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
• Article Data: 8

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

Description

4-deoxy Pyridoxine (DOP) is a vitamin B6 antimetabolite with diverse biological activities. It inhibits transport of pyridoxine , pyridoxal, and pyridoxamine in and reduces growth of S. carlsbergensis cells. DOP inhibits sphingosine-1-phosphate (S1P) lyase and reduces cyclic stretch-induced apoptosis in alveolar epithelial MLE-12 cells. DOP (5 mg, i.p.) reduces lysyl oxidase activity by 26% and reduces collagen and elastin crosslinking, resulting in limb abnormalities in chick embryos. It decreases latency to first seizure in mice (ED50 = 1 mmol/kg) and increases the occurrence and duration of myoclonic responses in baboons with photosensitive epilepsy. DOP reduces TNF-α and IL-6 production in mice infected with T. spiralis.

Chemical Properties

Solid

Uses

4-Deoxypyridoxine is the deoxy analogue of Pyridoxine (P991735). 4-Deoxypyridoxine is a vitamin B6 antimetabolite; 4-Deoxypyridoxine can induce a deficient status that alters the function and ultrastructure of EC similar to vascular disease.

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 
• 55522-60-6 5-chloromethyl-3-hydroxy-2,4-dimethylpyridinium chloride 
• 1350748-88-7 5-(hydroxymethyl)-2,4-dimethyl-6-(phenyldiazenyl)pyridin-3-ol 

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.

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.