54-47-7

• 常用中文名：磷酸吡哆醛
• 常用英文名：Pyridoxal phosphate
• CAS号：54-47-7
• 分子式：C₈H₁₀NO₆P
• 分子量：247.142
• 相关类别： 原料药 维生素类与矿物质类药 维生素B类药
• 发布时间：2018-09-24 07:35:23
• 更新时间：2024-01-02 08:28:20
• Pyridoxal phosphate 是维生素 B6 的活性形式,可以抑制 reverse transcriptases 的活性,用于迟发性运动障碍症的研究。

名称

• 中文名: 磷酸吡哆醛
• 英文名: pyridoxal 5'-phosphate
• 中文别名: 磷酸-5'-吡哆醛; 3-羟基-2-甲基-5-[(磷酰氧基)甲基]-4-吡啶甲醛; 吡哆醛-5-磷酸; 吡多醛-5-磷酸酯; 3-羟基-2-甲基-5-[(膦酰氧基)甲基]-4-吡啶甲醛; 辅去羧酶; PYRID氧杂L-5'-磷酸酯
• 英文别名: Pyridoxal-5-monophosphate; (4-Formyl-5-hydroxy-6-methyl-3-pyridinyl)methyl dihydrogen phosphate; Phosphate, Pyridoxal; (4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate; (4-Formyl-5-hydroxy-6-methyl-3-pyridinyl)methyldihydrogen-phosphat; Aderoxal; EINECS 200-208-3; Pyridoxal phosphate (6CI); (4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyldihydrogen-phosphat; Vitamin B6 phosphate; Pyridoxal 5-phosphate; Pyridoxal phosphate; MFCD00006333; 4-Pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[ (phosphonooxy)methyl]-; Pyridoxyl phosphate; Pyridoxal 5'-phosphic acid; Isonicotinaldehyde, 3-hydroxy-5-(hydroxymethyl)-2-methyl-, 5-(dihydrogen phosphate); 4-Pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-; 3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde

物化性质

• 密度: 1.6±0.1 g/cm3
• 沸点: 565.7±60.0 °C at 760 mmHg
• 熔点: 140-143ºC
• 分子式: C₈H₁₀NO₆P
• 分子量: 247.142
• 闪点: 296.0±32.9 °C
• 精确质量: 247.024567
• PSA: 126.76000
• LogP: -0.52
• 外观性状: 淡黄色粉末
• 蒸汽压: 0.0±1.6 mmHg at 25°C
• 折射率: 1.641
• 储存条件:

  本品应密封于4℃干燥避光保存。

• 分子结构:

  1、 摩尔折射率：54.40

  2、 摩尔体积（m³/mol）：150.8

  3、 等张比容（90.2K）：461.1

  4、 表面张力（dyne/cm）：87.3

  5、 极化率（10 ^-24cm ³）：21.56

• 计算化学:

  1.疏水参数计算参考值（XlogP）:-1.1

  2.氢键供体数量:3

  3.氢键受体数量:7

  4.可旋转化学键数量:4

  5.互变异构体数量:4

  6.拓扑分子极性表面积117

  7.重原子数量:16

  8.表面电荷:0

  9.复杂度:292

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：类白色或黄色粉末, 溶于稀酸中为无色，在碱中为黄色。几乎无臭、无味。

  2. 密度（g/mL,25/4℃）： 未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：140-143℃

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：微溶于醇，溶于200份水，不溶于氯仿、苯、丙酮、乙醚。在避光冷处稳定。

生物活性

• 描述: Pyridoxal phosphate 是维生素 B6 的活性形式,可以抑制 reverse transcriptases 的活性,用于迟发性运动障碍症的研究。
• 相关类别:
  信号通路 >> 抗感染 >> 逆转录酶
  研究领域 >> 神经疾病
  天然产物 >> 其他
• 靶点:

  Human Endogenous Metabolite

• 体外研究: 吡哆醛5'-磷酸盐严重抑制DNA聚合酶和RNase H.磷酸吡哆醛导致DNA合成速率的模拟降低[1]。与磷酸吡哆醛的缀合完全抑制NEIL2。在广泛的酶/底物比例范围内,吡哆醛磷酸盐缀合的NEIL2显示出比完整酶低得多的活性。磷酸吡哆醛结合后,NEIL2结合THF配体的能力完全丧失[2]。
• 参考文献:

  [1]. Modak MJ. Pyridoxal 5' phosphate: a selective inhibitor of oncornaviral DNA polymerases. Biochem Biophys Res Commun. 1976 Jul 12;71(1):180-7.

