Pyridoxine

HCID 1054

Basic information

CAS
65-23-6
Standard SMILES
Cc1ncc(CO)c(CO)c1O
InChIKey
LXNHXLLTXMVWPM-UHFFFAOYSA-N
Molecular formula
C8H11NO3
Average molar mass
169.18 g/mol
Monoisotopic mass
169.07389321

Overview

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 mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a member of methylpyridines, a vitamin B6, a monohydroxypyridine and a hydroxymethylpyridine.

Names & identifiers

Preferred name
Pyridoxine
IUPAC
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
English name
Pyridoxine
Molecular formula
C8H11NO3
Molecular weight
169.18

Names & synonyms

pyridoxine65-23-6PyridoxolPyridoxin3-hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridineAdermineGravidoxHydoxinPyridoxolum4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-5-Hydroxy-6-methyl-3,4-pyridinedimethanol
Show more names
PYRIDOXINE HCLPyridoxine (Vitamin B6)(5-hydroxy-6-Methylpyridine-3,4-diyl)diMethanolPYRIDOXIN HYDROCHLORIDE5-HYDROXY-6-METHYL-3,4-PYRIDINEDIMETHANOL HYDROCHLORIDEB6-HCLPridoxineADEMINE HCL
PiridoxinaPyridoxinumPiridossina3-Hydroxy-4,5-dimethylol-alpha-picolineHexabione2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridineVitamin V6

Database identifiers

CAS
65-23-6
PubChem CID
1054
DTXSID
DTXSID4023541
ChEMBL
CHEMBL1364
ChEBI
CHEBI:16709
UNII
KV2JZ1BI6Z
EC Number
200-603-0
Nikkaji
J2.095.349G、J2.356F

Properties

Computed structural properties

XLogP
-0.8
Topological polar surface area
73.6 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Vitamins and Derivatives
Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

CosmeticsHair conditioning; Antistatic; Skin conditioning
LogP-0.77
Food AdditivesUse unspecified -> FDA Substance added to food
Solubility79 mg/mL

Physicochemical properties

Melting point
214 · 214-215 °C(lit.)
Boiling point
298.46 °C · 298.46°C (rough estimate)
Density
1.2435 · 1.2435 (rough estimate)
refractive index
1.51 · 1.5100 (estimate)
storage temp.
2 · Inert atmosphere,2-8°C
solubility
2 O: · H2O: 0.1 g/mL at 20 °C, clear, colorless

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 3.8% (2 of 52) of reports.

Warning

H315 (96.2%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-

3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 28-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25773

Pyridoxine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary · 1 item

Has been tested in humans to relieve nausea and vomiting during pregnancy; Chronic ingestion of gram quantities can cause ataxia and sensory neuropathy; Has demonstrated testicular toxicity in rats; [REPROTOX] An irritant; May have cumulative adverse effects; [Alfa Aesar MSDS] See Pyridoxine hydrochloride.

Hazard Classes and CategoriesSkin Irrit. 2 (96.2%)

Toxicology

TreatmentAdminister charcoal as a slurry. (T273)
Exposure RoutesOral; parenteral (intramuscular). The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Pyridoxine is absorbed mainly in the jejunum.
Toxicity Summary · 1 item

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).

Signs and SymptomsToxic effects include convulsions, dyspnea, hypermotility, diarrhea, ataxia and muscle weakness.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

pyridoxine

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Safety data

F
8-10
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
UV1350000
hs_code
29362500

Chemistry & industry

Pharmacology

ATC Code · 4 items

A11HA02

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

A11HA02

Protein BindingPyridoxine 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.
Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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).

Biological Half-LifeThe total adult body pool consists of 16 to 25 mg of pyridoxine. Its half-life appears to be 15 to 20 days.
Metabolism/Metabolites · 2 items

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.

Hepatic. Half Life: 15-20 days

Uses & manufacturing

Uses · 3 items

The 4-methanol form of vitamin B6 that is converted to the coenzyme pyridoxal phosphate; [ChemIDplus] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Use (kg; approx.) in Germany (2009): >7500

For the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy.

U.S. Production2023: 661 lb
Consumer UsesOther
Industry UsesOther
Use ClassificationCosmetics -> Hair conditioning; Antistatic; Skin conditioning
General Manufacturing Information · 2 items

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

3,4-Pyridinedimethanol, 5-hydroxy-6-methyl-: ACTIVE

Applications · 6 items

DescriptionPyridoxine 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.

HistoryThe 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.

Usesantibacterial

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

UsesVitamin 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.

General DescriptionThe discovery of vitamin B6 is generally ascribed to Paul Gyrgy 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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
河北创之源生物科技有限公司13012111162
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

5 records

Compound notes

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