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ニコチン酸

ニコチン酸 化学構造式
59-67-6
CAS番号.
59-67-6
化学名:
ニコチン酸
别名:
ニコチン酸;ニシル;ニコサン3;ナイクリン;ニクリン;ニカギン;エファシン;3-ピリジンカルボン酸;アコチン;ニカンギン;ペロニン;ダスキル;ニコナシド;ナイアシン;アペラグリン;3-ピリジンカルボン酸塩;ニコチニプカ;ピリジン-3-カルボン酸;リニック;ニカシド
英語化学名:
Nicotinic acid
英語别名:
VB3;NICO;Niac;S115;Linic;Nicyl;Tinic;NIACIN;Akotin;Bionic
CBNumber:
CB0276607
化学式:
C6H5NO2
分子量:
123.11
MOL File:
59-67-6.mol

ニコチン酸 物理性質

融点 :
236-239 °C(lit.)
沸点 :
260C
比重(密度) :
1.473
屈折率 :
1.5423 (estimate)
闪点 :
193°C
貯蔵温度 :
2-8°C
溶解性:
18g/l
酸解離定数(Pka):
4.85(at 25℃)
外見 :
Powder
色:
White to off-white
PH:
2.7 (18g/l, H2O, 20℃)
水溶解度 :
1-5 g/100 mL at 17 ºC
Merck :
14,6525
BRN :
109591
安定性::
Stable. Incompatible with strong oxidizing agents. May be light sensitive.
InChIKey:
PVNIIMVLHYAWGP-UHFFFAOYSA-N
CAS データベース:
59-67-6(CAS DataBase Reference)
NISTの化学物質情報:
Niacin(59-67-6)
EPAの化学物質情報:
Nicotinic acid (59-67-6)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xi,T,F
Rフレーズ  36/37/38-36-39/23/24/25-23/24/25-11
Sフレーズ  26-36-24/25-45-36/37-16-7
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  1
RTECS 番号 QT0525000
8
自然発火温度 >365 °C Dust
TSCA  Yes
HSコード  29362990
有毒物質データの 59-67-6(Hazardous Substances Data)
毒性 LD50 s.c. in rats: 5 g/kg (Brazda, Coulson)
化審法 (5)-731
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P307+P311, P321,P405, P501
注意書き
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P311 医師に連絡すること。
P337+P313 眼の刺激が続く場合:医師の診断/手当てを受けること。

ニコチン酸 価格 もっと(55)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01FLC214893 ニコチン酸
Nicotinic acid
59-67-6 1g ¥6300 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01ACSVIT-005N ナイアシン
Niacin
59-67-6 1g ¥9300 2021-03-23 購入
東京化成工業 N0082 ニコチン酸 >99.0%(HPLC)(T)
Nicotinic Acid >99.0%(HPLC)(T)
59-67-6 500g ¥5600 2021-03-23 購入
東京化成工業 N0082 ニコチン酸 >99.0%(HPLC)(T)
Nicotinic Acid >99.0%(HPLC)(T)
59-67-6 25g ¥1600 2021-03-23 購入
関東化学株式会社(KANTO) 12829-2A ニコチン酸
Nicotinic acid
59-67-6 5g ¥2700 2021-03-23 購入

ニコチン酸 MSDS


3-Pyridinecarboxylic acid

ニコチン酸 化学特性,用途語,生産方法

外観

白色~ほとんど白色, 粉末又は塊

定義

本品は、次の化学式で表される複素環式化合物である。

溶解性

水酸化ナトリウム溶液および炭酸ナトリウム溶液に溶け、水にやや溶けにくく、エタノールに溶けにくく、エーテルに極めて溶けにくい。

解説

3-pyridinecarboxylic acid.C6H5NO2(123.11).ナイアシンともいう.ビタミンB複合体の一つで,抗ペラグラ因子.動物の肝臓,肉,酵母,豆類,穀物など生体内に広く存在する.ニコチン,3-ピコリン,3-エチルピリジンなどを濃硝酸,その他で酸化して合成される."針状晶.融点236.6 ℃.昇華性がある.水,エタノールに可溶,エーテル,ベンゼンに不溶.生体内ではトリプトファンから合成され,おもにニコチン酸アミド補酵素(NAD,NADP)の形で存在し,酸化還元反応に関与している.欠乏症は消化器および中枢神経系症状を伴う皮膚変化(ペラグラ)を起こす.[CAS 59-67-6]
森北出版「化学辞典(第2版)

