Pyridoxine
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Pyridoxine
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CAS No:
65-23-6
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Formula:
C8H11NO3
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Chemical Name:
Pyridoxine
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Synonyms:
3,4-Pyridinedimethanol,5-hydroxy-6-methyl-;Pyridoxol;5-Hydroxy-6-methyl-3,4-pyridinedimethanol;2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine;2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine;Pyridoxin;Pyridoxine;Adermin;Bezatin;Pirivitol;3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine;2087491-32-3
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CAS No:
Description
Pyridoxine is a pyridine derivative. Pyridoxine exerts antioxidant effects in cell model of Alzheimer's disease via the Nrf-2/HO-1 pathway.
Solid
Pyridoxine is 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 for synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid. It has a role as a cofactor, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a monohydroxypyridine, a vitamin B6, a member of methylpyridines and a hydroxymethylpyridine.|Pyridoxine is the 4-methanol form of vitamin B6, an important water-soluble vitamin that is naturally present in many foods. As its classification as a vitamin implies, Vitamin B6 (and pyridoxine) are essential nutrients required for normal functioning of many biological systems within the body. While many plants and microorganisms are able to synthesize pyridoxine through endogenous biological processes, animals must obtain it through their diet. More specifically, pyridoxine is converted to pyridoxal 5-phosphate in the body, which is an important coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. It's important to note that Vitamin B6 is the collective term for a group of three related compounds, pyridoxine, pyridoxal, and pyridoxamine, and their phosphorylated derivatives, pyridoxine 5'-phosphate, pyridoxal 5'-phosphate and pyridoxamine 5'-phosphate. Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in its biologically active coenzyme form pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA). Pyridoxine is used medically for the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy (due to [DB00951]'s mechanism of action which competitively inhibits the action of pyridoxine in the above-mentioned metabolic functions). It is also used in combination with [DB00366] (as the commercially available product Diclectin) for the treatment of nausea and vomiting in pregnancy.|Pyridoxine is a Vitamin B6 Analog. The chemical classification of pyridoxine is Vitamin B 6, and Analogs/Derivatives.|The 4-methanol form of VITAMIN B 6 which is converted to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990).
Pyridoxine Basic Attributes
169.18
169.18
200-386-2
KV2JZ1BI6Z
759148
DTXSID4023541
A11HA02|A - Alimentary tract and metabolism
2936250000
Characteristics
73.6
-0.8
Solid
1.4±0.1 g/cm3
159-162 °C
Sublimes
251.3±27.3 °C
1.621
79 mg/mL
2-8°C
134.6 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|130.75 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|135.69 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|148.49 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|136.03 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|134.4 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|144.3 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|132.4 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|132.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|134.7 Ų [M-H]-
Safety Information
NONH for all modes of transport
3
36/37/38
26-36
UV1350000
Xi
Stable. Incompatible with strong oxidizing agents.
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 50 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Oral Rat LD50 = 4 gm/kg. Toxic effects include convulsions, dyspnea, hypermotility, diarrhea, ataxia and muscle weakness.
Pyridoxine main active metabolite, pyridoxal 5’-phosphate, is released into the circulation (accounting for at least 60% of circulating vitamin B6) and is highly protein bound, primarily to albumin.
Drug Information
Pyridoxine is indicated for the treatment of vitamin B6 deficiency and for the prophylaxis of [DB00951]-induced peripheral neuropathy. It is also approved by Health Canada for the treatment of nausea and vomiting in pregnancy in a combination product with [DB00366] (as the commercially available product Diclectin).|FDA Label
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. Human studies have demonstrated that vitamin B6 deficiency affects cellular and humoral responses of the immune system. Vitamin B6 deficiency results in altered lymphocyte differentiation and maturation, reduced delayed-type hypersensitivity (DTH) responses, impaired antibody production, decreased lymphocyte proliferation and decreased interleukin (IL)-2 production, among other immunologic activities.
A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)
The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Pyridoxine is absorbed mainly in the jejunum. The Cmax of pyridoxine is achieved within 5.5 hours.|The major metabolite of pyridoxine, 4-pyridoxic acid, is inactive and is excreted in urine|Pyridoxine main active metabolite, pyridoxal 5’-phosphate, is released into the circulation (accounting for at least 60% of circulating vitamin B6) and is highly protein bound, primarily to albumin.
Pyridoxine is a prodrug primarily metabolized in the liver. The metabolic scheme for pyridoxine is complex, with formation of primary and secondary metabolites along with interconversion back to pyridoxine. Pyridoxine's major metabolite is 4-pyridoxic acid.
The total adult body pool consists of 16 to 25 mg of pyridoxine. Its half-life appears to be 15 to 20 days.
Vitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in its biologically active coenzyme form pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).
Pyridoxin
Pyridoxine Use and Manufacturing
500 ml with stirring, 150 ml of tetrahydrofuran was added to the three-necked flask of the thermometer and the condenser.25.3g (0.1mol)Ethyl 2-methyl-3-hydroxypyridine-4, 5-dicarboxylate, 9.49 g (0.25 mol) of sodium borohydride, Then, 7.5 g (0.125 mol) of glacial acetic acid was slowly added dropwise with stirring, and when glacial acetic acid was added dropwise, Control the temperature of the melt solution system to 30 ° C, After the completion of the dropwise addition, slowly heat up to 60 ° C, Reflux reaction 3 hours;After the reaction is completed, the solution system is cooled to 5 ° C, and 20percent dilute hydrochloric acid solution is added to the solution system.The pH of the solution system is adjusted to 2, and 20percent sodium hydroxide is added dropwise to the solution system.Adjust the pH to 14, when adding dilute hydrochloric acid and sodium hydroxide to the solution system, Control the temperature of the solution system below 10 ° C to prevent the addition of hydrochloric acid solution, The temperature in the solution system is too high; the system is filtered again, and the filter residue is washed twice with tetrahydrofuran.The washings and the filtrate were combined, and tetrahydrofuran was distilled off, and 150 ml of ethyl acetate was added to the residue, and the mixture was extracted three times.The extract phases were combined, and then ethyl acetate was evaporated under reduced pressure, and then 20 ml of anhydrous ethanol was added to the residue after concentration.And pass hydrogen chloride gas to saturation, then stand at room temperature for 3 hours, filter, After washing and drying, 19.3 g of vitamin B6 having a purity of 98.8percent was obtained, and the yield of vitamin B6 of the present example was 94percent
A form of vitamin B6It is a vitamin itself and can be used as a food additive. It can also be used as an intermediate of pyrithione hydrochloride. It can regulate the vitality of sebaceous glands, and can be used in cleansing and care products for facial oil control. Can also be used in hair care products to improve oily hair and healthy hair follicles.
3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-: ACTIVE
Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Cosmetics -> Antistatic; Hair conditioning; Skin conditioning
Computed Properties
Molecular Weight:169.18
XLogP3:-0.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:169.07389321
Monoisotopic Mass:169.07389321
Topological Polar Surface Area:73.6
Heavy Atom Count:12
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
Drug Function and Efficacy
Participates in the metabolism of certain amino acids and fats, reduces serum cholesterol, stimulates the production of white blood cells, and is used for retinopathy, optic neuritis, and leukocytopenia
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