Coclaurine

Base Information

• Chemical Name: Coclaurine
• CAS No.: 486-39-5
• Molecular Formula: C17H19 N O3
• Molecular Weight: 285.343
• UNII: CW1576313Y
• DSSTox Substance ID: DTXSID60197561
• Nikkaji Number: J6.009G
• Wikipedia: Coclaurine
• Wikidata: Q15633989
• Metabolomics Workbench ID: 50323
• ChEMBL ID: CHEMBL446211
• Mol file: 486-39-5.mol

Synonyms:1(R)-coclaurine;coclaurine;coclaurine, (+-)-isomer;coclaurine, (R)-isomer

Chemical Property of Coclaurine

Chemical Property:

• Vapor Pressure: 1.69E-10mmHg at 25°C
• Melting Point: 220-221°
• Refractive Index: 1.5400 (estimate)
• Boiling Point: 496.9°C at 760 mmHg
• PKA: 10.00±0.15(Predicted)
• Flash Point: 254.3°C
• PSA: 61.72000
• Density: 1.232g/cm³
• LogP: 2.86470
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 285.13649347
• Heavy Atom Count: 21
• Complexity: 330

Purity/Quality:

≥98% ^*data from raw suppliers

Coclaurine 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(NCCC2=C1)CC3=CC=C(C=C3)O)O
• Isomeric SMILES: COC1=C(C=C2[C@@H](NCCC2=C1)CC3=CC=C(C=C3)O)O

Technology Process of Coclaurine

There total 4 articles about Coclaurine 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:

(1S)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol (5843-65-2,17072-47-8,106032-53-5,22672-77-1) + S-adenosyl-L-methionine p-toluenesulfonate salt (52248-03-0) → Coclaurine (486-39-5)

Guidance literature:

With Coptis japonica cell lysate containing norcoclaurine 6-O-methyltransferase; magnesium chloride; In aq. buffer; at 37 ℃; for 1.5h; Reagent/catalyst; regioselective reaction; Enzymatic reaction;

DOI:10.1002/anie.202104476

Reference yield:

(1S)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol (5843-65-2,17072-47-8,106032-53-5,22672-77-1) + S-adenosyl-L-methionine p-toluenesulfonate salt (52248-03-0) → (S)-1-(4-hydroxybenzyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol + Coclaurine (486-39-5)

Guidance literature:

With Myxococcus xanthus cell lysate containing catechol-O-methyltransferase; magnesium chloride; In aq. buffer; at 37 ℃; for 1.5h; Enzymatic reaction;

DOI:10.1002/anie.202104476

Reference yield:

tyrosamine (51-67-2) → Coclaurine (486-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1: wild-type Thalictrum flavum cell lysate containing norcoclaurinesynthase; sodium pyruvate; Chromobacterium violaceum cell lysate containing transaminase; Candidatus Nitrosopumilus salaria cell lysate containing BD₃₁ tyrosinase; sodium hydroxide / aq. buffer / 8 h / 37 °C / pH 7.5 / Enzymatic reaction

2: magnesium chloride; Coptis japonica cell lysate containing norcoclaurine 6-O-methyltransferase / aq. buffer / 1.5 h / 37 °C / Enzymatic reaction

With sodium pyruvate; Candidatus Nitrosopumilus salaria cell lysate containing BD₃₁ tyrosinase; Chromobacterium violaceum cell lysate containing transaminase; Coptis japonica cell lysate containing norcoclaurine 6-O-methyltransferase; wild-type Thalictrum flavum cell lysate containing norcoclaurinesynthase; sodium hydroxide; magnesium chloride; In aq. buffer;

DOI:10.1002/anie.202104476

upstream raw materials:

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

S-adenosyl-L-methionine p-toluenesulfonate salt

tyrosamine

Downstream raw materials:

(S)-N-methylcoclaurine

-(S)-N-methylcoclaurine

Refernces

• 1、 Lu, Sheng-Teh,Tsai, Ian-Lih,Leou, Shiow-Piaw. "ALKALOIDS OF DEHAASIA TRIANDRA". . p. 615 - 620. Retrieved 2007/10/02.