Product Name

  • Name

    (S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol

  • EINECS
  • CAS No. 485-19-8
  • Article Data12
  • CAS DataBase
  • Density 1.217g/cm3
  • Solubility
  • Melting Point 125-126ºC
  • Formula C19H23 N O4
  • Boiling Point 504.9°Cat760mmHg
  • Molecular Weight 329.396
  • Flash Point 259.2°C
  • Transport Information
  • Appearance
  • Safety Poison by intravenous route. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 485-19-8 ((S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol)
  • Hazard Symbols
  • Synonyms 7-Isoquinolinol,1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-,(S)-; Reticuline (6CI,7CI,8CI); (+)-Reticuline; L-(+)-Reticuline; Reticulin;S-(+)-Reticuline; d-Reticuline
  • PSA 62.16000
  • LogP 2.82460

Synthetic route

reticuline
1699-46-3, 7096-86-8

reticuline

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
With borane-ammonia complex; recombinant monoamine oxidase D11 from Aspergillus niger; oxygen In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 48h; pH=7.7; Time; Resolution of racemate; Enzymatic reaction; enantioselective reaction;80%
1-(3'-benzyloxy-4'-methoxybenzyl)-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
916-40-5

1-(3'-benzyloxy-4'-methoxybenzyl)-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol; acetic acid under 2585.7 Torr; for 6h;0.026 g
isovanillin
621-59-0

isovanillin

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 75 percent / KOH / H2O / 5 h / Heating
2: 93 percent / NaBH4 / ethanol / 1.) room temperature, 18 h, 2.) reflux, 1 h
3: 96 percent / PBr3 / tetrahydrofuran / 1.5 h / 0 °C
4: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
5: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
6: K2CO3 / acetone / 14 h / Heating
7: lithium aluminum hydride / tetrahydrofuran / Heating
8: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
3-methoxy-4-(phenylmethoxy)benzaldehyde
2426-87-1

3-methoxy-4-(phenylmethoxy)benzaldehyde

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 73 percent / ammonium acetate / 1.5 h / Heating
2: 55 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 1.) reflux, 2 h, 2.) room temperature, overnight
3: formic acid / 48 h / 50 °C
4: 88 percent / ammonium sulfate / toluene / 48 h / Heating
5: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
6: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
7: K2CO3 / acetone / 14 h / Heating
8: lithium aluminum hydride / tetrahydrofuran / Heating
9: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine
22231-61-4

2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: formic acid / 48 h / 50 °C
2: 88 percent / ammonium sulfate / toluene / 48 h / Heating
3: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
4: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
5: K2CO3 / acetone / 14 h / Heating
6: lithium aluminum hydride / tetrahydrofuran / Heating
7: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
3-benzyloxy-4-methoxy-benzyl alcohol
1860-60-2

3-benzyloxy-4-methoxy-benzyl alcohol

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 96 percent / PBr3 / tetrahydrofuran / 1.5 h / 0 °C
2: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
3: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
4: K2CO3 / acetone / 14 h / Heating
5: lithium aluminum hydride / tetrahydrofuran / Heating
6: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
3-methoxy-4-benzyloxy-ω-nitrostyrolene
63909-38-6, 1860-56-6

3-methoxy-4-benzyloxy-ω-nitrostyrolene

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 55 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 1.) reflux, 2 h, 2.) room temperature, overnight
2: formic acid / 48 h / 50 °C
3: 88 percent / ammonium sulfate / toluene / 48 h / Heating
4: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
5: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
6: K2CO3 / acetone / 14 h / Heating
7: lithium aluminum hydride / tetrahydrofuran / Heating
8: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
4-methoxy-3-(benzyloxy)benzyl bromide
55667-12-4

4-methoxy-3-(benzyloxy)benzyl bromide

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
2: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
3: K2CO3 / acetone / 14 h / Heating
4: lithium aluminum hydride / tetrahydrofuran / Heating
5: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
vanillin
121-33-5

vanillin

KOH-solution

KOH-solution

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 88 percent / K2CO3 / ethanol
2: 73 percent / ammonium acetate / 1.5 h / Heating
3: 55 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 1.) reflux, 2 h, 2.) room temperature, overnight
4: formic acid / 48 h / 50 °C
5: 88 percent / ammonium sulfate / toluene / 48 h / Heating
6: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
7: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
8: K2CO3 / acetone / 14 h / Heating
9: lithium aluminum hydride / tetrahydrofuran / Heating
10: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
(S)-valinol-tert-butyl ether formamidine of 7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline
133320-18-0

(S)-valinol-tert-butyl ether formamidine of 7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
2: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
3: K2CO3 / acetone / 14 h / Heating
4: lithium aluminum hydride / tetrahydrofuran / Heating
5: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
1-(3'-benzyloxy-4'-methoxybenzyl)-7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline
19777-98-1

