pyridine-3-carboxylic acid

• ChemBase编号: 509
• 分子式: C6H5NO2
• 平均质量: 123.1094
• 单一同位素质量: 123.03202841
• SMILES: OC(=O)c1cccnc1
• Canonical SMILES: OC(=O)c1cccnc1
• InChI: InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
• InChIKey: PVNIIMVLHYAWGP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: pyridine-3-carboxylic acid
• IUPAC系统名: Pyridine-3-carboxylic acid
• IUPAC传统名: niacin
• 商标名: Akotin; Anti-Pellagra Vitamin; Apelagrin; Bionic; Daskil; Davitamon PP; Diacin; Direktan; Efacin; Kyselina Nikotinova; Linic; NICO; Naotin; Niac; Nicacid; Nicangin; Nico-Span; Nicocidin; Nicocrisina; Nicodan; Nicodelmine; Nicodon; Niconacid; Niconat; Niconazid; Nicorol; Nicosan 3; Nicoside; Nicosyl; Nicotamin; Nicotene; Nicotil; Nicotinipca; Nicotinsaure; Nicovasan; Nicovasen; Nicovel; Nicyl; Nipellen; Nyclin; P.P. Factor; Pellagra Preventive Factor; Pellagramin; Pellagrin; Pelonin; Peviton; PP Factor; Sk-Niacin; Tega-Span; Tinic; Vitaplex N; Niaspan; Simcor
• 别名: 尼可丁酸; 3-吡啶甲酸; 吡啶-3-羧酸; 尼亚生; 抗糙皮病因子; 维生素 B3; 烟酸; Acide Nicotinique; Acidum Nicotinicum; M-Pyridinecarboxylic Acid; NAH; Nicotine Acid; Nicotinic Acid; Pyridinecarboxylic Acid; Pyridylcarboxylic Acid; Vitamin B3; 3-Pyridinecarboxylic acid; niacin; Niacin; Niacinamide; Niacin(Nicotinic acid); Pyridine-3-carboxylic acid; 3-Carboxypyridine; Nicotinic acid; Pellagra preventive factor; 3-Carboxylpyridine; Akotin; Apelagrin; Niacor; Niaspan; Nicacid; Pelonin; Vitamin B5; Wampocap; β-Pyridinecarboxylic Acid; Bionic; Nicotinic acid; NICOTINIC ACID FREE ACID; 3-Picolinic acid; Vitamin B₃

登记号

• CAS号: 59-67-6
• EC号: 200-441-0
• MDL号: MFCD00006391
• Beilstein号: 109591
• 默克索引号: 146525
• PubChem SID: 24886386; 24897734; 24897668; 46507508; 24897443; 24886384; 160963972; 24886385; 24897445; 24871534
• PubChem CID: 938
• CHEBI ID: 15940
• ATC码: C04AC01; C10AD02
• CHEMBL: 573
• Chemspider ID: 913
• DrugBank ID: DB00627
• Gmelin ID: 3340
• IUPHAR配体索引: 1588
• KEGG ID: D00049
• 医学主题词(MeSH): Niacin
• 美国药典/FDA物质标识码: 2679MF687A
• 维基百科标题: Niacin

理论计算性质

JChem

• Acid pKa: 2.7856104
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): -1.3303725
• LogD (pH = 7.4): -2.8627489
• Log P: -0.16644564
• 摩尔折射率: 31.1573 cm^3
• 极化性: 11.793079 Å^3
• 极化表面积: 50.19 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.29
• LOG S: -0.17
• 溶解度: 8.31e+01 g/l

分子性质

理化性质

• 溶解度: 18 g L^-1 in water; 18 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO; Methanol; Water
• 外观: White Solid; White, translucent crystals
• 熔点: 189-202°C; 233-238 °C; 234-238 °C; 234-238 °C (dec.); 236.6; 236.85°C (510K); 236-239 °C(lit.); 236-239(subl.)°C; 236-239°C
• 闪点: 193 °C; 193°C; 293°C(559°F); 379.4 °F
• 自燃点: 365 °C
• 密度: 1.4; 1.467; 1.473 g cm^-3
• 折射率: 1.4936
• 蒸汽压: 5.7 x 10-6 mm Hg at 25 °C (estimated)
• 分配系数: 0.219
• 疏水性(logP): 0.4
• pKa: 2.201
• pKb: 11.796
• 等电点: 4.75
• 偶极距: 0.1271305813 D
• 标准摩尔燃烧焓 (ΔcH^o298): -2.73083 MJ mol^-1
• 标准摩尔生成焓 (ΔfH^o298): -344.9 kJ mol^-1

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• 保存注意事项: Irritant/Light Sensitive/Store under Argon
• RTECS编号: QT0525000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: 36; R36/37/38
• 安全公开号: 26; S26, S36
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• NFPA704:
  

