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539-15-1

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539-15-1 Usage

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

Different sources of media describe the Uses of 539-15-1 differently. You can refer to the following data:
1. 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.
2. 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.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 539-15-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 9 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 539-15:
(5*5)+(4*3)+(3*9)+(2*1)+(1*5)=71
71 % 10 = 1
So 539-15-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3

539-15-1 Well-known Company Product Price

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  • TCI America

  • (H1351)  Hordenine  >98.0%(GC)(T)

  • 539-15-1

  • 1g

  • 890.00CNY

  • Detail
  • TCI America

  • (H1351)  Hordenine  >98.0%(GC)(T)

  • 539-15-1

  • 5g

  • 2,990.00CNY

  • Detail
  • Sigma-Aldrich

  • (61207)  Hordenine  analytical standard

  • 539-15-1

  • 61207-50MG

  • 985.14CNY

  • Detail

539-15-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name hordenine

1.2 Other means of identification

Product number -
Other names 4-[2-(Dimethylamino)ethyl]phenol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:539-15-1 SDS

539-15-1Synthetic route

formaldehyd
50-00-0

formaldehyd

tyramine hydrochloride
60-19-5

tyramine hydrochloride

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate In methanol; water at 20℃;98%
tyrosamine
51-67-2

tyrosamine

formaldehyd
50-00-0

formaldehyd

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 20h; methylation;93%
With hydrogen; palladium on activated charcoal In methanol at 20℃; Methylation;93%
With sodium tris(acetoxy)borohydride In methanol at 20℃; for 18h;70%
4-(2-bromoethyl)phenol
14140-15-9

4-(2-bromoethyl)phenol

dimethyl amine
124-40-3

dimethyl amine

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
In methanol at 20℃;92%
at 20℃; im Rohr;
methanol
67-56-1

methanol

tyrosamine
51-67-2

tyrosamine

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With rhodium(III) chloride hydrate; potassium tert-butylate at 150℃; for 60h; Sealed tube; High pressure;76%
With palladium 10% on activated carbon; potassium tert-butylate at 130℃; for 30h;
2-(4-methoxyphenyl)-N,N-dimethylethylamine hydrochloride
6027-23-2

2-(4-methoxyphenyl)-N,N-dimethylethylamine hydrochloride

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With hydrogen bromide at 120 - 130℃;71.54%
4-methoxyphenethyl bromide
14425-64-0

4-methoxyphenethyl bromide

dimethyl amine
124-40-3

dimethyl amine

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
Stage #1: 4-methoxyphenethyl bromide; dimethyl amine In tetrahydrofuran at 20℃; for 18h;
Stage #2: With water; boron tribromide In hexane; dichloromethane at 0℃; for 0.666667h;
40%
4-methoxyphenethyl-dimethylamine
775-33-7

4-methoxyphenethyl-dimethylamine

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With hydrogenchloride at 160℃;
With phosphorus; hydrogen bromide at 110℃;
With hydrogenchloride at 160℃;
4-[2-(dimethylamino)ethyl]aniline
5636-52-2

4-[2-(dimethylamino)ethyl]aniline

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With sulfuric acid durch Diazotieren;
beim Diazotieren und Verkochen;
(4-hydroxyphenethyl)trimethylammonium iodide
1976-98-3

(4-hydroxyphenethyl)trimethylammonium iodide

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
bei der Destillation unter vermindertem Druck;
candicine chloride
3761-58-8

candicine chloride

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
bei der Destillation unter vermindertem Druck;
4-Methoxyphenethylamine
55-81-2

4-Methoxyphenethylamine

methyl iodide
74-88-4

methyl iodide

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With potassium hydroxide at 100℃; filtriert das entstand.Hordenin-methylaether-jodmethylat ab,entfernt aus dem Filtrat die primaere und sekundere Base durch Acetylieren mit Essigsaeureanhydrid und koht den so erhalt.Hordenin-methylaether mit Jodwasserstoffsaeure;
4-hydroxy-phenethyl iodide
6631-69-2

