Grundinformationen
- CAS
1124-11-4- Standard-SMILES
Cc1nc(C)c(C)nc1C- InChIKey
FINHMKGKINIASC-UHFFFAOYSA-N- Summenformel
- C8H12N2
- Durchschnittliche Molmasse
- 136,19 g/mol
- Monoisotopische Masse
- 136,10004838
Überblick
Tetramethylpyrazine is a member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups.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.
Namen und Bezeichner
- Bevorzugter Name
- Tetramethylpyrazine
- IUPAC
- 2,3,5,6-tetramethylpyrazine
- Lokaler Name
- 2,3,5,6-Tetramethyl-pyrazin
- Englischer Name
- Tetramethylpyrazine
- Summenformel
- C8H12N2
- Molmasse
- 136.19
Namen und Synonyme
2,3,5,6-TetramethylpyrazineTETRAMETHYLPYRAZINE1124-11-4LigustrazineChuanxiongzineTetrapyrazinechuanxingzineFEMA No. 3237CHUANXIONGQINTMPZ2,3,5,6,-Tetramethyl-1,4-pyrazineDTXSID6047070
Weitere Namen anzeigen
FEMA 3237Pyrazine,tetramethyl-Tetramethylpyrazin2,3,5,6-TetramethyLtetramethyl-pyrazinBS FactorLigustizine
V80F4IA5XGDTXCID4027070NSC-36080NSC-46451CHEBI:133246tetramethyl pyrazineRefChem:799162214-391-2
Datenbank-Bezeichner
- CAS
1124-11-4- PubChem CID
- 14296
- DTXSID
DTXSID6047070- ChEMBL
CHEMBL303697- ChEBI
CHEBI:133246- UNII
- V80F4IA5XG
- EC Number
- 214-391-2
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,3
- Polarare Oberfläche (TPSA)
- 25,8 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 87,8
Experimentelle und physikochemische Eigenschaften
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
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
190.00 °C. @ 760.00 mm Hg
190 °C
Melting Point86 °C
Physical Description
Solid
white crystals or powder with a musty, fermented, coffee odour
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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]
Gefahrenhinweise
Regulatory Information
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
Acute Tox. 4 (100%)
Acute toxicity (Oral) - Category 4
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29339990
- RTECS-Nr.
- UQ3905000
- risk_code
- 22-37/38-41-36/37/38
- hazard_code
- Xn,Xi
- safety_code
- 26-39-24/25-37/39-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
Cellular LocationsCytoplasm
Verwendung und Herstellung
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing InformationPyrazine, 2,3,5,6-tetramethyl-: ACTIVE
Anwendungen
Beschreibung2,3,5,6-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.
OccurrenceReported 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.
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