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니코틴산

니코틴산
니코틴산 구조식 이미지
카스 번호:
59-67-6
한글명:
니코틴산
동의어(한글):
니코틴산;3-카르복시피리딘;3-피리딘카르복실산;3-카르복실피리딘;3-피리딜카르복실산(3-PYRIDYLCARBOXYLICACID;3-피리딜카르복실산(3-PYRIDYLCARBOXYLICACID니아신;니아신;니코틴산;나이아신;3-카복실피리딘;3-피리딘카복실산;3-피리딜카복실산;니카시드
상품명:
Nicotinic acid
동의어(영문):
VB3;NICO;Niac;S115;Linic;Nicyl;Tinic;NIACIN;Akotin;Bionic
CBNumber:
CB0276607
분자식:
C6H5NO2
포뮬러 무게:
123.11
MOL 파일:
59-67-6.mol

니코틴산 속성

녹는점
236-239 °C(lit.)
끓는 점
260C
밀도
1.473
굴절률
1.5423 (estimate)
인화점
193°C
저장 조건
2-8°C
용해도
18g/l
산도 계수 (pKa)
4.85(at 25℃)
물리적 상태
Powder
색상
White to off-white
수소이온지수(pH)
2.7 (18g/l, H2O, 20℃)
수용성
1-5 g/100 mL at 17 ºC
Merck
14,6525
BRN
109591
안정성
Stable. Incompatible with strong oxidizing agents. May be light sensitive.
InChIKey
PVNIIMVLHYAWGP-UHFFFAOYSA-N
CAS 데이터베이스
59-67-6(CAS DataBase Reference)
NIST
Niacin(59-67-6)
EPA
Nicotinic acid (59-67-6)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi,T,F
위험 카페고리 넘버 36/37/38-36-39/23/24/25-23/24/25-11
안전지침서 26-36-24/25-45-36/37-16-7
유엔번호(UN No.) UN1230 - class 3 - PG 2 - Methanol, solution
WGK 독일 1
RTECS 번호 QT0525000
F 고인화성물질 8
자연 발화 온도 >365 °C Dust
TSCA Yes
HS 번호 29362990
유해 물질 데이터 59-67-6(Hazardous Substances Data)
독성 LD50 s.c. in rats: 5 g/kg (Brazda, Coulson)
기존화학 물질 KE-29937
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H370 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재) 특정 표적장기 독성 - 1회 노출 구분 1 위험 P260, P264, P270, P307+P311, P321,P405, P501
예방조치문구:
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P311 의료기관(의사)의 진찰을 받으시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P337+P313 눈에 대한 자극이 지속되면 의학적인 조치· 조언를 구하시오.

니코틴산 MSDS


3-Pyridinecarboxylic acid

니코틴산 C화학적 특성, 용도, 생산

개요

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.

화학적 성질

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.

물리적 성질

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

역사

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.

용도

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.

용도

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 to nicotinamide or to other derivatives exhibiting the biological activity of nicotinic acid. Vitamin (enzyme cofactor).

용도

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.

정의

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

상표명

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

일반 설명

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

일반 설명

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.

공기와 물의 반응

Water soluble.

반응 프로필

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

화재위험

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

생물학적 활성

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.

Biochem/physiol Actions

Nicotinic is an antioxidant and acts as a coenzyme in the form of nicotinamide adenine nucleotides(NAD). It modulates lipid metabolism and may be useful in treating dyslipidemia. Nicotinic acid reduces the low-density lipoprotein (LDL) synthesis and improves high-density lipoprotein (HDL) levels. Deficiency of niacin leads to enhanced lipid peroxidation and is implicated in Crohn′s disease Deficiency also impacts DNA repair and also leads to skin and gastrointestinal disorder pellagra.

Mechanism of action

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.

Pharmacokinetics

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..

Clinical Use

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.

부작용

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.

Safety Profile

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.

신진 대사

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.

Purification Methods

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.]

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