4-hydroxy-phenethyl iodide

dimethyl amine
124-40-3

dimethyl amine

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

4-(2-chloroethyl)phenol
28145-35-9

4-(2-chloroethyl)phenol

dimethyl amine
124-40-3

dimethyl amine

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With ethanol at 100℃;
tyramine hydrochloride
60-19-5

tyramine hydrochloride

[13C]Carbon monoxide
1641-69-6

[13C]Carbon monoxide

A

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

B

hordenine

hordenine

C

hordenine

hordenine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol for 16h; Ambient temperature; Title compound not separated from byproducts;A 1.6 % Spectr.
B 16.4 % Spectr.
C 82.0 % Spectr.
zeraconine

zeraconine

A

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

B

C20H29N

C20H29N

C

dihydrozeraconine

dihydrozeraconine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol for 24h;A 7 mg
B 10 mg
C 2 mg
ω-dimethylamino-4-oxy-acetophenone hydriodide

ω-dimethylamino-4-oxy-acetophenone hydriodide

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With phosphorus; hydrogen iodide at 125℃;
With phosphorus; hydrogen iodide at 125℃;
hordenine chloromethylate

hordenine chloromethylate

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
durch Destillation unter vermindertem Druck;
hordenine iodomethylate

hordenine iodomethylate

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
durch Destillation unter vermindertem Druck;
malt-germ

malt-germ

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

oxalate dimethyl-<β-(4-nitro-phenyl)-ethyl>-amine

oxalate dimethyl-<β-(4-nitro-phenyl)-ethyl>-amine

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
With hydrogenchloride; tin und Kochen das gebildete Amin mit verd.Schwefelsaeure unter Zusatz von NaNO2;
hydrogenchloride
7647-01-0

hydrogenchloride

N,N-dimethyl-2-(4-nitrophenyl)ethanamine
5339-05-9

N,N-dimethyl-2-(4-nitrophenyl)ethanamine

tin

tin

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
Behandeln der siedenden Loesung in verd.Schwefelsaeure mit Natriumnitrit;
hydrogen iodide
10034-85-2

hydrogen iodide

2-dimethylamino-1-(4-hydroxy-phenyl)-ethanone; hydriodide
114509-82-9

2-dimethylamino-1-(4-hydroxy-phenyl)-ethanone; hydriodide

red phosphorus

red phosphorus

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
at 125℃; im Rohr;
at 125℃; im Rohr;
N,N-dimethyl-2-(4-nitrophenyl)acetamide
90405-67-7

N,N-dimethyl-2-(4-nitrophenyl)acetamide

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium sulfide; xylene; phosphorus pentasulfide / 80 °C
2: alcohol; hydrochloric acid / Electrolysis.an Bleielektroden
3: diluted sulfuric acid / durch Diazotieren
View Scheme
Multi-step reaction with 2 steps
1: antimony pentoxide
2: beim Diazotieren und Verkochen
View Scheme
N,N-dimethyl(4-methoxyphenyl)thioacetamide
76579-52-7

N,N-dimethyl(4-methoxyphenyl)thioacetamide

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous-alcoholic hydrochloric acid / 20 °C / elektrolytische Reduktion an Bleikathode
2: hydrobromic acid; red phosphorus / 110 °C
View Scheme
N,N-dimethyl-2-(4-nitrophenyl)ethanethioamide
861643-06-3

N,N-dimethyl-2-(4-nitrophenyl)ethanethioamide

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: alcohol; hydrochloric acid / Electrolysis.an Bleielektroden
2: diluted sulfuric acid / durch Diazotieren
View Scheme
p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; palladium / Hydrogenation
2: concentrated aqueous hydrochloric acid / 160 °C
View Scheme
4-nitrophenylacetyl chloride
50434-36-1

4-nitrophenylacetyl chloride

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: benzene
2: potassium sulfide; xylene; phosphorus pentasulfide / 80 °C
3: alcohol; hydrochloric acid / Electrolysis.an Bleielektroden
4: diluted sulfuric acid / durch Diazotieren
View Scheme
2-(4-Methoxyphenyl)ethanol
702-23-8