1-(3'-benzyloxy-4'-methoxybenzyl)-7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: K2CO3 / acetone / 14 h / Heating
2: lithium aluminum hydride / tetrahydrofuran / Heating
3: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
(S)-7-Benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester
23523-84-4, 56114-15-9

(S)-7-Benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium aluminum hydride / tetrahydrofuran / Heating
2: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline
148776-16-3

7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 88 percent / ammonium sulfate / toluene / 48 h / Heating
2: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
3: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
4: K2CO3 / acetone / 14 h / Heating
5: lithium aluminum hydride / tetrahydrofuran / Heating
6: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
[1-[(S)-7-Benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-meth-(E)-ylidene]-((S)-1-tert-butoxymethyl-2-methyl-propyl)-amine

[1-[(S)-7-Benzyloxy-1-(3-benzyloxy-4-methoxy-benzyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-meth-(E)-ylidene]-((S)-1-tert-butoxymethyl-2-methyl-propyl)-amine

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
2: K2CO3 / acetone / 14 h / Heating
3: lithium aluminum hydride / tetrahydrofuran / Heating
4: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
3-benzyloxy-4-methoxybenzaldehyde
6346-05-0

3-benzyloxy-4-methoxybenzaldehyde

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 93 percent / NaBH4 / ethanol / 1.) room temperature, 18 h, 2.) reflux, 1 h
2: 96 percent / PBr3 / tetrahydrofuran / 1.5 h / 0 °C
3: t-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) -100 deg C, 4 h
4: hydrazine, acetic acid / ethanol; H2O / 2 h / Ambient temperature
5: K2CO3 / acetone / 14 h / Heating
6: lithium aluminum hydride / tetrahydrofuran / Heating
7: 0.026 g / hydrogen / 10percent Pd/C / acetic acid; methanol / 6 h / 2585.7 Torr
View Scheme
(-)-Norreticuline
4781-58-2

(-)-Norreticuline

S-Adenosyl-L-methionine
14031-35-7, 17176-17-9, 29908-03-0, 75044-81-4, 78548-84-2, 79647-17-9, 91279-78-6

S-Adenosyl-L-methionine

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
With ipecac alkaloid O-methyltransferase 3 Enzymatic reaction;
reticuline
1699-46-3, 7096-86-8

reticuline

A

(R)-reticuline
485-19-8, 1699-46-3, 3968-19-2, 7096-86-8, 14752-49-9

(R)-reticuline

B

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
With Escherichia coli monoamine oxidase MAO-N D11 Enzymatic reaction; enantioselective reaction;A n/a
B n/a
With recombinant monoamine oxidase D11 from Aspergillus niger In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 24h; pH=7.7; Resolution of racemate; Enzymatic reaction; enantioselective reaction;A n/a
B n/a
formaldehyd
50-00-0

formaldehyd

N-benzoyl-norreticuline
13168-51-9

N-benzoyl-norreticuline

A

(R)-reticuline
485-19-8, 1699-46-3, 3968-19-2, 7096-86-8, 14752-49-9

(R)-reticuline

B

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
With sodium cyanoborohydride; zinc(II) chloride In methanol at 20℃; for 24h; Overall yield = 96 %; Overall yield = 32.5 mg;
...Expand
dopamine
51-61-6

dopamine

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Conditions
ConditionsYield
With 4-morpholineethanesulfonic acid; ascorbate; isopropyl β-D-thiogalactopyranoside at 37℃; Enzymatic reaction;
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

(+)-reticuline N-oxide

(+)-reticuline N-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2.5h;66%
5-Chloro-1-phenyltetrazole
14210-25-4

5-Chloro-1-phenyltetrazole

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

7,11-O,O-bis(1-phenyl-1H-tetrazol-5-yl)reticuline

7,11-O,O-bis(1-phenyl-1H-tetrazol-5-yl)reticuline

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile for 24h; Reflux;63%
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

A

isoboldine
3019-51-0, 5164-93-2, 13529-67-4, 104597-61-7

isoboldine

B

(S)-(-)-pallidine
25650-75-3

(S)-(-)-pallidine

C

S-(-)-coreximine
483-45-4

S-(-)-coreximine

D

(S)-scoulerine
605-34-5, 6451-72-5, 6451-73-6, 6507-34-2

(S)-scoulerine

Conditions
ConditionsYield
With phosphate buffer; (S)-2-[3]pyridyl-pyrrolidine-1-carboxylic acid amide; NADPH; magnesium chloride at 37℃; for 2h; rat liver microsomes;A 7.5%
B 5.2%
C 21.1%
D 7.9%
...Expand
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

