Hordenine

Base Information

• Chemical Name: Hordenine
• CAS No.: 539-15-1
• Molecular Formula: C10H15NO
• Molecular Weight: 165.235
• Hs Code.: 29222990
• European Community (EC) Number: 208-710-4
• UNII: K3489CA082
• DSSTox Substance ID: DTXSID2046096
• Nikkaji Number: J6.381I
• Wikipedia: Hordenine
• Wikidata: Q119915
• Metabolomics Workbench ID: 38519
• ChEMBL ID: CHEMBL505789
• Mol file: 539-15-1.mol

Synonyms:hordenine;hordenine hydrochloride;hordenine sulfate (1:1);hordenine sulfate (2:1);N,N-dimethyltyramine

Chemical Property of Hordenine

Chemical Property:

• Appearance/Colour: White crystal
• Vapor Pressure: 0.00417mmHg at 25°C
• Melting Point: 117-118°
• Refractive Index: 1.542
• Boiling Point: 270.2 °C at 760 mmHg
• PKA: 10.05±0.26(Predicted)
• Flash Point: 123.5 °C
• PSA: 23.47000
• Density: 1.026 g/cm³
• LogP: 1.49630
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 165.115364102
• Heavy Atom Count: 12
• Complexity: 117

Purity/Quality:

98% ^*data from raw suppliers

Hordenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)CCC1=CC=C(C=C1)O
• 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.
• 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. 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.

Technology Process of Hordenine

There total 34 articles about Hordenine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + tyramine hydrochloride (60-19-5) → N,N-dimethyltyramine (539-15-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; In methanol; water; at 20 ℃;

DOI:10.1039/c8ra02052c

Reference yield: 93.0%

tyrosamine (51-67-2) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → N,N-dimethyltyramine (539-15-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 20h;

DOI:10.1016/S0040-4039(99)01099-0

Reference yield: 92.0%

4-(2-bromoethyl)phenol (14140-15-9) + dimethyl amine (124-40-3) → N,N-dimethyltyramine (539-15-1)

Guidance literature:

In methanol; at 20 ℃;

upstream raw materials:

tyrosamine

formaldehyd

4-methoxyphenethyl-dimethylamine

4-[2-(dimethylamino)ethyl]aniline

Downstream raw materials:

candicine chloride

p-hydroxyphenethyl alcohol

trans-4-ethylcyclohexanol

cis-4-ethylcyclohexanol

Refernces

• 1、 Russo, Cesar A.,Burton, Gerardo,Gros, Eduardo G.. "Metabolism of hordenine in Homogenates from Hordeum Vulgare Roots". . p. 71 - 74. Retrieved 1983.
• 2、 Frank,Marion. "". . p. 1641,1642. Retrieved 1956.
• 3、 -. "Preparation method of hordenine hydrochloride". . . Retrieved 2021/11/10.
• 4、 Goyal, Vishakha,Gahtori, Jyoti,Narani, Anand,Gupta, Piyush,Bordoloi, Ankur,Natte, Kishore. "Commercial Pd/C-Catalyzed N-Methylation of Nitroarenes and Amines Using Methanol as Both C1 and H2 Source". . p. 15389 - 15398. Retrieved 2019/12/04.