2-(4-Methoxyphenyl)ethanol

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous HI / 135 °C
View Scheme
2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl)acetonitrile
918344-20-4

2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl)acetonitrile

dimethyl amine
124-40-3

dimethyl amine

A

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

B

O-desmethylvenlafaxine
93413-62-8

O-desmethylvenlafaxine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol; water at 50℃; under 3750.38 Torr; for 10h; Product distribution / selectivity;
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

N,N-dimethyldibromotyramine
325151-61-9

N,N-dimethyldibromotyramine

Conditions
ConditionsYield
With bromine; tert-butylamine In toluene at -78 - 5℃; for 3h; Bromination;98%
With bromine; acetic acid at 20℃; for 3h;84%
With bromine; potassium bromide In water81%
1-Bromotetradecane
112-71-0

1-Bromotetradecane

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

N-(4-hydroxyphenethyl)-N,N-dimethyltetradecanaminium bromide

N-(4-hydroxyphenethyl)-N,N-dimethyltetradecanaminium bromide

Conditions
ConditionsYield
In acetonitrile for 48h; Reflux;93%
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

hexadecanyl bromide
112-82-3

hexadecanyl bromide

N-(4-hydroxyphenethyl)-N,N-dimethylhexadecanaminium bromide

N-(4-hydroxyphenethyl)-N,N-dimethylhexadecanaminium bromide

Conditions
ConditionsYield
In acetonitrile for 48h; Reflux;93%
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

2,6-diiodo-N,N-dimethyltyramine

2,6-diiodo-N,N-dimethyltyramine

Conditions
ConditionsYield
With mercury(II) diacetate; iodine In ethanol at 20℃; for 0.5h; Iodination;91%
With mercury(II) diacetate; iodine In ethanol at 20℃; for 0.5h; Iodination;85%
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

1-dodecylbromide
143-15-7

1-dodecylbromide

N-(4-hydroxyphenethyl)-N,N-dimethyldodecanaminium bromide

N-(4-hydroxyphenethyl)-N,N-dimethyldodecanaminium bromide

Conditions
ConditionsYield
In acetonitrile for 48h; Reflux;90%
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

methyl iodide
74-88-4

methyl iodide

(4-hydroxyphenethyl)trimethylammonium iodide
1976-98-3

(4-hydroxyphenethyl)trimethylammonium iodide

Conditions
ConditionsYield
In methanol for 12h;88%
at 110℃;
With ethanol
With diethyl ether
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

4-(2-(dimethylamino)ethyl)phenyl benzenesulfonate

4-(2-(dimethylamino)ethyl)phenyl benzenesulfonate

Conditions
ConditionsYield
In water; acetonitrile at 20℃; for 2h; Electrochemical reaction;85%
4-fluorobenzoic acid ethyl ester
451-46-7

4-fluorobenzoic acid ethyl ester

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

4-(4-(2-(dimethylamino)ethyl)phenoxy)benzoate

4-(4-(2-(dimethylamino)ethyl)phenoxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 120℃; Inert atmosphere;80%
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

3-(dimethylamino)propyl chloride hydrochloride
5407-04-5

3-(dimethylamino)propyl chloride hydrochloride

{3-[4-(2-dimethylamino-ethyl)-phenoxy]-propyl}-dimethyl-amine
325151-65-3

{3-[4-(2-dimethylamino-ethyl)-phenoxy]-propyl}-dimethyl-amine

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; for 28h; Alkylation;75%
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid diimide
112078-00-9

N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid diimide

2,9-bis-(2,6-diisopropyl-phenyl)-5,6,12,13-tetrakis-[4-(2-dimethylamino-ethyl)-phenoxy]-anthra[2,1,9-def;6,5,10-d'e'f']diisoquinoline-1,3,8,10-tetraone

2,9-bis-(2,6-diisopropyl-phenyl)-5,6,12,13-tetrakis-[4-(2-dimethylamino-ethyl)-phenoxy]-anthra[2,1,9-def;6,5,10-d'e'f']diisoquinoline-1,3,8,10-tetraone

