65-23-6

Basic information

• Product Name: 3,4-Pyridinedimethanol,5-hydroxy-6-methyl-
• Synonyms: Pyridoxol(8CI);2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine;2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine;5-Hydroxy-6-methyl-3,4-pyridinedimethanol;Adermin;Bezatin;Pirivitol;Pyridoxin;VB6
• CAS NO: 65-23-6
• Molecular Formula: C₈H₁₁NO₃
• Molecular Weight: 169.18
• EINECS: 200-603-0
• Product Categories: Heterocycle-Pyridine series;GANTRISIN;vitamin series;Inhibitors
• Mol File: 65-23-6.mol

Chemical Properties

• Melting Point: 159-162℃
• Boiling Point: 491.9 °C at 760 mmHg
• Flash Point: 251.3 °C
• Appearance: crystalline solid
• Density: 1.353 g/cm³
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.1?g/mL at?20?°C, clear, colorless
• PKA: pKa 5.00(H2O t = 25.0 I = 0.15 (mixed)) (Uncertain)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 3,4-Pyridinedimethanol,5-hydroxy-6-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Pyridinedimethanol,5-hydroxy-6-methyl-(65-23-6)
• EPA Substance Registry System: 3,4-Pyridinedimethanol,5-hydroxy-6-methyl-(65-23-6)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S36:
• WGK Germany: 3
• RTECS: UV1350000
• F: 8-10
• Hazardous Substances Data: 65-23-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Pyridinedimethanol,5-hydroxy-6-methylis used as an active pharmaceutical ingredient for the prevention and treatment of vitamin B6 deficiency. It is particularly useful in cases where deficiency is caused by inadequate dietary intake or as a result of taking certain medications, such as isoniazid or oral contraceptives.
Used in Skincare and Hair Care Products:
In the cosmetics industry, 3,4-Pyridinedimethanol,5-hydroxy-6-methylis used as a skin-conditioning agent. It is widely incorporated into hair products due to its beneficial effects on hair health and appearance.
Used in Nutritional Supplements:
As a form of Vitamin B6, 3,4-Pyridinedimethanol,5-hydroxy-6-methylis used in the formulation of nutritional supplements to support overall health and well-being. Vitamin B6 is essential for the proper functioning of the nervous system, maintaining healthy skin and red blood cells, and aiding in the metabolism of protein, carbohydrates, and fats.
Used in Antibacterial Applications:
3,4-Pyridinedimethanol,5-hydroxy-6-methylalso has antibacterial properties, making it a valuable component in the development of products designed to combat bacterial infections.
Physical Properties:
3,4-Pyridinedimethanol,5-hydroxy-6-methylappears as colorless crystals at room temperature. It is soluble in water and ethanol, and it is stable in acidic conditions but can be easily destroyed in alkaline environments. 3,4-Pyridinedimethanol,5-hydroxy-6-methylis resistant to high temperatures, although its stability may vary depending on the specific derivative.
General Description:
The discovery of Vitamin B6 is attributed to Paul Gy?rgy, who first identified it as a distinct vitamin in 1934. Pyridoxine (PN), pyridoxal (PL), and pyridoxamine (PM) are the three active forms of Vitamin B6, which can interconvert and participate in various enzyme reactions in the body. The major metabolite of 3,4-Pyridinedimethanol,5-hydroxy-6-methyl- is 4-pyridoxic acid, which is excreted in the urine.

Pharmacodynamics

Vitamin B6 (pyridoxine) is a water-soluble vitamin used in the prophylaxis and treatment of vitamin B6 deficiency and peripheral neuropathy in those receiving isoniazid (isonicotinic acid hydrazide, INH). Vitamin B6 has been found to lower systolic and diastolic blood pressure in a small group of subjects with essential hypertension. Hypertension is another risk factor for atherosclerosis and coronary heart disease. Another study showed pyridoxine hydrochloride to inhibit ADP- or epinephrine-induced platelet aggregation and to lower total cholesterol levels and increase HDL-cholesterol levels, again in a small group of subjects. Vitamin B6, in the form of pyridoxal 5'-phosphate, was found to protect vascular endothelial cells in culture from injury by activated platelets. Endothelial injury and dysfunction are critical initiating events in the pathogenesis of atherosclerosis.

