PYRIDOXINE

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.

CAS:    65-23-6
MF:    C8H11NO3
MW:    169.18
EINECS:    200-603-0

Synonyms
2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine;2-Methyl-3-hydroxy-4,5-dihydroxymethyl-pyridin;2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine;2-Picoline-4,5-dimethanol, 3-hydroxy-;3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-;3-hydroxy-2-picoline-5-dimethanol;3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine;3-Hydroxy-4,5-dimethylol-alpha-picoline

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. 
Pyridoxine is also used to treat drug induced deficiency in patients taking isoniazid or oral contraceptives.
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). 
Pyridoxine 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. 
Pyridoxine, 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.
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 Pyridoxine, it is converted intoto pyridoxal phosphate which is a coenzyme for synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid.
The discovery of Pyridoxine is generally ascribed to Paul Gyrgy who first realized there was a vitamin that was distinctly different from vitamin B2 in 1934. 
Pyridoxine 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 Pyridoxine 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.
Pyridoxine is a form of vitamin B6 found commonly in food and used as a dietary supplement. 
As a supplement Pyridoxine is used to treat and prevent pyridoxine deficiency, sideroblastic anaemia, pyridoxine-dependent epilepsy, certain metabolic disorders, side effects or complications of isoniazid use, and certain types of mushroom poisoning.
Pyridoxine is used by mouth or by injection.

Pyridoxine is usually well tolerated.
Occasionally side effects include headache, numbness, and sleepiness.
Normal doses are safe during pregnancy and breastfeeding.
Pyridoxine is in the vitamin B family of vitamins.
Pyridoxine is required by the body to metabolise amino acids, carbohydrates, and lipids.
Sources in the diet include meat, fish, fruit, vegetables, and grain.
Pyridoxine is in the vitamin B family of vitamins.
Pyridoxine is required by the body to make amino acids, carbohydrates, and lipids.
Sources in the diet include fruit, vegetables, and grain.
Pyridoxine is also required for muscle phosphorylase activity associated with glycogen metabolism.
Pyridoxine is a type of B vitamin. 
Pyridoxine, pyridoxal, and pyridoxamine are all forms of vitamin B6. 
Pyridoxine's found in certain foods and also made in a lab.
Pyridoxine is needed for the proper function of sugars, fats, and proteins in the body. Pyridoxine's also necessary for the development of the brain, nerves, skin, and many other parts of the body. 

Pyridoxine's found in cereals, legumes, and eggs, and often used with other B vitamins in vitamin B complex products.
People commonly use Pyridoxine for preventing and treating vitamin B6 deficiency. 
Pyridoxine is also used for heart disease, premenstrual syndrome (PMS), depression, morning sickness, Alzheimer disease, menstrual cramps, diabetes, and many other conditions, but there is no good scientific evidence to support many of these other uses.
Pyridoxine, or pyridoxine, is a water-soluble vitamin found naturally in many foods, as well as added to foods and supplements. 
Pyridoxine’ phosphate (PLP) is the active coenzyme form and most common measure of B6 blood levels in the body. 
Pyridoxine is a coenzyme that assists more than 100 enzymes to perform various functions, including the breakdown of proteins, carbohydrates, and fats; maintaining normal levels of homocysteine (since high levels can cause heart problems); and supporting immune function and brain health. 

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.
Pyridoxine is widely distributed in foods, including meats, whole-grain products (especially wheat), vegetables, and nuts. 
In the cereal grains, Pyridoxine 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 Pyridoxine 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.

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.
Cosmetics Ingredients Functions    HAIR CONDITIONING
ANTISTATIC
SKIN CONDITIONING
InChI: 1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
InChIKey: LXNHXLLTXMVWPM-UHFFFAOYSA-N
LogP: -0.770
CAS DataBase Reference: 65-23-6(CAS DataBase Reference)
NIST Chemistry Reference: Pyridoxine(65-23-6)
EPA Substance Registry System: Pyridoxine (65-23-6)

Physical properties    
Pyridoxine 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. 
Pyridoxine is resistant to high temperature, but pyridoxal and pyridoxamine are not.

