Higenamine

Base Information

• Chemical Name: Higenamine
• CAS No.: 5843-65-2
• Deprecated CAS: 17072-47-8
• Molecular Formula: C16H17NO3
• Molecular Weight: 271.316
• UNII: TBV5O16GAP
• DSSTox Substance ID: DTXSID70973974
• Wikipedia: Higenamine
• Wikidata: Q5754240
• Metabolomics Workbench ID: 125618
• ChEMBL ID: CHEMBL19344
• Mol file: 5843-65-2.mol

Synonyms:1(S)-norcoclaurine;1-(p-hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline;higenamine;higenamine hydrobromide, (+-)-isomer;higenamine hydrochloride, (S)-isomer;higenamine oxalate (1:1), (+-)-isomer;higenamine, tartrate (1:1), R-(R*,R*)-(+-)-isomer;norcoclaurine;O-demethylcoclaurine

Chemical Property of Higenamine

Chemical Property:

• Vapor Pressure: 1.56E-11mmHg at 25°C
• Melting Point: 208-210 °C
• Refractive Index: 1.666
• Boiling Point: 522.4 °C at 760 mmHg
• PKA: 9.72±0.40(Predicted)
• Flash Point: 209.6 °C
• PSA: 72.72000
• Density: 1.317 g/cm³
• LogP: 2.56170
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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:

98%,99%, ^*data from raw suppliers

Higenamine >98%,StandardReferencesGrade ^*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
• Recent ClinicalTrials: Pharmacokinetics and Pharmacodynamics of Higenamine in Chinese Healthy Subjects
• Uses: Demethyl-Coclaurine acts through inhibition of middle cerebral artery occlusion (MCAO)-mediated HMGB1 release in vivo. Useful towards ischemic injuries. (±)-Norcoclaurine can be used to prevent and treat of Alzheimer’s disease, bind to SARS-CoV-2 S protein:human ACE2 complex, as a bronchodilator to improve lung function in various respiratory diseases, and an antioxidant in lipid-like environments. It can also be used as a racemic salt-acidic compound to produce elevated and sustained ketosis.

Technology Process of Higenamine

There total 29 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: 69.0%

4-hydroxyphenylacetaldehyde (7339-87-9) + dopamine hydrochloride (62-31-7) → higenamine (5843-65-2)

Guidance literature:

In aq. phosphate buffer; water; at 37 ℃; for 1.25h;

DOI:10.1016/j.tetlet.2014.07.043

Reference yield: 44.0%

dopamine (51-61-6) + tyrosamine (51-67-2) → higenamine (5843-65-2)

Guidance literature:

tyrosamine; With pyridoxal 5'-phosphate; transaminase from chromobacterium violaceum; sodium pyruvate; sodium L-ascorbate; In aq. phosphate buffer; acetonitrile; at 37 ℃; for 6h; pH=7.5; Inert atmosphere; Enzymatic reaction;

dopamine; In aq. phosphate buffer; acetonitrile; at 60 ℃; for 18h; Inert atmosphere;

DOI:10.1002/anie.201902761

upstream raw materials:

p-hydroxyphenethyl alcohol

4-hydroxyphenylacetaldehyde

dopamine hydrochloride

dopamine

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

C₂₁H₂₅NO₅

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

(1R)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Refernces

• 1、 Andexer, Jennifer N.,Cárdenas-Fernández, Max,Hailes, Helen C.,Méndez-Sánchez, Daniel,Richter, Michael,Roddan, Rebecca,Siegrist, Jutta,Subrizi, Fabiana,Thair, Benjamin,Wang, Yu,Ward, John M.. "Multienzyme One-Pot Cascades Incorporating Methyltransferases for the Strategic Diversification of Tetrahydroisoquinoline Alkaloids". supporting information. p. 18673 - 18679. Retrieved 2021/07/19.
• 2、 -. "Synthesis technology of higenamine and pharmaceutical salt of higenamine". . . Retrieved 2019/09/14.