Toxicity

Oral Rat LD50 = 4 gm/kg. Toxic effects include convulsions, dyspnea, hypermotility, diarrhea, ataxia and muscle weakness.

References

[1] http://www.webmd.com [2] https://dailymed.nlm.nih.gov

History

The discovery of vitamin was tortuous and legendary. After fat-soluble A and water soluble B were discovered by the year of 1915, the discovery of vitamins entered into a rapid developed period. In separation process of riboflavin by Kuhn and his colleagues, they noticed the unusual relationship between growth-promoting activ ity and fluorescence of extracts. Then they supposed that the existence of no fluorescent substances were very necessary for growth-promoting activity of riboflavin. And they considered this phenomenon as the evidence of a second chem ical existence in the thermostable complex. At last, they named this substance as vitamin B6 .Vitamin B6 is widely distributed in foods, including meats, whole-grain products (especially wheat), vegetables, and nuts. In the cereal grains, vitamin B6 is concen trated primarily in the germ and aleuronic layer. Thus, the refining of grains in the production of flours, which removes much of these fractions, results in substantial reductions of vitamin B6 content. The chemical forms of vitamin B6 tend to vary among foods between plant and animal origin: plant tissues contain most pyridox ine (the free alcohol form, pyridoxol), whereas animal tissues contain most pyri doxal and pyridoxamine.

Indications

Vitamin B6 deficiency

World Health Organization (WHO)

Pyridoxine (vitamin B6) is listed in theWHO Model List of Essential Drugs.

Biological Activity

pyridoxine (pyridoxol, vitamin b6, gravidox), also known as vitamin b6, is a form of vitamin b6 found commonly in food and used as dietary supplement. pyridoxine exerts antioxidant effects in cell model of alzheimer's disease via the nrf-2/ho-1 pathway.

Biochem/physiol Actions

Pyridoxine plays a key role in cell maintenance and amino acid metabolism. Deficiency of vitamin B6 leads to anemia especially in pregnant women and seizures in newborns. It serves as cofactor for heme biosynthesis during δ-amino levulinic acid formation, γ-aminobutyric acid (GABA) transaminase and glutamic acid decarboxylase. Vitamin B6 also helps in reactive oxygen species (ROS) scavenging and helps plants in overcoming the abiotic and biotic stress.

Pharmacology

The metabolically active form of vitamin B6 is pyridoxal phosphate, which serves as a coenzyme of numerous enzymes, most of which are involved in the metabolism of amino acids. Vitamin B6 functions through the following general mechanisms: decarboxylation, transamination, racemization, elimination, replacement reactions, and β-group interconversions.Pyridoxal phosphate is practically involved in all amino acid metabolism reac tions, such as transaminations, transsulfuration, and selenoamino acid metabolism, in both their biosynthesis and their catabolism. Vitamin B6 also plays an important role in the tryptophan–niacin conversion, histamine synthesis, neurotransmitter syn thesis, and hemoglobin synthesis.Vitamin B6 has two roles in gluconeogenesis, transaminations and glycogen uti lization. It is required for the utilization of glycogen to release glucose by serving as a coenzyme of glycogen phosphorylase.

Clinical Use

Pyridoxine is indicated in the treatment and prevention of known or suspected vitamin B6 deficiency, which is most likely to occur in the setting of alcoholism in developed countries. At least seven genetic disorders that result in a vitamin B6 deficiency syndrome in the presence of an adequate dietary intake have been identified. These result from defects in enzymes that are responsible for the bioactivation or utilization of vitamin B6.

