186534-02-1

Basic information

• Product Name: Pyrazinecarboxaldehyde, trimethyl- (9CI)
• Synonyms: Pyrazinecarboxaldehyde, trimethyl- (9CI);3,5,6-TRIMETHYLPYRAZINE-2-CARBALDEHYDE;2-Pyrazinecarboxaldehyde, 3,5,6-triMethyl-;Pyrazinecarboxaldehyde, triMethyl-;3,5,6-Trimethylpyrazine-2-carboxaldehyde
• CAS NO: 186534-02-1
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.1778
• Product Categories: ALDEHYDE;PIPERIDINE
• Mol File: 186534-02-1.mol

Chemical Properties

• Boiling Point: 231.8±35.0℃ (760 Torr)
• Flash Point: 96.8±32.4℃
• Appearance: /
• Density: 1.101±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.553
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 1.06±0.10(Predicted)
• CAS DataBase Reference: Pyrazinecarboxaldehyde, trimethyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrazinecarboxaldehyde, trimethyl- (9CI)(186534-02-1)
• EPA Substance Registry System: Pyrazinecarboxaldehyde, trimethyl- (9CI)(186534-02-1)

Safety Data

• Hazardous Substances Data: 186534-02-1(Hazardous Substances Data)

Usage

Uses

Used in the Food Industry:
Pyrazinecarboxaldehyde, trimethyl(9CI) is used as a flavoring agent for its nutty, earthy, and roasted notes, enhancing the taste and aroma of various food products.
Used in the Fragrance Industry:
Pyrazinecarboxaldehyde, trimethyl(9CI) is utilized in the production of fragrances, contributing to the creation of unique and appealing scents for a wide range of products, including perfumes, cosmetics, and personal care items.
Used in Pharmaceutical Synthesis:
Pyrazinecarboxaldehyde, trimethyl(9CI) serves as an intermediate in the synthesis of pharmaceuticals, playing a crucial role in the development of new drugs and medicinal compounds.
Used in Chemical Synthesis:
Pyrazinecarboxaldehyde, trimethyl(9CI) is also employed as an intermediate in the synthesis of various chemicals, contributing to the production of a broad spectrum of chemical products.
Safety Precautions:
While Pyrazinecarboxaldehyde, trimethyl(9CI) is considered relatively low in toxicity, it can cause irritation to the skin, eyes, and respiratory system. Therefore, it should be handled with care in a well-ventilated area to minimize potential health risks.

InChI:InChI=1/C8H10N2O/c1-5-6(2)10-8(4-11)7(3)9-5/h4H,1-3H3

Upstream product

• 76494-51-4 2,3,5,6-tetramethylpyrazine hydrochloride 
• 79074-43-4 (3,5,6-trimethylpyrazin-2-yl)methyl acetate 
• 22978-83-2 2,3,5,6-tetramethylpyrazine mono N-oxide 
• 1124-11-4 Tetramethylpyrazine 
• 75907-74-3 2-Pyrazinemethanol,3,5,6-trimethyl 

Downstream Products

• 1332730-39-8 methyl 3,5,6-trimethylpyrazine-2-carboxylate 
• 1000672-87-6 (E)-2-(3-cyanostyryl)-3,5,6-trimethylpyrazine 
• 1000672-80-9 (E)-2-(4-methylstyryl)-3,5,6-trimethylpyrazine 
• 1000672-79-6 (E)-2-(2-methylstyryl)-3,5,6-trimethylpyrazine 
• 1000672-86-5 (E)-2-(2-cyanostyryl)-3,5,6-trimethylpyrazine 

Relevant articles and documents

Synthesis of colletotrichumine A

A short synthesis of colletotrichumine A, an oxindole-pyrazine alkaloid isolated from the pathogenic fungus Colletotrichum capsici, is described.