(S)-(+)-<2',6',8-3H3>reticuline
74080-69-6

(S)-(+)-<2',6',8-3H3>reticuline

Conditions
ConditionsYield
With tritium oxide; potassium tert-butylate at 100℃; for 110h; sealed tube;
With tritium oxide; potassium tert-butylate at 100℃; for 110h;
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

(S)-scoulerine
605-34-5, 6451-72-5, 6451-73-6, 6507-34-2

(S)-scoulerine

Conditions
ConditionsYield
enzymatic reaction with berberine bridge enzyme;
berberine bridge enzyme Mechanism; stereochemistry of enzymatic berberine bridge formation;
With glycine-NaOH buffer; berberine bridge-forming enzyme In water at 30℃; for 1h; Mechanism; further benzylisoquinolines; tritium labelling (-N-CT3) experiments;
With berberine bridge enzyme; tris hydrochloride at 37℃; for 2h; pH=8.8; Enzymatic reaction;
With berberine bridge enzyme Enzymatic reaction;
acetic anhydride
108-24-7

acetic anhydride

(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

L-Reticulin-diacetat
14199-49-6

L-Reticulin-diacetat

Conditions
ConditionsYield
With pyridine at 20℃;
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

(1S,2S)-reticuline Nα-oxide

(1S,2S)-reticuline Nα-oxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 20 °C
2: m-CPBA / CH2Cl2
3: 1.6 mg / aq. NH4OH / methanol / 20 °C
View Scheme
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

C23H27NO7

C23H27NO7

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 20 °C
2: m-CPBA / CH2Cl2
View Scheme
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

(1S,2R)-reticuline Nβ-oxide

(1S,2R)-reticuline Nβ-oxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 20 °C
2: m-CPBA / CH2Cl2
3: 1.3 mg / aq. NH4OH / methanol / 20 °C
View Scheme
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

columbamine
3621-36-1

columbamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: enzymatic reaction with berberine bridge enzyme
2: S-adenosyl-L-methionine / enzymatic reaction with (S)-scoulerine-9-O-methyltransferase
3: enzymatic reaction with (S)-tetrahydroprotoberberine oxidase
View Scheme
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

(-)-isocorypalmine
6487-33-8, 6989-84-0, 53447-14-6, 483-34-1

(-)-isocorypalmine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: enzymatic reaction with berberine bridge enzyme
2: S-adenosyl-L-methionine / enzymatic reaction with (S)-scoulerine-9-O-methyltransferase
View Scheme
(+)-(S)-reticuline
485-19-8

(+)-(S)-reticuline

Nandinine
572-76-9

Nandinine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: recombinant berberine bridge enzyme; recombinant CYP719A13 enzyme from Argemone mexicana; recombinant CYP719A14 enzyme from Argemone mexicana; recombinant cytochrome P450 reductase from Eschscholzia californica; NADPH / 1 h / 30 °C / pH 8 / Enzymatic reaction
2: recombinant CYP719A13 enzyme from Argemone mexicana; NADPH / 0.17 h / 30 °C / pH 8 / Enzymatic reaction
View Scheme

Streptomycin c Chemical Properties

IUPAC  Name: 1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol 
Molecular Formula: C19H23NO4
Molecular Weight: 329.39022
Freely Rotating Bonds: 6
Polar Surface Area: 40.16 Å2
Index of Refraction: 1.603
Molar Refractivity: 92.98 cm3
Molar Volume: 270.4 cm3
Polarizability: 36.86× 10-24 cm3
Surface Tension: 49.7 dyne/cm
Density: 1.217 g/cm3
Flash Point: 259.2 °C
Enthalpy of Vaporization: 80.38 kJ/mol
Boiling Point: 504.9 °C at 760 mmHg
Vapour Pressure: 8.11E-11 mmHg at 25°C 
The Cas Register Number of  Streptomycin c is 485-19-8.The chemical synonyms of Streptomycin c (CAS NO.485-19-8) are (+)-Reticuline ; (R)-Reticuline ; (R,S)-Reticuline ; (S)-Reticuline ; 1-(3-Hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol ; 1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol ; 2-Methyl-7-hydroxy-6-methoxy-1-(3-hydroxy-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline  and 7-isoquinolinol, 1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl- .The molecular structure of Streptomycin c (CAS NO.485-19-8) is.

Streptomycin c Uses

 Streptomycin c (CAS NO.485-19-8) is used in organic synthesis.

Streptomycin c Toxicity Data With Reference

1.    

scu-mus LD50:865 mg/kg

     85ERAY    Antibiotics: Origin, Nature, and Properties. 1 (1978),570.
2.    

ivn-mus LD50:154 mg/kg

     85ERAY    Antibiotics: Origin, Nature, and Properties. 1 (1978),570.

Streptomycin c Safety Profile

Poison by intravenous route. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NOx.

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