Plant cell reports, 1(6), 236-239 (1982-12-01)
Hordenine is biosynthesized in young roots of barley by subsequent N-methylation of tyramine. It was shown that two distinct enzymes are responsible for these methylation reactions. They differed in their pH-optimum, their stability in dependence of the pH-value, and were
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
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| H40009-5G | 04061831826999 |
| 04476-1G | 04061826007891 |
| 04476-100MG | 04061838630698 |