Uses    
Pyridoxine is a skin-conditioning agent that is also widely used in hair products.
Pyridoxine, a water-soluble vitamin with a solubility of 1 g in 5 ml of water. 
Pyridoxine functions in the utilization of protein and is an essential nutrient in enzyme reactions. 
Pyridoxine is necessary for proper growth. 
During processing, there is a loss due to leaching of the vitamin in water. 
Pyridoxine is destroyed by high temperatures, high irradiation, and exposure to light. 
During storage, loss increases with temperature and storage time. 
Pyridoxine is found in liver, eggs, and meats.

Medical uses
As a treatment (oral or injection), Pyridoxine is used to treat or prevent pyridoxine deficiency, sideroblastic anaemia, pyridoxine-dependent epilepsy, certain metabolic disorders, side effects of isoniazid treatment and certain types of mushroom poisoning.
Pyridoxine is an antibiotic used for the treatment of tuberculosis. 
Pyridoxine's common side effects include numbness in the hands and feet.
Co-treatment with vitamin B6 alleviates the numbness.
Pyridoxine-dependent epilepsy is a type of rare infant epilepsy that does not improve with typical anti-seizure medications.
Pyridoxine in combination with doxylamine is used as a treatment for morning sickness in pregnant women.

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 Pyridoxine 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.

Pharmacology    
The metabolically active form of Pyridoxine is pyridoxal phosphate, which serves as a coenzyme of numerous enzymes, most of which are involved in the metabolism of amino acids. 
Pyridoxine functions through the following general mechanisms: decarboxylation, transamination, racemization, elimination, replacement reactions, and β-group interconversions.
Pyridoxine 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. 
Pyridoxine also plays an important role in the tryptophan–niacin conversion, histamine synthesis, neurotransmitter syn thesis, and hemoglobin synthesis.
Pyridoxine has two roles in gluconeogenesis, transaminations and glycogen uti lization. 
Pyridoxine is required for the utilization of glycogen to release glucose by serving as a coenzyme of glycogen phosphorylase.

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

Synthesis
1. 150 mL of tetrahydrofuran was added to a 500 mL three-necked flask equipped with a thermometer and condenser tube. 
2. 25.3 g (0.1 mol) of ethyl 2-methyl-3-hydroxypyridine-4,5-dicarboxylate and 9.49 g (0.25 mol) of sodium borohydride were added sequentially. 
3. 7.5 g (0.125 mol) of glacial acetic acid was added slowly dropwise with stirring and the temperature of the reaction system was controlled at 30 °C. 4. 
4. After the dropwise addition, the reaction was slowly heated to 60 °C and refluxed for 3h. 
5. After completion of the reaction, the reaction solution was cooled to 5 °C, and the pH was adjusted to 2 by adding 20% dilute hydrochloric acid solution. 
6. Slowly add 20% sodium hydroxide solution dropwise, adjust the pH to 14, control the solution temperature below 10 ℃. 
7. Filter the reaction mixture and wash the filtrate with tetrahydrofuran twice. 
8. Combine the washings and filtrate and distill to remove the tetrahydrofuran. 
9. 150 mL of ethyl acetate was added to the residue and extracted three times. 
10. The organic phases were combined and the ethyl acetate was evaporated under reduced pressure. 
11. Concentrate and add 20 mL of anhydrous ethanol and pass through hydrogen chloride gas to saturation. 
12. Let stand at room temperature for 3 hours, filter, wash and dry to obtain 19.3 g of pyridoxine with 98.8% purity and 94% yield.

Side effects
Pyridoxine is usually well tolerated, though overdose toxicity is possible.
Occasionally side effects include headache, numbness, and sleepiness.
Pyridoxine overdose can cause a peripheral sensory neuropathy characterized by poor coordination, numbness, and decreased sensation to touch, temperature, and vibration.
Healthy human blood levels of pyridoxine are 2.1–21.7 ng/mL. 
Normal doses are safe during pregnancy and breastfeeding.