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃;62%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 0.25h; Inert atmosphere;
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 15h; Inert atmosphere;
methyl-phenyl-carbamic acid 4-hydroxymethyl-phenyl ester
548770-60-1

methyl-phenyl-carbamic acid 4-hydroxymethyl-phenyl ester

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

methyl-phenyl-carbamic acid 4-[4-(2-dimethylamino-ethyl)-phenoxymethyl]-phenyl ester
548770-73-6

methyl-phenyl-carbamic acid 4-[4-(2-dimethylamino-ethyl)-phenoxymethyl]-phenyl ester

Conditions
ConditionsYield
52%
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

C22H29NO5S

C22H29NO5S

(4R,4aR,6aS,10aR,13bS,14S)-8-((4-(2-(dimethylamino)ethyl)-phenoxy)methyl)-4-methyl-2,3,4,4a,5,6,9,10-octahydro-1H-6a,13b,9-(epiethane[1,1,2]triyl)-4,13-methanodibenzo-[2,3:6,7]cyclohepta[1,2-d]oxazol-12(13aH)-one

(4R,4aR,6aS,10aR,13bS,14S)-8-((4-(2-(dimethylamino)ethyl)-phenoxy)methyl)-4-methyl-2,3,4,4a,5,6,9,10-octahydro-1H-6a,13b,9-(epiethane[1,1,2]triyl)-4,13-methanodibenzo-[2,3:6,7]cyclohepta[1,2-d]oxazol-12(13aH)-one

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h;50%
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

N,N-dimethyldichlorotyramine
325151-62-0

N,N-dimethyldichlorotyramine

Conditions
ConditionsYield
With sulfuryl dichloride at 65℃; for 6h; Chlorination;40%
ethyl bromide
74-96-4

ethyl bromide

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

ethyl-(4-hydroxy-phenethyl)-dimethyl-ammonium; bromide
108848-21-1

ethyl-(4-hydroxy-phenethyl)-dimethyl-ammonium; bromide

Conditions
ConditionsYield
With ethanol
methylene chloride
74-87-3

methylene chloride

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

candicine chloride
3761-58-8

candicine chloride

Conditions
ConditionsYield
With methanol
chloroethane
75-00-3

chloroethane

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

ethyl-(4-hydroxy-phenethyl)-dimethyl-ammonium; chloride
108847-83-2

ethyl-(4-hydroxy-phenethyl)-dimethyl-ammonium; chloride

Conditions
ConditionsYield
With ethanol at 100 - 110℃;
iodoethyl carbamate
94392-36-6

iodoethyl carbamate

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

(2-carbamoyloxy-ethyl)-(4-hydroxy-phenethyl)-dimethyl-ammonium; iodide

(2-carbamoyloxy-ethyl)-(4-hydroxy-phenethyl)-dimethyl-ammonium; iodide

Conditions
ConditionsYield
With methanol
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

p-hydroxyphenethyl alcohol
501-94-0

p-hydroxyphenethyl alcohol

Conditions
ConditionsYield
With yeast
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

A

trans-4-ethylcyclohexanol
19781-62-5

trans-4-ethylcyclohexanol

B

cis-4-ethylcyclohexanol
19781-61-4

cis-4-ethylcyclohexanol

Conditions
ConditionsYield
With ethanol; nickel at 155℃; under 51485.6 Torr; Hydrogenation;
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

candicine chloride
3761-58-8

candicine chloride

N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

acetic anhydride
108-24-7

acetic anhydride

1-acetoxy-4-(2-dimethylamino-ethyl)-benzene
95469-40-2

1-acetoxy-4-(2-dimethylamino-ethyl)-benzene

Conditions
ConditionsYield
at 100℃;
N,N-dimethyltyramine
539-15-1

N,N-dimethyltyramine

cinnamoyl chloride
102-92-1

cinnamoyl chloride

1-cinnamoyloxy-4-(2-dimethylamino-ethyl)-benzene

1-cinnamoyloxy-4-(2-dimethylamino-ethyl)-benzene

Conditions
ConditionsYield
With pyridine

539-15-1Relevant articles and documents

THE BIOSYNTHESIS OF SCELETIUM ALKALOIDS IN SCELETIUM SUBVELUTINUM

Herbert, Richard B.,Kattah, Abdullah E.

