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Principaux documents

04476

Sigma-Aldrich

Hordenine

≥97.0% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C10H15NO
Numéro CAS:
Poids moléculaire :
165.23
Numéro Beilstein :
2207615
Numéro CE :
Numéro MDL:
Code UNSPSC :
41116107
ID de substance PubChem :
Nomenclature NACRES :
NA.25

Niveau de qualité

Pureté

≥97.0% (HPLC)

Forme

powder or crystals

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

[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
Daopeng Tan et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 35(19), 2572-2575 (2010-12-24)
To investigate the alkaloids from Senecio scandens. Compounds were isolated with silica gel and Sephadex LH-20 column chromatography and their structures were determined by spectral analysis and chemical evidence. The hepatic cytotoxicity of isolated compounds was tested by MTT method

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