148-51-6

Basic information

• Product Name: 4-Deoxypyridoxine hydrochloride
• Synonyms: 5-(Hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride;Deoxypyridoxine hydrochloride;4-Deoxypyridoxine hydrochloride ,98%;5-(HydroxyMethyl)-2,4-diMethyl-3-hydroxypyridine HCl;2,4-DiMethyl-3-hydroxy-5-hydroxyMethylpyridine Hydrochloride;3-Hydroxy-5-hydroxyMethyl-2,4-diMethylpyridine Hydrochloride;4-DesoxyaderMin Hydrochloride;4-Desoxypyridoxine Hydrochloride
• CAS NO: 148-51-6
• Molecular Formula: C₈H₁₁NO₂*ClH
• Molecular Weight: 189.64
• EINECS: 205-714-8
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Biochemistry;Vitamin Derivatives;Vitamins;DA - DHForensic and Veterinary Standards;Alphabetic;Chemical Structure;D;Drugs&Metabolites;Neat CompoundsDrugs of Abuse;Others;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 148-51-6.mol

Chemical Properties

• Melting Point: 274°C(dec.)(lit.)
• Boiling Point: 414.1 °C at 760 mmHg
• Flash Point: 204.2 °C
• Appearance: White to off white crystalline powder
• Density: 1.201 g/cm³
• Vapor Pressure: 1.34E-07mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• Stability: Hygroscopic
• CAS DataBase Reference: 4-Deoxypyridoxine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Deoxypyridoxine hydrochloride(148-51-6)
• EPA Substance Registry System: 4-Deoxypyridoxine hydrochloride(148-51-6)

Safety Data

• WGK Germany: 3
• RTECS: UT4800000
• Hazardous Substances Data: 148-51-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
4-Deoxypyridoxine hydrochloride is used as a pharmaceutical agent for inducing a vitamin B6 deficient status, which can alter the function and ultrastructure of endothelial cells (EC) in a manner similar to vascular disease. This property makes it a valuable tool for studying the effects of vitamin B6 deficiency on cellular processes and vascular health.
Used in Research Applications:
In research, 4-Deoxypyridoxine hydrochloride is used as a tool to study the effects of vitamin B6 deficiency on various cellular processes. It is particularly useful in investigating the role of vitamin B6 in the growth of S. carlsbergensis cells, as well as its impact on the activity of lysyl oxidase, which is involved in collagen and elastin crosslinking.
Used in Neurological Applications:
4-Deoxypyridoxine hydrochloride is used as a compound to study its effects on neurological conditions. It has been shown to decrease latency to first seizure in mice and increase the occurrence and duration of myoclonic responses in baboons with photosensitive epilepsy. This makes it a valuable tool for understanding the role of vitamin B6 in neurological function and the potential development of treatments for seizure disorders.
Used in Immunological Applications:
In the field of immunology, 4-Deoxypyridoxine hydrochloride is used to study its effects on the immune system. It has been shown to reduce the production of TNF-α and IL-6 in mice infected with T. spiralis, suggesting that it may play a role in modulating immune responses. This application could be useful in the development of therapies for autoimmune diseases and other conditions involving immune system dysregulation.
Used in Material Science Applications:
As a solid compound, 4-Deoxypyridoxine hydrochloride may also have potential applications in material science, particularly in the development of new materials with unique properties. Its chemical properties and interactions with other compounds could be harnessed to create novel materials with specific applications in various industries.

InChI:InChI=1/C8H11NO2.ClH/c1-5-7(4-10)3-9-6(2)8(5)11;/h3,10-11H,4H2,1-2H3;1H

Upstream product

• 65-23-6 5-hydroxy-6-methyl-3,4-pyridinedimethanol 
• 58-56-0 pyridoxal hydrochloride 

Downstream Products

• 57183-08-1 (5-(benzyloxy)-4,6-dimethylpyridin-3-yl)methanol 
• 53580-72-6 2,4-dimethyl-5-hydroxymethyl-3-acetoxypyridine 
• 1350748-88-7 5-(hydroxymethyl)-2,4-dimethyl-6-(phenyldiazenyl)pyridin-3-ol 
• 55522-60-6 5-chloromethyl-3-hydroxy-2,4-dimethylpyridinium chloride 

Relevant articles and documents

Inhibition of colitis by ring-modified analogues of 6-acetamido-2,4,5-trimethylpyridin-3-ol

6-Aminopyridin-3-ol scaffold has shown an excellent anti-inflammatory bowel disease activity. Various analogues with the scaffold were synthesized in pursuit of the diversity of side chains tethering on the C(6)-position. Structure-activity relationship among the analogues was investigated to understand the effects of the side chains and their linkers on their anti-inflammatory activities. In this study, structural modification moved beyond side chains on the C(6)-position and reached to pyridine ring itself. It expedited us to synthesize diverse ring-modified analogues of a representative pyridine-3-ol, 6-acetamido-2,4,5-trimethylpyridin-3-ol (9). In the evaluation of compounds on their inhibitory actions against TNF-α-induced adhesion of monocytic cells to colonic epithelial cells, an in vitro model mimicking colon inflammation, the effects of compounds 9, 17, and 19 were greater than tofacitinib, an orally available anti-colitis drug, and compound 17 showed the greatest activity. In addition, TNF-α-induced angiogenesis, which permits more inflammatory cell migration into inflamed tissues, was significantly blocked by compounds 17 and 19 in a concentration-dependent manner. In the comparison of in vivo therapeutic effects of compounds 9, 17, and 19 on dextran sulfate sodium (DSS)-induced colitis in mice, compound 17 was the most potent and efficacious, and compound 19 was better than compound 9 which showed a similar degree of inhibitory effect to tofacitinib. Taken together, it seems that either the trimethyl system or the hydroxyl group on the pyridinol ring is essential to the activity. This finding might become a new milestone in the development of pyridinol-based anti-inflammatory bowel disease agents.

