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04476

Sigma-Aldrich

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:
539-15-1
Molecular Weight:
165.23
Beilstein:
2207615
EC Number:
208-710-4
MDL number:
MFCD00051462
UNSPSC Code:
41116107
PubChem Substance ID:
329747931
NACRES:
NA.25

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

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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. 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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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[Not Available].
R HAZARD et al.
Comptes rendus des seances de la Societe de biologie et de ses filiales, 139, 630-630 (1945-07-01)
The biogenesis of alkaloids. XVI. Hordenine metabolism in barley.
Frank, A. W. and Marion, L.
Canadian Journal of Chemistry, 34, 1641-1646 (1956)
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
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
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