用途

脱水酵素補酵素です。酸化還 元反応に作用します。

化粧品の成分用途

ヘアコンディショニング剤、皮膚コンディショニング剤

効能

脂質異常症治療薬, 血管拡張薬, ニコチン酸補充薬

商品名

ナイクリン (トーアエイヨー)

説明

Niacin is an additive to food on the basis of its nutrient supplement qualities as a vitamin (as an enzyme co-factor). This water-soluble vitamin of the B complex occurs in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. A deficiency of niacin results in the disease, pellagra.

化学的特性

NIACIN is sometimes referred to as nicotinic acid or nicotinamide and earlier called the P-P factor, antipellagra factor, antiblacktongue factor, and vitamin B4, niacin is available in several forms (niacin, niacinamide, niacinamide ascorbate, etc.) for use as a nutrient and dietary supplement. Niacin is frequently identified with the B complex vitamin grouping. Early in the research on niacin, a nutritional niacin deficiency was identified as the cause of pellagra in humans, blacktongue in dogs, and certain forms of dermatosis in humans. Niacin deficiency is also associated with perosis in chickens as well as poor feathering of the birds.

物理的性質

Nicotinic acid and nicotinamide are colorless crystalline substances. Each is insol uble or only sparingly soluble in organic solvents. Nicotinic acid is slightly soluble in water and ethanol; nicotinamide is very soluble in water and moderately soluble in ethanol
Nicotinic acid is amphoteric and forms salts with acids as well as bases. Its car boxyl group can form esters and anhydrides and can be reduced. Both nicotinic acid and nicotinamide are very stable in dry form, but in solution nicotinamide is hydro lyzed by acids and bases to yield nicotinic ac
The coenzyme forms of niacin are the pyridine nucleotides, NAD(H) and NADP(H). In each of these compounds, the electron-withdrawing effect of the N-1 atom and the amide group of the oxidized pyridine nucleus enables the pyridine C-4 atom to react with many nucleophilic agents (e.g., sulfite, cyanide, and hydride ions). It is the reaction with hydride ions (H?) that is the basis of the enzymatic hydrogen transfer by the pyridine nucleotides; the reaction involves the transfer of two electrons in a single step
Several substituted pyridines are antagonists of niacin in biological systems: pyridine-3-sulfonic acid, 3-acetylpyridine, isonicotinic acid hydrazine, 17 and 6-aminonicotinamide

来歴

Huber first synthesized nicotinic acid in 1867. In 1914, Funk isolated nicotinic acid from rice polishings. Goldberger, in 1915, demonstrated that pellagra is a nutritional deficiency. In 1917, Chittenden and Underhill demonstrated that canine blacktongue is similar to pellagra. In 1935, Warburg and Christian showed that niacinamide is essential in hydrogen transport as diphosphopyridine nucleotide (DPN). In the following year, Euler et al. isolated DPN and determined its structure. In 1937, Elvhehjem et al. cured blacktongue by administration of niacinamide derived from liver. In the same year, Fouts et al. cured pellagra with niacinamide. In 1947, Handley and Bond established conversion of tryptophan to niacin by animal tissues.

使用

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.
Niacin is a water-soluble b-complex vitamin that is necessary for the growth and health of tissues. It prevents pellagra. It has a solubility of 1 g in 60 ml of water and is readily soluble in boiling water. It is relatively stable in storage and no loss occurs in ordinary cooking. Sources include liver, peas, and fish. It was originally termed nicotinic acid and also functions as a nutrient and dietary supplement.

使用

niacin is also known as vitamin B3. It is a water-soluble conditioning agent that improves rough, dry, or flaky skin, helping smooth the skin and improve its suppleness. niacin enhances the appearance and feel of hair, by increasing body, suppleness, or sheen, or by improving the texture of hair that has been damaged physically or by chemical treatment. When used in the formulation of skin care products, niacinamide and niacin enhance the appearance of dry or damaged skin by reducing flaking and restoring suppleness.

定義

ChEBI: A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.

brand name

Niacor (Upsher Smith); Niaspan (KOS); Nicolar (Sanofi Aventis); Wampocap (Medpointe).