PHARMACEUTICAL COMPOSITION CONTAINING, AS ACTIVE INGREDIENT, 7-AZAINDOLIN-2-ONE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

The present invention relates to a 7-azaindolin-2-one derivative or a pharmaceutically acceptable salt thereof, and the 7-azaindolin-2-one derivative or the pharmaceutically acceptable salt thereof can be favorably used as a medicinal material for inhibiting cancer growth and cancer metastasis.

Synthesis and biological activity of quaternary phosphonium salts based on 3-hydroxypyridine and 4-deoxypyridoxine

Methods for the synthesis of quaternary phosphonium salts based on 3-hydroxypyridine and 4-deoxypyridoxine were developed. Some of obtained compounds possess high antibacterial and antitumor activity in vitro.

5-Hydroxy-7-azaindolin-2-one, a novel hybrid of pyridinol and sunitinib: Design, synthesis and cytotoxicity against cancer cells

Angiogenesis plays important roles in tumor growth and metastasis. Sunitinib (Sutent) is an antitumor agent targeting receptor tyrosine kinases which are involved in angiogenesis as well as cancer cell growth and survival. Using the pyridin-3-ol scaffold, which was previously reported as an excellent antioxidant and antiangiogenic platform, we have synthesized sunitinib mimics 6 by hybridizing bicyclic pyridinol 4 as a key scaffold and pyrrole-2-carbaldehydes 7 as side chains. Cytotoxicity assays showed that compounds 6 have comparable to better anticancer activity than sunitinib against five different cancer cell lines. In addition, compounds 6 showed even lower levels of cytotoxicity against normal cells, resulting in up to 26-fold better safety windows, than sunitinib. Signaling pathway-associated transcription factor reporter assay and western blot analyses revealed that apoptosis induction in MDA-MB-231 human breast cancer cells by 6F is mainly mediated through the p53 increase and down-regulation of phospho-signal transducer and activator of transcription 3 (STAT3) and its target gene products, cyclin D, Bcl-2, and survivin. The data strongly suggest that our hybrid compounds can provide a novel anticancer scaffold with improved and safer cytotoxicity profiles than sunitinib.

INHIBITORS OF HEMEPROTEIN-CATALYZED LIPID PEROXIDATION

Compounds, compositions and methods related to the prevention or treatment of isoprostane-mediated tissue damage in a mammalian subject in need thereof.

Pyridoxine-derived bicyclic amido-, ureido-, and carbamato-pyridinols: Synthesis and antiangiogenic activities

We recently developed an efficient and practical synthesis for a novel series of pyridoxine-derived 6-amido-2,4,5-trimethylpyridin-3-ols and found that this novel scaffold has outstanding activity to inhibit angiogenesis measured by the quantitative chick embryo chorioallantoic membrane (CAM) assay. As an effort to extend the scope of the amidopyridinol scaffold, we here report the synthesis and antiangiogenic activities of a series of bicyclic versions of the amidopyridinol including five- and six-membered cyclic amide-, cyclic urea-, and cyclic carbamate-fused pyridinols. The six membered bicyclic derivatives were prepared by the reported procedures, and the five-membered ring-fused ones were synthesized by new synthetic methods developed in this study. CAM assays showed that both six- and five-membered lactam-fused pyridinols have activities comparable to sunitinib malate, the positive control, in inhibition of vascular endothelial growth factor-induced angiogenesis. On the other hand, the urea and the carbamate derivatives showed modest to moderate antiangiogenic activities. In summary, some bicyclic aminopyridinols can provide a good platform for structural exploitation in future medicinal chemistry work.

Preparation and investigation of vitamin B6-derived aminopyridinol antioxidants

3-Pyridinols bearing amine substitution para to the hydroxylic moiety have previously been shown to inhibit lipid peroxidation more effectively than typical phenolic antioxidants, for example, α-tocopherol. We report here high-yielding, large-scale syntheses of mono- and bicyclic aminopyridinols from pyridoxine hydrochloride (i.e., vitamin B6). This approach provides straightforward, scaleable access to novel, potent, molecular scaffolds whose antioxidant properties have been investigated in homogeneous solutions and in liposomal vesicles. These molecular aggregates mimic cell membranes that are the targets of oxidative damage in vivo.

Studies on anticoccidial agents. 1. Synthesis and anticoccidial activity of 4 deoxypyridoxol and its esters

Methods for syntheses of 4 deoxypyridoxine and 2 ethyl 2 demethylpyridoxine from pyridoxine were developed. α5 O Monoacyl 4 deoxypyridosines were, in general, obtained by selective hydrolysis of 3,α5 O diacyl 4 deoxypyridoxines. 4 Deoxypyridoxine and its esters showed anticoccidial activity against Eimeria acervulina. (19 references.)