Safety Profile

Moderately toxic by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects: ataxia, local anesthetic, paresthesia. When heated to decomposition it emits toxic fumes of Nox

Veterinary Drugs and Treatments

Pyridoxine use in veterinary medicine is relatively infrequent. It may be of benefit in the treatment of isoniazid (INH) or crimidine (an older rodenticide) toxicity. Pyridoxine deficiency is apparently extremely rare in dogs or cats able to ingest food. Cats with severe intestinal disease may have a greater requirement for pyridoxine in their diet. Experimentally, pyridoxine has been successfully used in dogs to reduce the cutaneous toxicity associated with doxorubicin containing pegylated liposomes (Doxil?). Pyridoxine has been demonstrated to suppress the growth of feline mammary tumors (cell line FRM) in vitro. In humans, labeled uses for pyridoxine include pyridoxine deficiency and intractable neonatal seizures secondary to pyridoxine dependency syndrome. Unlabeled uses include premenstrual syndrome (PMS), carpal tunnel syndrome, tardive dyskinesia secondary to antipsychotic drugs, nausea and vomiting in pregnancy, hyperoxaluria type 1 and oxalate kidney stones, and for the treatment of isoniazid (INH), cycloserine, hydrazine or Gyometra mushroom poisonings.

InChI:InChI=1/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3

Upstream product

• 15741-69-2 4,5-bis-hydroxymethyl-2-methyl-pyridin-3-ylamine 
• 100193-34-8 5-acetoxy-6-methyl-pyridine-3,4-dicarboxylic acid dimethyl ester 
• 67-56-1 methanol 
• 84878-62-6 N-[1-(3,4-bis-acetoxymethyl-[2]furyl)-ethyl]-acetamide 
• 50-99-7 D-glucose 
• 66-72-8 pyridoxal 
• 2397-71-9 5-hydroxy-6-methylpyridine-3,4-dicarboxylic acid diethyl ester 
• 21768-45-6 (-)-2S,3S-2-amino-3,4-dihydroxybutyric acid 
• 60299-43-6 1-deoxy-D-xylulose 
• 2280-44-6 D-Glucose 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 15066-64-5 1-(3,4-bis-hydroxymethyl-[2]furyl)-ethylamine 
• 220092-30-8 <5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl>methyl acetate 

Downstream Products

• 633-72-7 4,5-bis-hydroxymethyl-3-methoxy-2-methyl-pyridine 
• 6273-67-2 3-hydroxy-4,5-bis-hydroxymethyl-2-methyl-1-phenacyl-pyridinium; bromide 
• 61-67-6 4-deoxypyridoxine 
• 6560-46-9 5-hydroxy-4-hydroxymethyl-6-methyl-pyridine-3-carbaldehyde 
• 5196-20-3 7-hydroxy-6-methyl-1,3-dihydrofuro<3,4-c>pyridin 
• 524-07-2 5-hydroxy-4-hydroxymethyl-6-methyl-nicotinic acid 
• 149950-42-5 5'-O-(β-D-fructofuranosyl)-pyridoxine 
• 149950-43-6 5'-O-<β-D-fructofuranosyl-(2->1)-β-D-fructofuranosyl>-pyridoxine 
• 66-72-8 pyridoxal 
• 82-82-6 4-pyridoxic acid 
• 1464-33-1 ginkgotoxin 
• 1392100-18-3 3-O-benzyl-α4,α5-di-O-(3-hydroxypropyl)-6-(trifluoromethyl)pyridoxine 
• 1392100-03-6 3,α4,α5-tri-O-benzyl-6-iodopyridoxine 
• 1392100-05-8 3,α4,α5-tri-O-benzyl-6-(trifluoromethyl)pyridoxine 

