4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol

• ChemBase ID: 50
• Molecular Formular: C8H11NO3
• Molecular Mass: 169.17784
• Monoisotopic Mass: 169.07389322
• SMILES: Oc1c(c(CO)cnc1C)CO
• Canonical SMILES: OCc1c(CO)cnc(c1O)C
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
• IUPAC Traditional name: pyridoxine
• Brand Name: Aderoxine; Alestrol; Becilan; Beesix; Benadon; Bonasanit; Campoviton 6; Gravidox; Hexa-Betalin; Hexavibex; Hexermin; Hexermine; Hexobion; Hydoxin; Nestrex; Pydox; Pyridipca; Pyridox; Pyridoxine-HCl Microencapsulated; Rodex TD; Tex Six T.R.; Vitamin B6; Vitaped
• Synonyms: Pyridoxine; 3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine; 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol; Vitamin B6; Adermin hydrochloride; Adermine hydrochloride; Aderomine hydrochloride; Pyridoxine HCl; Pyridoxine Chloride; Pyridoxin hydrochloride; Pyridoxine hydrochloride; Pyridoxine hydrogen chloride; Pyridoxinium Chloride; Pyridoxinum Hydrochloricum; Pyridoxol hydrochloride; PN; Hexabione hydrochloride; Pyridoxine; Pyridoxol; 吡哆醇; 维生素 B6; 吡哆素

Database IDs

• CAS Number: 65-23-6
• EC Number: 200-603-0
• MDL Number: MFCD00006335
• PubChem SID: 160963513; 46508560; 24898690
• PubChem CID: 1054
• CHEBI ID: 16709
• ATC CODE: A11HA02
• CHEMBL: 1364
• Chemspider ID: 1025
• DrugBank ID: DB00165
• KEGG ID: D08454
• Wikipedia Title: Pyridoxine

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.39743
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.2796693
• LogD (pH = 7.4): -0.96294767
• Log P: -0.9513213
• Molar Refractivity: 44.1053 cm^3
• Polarizability: 16.756275 Å^3
• Polar Surface Area: 73.58 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.57
• LOG S: -1.02
• Solubility (Water): 1.61e+01 g/l

PROPERTIES

Physical Property

• Solubility: 2.2E+005 mg/L
• Melting Point: 159 - 162°C; 159-162 °C; 159-162 °C(lit.)
• Hydrophobicity(logP): -0.77 [SANGSTER (1993)]; -0.795

Safety Information

• RTECS: UV1300000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: ≥98%; 95%; 95+%; 98%
• Empirical Formula (Hill Notation): C8H11NO3

DETAILS

DrugBank - DB00165

• Drug Groups: approved; nutraceutical
• Description: Pyridoxine is the 4-methanol form of vitamin B6 and is converted to pyridoxal 5-phosphate in the body. Pyridoxal 5-phosphate is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. Although pyridoxine and vitamin B6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading. [PubChem]
• Indication: For the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy.
• Pharmacology: 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.
• Toxicity: Oral Rat LD50 = 4 gm/kg. Toxic effects include convulsions, dyspnea, hypermotility, diarrhea, ataxia and muscle weakness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Pyridoxine is absorbed mainly in the jejunum.
• Half Life: 15-20 days
• Protein Binding: 22%
• External Links: Wikipedia; PDRhealth; Drugs.com

Sigma Aldrich - P5669

Biochem/physiol Actions
Pyridoxine (Vitamin B6) is a form of vitamin B6. Other forms include the aldehyde pyridoxal and the amide pyridoxamine. Pyridoxine is used in cell culture and other applications as a precursor to pyridoxal phosphate.