2196-60-3

Basic information

• Product Name: Coclaurine
• Synonyms: Coclaurine;(1R)-1-(4-Hydroxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-ol;(R)-1,2,3,4-Tetrahydro-1-(4-hydroxybenzyl)-6-methoxyisoquinolin-7-ol;(R)-Coclaurine;Sanjoinine K;(1R)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-7-isoquinolinol
• CAS NO: 2196-60-3
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.3377
• Mol File: 2196-60-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 222-224 °C
• Boiling Point: 496.9°Cat760mmHg
• Flash Point: 254.3°C
• Appearance: /
• Density: 1.232g/cm³
• Vapor Pressure: 1.69E-10mmHg at 25°C
• Refractive Index: 1.62
• PKA: 10.00±0.15(Predicted)
• CAS DataBase Reference: Coclaurine(CAS DataBase Reference)
• NIST Chemistry Reference: Coclaurine(2196-60-3)
• EPA Substance Registry System: Coclaurine(2196-60-3)

Safety Data

• Hazardous Substances Data: 2196-60-3(Hazardous Substances Data)

Usage

Description

Coclaurine is a tetrahydroisoquinoline alkaloid derived from plants, characterized by its white crystalline powder form and solubility in various organic solvents such as methanol, ethanol, and DMSO. It possesses anti-aging activity and is recognized for its role as a nicotinic acetylcholine receptor antagonist, making it a potential candidate for pharmaceutical and cosmetic applications.

Uses

Used in Pharmaceutical Applications:
Coclaurine is used as a nicotinic acetylcholine receptor antagonist for its potential therapeutic effects on various conditions related to the nervous system. Its ability to modulate receptor activity may contribute to the development of treatments for neurological disorders and cognitive enhancement.
Used in Cosmetic Applications:
Coclaurine is used as an anti-aging agent in the cosmetic industry, capitalizing on its ability to promote skin health and slow down the aging process. Its incorporation into skincare products may help improve skin elasticity, reduce the appearance of fine lines and wrinkles, and provide overall rejuvenation.
Used in Chemical Research:
As a tetrahydroisoquinoline alkaloid, Coclaurine serves as an important compound in chemical research, particularly in the study of natural products and their potential applications in medicine and pharmacology. Its unique chemical properties and structural features make it a valuable subject for further investigation and development.

InChI:InChI=1/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m1/s1

Synthetic route

(+)-1-(R)-coclaurine (2196-60-3) + acetic anhydride (108-24-7) → Acetic acid (R)-1-(4-acetoxy-benzyl)-2-acetyl-6-methoxy-1,2,3,4-tetrahydro-isoquinolin-7-yl ester (3422-43-3, 96370-47-7)

Conditions	Yield
With pyridine for 15h; Ambient temperature;

(+)-1-(R)-coclaurine (2196-60-3) + S-(5’-adenosyl)-L-methionine chloride → (-)-(R)-(N)-methylcoclaurine (5096-70-8)

Conditions	Yield
With potassium phosphate buffer; sodium L-ascorbate; coclaurine N-methyltransferase In water at 30℃; for 1h; pH=7.0; Kinetics; Further Variations:; relative activity (vs (S)-coclaurine);

Downstream Products

• 5096-70-8 (-)-(R)-(N)-methylcoclaurine 

Related news

The crystal structure of Coclaurine (cas 2196-60-3) hydrobromide monohydrate and the absolute configuration of Coclaurine (cas 2196-60-3)07/15/2019

The structure and absolute configuration of coclaurine has been determined by X-ray analysis of its hydrobromide monohydrate. The (+)-enantiomer has the D-configuration. The chirality of the molecular structure is correlated with circular dichroism measurements.detailed

Purification and characterization of Coclaurine (cas 2196-60-3) N-methyltransferase from cultured Coptis japonica cells07/13/2019

S-Adenosyl-l-methionine (SAM): coclaurine N-methyltransferase (CNMT), which catalyzes the transfer of a methyl group from S-adenosyl-l-methionine to the amino group of the tetrahydrobenzylisoquinoline alkaloid coclaurine, was purified 340-fold from Coptis japonica cells in 1% yield to give an al...detailed