57231-32-0

Basic information

• Product Name: (R)-1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-2-methylisoquinoline-6,7-diol
• Synonyms: (R)-1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-2-methylisoquinoline-6,7-diol;(1R)-1β-(3,4-Dihydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol;(1R)-1β-[(3,4-Dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-2-methyl-6,7-isoquinolinediol;Einecs 260-636-1
• CAS NO: 57231-32-0
• Molecular Formula: C17H19NO4
• Molecular Weight: 301.33706
• EINECS: 260-636-1
• Mol File: 57231-32-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 548°Cat760mmHg
• Flash Point: 323°C
• Appearance: /
• Density: 1.373g/cm³
• Vapor Pressure: 1.28E-12mmHg at 25°C
• Refractive Index: 1.685
• CAS DataBase Reference: (R)-1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-2-methylisoquinoline-6,7-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-2-methylisoquinoline-6,7-diol(57231-32-0)
• EPA Substance Registry System: (R)-1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-2-methylisoquinoline-6,7-diol(57231-32-0)

Safety Data

• Hazardous Substances Data: 57231-32-0(Hazardous Substances Data)

Usage

General Description

(R)-1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-2-methylisoquinoline-6,7-diol, also known as tetrahydroberberine, is a chemical compound that belongs to the isoquinoline alkaloids. It is derived from the plant Berberis aristata and has been traditionally used in Ayurvedic medicine for its antioxidant and anti-inflammatory properties. Tetrahydroberberine has been studied for its potential therapeutic effects on various health conditions, including diabetes, obesity, and cardiovascular diseases. It has been shown to have hypoglycemic and hypolipidemic properties, making it a promising candidate for the treatment of metabolic disorders. Additionally, tetrahydroberberine has demonstrated neuroprotective effects and has been investigated for its potential use in the management of neurodegenerative diseases.

InChI:InChI=1/C17H19NO4/c1-18-5-4-11-8-16(21)17(22)9-12(11)13(18)6-10-2-3-14(19)15(20)7-10/h2-3,7-9,13,19-22H,4-6H2,1H3/t13-/m1/s1

Upstream product

• 56632-97-4 6,7-bis-benzyloxy-1-(3,4-bis-benzyloxy-benzyl)-3,4-dihydro-isoquinoline 
• 4747-99-3 Norlaudanosolin 
• 79832-22-7 6,7-bisbenzyloxy-1-(3,4-bisbenzyloxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 94757-36-5 4,5,3',4'-tetramethoxy-2-vinyl-stilbene 

Downstream Products

• 24993-28-0 [2-(3,4-dimethoxy-styryl)-4,5-dimethoxy-phenethyl]-dimethyl-amine 

Relevant articles and documents

Compositions and methods for producing benzylisoquinoline alkaloids

The present invention relates to host cells that produce compounds that are characterized as benzylisoquinolines, as well as select precursors and intermediates thereof. The host cells comprise one, two or more heterologous coding sequences wherein each of the heterologous coding sequences encodes an enzyme involved in the metabolic pathway of a benzylisoquinoline, or its precursors or intermediates from a starting compound. The invention also relates to methods of producing the benzylisoquinoline, as well as select precursors and intermediates thereof by culturing the host cells under culture conditions that promote expression of the enzymes that produce the benzylisoquinoline or precursors or intermediates thereof.

Biosynthesis. Part 24. Speculative Incorporation Experiments with 1-Benzylisoquinolines and a Logical Approach via C6-C2 and C6-C3 Precursors to the Biosynthesis of Hasubanonine and Protostephanine

Many possible 1-benzyltetrahydroisoquinolines have been examined as possible advanced precursors of the alkaloids hasubanonine (1) and protostephanine (2) in Stephania japonica plants, but none was incorporated significantly.Administration of various precursor molecules having only one aromatic ring, such as tyrosine, has demonstrated that both alkaloids are derived from two different C6-C2 biogenetic units.The subsequent failure of further 1-benzyltetrahydroisoquinolines and bisphenethylamines to be incorporated suggested the intermediacy of either (a) modified 1-benzylisoquinolines or (b) trioxygenated C6-C2 building blocks.Precursors designed to examine the first possibility, such as 1-benzyl-3,4-dihydroisoquinolines or 1-benzyl-1-carboxytetrahydroisoquinolines, were not incorporated into (1) and (2) whereas two 3',4',5'-trioxygenated 2-phenylethylamines were incorporated.These findings allow further delineation of the requirements for later precursors of the alkaloids (1) and (2).