Higenamine hydrochloride

Base Information

• Chemical Name: Higenamine hydrochloride
• CAS No.: 11041-94-4
• Molecular Formula: C16H17NO3^.HCl
• Molecular Weight: 307.777
• Hs Code.: 2933499090
• UNII: PQ432PID6E
• DSSTox Substance ID: DTXSID10911673
• Wikidata: Q27286703
• Mol file: 11041-94-4.mol

Synonyms:Higenamine hydrochloride;11041-94-4;Higenamine HCl;Demethyl;6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride;(+-)-Demethylcoclaurine hydrochloride;Demethylcoclaurine hydrochloride;MFCD01717353;Higenamine (hydrochloride);UNII-PQ432PID6E;PQ432PID6E;1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrochloride;11041-94-4 (HCl);1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrochloride;(+-)-1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediol hydrochloride;6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-, hydrochloride, (+-)-;6,7-Dihydroxy-1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline HCl;1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride;6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-, hydrochloride (1:1);norcoclaurine HCl;6,7-ISOQUINOLINEDIOL, 1,2,3,4-TETRAHYDRO-1-((4-HYDROXYPHENYL)METHYL)-, HYDROCHLORIDE (1:1);Demethylcoclaurine HCl;Higenamine?Hydrochloride;HY-N2037A;DTXSID10911673;(+/-)-Higenamine HCl - natural;BCP07397;(+/-)-Higenamine HCl - synthetic;s3960;AKOS025287070;CCG-267555;_x000D_67-Dihydroxy-1-(4-Hydroxybenzyl)-1234-tetrahydroisoquinoline Hydrochloride;1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediol hydrochloride;1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol hydro chloride (1:1);AC-26395;AS-10415;LS-85615;SY029900;XH163199;CS-0016803;FT-0696741;(+/-)-DEMETHYLCOCLAURINE HYDROCHLORIDE;EN300-822191;DEMETHYLCOCLAURINE HYDROCHLORIDE, (+/-)-;J-503750;Q27286703;Z2940609369;1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol hydrochloride;1-[(4-Hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol--hydrogen chloride (1/1);6,7-ISOQUINOLINEDIOL, 1,2,3,4-TETRAHYDRO-1-((4-HYDROXYPHENYL)METHYL)-, HYDROCHLORIDE, (+/-)-

Chemical Property of Higenamine hydrochloride

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.56E-11mmHg at 25°C
• Boiling Point: 522.4 °C at 760 mmHg
• Flash Point: 209.6 °C
• PSA: 72.72000
• LogP: 3.36370
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 307.0975211
• Heavy Atom Count: 21
• Complexity: 317

Purity/Quality:

99% ^*data from raw suppliers

Higenamine Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O.Cl
• Description: Higenamine is a chemical found in several plants including aconite, Annona squamosa, Nandina domestica (sacred bamboo), and others. HigenaMine Hydrochloride is the hydrochloride form of higenamine.
• Uses: Higenamine HCl (norcoclaurine) is a plant-based alkaloid widely used as nutritional supplement in food and beverage industries.

Technology Process of Higenamine hydrochloride

There total 8 articles about Higenamine hydrochloride 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:

6,7-bisbenzyloxy-1-(4-benzyloxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (117765-29-4) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; for 2h;

DOI:10.1039/P19810002016

Reference yield:

2-[4-(benzyloxy)phenyl]acetonitrile (838-96-0) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium hydroxide, water / ethane-1,2-diol / 18 h / Heating

2: oxalyl chloride, DMF / benzene / 1 h / 20 °C

3: sodium hydrogen carbonate / CH₂Cl₂; H₂O / 1.5 h

4: phosphorus oxychloride / acetonitrile / 0.42 h / Heating

5: sodium borohydride / methanol / 0.75 h / 0 °C

6: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; oxalyl dichloride; water; hydrogen; sodium hydrogencarbonate; N,N-dimethyl-formamide; trichlorophosphate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; ethylene glycol; acetonitrile; benzene;

DOI:10.1039/P19810002016

Reference yield:

3,4-bis(benzyloxy)-β-nitrostyrene (1699-54-3) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / lithium aluminium hydride / tetrahydrofuran / 1.25 h / Heating

2: sodium hydrogen carbonate / CH₂Cl₂; H₂O / 1.5 h

3: phosphorus oxychloride / acetonitrile / 0.42 h / Heating

4: sodium borohydride / methanol / 0.75 h / 0 °C

5: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; sodium hydrogencarbonate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1039/P19810002016

upstream raw materials:

6,7-bisbenzyloxy-1-(4-benzyloxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

2-[4-(benzyloxy)phenyl]acetonitrile

3,4-bis(benzyloxy)-β-nitrostyrene

2-(4-(benzyloxy)phenyl)acetyl chloride

Refernces