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테트라메틸피라진

Tetramethylpyrazine

HCID 14296
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
1124-11-4
표준 SMILES
Cc1nc(C)c(C)nc1C
InChIKey
FINHMKGKINIASC-UHFFFAOYSA-N
분자식
C8H12N2
평균 분자량
136.19 g/mol
단동위원소 질량
136.10004838

개요

Tetramethylpyrazine is a member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups. An alkaloid extracted from Chuanxiong (Ligusticum wallichii). It has a role as an antineoplastic agent, a vasodilator agent, a platelet aggregation inhibitor, a neuroprotective agent, an apoptosis inhibitor and a bacterial metabolite. It is an alkaloid and a member of pyrazines.

이름 및 식별자

우선 이름
Tetramethylpyrazine
IUPAC
2,3,5,6-tetramethylpyrazine
현지명
테트라메틸피라진
영어명
Tetramethylpyrazine
분자식
C8H12N2
분자량
136.19

이름 및 동의어

2,3,5,6-TetramethylpyrazineTETRAMETHYLPYRAZINE1124-11-4LigustrazineChuanxiongzineTetrapyrazinechuanxingzineFEMA No. 3237CHUANXIONGQINTMPZ2,3,5,6,-Tetramethyl-1,4-pyrazineDTXSID6047070
이름 더 보기
2,3,5,6-사메틸피라진테트라메틸피라진FEMA 3237Pyrazine,tetramethyl-Tetramethylpyrazin2,3,5,6-TetramethyLtetramethyl-pyrazinBS FactorLigustizine
V80F4IA5XGDTXCID4027070NSC-36080NSC-46451CHEBI:133246tetramethyl pyrazineRefChem:799162214-391-2

데이터베이스 식별자

CAS
1124-11-4
PubChem CID
14296
DTXSID
DTXSID6047070
ChEMBL
CHEMBL303697
ChEBI
CHEBI:133246
UNII
V80F4IA5XG
EC Number
214-391-2

물성

구조 계산 물성

XLogP
1.3
극성 표면적
25.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
10
형식 전하
0
복잡도
87.8

실험 및 물리화학적 성질

SpringerMaterials PropertiesCrystal structure
FragrancesFragrance Ingredient (2,3,5,6-Tetramethylpyrazine) -> IFRA transparency List
LogP1.28
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 3건

slightly soluble in water; soluble in oils, propylene glycol, organic solvents

very soluble (in ethanol)

<0.1 [ug/mL] (The mean of the results at pH 7.4)

Boiling Point · 2건

190.00 °C. @ 760.00 mm Hg

190 °C

Melting Point86 °C
Physical Description · 2건

Solid

white crystals or powder with a musty, fermented, coffee odour

물리화학적 성질

안전 및 규제

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

GHS 분류

GHS Classification · 6건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1685 reports by companies from 8 notifications to the ECHA C&L Inventory.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

유해성 정보

Regulatory Information · 3건

Chemical: Pyrazine, tetramethyl-

Regulation (EC) No 1831/2003 (amended)

2,3,5,6-Tetramethylpyrazine: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and Categories · 2건

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
UQ3905000
HS 번호
29339990
risk_code
22-37/38-41-36/37/38
hazard_code
Xn,Xi
safety_code
26-39-24/25-37/39-36
기존화학 물질
KE-33627
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
Cellular LocationsCytoplasm

용도 및 제조

Use Classification · 3건

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing InformationPyrazine, 2,3,5,6-tetramethyl-: ACTIVE
응용 분야 · 5건

개요2,3,5,6-Tetramethylpyrazine is an alkaloid that has been found in L. wallichii and has diverse biological activities. It reduces kainate-induced increases in production of reactive oxygen species (ROS) and cytotoxicity in primary rat hippocampal neurons when used at a concentration of 5 μM. 2,3,5,6-Tetramethylpyrazine (0.1 mM) induces vasodilation in precontracted isolated and endothelium-denuded rat tail artery strips and reduces blood pressure in anesthetized rats. It decreases infarct volume, caspase-3 activation, and hypoxia-inducible factor-1α (HIF-1α) levels in a rat model of focal cerebral ischemia induced by middle cerebral artery occlusion (MCAO) when administered at a dose of 20 mg/kg.

출처Reported found in French fried potato, bell pepper, wheat bread, emmental cheese, Swiss cheese, Camembert cheese, Gruyere cheese, boiled and cooked beef, grilled and roasted beef, fried beef, cooked lamb and mutton, lamb and mutton liver, grilled and roasted uncured pork, beer, black tea, green tea. Also reported present in cocoa products, coffee, dairy products, oatmeal, galbanum oil, roasted peanuts, soybean, beans, mushroom, trassi, coriander seed, rice bran, trassi, sukiyaki, soy sauce, malt, licorice, dried bonito, wild rice, shrimp, crab, clam, scallop, filberts, rum, sake, wine, whiskey, burley tobacco and soy products.