Relevant articles and documents

Pyridoxamine, a scavenger agent of carbohydrates

Pyridoxamine has been found to inhibit protein glycation and to avoid the formation of advanced glycation end-products (AGEs). One of the mechanisms by which pyridoxamine can inhibit glycation involves the scavenger of carbonyl groups with glycation capacity. In this work, we conducted a kinetic study of the reactions of pyridoxamine with various carbohydrates under physiological pH and temperature. The reactions involving hexoses were found to give a tricyclic compound (5) in addition to pyridoxal and pyridoxine. Such a tricyclic compound inhibits the Amadori rearrangement and the formation of other carbonyl compounds with glycating properties. The reactions involving pentoses gave compound 7 and pyridoxal - by transamination of the Schiff base. The transamination reaction enhances the inhibitory action of pyridoxamine. The formation rate constants for the Schiff base, k3, were found to be similar to those for the reactions of D-glucose with amino acids, which suggests competition between pyridoxamine and terminal amino residues in proteins for glycating sites in sugars. These constants are dependent on the electrophilic character of the carbonyl carbon in the carbohydrate.

Purification and characterization of pyridoxine 5′-phosphate phosphatase from Sinorhizobium meliloti

Here we report the purification and biochemical characterization of a pyridoxine 5′-phosphate phosphatase involved in the biosynthesis of pyridoxine in Sinorhizobium meliloti. The phosphatase was localized in the cytoplasm and purified to electrophoretic homogeneity by a combination of EDTA/lysozyme treatment and five chromatography steps. Gel-filtration chromatography with Sephacryl S-200 and SDS/PAGE demonstrated that the protein was a monomer with a molecular size of approximately 29kDa. The protein required divalent metal ions for pyridoxine 5′-phosphate phosphatase activity, and specifically catalyzed the removal of Pi from pyridoxine and pyridoxal 5′-phosphates at physiological pH (about 7.5). It was inactive on pyridoxamine 5′-phosphate and other physiologically important phosphorylated compounds. The enzyme had the same Michaelis constant (K m) of 385 μM for pyridoxine and pyridoxal 5′-phosphates, but its specific constant [maximum velocity (Vmax)/Km] was nearly 2.5 times higher for the former than for the latter.

Biosynthesis of vitamin B6 in Rhizobium: in vitro synthesis of pyridoxine from 1-deoxy-D-xylulose and 4-hydroxy-L-threonine.

Pyridoxine (vitamin B6) in Rhizobium is synthesized from 1-deoxy-D-xylulose and 4-hydroxy-L-threonine. To define the pathway enzymatically, we established an enzyme reaction system with a crude enzyme solution of R. meliloti IFO14782. The enzyme reaction system required NAD+, NADP+, and ATP as coenzymes, and differed from the E. coli enzyme reaction system comprising PdxA and PdxJ proteins, which requires only NAD+ for formation of pyridoxine 5'-phosphate from 1-deoxy-D-xylulose 5-phosphate and 4-(phosphohydroxy)-L-threonine.

Preparation method of high content vitamin B6

The invention relates to a preparation method of a high content vitamin B6. According to the method, 1,5-dihydro-3,3-disubstituent group-8-methyl-9-alkyl carbonyl oxypyrido [3,4-e]-1,3-dioxane is prepared by the Diels-Alder addition reaction, aromatization reaction and esterification reaction of 4-methyl-5-alkoxyl-oxazole and 2,2-disubstituent group-4,7-dihydro-1,3-dioxepine in the presence of ananhydride through the "one-pot method", and then vitamin B6 is prepared by deprotection. According to the method, the stability of the raw materials of 4-methyl-5-alkoxyl-oxazole and 2,2-disubstituentgroup-4,7-dihydro-1,3-dioxepine are ensured, the reaction is thorough, and the selectivity is high, so that the method provides guarantees for the preparation of high content medicinal vitamin B6.