一般的な説明

Nicotinic acid, 3-pyridinecarboxylicacid (Niacin), is effective in the treatment of all types ofhyperlipoproteinemia except type I, at doses above thosegiven as a vitamin supplement. The drug reduces VLDLsynthesis and, subsequently, its plasma products, IDL andLDL. Plasma triglyceride levels are reduced because of thedecreased VLDL production. Cholesterol levels are lowered,in turn, because of the decreased rate of LDL formationfrom VLDL. Although niacin is the drug of choicefor type II hyperlipoproteinemias, its use is limited becauseof the vasodilating side effects. Flushing occurs inpractically all patients but generally subsides when thedrug is discontinued.
The hypolipidemic effects of niacin may be caused byits ability to inhibit lipolysis (i.e., prevent the release ofFFAs and glycerol from fatty tissues). Therefore, there is areduced reserve of FFA in the liver and diminution oflipoprotein biosynthesis, which reduces the production ofVLDL. The decreased formation of lipoproteins leads to apool of unused cholesterol normally incorporated inVLDL. This excess cholesterol is then excreted throughthe biliary tract.

一般的な説明

Odorless white crystalline powder with a feebly acid taste. pH (saturated aqueous solution) 2.7. pH (1.3% solution) 3-3.5.

空気と水の反応

Water soluble.

反応プロフィール

Nicotinic acid is incompatible with strong oxidizers. Nicotinic acid is also incompatible with sodium nitrite.

火災危険

Flash point data for Nicotinic acid are not available; however, Nicotinic acid is probably combustible.

生物活性

Nicotinic acid can be converted to nicotinamide in the animal body and, in this form, is found as a component of two oxidation-reduction coenzymes, NAD and NADP.The nicotinamide portion of the coenzyme transfers hydrogens by alternating between an oxidized quaternary nitrogen and a reduced tertiary nitrogen. Enzymes that contain NAD or NADP are usually called dehydrogenases. They participate in many biochemical reactions of lipid, carbohydrate, and protein metabolism. An example of an NAD-requiring system is lactic dehydrogenase which catalyzes the conversion of lactic acid to pyruvic acid.

作用機序

Nicotinic acid decreases formation and secretion of VLDL by the liver.This action appears secondary to its ability to inhibit fatty acid mobilization from adipose tissue. Circulating free fatty acids provide the main source of fatty acids for hepatic triglyceride synthesis, and lowering triglyceride synthesis lowers VLDL formation and secretion by the liver. Since plasma VLDL is the source of LDL, lowering VLDL can ultimately lower LDL. In addition, nicotinic acid shifts LDL particles to larger (more buoyant) sizes. The larger LDL particles are thought to be less atherogenic. Nicotinic acid can also significantly increase plasma HDL levels; the mechanism is unknown.

薬物動態学

Nicotinic acid is readily absorbed. Peripheral vasodilation is seen within 20 minutes, and peak plasma concentrations occur within 45 minutes. The half-life of the compound is approximately one hour, thus necessitating frequent dosing or an extended-release formulation. Extended release tablets produce peripheral vasodilation within 1 hour, reach peak plasma concentrations within 4 to 5 hours, and have a duration of 8 to 10 hours.
Dosing of nicotinic acid should be titrated to minimize adverse effects. An initial dose of 50 to 100 mg t.i.d. often is used with immediaterelease tablets. The dose then is gradually increased by 50 to 100 mg every 3 to 14 days, up to a maximum of 6 g/day, as tolerated. Therapeutic monitoring to assess efficacy and prevent toxicity is essential until a stable and effective dose is reached. Similar dosing escalations are available for extended-release products, with doses normally starting at 500 mg once daily at bedtime..

臨床応用

Nicotinic acid has been esterified to prolong itshypolipidemic effect. Pentaerythritol tetranicotinate hasbeen more effective experimentally than niacin in reducingcholesterol levels in rabbits. Sorbitol and myo-inositolhexanicotinate polyesters have been used in the treatment ofpatients with atherosclerosis obliterans.The usual maintenance dose of niacin is 3 to 6 g/daygiven in three divided doses. The drug is usually given atmealtimes to reduce the gastric irritation that often accompanieslarge doses.

