17459-85-7

Basic information

• Product Name: 1-benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• Synonyms: 1-benzyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline; 6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-(phenylmethyl)-; 6,7-Isoquinolinediol, 1-benzyl-1,2,3,4-tetrahydro-
• CAS NO: 17459-85-7
• Molecular Formula: C₁₆H₁₇NO₂
• Molecular Weight: 255.3117
• Mol File: 17459-85-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 459.6°C at 760 mmHg
• Flash Point: 175.1°C
• Density: 1.23g/cm³
• Vapor Pressure: 4.55E-09mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: 1-benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol(17459-85-7)
• EPA Substance Registry System: 1-benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol(17459-85-7)

Safety Data

• Hazardous Substances Data: 17459-85-7(Hazardous Substances Data)

Upstream product

• 51-61-6 dopamine 
• 122-78-1 phenylacetaldehyde 
• 62-31-7 dopamine hydrochloride 
• 3423-37-8 1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 4876-00-0 1-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinoline 

Relevant articles and documents

Synthesis, Purification, and Selective β2-AR Agonist and Bronchodilatory Effects of Catecholic Tetrahydroisoquinolines from Portulaca oleracea

A green, biomimetic, phosphate-mediated Pictet-Spengler reaction was used in the synthesis of three catecholic tetrahydroisoquinolines, 1, 2, and 12, present in the medicinal plant Portulaca oleracea, as well as their analogues 3-11, 13, and 14, with dopa

Asymmetric synthesis of tetrahydroisoquinolines by enzymatic Pictet-Spengler reaction

Norcoclaurine synthase (NCS) catalyzes the stereo-selective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as the first step of benzylisoquinoline alkaloid synthesis in plants. Recent studies suggested that NCS shows relatively relaxed substrate specificity toward aldehydes, and thus, the enzyme can serve as a tool to synthesize unnatural, optically active tetrahydroisoquinolines. In this study, using an N-terminally truncated NCS from Coptis japonica expressed in Escherichia coli, we examined the aldehyde substrate specificity of the enzyme. Herein, we demonstrate the versatility of the enzyme by synthesizing 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline and 6,7-dihydroxy-1-propyl-1,2,3,4-tetrahydroisoquinoline in molar yields of 86.0 and 99.6% and in enantiomer excess of 95.3 and 98.0%, respectively. The results revealed the enzyme is a promising catalyst that functions to stereoselectively produce various 1-substituted-1,2,3,4-tetrahydroisoquinolines.

Biocatalytic production of tetrahydroisoquinolines

The promiscuity of the enzyme norcoclaurine synthase is described. This biocatalyst yielded a diverse array of substituted tetrahydroisoquinolines by cyclizing dopamine with various acetaldehydes in a Pictet-Spengler reaction. This enzymatic reaction may provide a biocatalytic route to a range of tetrahydroisoquinoline alkaloids.