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피리독신

Pyridoxine

HCID 1054
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
65-23-6
표준 SMILES
Cc1ncc(CO)c(CO)c1O
InChIKey
LXNHXLLTXMVWPM-UHFFFAOYSA-N
분자식
C8H11NO3
평균 분자량
169.18 g/mol
단동위원소 질량
169.07389321

개요

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.

이름 및 식별자

우선 이름
Pyridoxine
IUPAC
4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
현지명
피리독신
영어명
Pyridoxine
분자식
C8H11NO3
분자량
169.18

이름 및 동의어

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
이름 더 보기
비타민B6피리독신PYRIDOXINE 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

데이터베이스 식별자

CAS

물성

구조 계산 물성보충 중

XLogP
-0.8
극성 표면적
73.6 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
4
회전 가능 결합 수
2
무거운 원자 수
12
형식 전하
0
복잡도
142

실험 및 물리화학적 성질

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

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

CosmeticsHair conditioning; Antistatic; Skin conditioning
LogP-0.77
Food AdditivesUse unspecified -> FDA Substance added to food
Solubility79 mg/mL
Human Drugs · 5건

Breast Feeding; Lactation; Milk, Human; Vitamins

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Vitamins and minerals

Melting Point · 2건

159-162 °C

159 - 162 °C

Vapor Pressure0.00000028 [mmHg]
Physical Description · 3건

Dry Powder

White powder; [Alfa Aesar MSDS]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 4건

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 · 1건

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%)

독성 정보

화학 및 산업

약리 정보

ATC Code · 4건

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 · 1건

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 · 1건

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).

관련 반응

5건
반응 기록 만들기
HRID 198087 반응식
HRID 198087반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 839525 반응식
HRID 839525반응물로uspto-grants-1978_06
HRID 1350549 반응식
HRID 1350549생성물로uspto-grants-2007_05
HRID 1972117 반응식
HRID 1972117생성물로uspto-grants-2013_04
HRID 2222062 반응식
HRID 2222062생성물로uspto-grants-2008_05

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
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

Solid

Ionization Efficiency · 6건

Positive

3.28

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section · 6건

133.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID1040792]

134.4 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]

134.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

126.18 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

135.69 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

물리화학적 성질

녹는점
214 · 214-215 °C(lit.)
끓는 점
298.46 °C · 298.46°C (rough estimate)
밀도
1.2435 · 1.2435 (rough estimate)
굴절률
1.51 · 1.5100 (estimate)
저장 조건
2 · Inert atmosphere,2-8°C
용해도
2 O: · H2O: 0.1 g/mL at 20 °C, 투명, 무색
산도 계수 (pKa)
5 · pKa 5.00(H2O t = 25.0 I = 0.15 (mixed)) (Uncertain)
물리적 상태
고체
색상
흰색에서 황백색까지
냄새
냄새 없는
BCS Class
1 · 1,3
안정성
안정적인. 강한 산화제와 호환되지 않습니다.
화장품 원료 기능
헤어 컨디셔닝대전방지제피부 컨디셔닝
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
SMILES
Cc1ncc(CO)c(CO)c1O
LogP
-0.77 · -0.770
NIST
2 · 2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridine(65-23-6)
EPA
3 · 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- (65-23-6)

화학적 성질

crystalline solid

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 · 1건

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 · 5건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

pyridoxine

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataLD50: 4 gm/kg (oral, rat)

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
UV1350000
HS 번호
29362500
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36
기존화학 물질
KE-20694
F 고인화성물질
8-10
스토리지 클래스
11 - Combustible Solids
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 · 2건

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

FDA Pharmacological Classification · 6건

KV2JZ1BI6Z

PYRIDOXINE

Established Pharmacologic Class [EPC] - Vitamin B6 Analog

Chemical/Ingredient structural concept [Chemical/Ingredient] - Vitamin B 6

Chemical/Ingredient structural concept [Chemical/Ingredient] - Analogs/Derivatives

Pyridoxine is a Vitamin B6 Analog. The chemical classification of pyridoxine is Vitamin B 6 and Analogs/Derivatives.

MeSH Pharmacological ClassificationA group of water-soluble vitamins, some of which are COENZYMES.
Absorption, Distribution and Excretion · 3건

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.

Tissue LocationsErythrocyte
Cellular LocationsExtracellular
Metabolite PathwaysHypophosphatasia

용도 및 제조

Uses · 3건

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 · 2건

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

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

응용 분야 · 3건

역사The 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.

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

일반 설명The 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.

상·하류 제품 정보

상류 원료

수크로스(설탕)3-amino-4,5-bis(aminomethyl)2-methylpyridine trihydrochloride1,5-dihydro-3-isopropyl-8-methyl-[1,3]dioxepino[5,6-c]pyridin-9-ol1,5-dihydro-3-isopropyl-8-methyl-[1,3]dioxepino[5,6-c]pyridin-9-yl acetate디메틸5-히드록시-6-메틸피리딘-3,4-디카르복실레이트diethyl 5-hydroxy-6-methylpyridine-3,4-dicarboxylate3,4-피리딘디카르복실산,5-히드록시-6-메틸-Glycine, N-[[3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinyl]methyl]-4-피리독산D-Altrose피리독살D-(+)-Allosepyridoxamine

하류 제품

인산피리독살5-클로로메틸-3-하이드록시-4-하이드록시메틸-2-메틸피리딘1,3-dihydro-6-methylfuro[3,4-c]pyridin-7-ol
추가 설명 · 1건

정의ChEBI: 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.