副作用

Compliance with nicotinic acid therapy can be poor because the drug can produce an intense cutaneous flush. This can be reduced by beginning the drug in stepped doses of 250 mg twice daily and increasing the dose monthly by 500 to 1000 mg per day to a maximum of 3000 mg per day.Taking nicotinic acid on a full stomach (end of meal) and taking aspirin before dosage can reduce the severity of flushing. Time-release forms of nicotinic acid may also decrease cutaneous flushing. Nicotinic acid can cause gastrointestinal (GI) distress,liver dysfunction (especially at high doses), decreased glucose tolerance, hyperglycemia, and hyperuricemia. Thus, it is contraindicated in patients with hepatic dysfunction, peptic ulcer, hyperuricemia, or diabetes mellitus. A paradox associated with nicotinic acid is that it is the most widely available hypolipidemic drug (it is sold over the counter), yet its use requires the closest management by the physician.

安全性プロファイル

Poison by intraperitoneal route. Moderately toxic by ingestion, intravenous, and subcutaneous routes. Human systemic effects: change in clotting factors, changes in platelet count. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits toxic fumes of NOx.

Chemical Synthesis

Nicotinic acid, pyridine-3-carboxylic acid (20.2.9) is synthesized industrially by heating a paraldehyde trimer of acetaldehyde, under pressure with ammonia, which leads to the formation of 2-methyl-5-ethylpyridine, followed by oxidation with nitric acid which gives the desired product.

代謝

Nicotinic acid is a B-complex vitamin that is converted to nicotinamide, NAD+ , and NADP+ .The latter two compounds are coenzymes and are required for oxidation/reduction reactions in a variety of biochemical pathways. Additionally, nicotinic acid is metabolized to a number of inactive compounds, including nicotinuric acid and N-methylated derivatives. Normal biochemical regulation and feedback prevent large doses of nicotinic acid from producing excess quantities of NAD+ and NADP+ .Thus, small doses of nicotinic acid, such as those used for dietary supplementation, will be primarily excreted as metabolites, whereas large doses, such as those used for the treatment of hyperlipoproteinemia, will be primarily excreted unchanged by the kidney.

純化方法

Crystallise the acid from *benzene, EtOH or H2O. It sublimes without decomposition. [McElvain Org Synth Coll Vol I 385 1941, Beilstein 22 III/IV 439, 22/2 V 57.]

ニコチン酸 上流と下流の製品情報

原材料

準備製品


ニコチン酸 生産企業

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59-67-6(ニコチン酸)キーワード:


  • 59-67-6
  • BETA-PICOLINIC ACID
  • AKOS BBS-00003719
  • ACIDUM-NICOTINICUM
  • 3-PICOLINIC ACID
  • 3-CARBOXYPYRIDINE
  • RARECHEM AL BO 0217
  • TIMTEC-BB SBB004279
  • NICOTINIC ACID
  • NICONACID
  • NIACIN
  • PELLAGRA PREVENTIVE FACTOR
  • PYRIDINE-3-CARBOXYLATE
  • PYRIDINE-3-CARBOXYLIC ACID
  • PYRIDINE-BETA-CARBOXYLIC ACID
  • VITAMIN B3
  • 3-Carboxylpyridine
  • Vitamin B5
  • Acide nicotinique
  • acidenicotinique
  • Akotin
  • anti-Pellagra vitamin
  • Nicangin
  • NICO
  • Nico-400
  • Nicobid
  • Nicocap
  • Nicocidin
  • Nicocrisina
  • Nicodan
  • Nicodelmine
  • ニコチン酸
  • ニシル
  • ニコサン3
  • ナイクリン
  • ニクリン
  • ニカギン
  • エファシン
  • 3-ピリジンカルボン酸
  • アコチン
  • ニカンギン
  • ペロニン
  • ダスキル
  • ニコナシド
  • ナイアシン
  • アペラグリン
  • 3-ピリジンカルボン酸塩
  • ニコチニプカ
  • ピリジン-3-カルボン酸
  • リニック
  • ニカシド
  • ニコデルミン
  • ニコ-スパン
  • ペラグリン
  • ニコラル
  • ニアシン
  • ニコチン酸 [MALDI-TOF/MS マトリックス用]
  • ニコチン酸標準品
  • ニコチン酸 (JP17)
  • ビタミン
  • マトリックス素材 (MALDI-TOF-MS)
  • 分析化学
  • 生化学
  • 質量分析用試薬
  • ビタミンB群
  • 代謝産物
  • 代謝作用薬
  • 血管拡張薬
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