(+)-Higenamine

Base Information

• Chemical Name: (+)-Higenamine
• CAS No.: 106032-53-5
• Molecular Formula: C16H17 N O3
• Molecular Weight: 271.316
• UNII: 6016M93W29
• DSSTox Substance ID: DTXSID90331552
• Nikkaji Number: J444.133H
• Wikidata: Q27103301
• Metabolomics Workbench ID: 51442
• ChEMBL ID: CHEMBL501778
• Mol file: 106032-53-5.mol

Synonyms:(+)-HIGENAMINE;106032-53-5;(R)-(+)-Higenamine;(R)-Norcoclaurine;Higenamine, (+)-;(+)-Demethylcoclaurine;UNII-6016M93W29;CHEMBL501778;6016M93W29;CHEBI:27751;6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-, (1R)-;6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-, (R)-;(1R)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol;(1R)-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;6,7-Dihydroxy-(1R)-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline;6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-, (1R)-;SCHEMBL5898913;DTXSID90331552;BDBM50242856;C06347;EN300-22053210;Q27103301

Chemical Property of (+)-Higenamine

Chemical Property:

• Vapor Pressure: 1.56E-11mmHg at 25°C
• Boiling Point: 522.4°Cat760mmHg
• PKA: 9.72±0.40(Predicted)
• Flash Point: 209.6°C
• PSA: 72.72000
• Density: 1.317g/cm³
• LogP: 2.56170
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 271.12084340
• Heavy Atom Count: 20
• Complexity: 317

Purity/Quality:

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
• Isomeric SMILES: C1CN[C@@H](C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O

Technology Process of (+)-Higenamine

There total 27 articles about (+)-Higenamine 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: 99.0%

dopamine (51-61-6) + 4-hydroxyphenylacetaldehyde (7339-87-9) → (1S)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol (5843-65-2,17072-47-8,106032-53-5,22672-77-1)

Guidance literature:

With CjNCS₂; In acetonitrile; at 37 ℃; for 3h; pH=7.4; Enzymatic reaction;

DOI:10.1002/adsc.201200641

Reference yield:

tyrosamine (51-67-2) → (1S)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol (5843-65-2,17072-47-8,106032-53-5,22672-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Cytochrome P₄₅₀ 2D₆ / Enzymatic reaction

2: Norcoclaurine synthase / Enzymatic reaction

With Cytochrome P₄₅₀ 2D₆; Norcoclaurine synthase;

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → (1S)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol (5843-65-2,17072-47-8,106032-53-5,22672-77-1)

Guidance literature:

Multi-step reaction with 3 steps

1: AbPPO / Enzymatic reaction

2: L-tyrosine/dopa decarboxylase / Enzymatic reaction

3: Norcoclaurine synthase / Enzymatic reaction

With AbPPO; L-tyrosine/dopa decarboxylase; Norcoclaurine synthase;

upstream raw materials:

(3,4-Dimethoxyphenyl)acetic acid

(S)-(+)-2-(3,4-dimethoxyphenyl)-N-(1-phenylethyl)acetamide

(S)-(-)-[2-(3,4-dimethoxyphenyl)ethyl](1-phenylethyl)amine

N-[2-(3,4-dimethoxyphenyl)ethyl]-N-[1-((1S)-phenyl)ethyl]-2-(4-methoxyphenyl)acetamide

Downstream raw materials:

(2S)-1-((1S)-6,7-dihydroxy-1-(4-hydroxybenzyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-one

Coclaurine

Refernces

• 1、 Wang, Yu,Tappertzhofen, Nadine,Méndez-Sánchez, Daniel,Bawn, Maria,Lyu, Boyu,Ward, John M.,Hailes, Helen C.. "Design and Use of de novo Cascades for the Biosynthesis of New Benzylisoquinoline Alkaloids". supporting information. p. 10120 - 10125. Retrieved 2019/06/27.
• 2、 Wu, Hsin-Pei,Lu, Tai-Ni,Hsu, Nai-Yun,Chang, Che-Chien. "Absolute stereochemical assignment of SCH 71450, a selective dopamine D4 receptor antagonist, through enantioselective epimer synthesis". . p. 2898 - 2905. Retrieved 2013/07/05.