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65-23-6 molecular structure
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4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol

ChemBase ID: 50
Molecular Formular: C8H11NO3
Molecular Mass: 169.17784
Monoisotopic Mass: 169.07389322
SMILES and InChIs

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

Cite this record

CBID:50 http://www.chembase.cn/molecule-50.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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
Pyridoxine
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine
Pyridoxol
吡哆醇
维生素 B6
吡哆素
CAS Number
65-23-6
EC Number
200-603-0
MDL Number
MFCD00006335
PubChem SID
46508560
160963513
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.39743  H Acceptors
H Donor LogD (pH = 5.5) -1.2796693 
LogD (pH = 7.4) -0.96294767  Log P -0.9513213 
Molar Refractivity 44.1053 cm3 Polarizability 16.756275 Å3
Polar Surface Area 73.58 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.57  LOG S -1.02 
Solubility (Water) 1.61e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
2.2E+005 mg/L expand Show data source
Melting Point
159 - 162°C expand Show data source
159-162 °C expand Show data source
159-162 °C(lit.) expand Show data source
Hydrophobicity(logP)
-0.77 [SANGSTER (1993)] expand Show data source
-0.795 expand Show data source
RTECS
UV1300000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Gene Information
human ... CYP1A2(1544) expand Show data source
Purity
≥98% expand Show data source
95% expand Show data source
95+% expand Show data source
98% expand Show data source
Empirical Formula (Hill Notation)
C8H11NO3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia
DrugBank - DB00165 external link
Item Information
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 external link
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.

REFERENCES

REFERENCES

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