Environmentally friendly preparation method for vitamin B6

The invention relates to an environmentally friendly preparation method for vitamin B6. The method comprises the following steps: carrying out a condensation reaction on a carbonyl compound and 2-cyano-2-cis-butene-1,4-diol which is used as a starting material, protecting hydroxyl groups to obtain 2,2-disubstituted-5-cyano-4,7-dihydro-1,3-dioxepine, carrying out a formylation reaction on the 2,2-disubstituted-5-cyano-4,7-dihydro-1,3-dioxepine, carbon monoxide and hydrogen to prepare 2,2-disubstituted-5-cyano-6-formyl-1,3-dioxetpin, condensing the 2,2-disubstituted-5-cyano-6-formyl-1,3-dioxetpin and 2-aminopropionate or its hydrochloride, and removing the carbonyl compound to prepare the vitamin B6. The method does not use a 4-methyl-5-alkoxyoxazole intermediate which is expensive and generates a large amount of wastewater in the production process, so the method has the advantages of environmentally friendly process, high reaction selectivity, high product purity, high atom economy, and suitableness for industrial production.

Method for preparing vitamin B6 by reduction method

The invention discloses a method for preparing a vitamin B6 in a reduction manner. The method comprises the following steps of (a), dissolving 2-methyl-3-hydroxypyridine-4,5-diformate in a solvent, adding a weak reducer and an organic acid, raising a temperature to 40 to 90 DEG C, carrying out a reflux reaction for 2h to 5h, and cooling the temperature, so as to obtain a solution system; (b), adding hydrochloric acid into the solution system to regulate to be acidic, then adding sodium hydroxide to regulate to be alkaline, filtering, extracting filtrate, and introducing a HCl gas into an extract phase, so as to obtain a saturated solution; (c), standing the saturated solution at room temperature for devitrification, filtering, washing, oven-drying, recrystallizing and filtering, wherein inthe step (a), the weak reducer is sodium borohydride or potassium borohydride; the organic acid is one of formic acid, acetic acid, oxalic acid, trifluoroacetic acid, propionic acid, benzoic acid andtartaric acid. By the combination of the low-cost weak reducer sodium borohydride or potassium borohydride and the organic acid which are adopted by the method to prepare the vitamin B6, the ester isjointly reduced, and a reaction condition is mild.

Effect of structure of nucleophile and substrate on the quaternization of heterocyclic amines

The influence of the nature of the quaternizing agent and substrate on the quaternization of heterocyclic amines, derivatives of pyridine, ss-picoline, nicotinamide, pyridoxine, was studied. The synthesized compounds were characterized by IR spectroscopy and elemental analysis. The conclusions were made about the effect of the structure of nucleophile and substrate on the process of quaternization reaction. Pleiades Publishing, Ltd., 2010.

STABLE VITAMIN B6 DERIVATIVE

A compound represented by the following general formula (I) or a salt thereof: wherein R1 represents a glycosyl group, a phosphate group, or a cyclic phosphate group bound to R2; R2 represents -CH2OH, -CHO, -CH2NH2, -CH2-amino acid residue, or -CH2-OPO2H; and R3 represents hydrogen atom, or -PO3H2, and a composition for cosmetics, medicaments, foodstuffs, and/or feeds containing the aforementioned compound or a salt thereof.

Novel compositions for the delivery of negatively charged molecules

This invention features permeability enhancer molecules, and methods, to increase membrane permeability of various molecules, such as nucleic acids, polynucleotides, oligonucleotides, enzymatic nucleic acid molecules, antisense nucleic acid molecules, 2-5A antisense chimeras, triplex forming oligonucleotides, decoy RNAs, dsRNAs, siRNAs, aptamers, or antisense nucleic acids containing nucleic acid cleaving chemical groups, peptides, polypeptides, proteins, carbohydrates, steroids, metals and small molecules, thereby facilitating cellular uptake of such molecules.

Silane reduction of 5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid diethyl ester: Synthesis of vitamin B6

Alternative methods for the synthesis of pyridoxine have been investigated. The key intermediate, 5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid diethyl ester (5), was reduced with either a silane monomer (MeSiH(OEt)2) or a polysiloxane (polymethylhydrosiloxane, PMHS) to afford crude pyridoxine. An isolation technique utilizing a commercially available resin was devised, affording the desired product, vitamin B6, in an overall yield of 38-54% and a purity of 76%.