  [2]. Grin IR, et al. Inactivation of NEIL2 DNA glycosylase by pyridoxal phosphate reveals a loop important for substrate binding. Biochem Biophys Res Commun. 2010 Mar 26;394(1):100-5.

MSDS

Name: Pyridoxal 5-Phosphate 99% (Titr.) Material Safety Data Sheet Synonym: 3-Hydroxy-2-Methyl-5-(Phosphonoxy)-4-Pyridinecarboxaldehyde; 1-Iodohexadecane CAS: 54-47-7 Section 1 - Chemical Product MSDS Name:Pyridoxal 5-Phosphate 99% (Titr.) Material Safety Data Sheet Synonym:3-Hydroxy-2-Methyl-5-(Phosphonoxy)-4-Pyridinecarboxaldehyde; 1-Iodohexadecane Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 54-47-7 4-Pyridinecarboxaldehyde,3-Hydroxy-2-M 99 200-208-3 Hazard Symbols: None Listed. Risk Phrases: None Listed. Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Light sensitive. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: May cause irritation of the digestive tract. Low hazard for usual industrial handling. Inhalation: May cause respiratory tract irritation. Low hazard for usual industrial handling. Chronic: None Section 4 - FIRST AID MEASURES Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. If irritation develops, get medical aid. Skin: Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse. Ingestion: Never give anything by mouth to an unconscious person. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Get medical aid if irritation or symptoms occur. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid if cough or other symptoms appear. Notes to Physician: Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extinguishing Media: Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. No special precautions indicated. Store protected from light. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 54-47-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Powder Color: light yellow Odor: Not available. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: Not available. Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: Specific Gravity/Density: Molecular Formula: C8H10NO6P Molecular Weight: 247.14 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, light, dust generation, excess heat, strong oxidants. Incompatibilities with Other Materials: Strong oxidizing agents. Hazardous Decomposition Products: Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide, oxides of potassium. Hazardous Polymerization: Has not been reported Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 54-47-7: UV1207000 LD50/LC50: CAS# 54-47-7: Oral, mouse: LD50 = 4640 mg/kg; Oral, rat: LD50 = 5900 mg/kg. Carcinogenicity: 4-Pyridinecarboxaldehyde,3-Hydroxy-2-Methyl-5-(Phosphonooxy) - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material. Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: Not available. Risk Phrases: Safety Phrases: S 24/25 Avoid contact with skin and eyes. S 28A After contact with skin, wash immediately with plenty of water. S 37 Wear suitable gloves. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 54-47-7: 1 Canada CAS# 54-47-7 is listed on Canada's DSL List. CAS# 54-47-7 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 54-47-7 is listed on the TSCA inventory. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 1 、急性毒性：大鼠经口LD50： 5900 mg/kg；大鼠皮下LD50：850 mg/kg；小鼠经口LD50：4640mg/kg；小鼠皮下：870 mg/kg； 小鼠静脉LD50：530 mg/kg；小鼠肌内LD50：1150 mg/kg； 2、致突变性：DNA的damageTEST系统：细菌-大肠杆菌：50umol/L CHEMICAL IDENTIFICATION RTECS NUMBER : UV1207000 CHEMICAL NAME : Pyridoxal, 5-(dihydrogen phosphate) CAS REGISTRY NUMBER : 54-47-7 LAST UPDATED : 199701 DATA ITEMS CITED : 11 MOLECULAR FORMULA : C8-H10-N-O6-P MOLECULAR WEIGHT : 247.16 WISWESSER LINE NOTATION : T6NJ B1 CQ DVH E1OPQQO HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 5900 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 850 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 4640 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 870 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 530 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1150 mg/kg TOXIC EFFECTS : Behavioral - antipsychotic TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - species unspecified DOSE/DURATION : >3 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Mammal - species unspecified DOSE/DURATION : 550 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value MUTATION DATA TYPE OF TEST : DNA damage TEST SYSTEM : Bacteria - Escherichia coli DOSE/DURATION : 50 umol/L REFERENCE : FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 34,530,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3949 No. of Facilities: 577 (estimated) No. of Industries: 2 No. of Occupations: 5 No. of Employees: 5538 (estimated) No. of Female Employees: 3978 (estimated)

安全

• 安全声明 (欧洲): 22-24/25
• WGK德国: 3
• 海关编码: 2936250000

合成路线

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制备

【方法一】
吡哆胺二盐酸盐与无水磷酸反应成吡哆胺磷酸酯，后者再经二氧化锰氧化制得。
【方法二】
以吡哆醇为原料。

海关

海关编码	2933399090
中文概述	2933399090. 其他结构含非稠合吡啶环的化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%