, p. 141 - 144 (1989)

Six Sceletium (Mesembrine) alkaloids (1)-(6) are identified, together with N,N-dimethyltyramine (10) as constituents of Sceletium subvelutinum.The alkaloids (1)-(6) incorporate label from radioactive tyramine (8) and 4-hydroxyphenylpropionic acid (12) as expected; notably -4-hydroxydihydrocinnamaldehyde is a more efficient alkaloid precursor than the acid (12).Preliminary evidence locates the amine (16) potentially as a key precursor for Sceletium alkaloids; (14) is less efficiently incorporated.

STRUCTURE OF THE NEW DITERPENE ALKALOID ZERACONINE AND ITS N-OXIDE

Vaisov, Z. M.,Yunusov, M. S.

, p. 337 - 338 (1987)

The structures of the new diterpene alkaloid zeraconine and its N-oxide, isolated from Aconitum zeravschanicum, have been established on the basis of spectral characteristics and chemical transformations.

Preparation method of hordenine hydrochloride

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Paragraph 0042-0045, (2021/11/10)

The invention discloses a preparation method of hordenine hydrochloride. The preparation method comprises the following steps: taking 4-(2-bromoethyl)phenol as a raw material, adding ethanol to prepare a solution, dropwise adding excessive dimethylamine solution, and stirring at a lower temperature to carry out amination reaction to obtain hordenine hydrobromide. The proper excessive dimethylamine is adopted, so that the quaternization side reaction is effectively inhibited, the solvent dispersion effect is also played, the contact reaction opportunity of the hordenine product generated in the first reaction and the 4-(2-bromoethyl)phenol added later is greatly reduced, the high product yield can be kept, and meanwhile the low preparation cost is achieved; 4-(2-bromoethyl) phenol is added into ethanol to prepare a dilute solution of ethanol, and the dilute solution of ethanol is dropwise added into a dimethylamine solution to improve the dispersity of 4-(2-bromoethyl) phenol in a reaction system and inhibit quaternization side reaction; and the amination reaction is carried out by stirring at a relatively low temperature of 10-25 DEG C, so that the occurrence of quaternization side reaction is inhibited, and a relatively good reaction effect is achieved.

Commercial Pd/C-Catalyzed N-Methylation of Nitroarenes and Amines Using Methanol as Both C1 and H2 Source

Goyal, Vishakha,Gahtori, Jyoti,Narani, Anand,Gupta, Piyush,Bordoloi, Ankur,Natte, Kishore

, p. 15389 - 15398 (2019/12/04)

Herein, we report commercially available carbon-supported-palladium (Pd/C)-catalyzed N-methylation of nitroarenes and amines using MeOH as both a C1 and a H2 source. This transformation proceeds with high atom-economy and in an environmentally friendly way via borrowing hydrogen mechanism. A total of >30 structurally diverse N-methylamines, including bioactive compounds, were selectively synthesized with isolated yields of up to 95%. Furthermore, selective N-methylation and deuteration of nimesulide, a nonsteroidal anti-inflammatory drug, were realized through the late-stage functionalization.

Desvenlafaxine succinate impurities as well as preparation method and use thereof

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Paragraph 0045, (2018/06/15)

The invention discloses desvenlafaxine succinate impurities, i.e., desvenlafaxine succinate impurity 2 and desvenlafaxine succinate impurity I. In addition, the invention further discloses a preparation method of a desvenlafaxine succinate impurity 2, a desvenlafaxine succinate impurity 5, a desvenlafaxine succinate impurity 6, a desvenlafaxine succinate impurity 7, a desvenlafaxine succinate impurity H and a desvenlafaxine succinate impurity I. According to the desvenlafaxine succinate related impurities and preparation thereof, provided by the invention, a foundation for quality research onintermediates, raw pharmaceutical materials and compositions of desvenlafaxine succinate is laid.

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