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Hordenine

Product Name
Hordenine
CAS No.
539-15-1
Chemical Name
Hordenine
Synonyms
Hordenin;Hordeine;Anhalin;Cactine;Anhaline;Hordetin;Ordenina;Ordenine;Eremursin;Hordenine
CBNumber
CB4747471
Molecular Formula
C10H15NO
Formula Weight
165.23
MOL File
539-15-1.mol
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Hordenine Property

Melting point:
117-118°
Boiling point:
bp11 173°
Density 
1.0203 (rough estimate)
refractive index 
1.4820 (estimate)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
10.05±0.26(Predicted)
form 
Solid
color 
Pale Yellow to Dark Beige
Merck 
14,4746
BRN 
2207615
LogP
1.400 (est)
CAS DataBase Reference
539-15-1(CAS DataBase Reference)
NIST Chemistry Reference
Phenol, 4-[2-(dimethylamino)ethyl]-(539-15-1)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36-43
Safety Statements 
26-36/37
WGK Germany 
3
HS Code 
29222990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
04476
Product name
Hordenine
Purity
≥97.0% (HPLC)
Packaging
100mg
Price
$98.9
Updated
2025/07/31
Sigma-Aldrich
Product number
PHL80469
Product name
Hordenine
Purity
phyproof? Reference Substance
Packaging
50mg
Price
$337
Updated
2025/07/31
Sigma-Aldrich
Product number
04476
Product name
Hordenine
Purity
≥97.0% (HPLC)
Packaging
1g
Price
$733
Updated
2025/07/31
TCI Chemical
Product number
H1351
Product name
Hordenine
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$38
Updated
2025/07/31
TCI Chemical
Product number
H1351
Product name
Hordenine
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$115
Updated
2025/07/31
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Hordenine Chemical Properties,Usage,Production

Description

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 (Ki = 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.

Chemical Properties

Light yellow solid

Uses

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.

Uses

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.

Purification Methods

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.]

References

[1] D L LIU  J V L. Biologically active secondary metabolites of barley. II. Phytotoxicity of barley allelochemicals.[J]. Journal of Chemical Ecology, 1993, 19 10: 2231-2244. DOI: 10.1007/bf00979660
[2] SANG-CHEOL KIM . Hordenine, a single compound produced during barley germination, inhibits melanogenesis in human melanocytes[J]. Food Chemistry, 2013, 141 1: Pages 174-181. DOI: 10.1016/j.foodchem.2013.03.017
[3] MEYER E. Separation of two distinct S-adenosylmethionine dependent N-methyltransferases involved in hordenine biosynthesis in Hordeum vulgare.[J]. Plant Cell Reports, 1982, 1 6: 236-239. DOI: 10.1007/bf00272627
[4] THOMAS SOMMER. Identification of the Beer Component Hordenine as Food-Derived Dopamine D2 Receptor Agonist by Virtual Screening a 3D Compound Database.[J]. ACS Applied Electronic Materials, 2017: 44201. DOI: 10.1038/srep44201
[5] IRINA STEINER. A sensitive method for the determination of hordenine in human serum by ESI+ UPLC-MS/MS for forensic toxicological applications[J]. Analytical and Bioanalytical Chemistry, 2016, 408 9: 2285-2292. DOI: 10.1007/s00216-016-9324-3

Hordenine Preparation Products And Raw materials

Raw materials

Preparation Products

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Hordenine Suppliers

Americas 1 Canada 1 China 325 Czech Republic 1 Europe 1 Germany 5 India 6 Japan 1 Switzerland 2 United Kingdom 7 United States 29 Global 379
AdooQ BioScience, LLC
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HBCChem, Inc.
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EMMX Biotechnology LLC
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888-539-0666
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888-539-0666
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info@emmx.com
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Target molecule Corp.
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857-239-0968
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View Lastest Price from Hordenine manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
Hordenine 539-15-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-13
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Hordenine 539-15-1
Price
US $200.00-85.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-23
Henan Aochuang Chemical Co.,Ltd.
Product
Hordenine 539-15-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-09-29

539-15-1, HordenineRelated Search:

4-Ethylphenol Acetaminophen Maltitol Maltodextrin Phenol Ethyl maltol N,N-Dimethyl-1,4-phenylenediamine 4-Aminophenol 3-Aminophenol Xylenol Maltose Phenol Red Sophoridine 2-Aminophenol Venlafaxine hydrochloride (2RS)-2-(Cyclohex-1-enyl)-2-(4-Methoxyphenyl)-N,N-diMethylethanaMine Hydrochloride D,L-N,N-Didesmethyl-N-(4-methoxyphenethyl) Venlafaxine Venlafaxine

  • AKOS 227-22
  • Hordenine, froM D.tiliaefoliuM G.Don
  • Anhalin
  • Anhaline
  • N,N-(DiMethyl-d6)tyraMine
  • Ordenina-d6
  • p-[2-[(DiMethyl-d6)aMino]ethyl]phenol
  • Peyocactine-d6
  • p-Hydroxy-N,N-(diMethyl-d6)phenethylaMine
  • Anhaline 4-[2-(Dimethylamino)ethyl]phenol 4-Hydroxy-N,N-dimethylphenethylamine
  • Hordenine SynonyMs 4-(2-DiMethylaMinoethyl)phenol
  • Venlafaxine Impurity (4-(2-(Dimethylamino)ethyl)-Phenol)
  • Hordenine 4-(2-Dimethylaminoethyl)phenol
  • Eremursin
  • Venlafaxine Impurity
  • Hordenine, 98%, from D.tiliaefolium G.Don
  • Desvenlafaxine Impurity 8
  • Cactine
  • Eremursine
  • Hordenin
  • Hordetin
  • N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamine
  • N,N-Dimethyl-4-hydroxy-beta-phenethylamine
  • N,N-Dimethyl-p-hydroxyphenethylamine
  • N,N-Dimethyltyramine
  • Ordenina
  • Ordenine
  • p-[2-(Dimethylamino)ethyl]phenol
  • Peyocactine
  • Phenol, 4-[2-(dimethylamino)ethyl]-
  • Phenol, p-[2-(dimethylamino)ethyl]-
  • p-Hydroxy-N,N-dimethylphenethylamine
  • p-[2-(dimethylamino)ethyl]phenol sulphate
  • N,N-dimethyl-p-hydroxyphenylethyl
  • HORDENINE(FREE BASE)(P)
  • Dimethyl[2-(4-hydroxyphenyl)ethyl]amine
  • Hordenine
  • 4-(2-Dimethylaminoethyl)phenol
  • N,N-DiMethyl-4-hydroxy-β-phenethylaMine
  • 4-[2-(DiMethyl-d6)aMinoethyl]phenol
  • Anhalin-d6
  • Anhaline-d6
  • Cactine-d6
  • Hordenin-d6
  • N,N-(DiMethyl-d6)-4-hydroxy-β-phenethylaMine
  • N,N-(DiMethyl-d6)-p-hydroxyphenethylaMine
  • Hordeine
  • Hordenine&gt
  • 4-Hydroxy-N,N-dimethylphenethylamine
  • Hordenine USP/EP/BP
  • Hordenine (Ordenina
  • TIANFU-CHEM CAS:539-15-1 Hordenine
  • hordeniniumsulfat
  • Barley malt alkali
  • Hordenine (25 mg) (4-(2-(dimethylamino)ethyl)phenol)
  • Hordenine, ≥ 98.0%
  • Hordenine in methanol
  • Effexor 29