  1

  1

  0
• GHS危险声明: H319
• GHS警示性声明: P280-P264-P305+P351+P338-P337+P313; P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 给药途径: Intramuscular, Oral
• 半衰期: 20-45 min
• 相关基因信息: human ... CYP1A2(1544)rat ... Chrnb2(54239)

产品相关信息

• 纯度: ≥99%; ≥98%; ≥99.0% (HPLC); ≥99.5%; ≥99.5% (HPLC); 97%; 98%; 99%
• 级别: analytical standard; matrix substance for MALDI-MS; Ph Eur; purum; SAJ special grade
• 成盐信息: Free Base
• 包装: ampule of 1000 mg
• 适用性: meets USP testing specifications; plant cell culture tested; suitable for cell culture; suitable for insect cell culture; suitable for plant cell culture
• 燃烧残渣: <0.05%; ≤0.05%
• 杂质: ≤0.2% water
• 痕量阳离子: Ba: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• 干燥失重: ≤0.2% loss on drying
• 产品质量级别: PREMIUM
• 特征: standard type water soluble vitamin
• 适用分析物: oligonucleotides; peptides; proteins
• 药典: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C6H5NO2

详细说明

MP Biomedicals - 02194716

Cell Culture Reagent
Purity: 99+%
Crystalline
Free Acid

MP Biomedicals - 02102446

Purity: 99+%
Crystalline
Free Acid

DrugBank - DB00627

• Drug Groups: approved; nutraceutical; investigational
• Description: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has pellagra-curative, vasodilating, and antilipemic properties. [PubChem]
• Indication: For the treatment of type IV and V hyperlipidemia. It is indicated as ajunctive therapy.
• Pharmacology: Niacin and niacinamide are indicated for prevention and treatment of vitamin B3 deficiency states. Vitamin B3 (Niacin) also acts to reduce LDL cholesterol, triglycerides, and HDL cholesterol. The magnitude of individual lipid and lipoprotein responses may be influenced by the severity and type of underlying lipid abnormality. The increase in total HDL is associated with a shift in the distribution of HDL subfractions (as defined by ultra-centrifugation) with an increase in the HDL2:HDL3 ratio and an increase in apolipoprotein A-I content. Vitamin B3 (Niacin) treatment also decreases the serum levels of apolipoprotein B-100 (apo B), the major protein component of the VLDL (very low-density lipoprotein) and LDL fractions, and of lipoprotein-a, a variant form of LDL independently associated with coronary risk.
• Toxicity: Nicotinic acid can cause vasodilation of cutaneous blood vessels resulting in increased blood flow, principally in the face, neck and chest. This produces the niacin- or nicotinic acid-flush. The niacin-flush is thought to be mediated via the prostaglandin prostacyclin. Histamine may also play a role in the niacin-flush. Flushing is the adverse reaction first observed after intake of a large dose of nicotinic acid, and the most bothersome one. LD₅₀ 7000 mg/kg (Rat)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Both nicotinic acid and nicotinamide are efficiently absorbed from the stomach and small intestine.
• Half Life: 20-45 minutes.
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1744

Research Area: Metabolic Disease
Biological Activity:
Niacin(Nicotinic acid) is a water-soluble vitamin belonging to the vitamin B family, which occurs in many animal and plant tissues, with antihyperlipidemic activity. Niacin is converted to its active form niacinamide, which is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and its phosphate form, NADP. These coenzymes play an important role in tissue respiration and in glycogen, lipid, amino acid, protein, and purine metabolism. [1, 2]

Sigma Aldrich - 72309

Other Notes
Coenzyme and Cofactors, vol 2: Pyridine Nucleotide Coenzymes1,2

Sigma Aldrich - N4126

Biochem/physiol Actions
降低肝脏极低密度脂蛋白和载脂蛋白 B 的产量。
包装
1 kg in poly bottle
5, 100, 500 g in poly bottle

Toronto Research Chemicals - N429250

Nicotinic acid. It is a precursor of the coenzymes NAD and NADP. Widely distributed in nature; appreciable amounts are found in liver , fish, yeast and cereal grains. Dietary deficiency is associated with pellagra. The term “niacin” has also been applied

参考文献

• http://www.cancer.gov/drugdictionary/?CdrID=38351
• http://en.wikipedia.org/wiki/Niacin
• Darby, W.J., et al.: Nutr. Rev., 33, 289 (1975)
• Black, A., et al.: Eur. J. Clin. Nutr., 54, 395 (1975)
• Cole, T., et al.: Br. Med. J., 320, 1240 (1975)
• Forshee, R., et al.: J. Nutr., 134, 2733 (1975)