tetramethylpyrazine

• ChemBase ID: 69945
• Molecular Formular: C8H12N2
• Molecular Mass: 136.19428
• Monoisotopic Mass: 136.10004839
• SMILES: c1(c(nc(c(n1)C)C)C)C
• Canonical SMILES: Cc1nc(C)c(nc1C)C
• InChI: InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
• InChIKey: FINHMKGKINIASC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetramethylpyrazine
• IUPAC Traditional name: tetramethylpyrazine; pyrazine, tetramethyl-
• Synonyms: 2,3,5,6-Tetramethylpyrazine; 2,3,5,6-TETRAMETHYL PYRAZINE; Ligustrazine; Chuanxiongzine; Tetramethylpyrazine; 2,3,5,6-Tetramethylpyrazine; 2,3,5,6-四甲基吡嗪; 2,3,5,6-四甲基哌嗪

Database IDs

• CAS Number: 1124-11-4
• EC Number: 214-391-2
• MDL Number: MFCD00006146
• Beilstein Number: 113100
• PubChem SID: 162035670; 24901576; 24851081; 24901575
• PubChem CID: 14296
• FEMA ID: 3237
• Council of Europe Number: 734
• Flavis Number: 14.018

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.06317192
• LogD (pH = 7.4): 0.063379
• Log P: 0.063381635
• Molar Refractivity: 40.1102 cm^3
• Polarizability: 15.593656 Å^3
• Polar Surface Area: 25.78 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 77-80 °C(lit.); 83-86°C; 84-86°C; 85-87 °C
• Boiling Point: 190 °C(lit.); 190°C; 190°C
• Density: 1.08
• Organoleptic: chocolate; musty; coffee; chocolate; musty; fatty; coffee

Safety Information

• Storage Warning: IRRITANT
• RTECS: UQ3905000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 22-37/38-41; R:22
• Safety Statements: 26-36/37; 26-39; S:36/37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002

Pharmacology Properties

• Allergens: no known allergens
• Mechanism of Action: Apoptosis inhibitor; Free radicals scavenger

Product Information

• Purity: ≥98%; ≥98.0% (GC); 95+%; 98%; 98+%
• Grade: FG; Halal; Kosher; natural; NI; purum
• Impurities: ≤2% water; ≤2.0% water (Karl Fischer)
• Biological Source: Metab. from Bacillus subtilis; isol. from Galbanum oil. Also in Ligusticum wallichii
• Application(s): Bactericidal agent; Fragrance and flavouring ingredient; Neuroprotective; Protect against pulmonary fibrosis; Protect against renal ischemia/reperfusion injury; Pulmonary vasodilator; Shows antiinflammatory activity
• Empirical Formula (Hill Notation): C8H12N2

DETAILS

MP Biomedicals - 05212219

MP Biomedicals Rare Chemical collection

Sigma Aldrich - W323713

Packaging
1 kg in poly bottle
1 sample in glass bottle
25, 100 g in poly bottle

Sigma Aldrich - 183938

Packaging
25, 100 g in poly bottle

Sigma Aldrich - W323705

Packaging
1 kg in poly bottle
1 sample in glass bottle
250 g in poly bottle
5 kg in poly drum

REFERENCES

• 1. Feng L, Ke N, Cheng F, Guo Y, Li S, Li Q, Li Y. The Protective Mechanism of ligustrazine Against Renal Ischemia/Reperfusion Injury. J Surg Res. 2009 May 14.
• 2. Dai L, Hou J, and Cai HR. Using ligustrazine and Angelica sinensis treat the bleomycin-induced pulmonary fibrosis in rats.
• Chinese journal of tuberculosis and respiratory diseases 1996; 19(1): 26-28.
• 3. Fan LH, Wang KZ, Cheng B, Wang CS, Dang XQ. Anti-apoptotic and neuroprotective effects of Tetramethylpyrazine following spinal cord ischemia in rabbits. BMC Neurosci. 2006 Jun 14;7:48.
• Has been used as a component of a buffer to control the acid-catalyzed ring-opening of epoxides: J. Chem. Soc., Perkin 2, 1309 (1972).