Ligusticum walliichi has a long medicinal history in China and is used in the treatment of headache, promoting blood and Qi circulation, curing chills and alleviating pain”. Clinically, it is mainly used for the treatment of cardiovascular and cerebrovascular diseases. Ligustrazine (2,3,5,6-tetramethylpyrazine) is the main active ingredient of Ligusticum walliich. It was first isolated in 1962 .In recent years, studies have found that ligustrazine can inhibit the activity of the cerebral cortex and medullary respiratory center, excite vasomotors, induce the expansion of peripheral blood vessels, promote the blood flow of the coronary artery and lower limbs, and reduce blood pressure. Ligustrazine can also paralyze the nerve center and has sedative and analgesic effects.Studies have suggested that ligustrazine has a variety of new effects, including improving leptomeningeal and peripheral microcirculation and increasing cerebral blood flow, and its effect is better than that of papaverine. Ligustrazine can also protect against experimental cerebral ischemia and alleviate brain edema and the deposition of fibrin in microvessels. Ligustrazine is also used in the treatment of pulmonary heart disease, heart failure, dilated heart disease, portal hypertension, type II diabetes mellitus, tumor and coronary heart disease, and restenosis after stent implantation .

관련 반응

22건
반응 기록 만들기
HRID 443329 반응식
HRID 443329반응물로uspto-grants-1981_04
HRID 443330 반응식
HRID 443330반응물로uspto-grants-1981_04
HRID 443331 반응식
HRID 443331반응물로uspto-grants-1981_04
HRID 443332 반응식
HRID 443332반응물로uspto-grants-1981_04
HRID 443334 반응식
HRID 443334반응물로uspto-grants-1981_04
HRID 633772 반응식
HRID 633772반응물로uspto-grants-2016_04
HRID 633773 반응식
HRID 633773반응물로uspto-grants-2016_04
HRID 633774 반응식
HRID 633774반응물로uspto-grants-2016_04
1 / 3 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Nikkaji
J39.647H
녹는점
77 · 77-80 °C(lit.)
끓는 점
190 °C · 190 °C(lit.)
밀도
1.08 · 1.08
굴절률
1.588 · 1.5880 (estimate)
FEMA
3237 · 3237 | 2,3,5,6-TETRAMETHYLPYRAZINE
인화점
128 · 128-130°C/200mm
저장 조건
Sealed in dry,Room Temperature
용해도
4 g/L · 4g/L
산도 계수 (pKa)
3.2 · 3.20±0.10(Predicted)
물리적 상태
Solid
색상
흰색에서 황백색까지
냄새
10 % · 디프로필렌 글리콜 중 10.00%. 고소한 곰팡내 나는 초콜릿 커피 코코아 갈색 라드 탄
냄새 유형
견과류
생물학적 소스
synthetic
수용성
물에 용해됩니다(20°C에서 4g/L).
JECFA Number
780 · 780
BRN
113100 · 113100
안정성
안정적인. 강산, 강산화제와 호환되지 않습니다.
화장품 원료 기능
향수
InChI
1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
InChIKey
FINHMKGKINIASC-UHFFFAOYSA-N
SMILES
Cc1nc(C)c(C)nc1C
LogP
1.56 · 1.56
NIST
Pyrazine, tetramethyl-(1124-11-4)
EPA
Tetramethylpyrazine (1124-11-4)

화학적 성질

2,3,5,6-Tetramethylpyrazine has musty, fermented, coffee odor

역사

용도etramethylpyrazine is an anti-inflammatory compound isolated from the fermented food natto. Tetramethylpyrazine demonstrated in vivo nootropic activity in rats.

일반 설명2,3,5,6-Tetramethylpyrazine has been isolated from Ephedra sinica. It is useful in the treatment of several disorders such as asthma, heart failure, rhinitis and urinary incontinence. It is a flavor ingredient of tobacco. It forms cocrystal with 4-hydroxybenzoic acid which exhibits supramolecular synthon polymorphism.

제조 방법

From2,5-dimethylpyrazine by ring alkylationwithMeLi; also by condensation of 2,3-butanedionewith 2,3-butanediamine.

상·하류 제품 정보

상류 원료

메틸피라진2,3-부탄디온Acetylacetone아질산 나트륨Ethanol solution에틸 니트리트(아질산에틸)1,4-디아미노부탄

하류 제품

Trimethyl thiazole

공급사100 곳

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추가 설명

정의ChEBI: A member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups. An alkaloid extracted from Chuanxiong (Ligusticum wallichii).