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2,3,5,6-テトラメチルピラジン

Tetramethylpyrazine

HCID 14296
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
1124-11-4
標準SMILES
Cc1nc(C)c(C)nc1C
InChIKey
FINHMKGKINIASC-UHFFFAOYSA-N
分子式
C8H12N2
平均分子量
136.19 g/mol
単同位体質量
136.10004838

概要

Tetramethylpyrazine is a member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups.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.

名称と識別子

優先名称
Tetramethylpyrazine
IUPAC
2,3,5,6-tetramethylpyrazine
現地名
2,3,5,6-テトラメチルピラジン
英語名
Tetramethylpyrazine
分子式
C8H12N2
分子量
136.19

名称と別名

2,3,5,6-TetramethylpyrazineTETRAMETHYLPYRAZINE1124-11-4LigustrazineChuanxiongzineTetrapyrazinechuanxingzineFEMA No. 3237CHUANXIONGQINTMPZ2,3,5,6,-Tetramethyl-1,4-pyrazineDTXSID6047070
名称をさらに表示
2,3,5,6-テトラメチルピラジンテトラメチルピラジンリグストラジン2,3,5,6,-テトラメチルl-1,4-ピラジン2,3,5,6-テトラメチルピラジン, 98+%テトラメチルピラジン, 2,3,5,6-FEMA 3237Pyrazine,tetramethyl-Tetramethylpyrazin2,3,5,6-TetramethyLtetramethyl-pyrazinBS FactorLigustizine
V80F4IA5XGDTXCID4027070NSC-36080NSC-46451CHEBI:133246tetramethyl pyrazineRefChem:799162214-391-2

データベース識別子

CAS
1124-11-4
PubChem CID
14296
DTXSID
DTXSID6047070

物性

構造計算による物性

XLogP
1.3
極性表面積
25.8 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
10
形式電荷
0
複雑度
87.8

実験および物理化学的性質

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 · 3 件

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 · 2 件

190.00 °C. @ 760.00 mm Hg

190 °C

Melting Point86 °C
Physical Description · 2 件

Solid

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

物理化学的性質

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

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]

危険有害性情報

Regulatory Information · 3 件

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 · 2 件

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

安全データ

wgk
3
tsca
TSCA listed
rtecs
UQ3905000
hs_code
29339990
risk_code
22-37/38-41-36/37/38
化審法
(5)-951
hazard_code
Xn,Xi
safety_code
26-39-24/25-37/39-36
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

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

用途と製造

Use Classification · 3 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing InformationPyrazine, 2,3,5,6-tetramethyl-: ACTIVE
応用分野 · 7 件

用途ナッツ類のばい焼香を有する食品調合香料

用途有機合成原料。

説明2,3,5,6-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.

天然物の起源Reported 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.

関連反応

22 件
反応記録を作成
HRID 443329 の反応式
HRID 443329反応物としてuspto-grants-1981_04
HRID 443330 の反応式
HRID 443330反応物としてuspto-grants-1981_04
HRID 443331 の反応式
HRID 443331反応物としてuspto-grants-1981_04
HRID 443332 の反応式
HRID 443332反応物としてuspto-grants-1981_04
HRID 443334 の反応式
HRID 443334反応物としてuspto-grants-1981_04
HRID 633772 の反応式
HRID 633772反応物としてuspto-grants-2016_04
HRID 633773 の反応式
HRID 633773反応物としてuspto-grants-2016_04
HRID 633774 の反応式
HRID 633774反応物としてuspto-grants-2016_04
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
ChEMBL
CHEMBL303697
ChEBI
CHEBI:133246
UNII
V80F4IA5XG
EC Number
214-391-2
Nikkaji
J39.647H
融点
77 · 77-80 °C(lit.)
沸点
190 °C · 190 °C(lit.)
比重(密度)
1.08 · 1.08
屈折率
1.588 · 1.5880 (estimate)
FEMA
3237 · 3237 | 2,3,5,6-TETRAMETHYLPYRAZINE
闪点
128 · 128-130°C/200mm
貯蔵温度
Sealed in dry,Room Temperature
溶解性
4 g/リットル · 4g/リットル
酸解離定数(Pka)
3.2 · 3.20±0.10(Predicted)
外見
Solid
色
ホワイトからオフホワイト
臭い (Odor)
10 %。ナッツっぽいかび臭いチョコレートコーヒーココアブラウンラード焦げ · ジプロピレングリコール中10.00%。ナッツっぽいかび臭いチョコレートコーヒーココアブラウンラード焦げ
においのタイプ
ナッティ
由来生物
synthetic
水溶解度
水に溶けます (20°C で 4 g/L)。
JECFA Number
780 · 780
BRN
113100 · 113100
安定性
安定。強酸、強酸化剤とは相容れない。
化粧品成分の機能
香料
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
CAS データベース
1124 · 1124-11-4(CAS DataBase Reference)
NISTの化学物質情報
Pyrazine, tetramethyl-(1124-11-4)
EPAの化学物質情報
Tetramethylpyrazine (1124-11-4)

化学的性質

化学的特性2,3,5,6-Tetramethylpyrazine has musty, fermented, coffee odor

来歴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 .

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

一般的な説明2,3,5,6-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.

調製方法

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

上流・下流製品情報

上流原料

2-メチルピラジンジアセチルAcetylacetone亜硝酸ナトリウムEthanol solution亜硝酸エチル (約15%エタノール溶液, 約1.6mol/L)1,4-ジアミノブタン

下流製品

2,4,5-トリメチルチアゾール

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補足説明

定義ChEBI: 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).