1464-33-1

Basic information

• Product Name: 4-methoxymethylpyridoxine
• Synonyms: 4-methoxymethylpyridoxine;3-Hydroxy-5-hydroxymethyl-4-methoxymethyl-2-methylpyridine;3-Hydroxy-5-hydroxymethyl-4-methoxymethyl-2-picoline;5-hydroxy-4-(methoxymethyl)-6-methyl-3-pyridinemethano;5-hydroxy-4-(methoxymethyl)-6-methyl-3-pyridinemethanol;5-Hydroxy-4-methoxymethyl-6-methyl-3-pyridinemethanol;alpha(sup 4)-o-methylpyridoxol;5-(hydroxymethyl)-4-(methoxymethyl)-2-methylpyridin-3-ol
• CAS NO: 1464-33-1
• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.206
• Mol File: 1464-33-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 181°C
• Boiling Point: 316.88°C (rough estimate)
• Flash Point: 198.3°C
• Appearance: /
• Density: 1.1967 (rough estimate)
• Refractive Index: 1.4760 (estimate)
• CAS DataBase Reference: 4-methoxymethylpyridoxine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxymethylpyridoxine(1464-33-1)
• EPA Substance Registry System: 4-methoxymethylpyridoxine(1464-33-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1464-33-1(Hazardous Substances Data)

Usage

General Description

4-methoxymethylpyridoxine is a chemical compound that is derived from pyridoxine, also known as vitamin B6. It is a derivative of vitamin B6 that has a methoxy group and a methyl group attached to the pyridine ring. 4-methoxymethylpyridoxine has been studied for its potential therapeutic properties, particularly in the treatment of inflammation and oxidative stress. It is believed to have antioxidant and anti-inflammatory effects, making it a promising candidate for the development of new drugs for various conditions. Additionally, 4-methoxymethylpyridoxine has been found to have neuroprotective effects and may play a role in preventing or treating neurodegenerative diseases. Further research is needed to fully understand the potential benefits and mechanisms of action of this compound.

InChI:InChI=1/C9H13NO3/c1-6-9(12)8(5-13-2)7(4-11)3-10-6/h3,11-12H,4-5H2,1-2H3

Synthetic route

methanol (67-56-1) + 5-hydroxy-6-methyl-3,4-pyridinedimethanol (65-23-6) → ginkgotoxin (1464-33-1)

Conditions	Yield
In neat (no solvent) at 105℃; for 96h; regioselective reaction;	58%
In water at 15℃; Irradiation;	15%

methanol (67-56-1) + pyridoxine hydrochloride → ginkgotoxin (1464-33-1)

Conditions	Yield
With toluene-4-sulfonic acid at 110℃; for 3h; Sealed tube; Microwave irradiation;	56%

diazomethane (186581-53-3, 908094-01-9) + ginkgotoxin (1464-33-1) → 2-Methyl-3-methoxy-4-methoxymethyl-5-hydroxymethylpyridine (19175-11-2)

Conditions	Yield
In diethyl ether; ethanol at 5 - 10℃;

ginkgotoxin (1464-33-1) → 5-hydroxy-6-methyl-3,4-pyridinedimethanol (65-23-6)

Conditions	Yield
With sulfuric acid at 150℃; for 12h;	85.5 % Chromat.

ginkgotoxin (1464-33-1) → 4'-O-methylpyridoxine-5'-phosphate

Conditions	Yield
Stage #1: ginkgotoxin With phosphorus pentoxide at 60℃; for 3.5h; Stage #2: With water for 0.583333h; Heating; Further stages.;

Upstream product

• 67-56-1 methanol 
• 65-23-6 5-hydroxy-6-methyl-3,4-pyridinedimethanol 

Downstream Products

• 65-23-6 5-hydroxy-6-methyl-3,4-pyridinedimethanol 

Relevant articles and documents

Photogeneration of an o-quinone methide from pyridoxine (vitamin B6) in aqueous solution

Photolysis (254, 266 or 308 nm) of pyridoxine (vitamin B6) in aqueous solution gives an o-quinone methide efficiently which is trapped by MeOH and ethyl vinyl ether.

A regioselective etherification of pyridoxine via an ortho-pyridinone methide intermediate

The catalyst-free, regioselective synthesis of 4′-O-substituted pyridoxine derivatives under solventless conditions is described. The methodology relies on the highly regioselective formation of the ortho-pyridinone methide from pyridoxine and subsequent oxa-Michael addition of alcohol nucleophiles. This methodology provides good to excellent yields for primary and secondary alcohols and moderate yields for tertiary alcohols.