1464-33-1

Usage

Uses

Used in Pharmaceutical Industry:
4-methoxymethylpyridoxine is used as a therapeutic agent for its potential to mitigate inflammation and oxidative stress. Its antioxidant and anti-inflammatory properties make it a promising candidate for the development of new drugs aimed at treating various conditions associated with these processes.
Used in Neuroprotective Applications:
In the field of neurology, 4-methoxymethylpyridoxine is utilized for its neuroprotective effects, suggesting a role in the prevention or treatment of neurodegenerative diseases. 4-methoxymethylpyridoxine's ability to protect neurons could lead to advancements in managing conditions such as Alzheimer's and Parkinson's diseases, where oxidative stress and inflammation are implicated in disease progression.
Further research is essential to fully elucidate the mechanisms of action and the extent of the potential benefits of 4-methoxymethylpyridoxine, ensuring its safe and effective application in medical treatments.

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 academic research and scientific papers

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.

Quantification of a botanical negative marker without an identical standard: Ginkgotoxin in Ginkgo biloba

A new strategy for the analysis of natural products uses a combination of quantitative 1H NMR (qHNMR) and adsorbent-free countercurrent separation (CS) methodology to establish a quantification method for ginkgotoxin (4′-O-methylpyridoxine) in Ginkgo biloba preparations. The target analyte was concentrated in a one-step CS process using the ChMWat +2 solvent system (CHCl3-MeOH-H2O, 10:5:5) and subsequently assayed by qHNMR. While commercial G. biloba seeds contained 59 μg of ginkgotoxin per seed, the compound was below the limit of detection (9 ppm) in a typical leaf extract. Due to the enrichment potential and loss-free operation of CS, the combination of CS and qHNMR is a generally suitable approach for threshold assays aimed at quantifying target compounds such as botanical negative markers at the low ppm level. As the proof of principle is demonstrated for relatively small CS capacities (20 mL, 1:40 loading) and modest NMR sensitivity (n = 16, 400 MHz, 5 mm RT probe), the approach can be adapted to quantification at the ppb level. The procedure enables the quantification of a botanical negative marker in the absence of identical reference material, which otherwise is a prerequisite for LC-based assays.

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.