CAS No.485-19-8,(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol Suppliers

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Basic Information

Molecular Structure:
CAS No.:	485-19-8
Name:	(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol
Article Data:	12

Formula:	C19H23 N O4
Molecular Weight:	329.396
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
Density:	1.217g/cm³
Melting Point:	125-126ºC
Boiling Point:	504.9°Cat760mmHg
Flash Point:	259.2°C
Safety:	Poison by intravenous route. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NO_x.
PSA:	62.16000
LogP:	2.82460

Synthetic route

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

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

Conditions

Conditions	Yield
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%

: 916-40-5
1-(3'-benzyloxy-4'-methoxybenzyl)-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

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

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; acetic acid under 2585.7 Torr; for 6h;	0.026 g

: 621-59-0
isovanillin

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

Conditions

Conditions	Yield
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

Yield

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

: 2426-87-1
3-methoxy-4-(phenylmethoxy)benzaldehyde

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

Conditions

Conditions	Yield
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

Yield

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

: 22231-61-4
2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine

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

Conditions

Conditions	Yield
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

Yield

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

: 1860-60-2
3-benzyloxy-4-methoxy-benzyl alcohol

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

Conditions

Conditions	Yield
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

Yield

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

: 63909-38-6, 1860-56-6
3-methoxy-4-benzyloxy-ω-nitrostyrolene

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

Conditions

Conditions	Yield
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

Yield

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

: 55667-12-4
4-methoxy-3-(benzyloxy)benzyl bromide

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

Conditions

Conditions	Yield
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

: 121-33-5
vanillin

KOH-solution: KOH-solution

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

Conditions

Conditions	Yield
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

Yield

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

: 133320-18-0
(S)-valinol-tert-butyl ether formamidine of 7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline

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

Conditions

Conditions	Yield
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

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Chemistry

IUPAC Name: 1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Molecular Formula: C₁₉H₂₃NO₄Molecular 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^-24cm³
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.

Uses

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

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.

Safety Profile

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