Pyridoxine Chemical Properties

Melting point:

214-215 °C(lit.)

Boiling point:

298.46°C (rough estimate)

Density 

1.2435 (rough estimate)

refractive index 

1.5100 (estimate)

storage temp. 

Inert atmosphere,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)

form 

Solid

color 

White to Off-White

Odor

Odorless

BCS Class

1,3

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

LXNHXLLTXMVWPM-UHFFFAOYSA-N

LogP

-0.770

CAS DataBase Reference

65-23-6(CAS DataBase Reference)

NIST Chemistry Reference

2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridine(65-23-6)

EPA Substance Registry System

3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- (65-23-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UV1350000

F 

8-10

HS Code 

29362500

MSDS

• Language:English Provider:2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Pyridoxine Usage And Synthesis

Description

Pyridoxine hydrochloride provides pyridoxine, which is also known as vitamin B6. Vitamin B6 is naturally found in foods such as cereals, beans, vegetables, liver, meat, and eggs.  Vitamin B6 functionalizes as a coenzyme in the metabolism of protein, carbohydrate, and fat. Vitamin 6 is needed to maintain the health of nerves, skin, and red blood cells.
Pyridoxine is used to prevent or treat vitamin B6 deficiency caused by inadequate dietary intake. It is also used to treat drug induced deficiency in patients taking isoniazid or oral contraceptives.

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

Chemical Properties

crystalline solid

Physical properties

It is one kind of B vitamins, containing pyridoxine or pyridoxal or pyridoxamine. Appearance: colorless crystals at room temperature. Solubility: soluble in water and ethanol. Stability: stable in acid liquor but easily destroyed in alkali liquor. Pyridoxol is resistant to high temperature, but pyridoxal and pyridoxamine are not.

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.

Uses

antibacterial

Uses

pyridoxine HCL is a skin-conditioning agent that is also widely used in hair products.

Uses

Vitamin B6, a water-soluble vitamin with a solubility of 1 g in 5 ml of water. It functions in the utilization of protein and is an essential nutrient in enzyme reactions. It is necessary for proper growth. During processing, there is a loss due to leaching of the vitamin in water. It is destroyed by high temperatures, high irradiation, and exposure to light. During storage, loss increases with temperature and storage time. It is found in liver, eggs, and meats.

Definition

ChEBI: A hydroxymethylpyridine with hydroxymethyl groups at positions 4 and 5, a hydroxy group at position 3 and a methyl group at position 2. The 4-methanol form of vitamin B6, it is converted intoto pyridoxal phosphate which is a coenzyme f r synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid.

Indications

Vitamin B6 deficiency

brand name

Hexa-Betalin (Lilly).

World Health Organization (WHO)

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

General Description

The discovery of vitamin B₆ is generally ascribed to Paul Gy?rgy who first realized there was a vitamin that was distinctly different from vitamin B₂ in 1934. Pyridoxine (PN) is the C⁴ hydroxymethyl derivative, pyridoxal (PL) is the C⁴ formyl derivative and pyridoxamine (PM) is the C⁴ aminomethyl derivative of 5-(hydroxymethyl)- 2-methylpyridin-3-ol). Each of these are also converted to their corresponding 5'-phosphate derivatives referred to as pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP), and pyridoxamine 5'-phosphate (PMP), respectively . Because of their ability to interconvert, all are considered active forms of vitamin B₆ in vivo. Although PLP is the major coenzyme form, PMP can also function as a coenzyme primarily in aminotransferases. The major metabolite is 4-pyridoxic acid, which is excreted in the urine.

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.

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