Discovery of potential anticancer multi-targeted ligustrazine based cyclohexanone and oxime analogs overcoming the cancer multidrug resistance

The drug research and development nowadays is focusing on multi-target drugs. In the treatment of cancer, therapies using drugs inhibiting one numerous targets signify a novel viewpoint. In comparison with traditional therapy, multi-targeted drugs directly aim cell subpopulations which are involved in progression of tumor. The current study comprises the synthesis of 34 novel ligustrazine-containing α, β-unsaturated carbonyl-based compounds and oximes. The growth of 5 various cancer cell types was strongly inhibited by ligustrazine-containing oximes as revealed by biological evaluation. A strong SAR was provided by the antiproliferative activity. The mechanistic effects of most active antiproliferative compounds on tubulin polymerization, EGFR TK kinases, KAF and BRAFV600E were investigated, followed by in?vitro investigation of reversal of efflux-based resistance developed by cancer cells. EGFR was strongly inhibited by two oximes 7e and 8o. Out of all linkers including positive control, 1-isopropyl-piperidin-4-one linker-bearing compounds showed best inhibition of FAK. The strongest inhibitory activity of BRAFV600E was showed by compound 5e with an IC50 of 0.7?μM. Analogs such as 5 and 7 (b,e,f) exhibited a dual role as anticancer as well as MDR reversal agents. For understanding the target protein integrations with new compounds, molecular docking studies were also carried out.

Synthesis and relationship of stability and biological activity of new DSS and TMP conjugates

A series of novel conjugates of danshensu (DSS) and tetramethylpyrazine (TMP) were designed and synthesized. Their stability toward hydrolysis by carboxylesterase and cardioprotective effect against t-BHP- and doxorubicin-induced damage were evaluated in H9c2 cells. The results revealed that increasing steric hindrance with bulky groups at the linkage position between DSS and TMP prolonged the half-life and also markedly increased the protective effect. Compound 7 was the most potent in protecting against t-BHP- and doxorubicin-induced damage. The protective effect of compound 7 may in part be attributed to its promotion of mitochondrial biogenesis. This journal is

Synthesis and biological evaluation of ligustrazine derivatives

Synthesized ligustrazine derivatives (1a, 1b, 1c (novel)) were structurally confirmed by mass spectrometry,1H NMR, and 13C NMR. The cytotoxic activities of all derivatives were evaluated by MTS assay in three human prostate cancer cell lines (PC-3, LNCaP, and DU145) and in the A549 human lung cancer cell line. Compound 1a exhibited strong cytotoxic activity against PC-3 cells (IC50 3.63μM). In addition, compounds 1-1c showed moderate α1-adrenergic receptor (AR) subselective antagonistic and β2-AR agonistic effects, indicating potential use for the treatment of chronic obstructive pulmonary disease. Molecular docking results showed 1b bound to one region of the active site in β2-AR, but 1, 1a, and 1c bound to a different region.

Synthesis and biological evaluation of novel ligustrazine-chalcone derivatives as potential anti-triple negative breast cancer agents

A series of novel ligustrazine-chalcone hybrids were synthesized and evaluated for their in vitro and in vivo antitumor activities. The results showed that most of these compounds exhibited significant in vitro cytotoxicity against MDA-MB-231, MCF-7, A549

Discovery of a new tetramethylpyrazine based chalcone with α, β-unsaturated ketone moiety as a potential anticancer agent

In this study, a new ligustrazine-based chalcone molecule has been synthesized that contains an extra α, β-Unsaturated ketone moiety along with α, the β-Unsaturated carbonyl group of chalone. A new tetramethylpyrazine (TMP) based aldehyde was synthesized to make the TMP (ligustrazine) as part of chalcone and then it was reacted with newly synthesized ketone containing additional α, β-Unsaturated ketone moiety. After characterization, this new compound was evaluated for its effect on different types of cancer cell lines and very promising results were obtained. The growth of these cancer cells was inhibited by newly designed and synthesized compounds, especially for colon and pancreatic cancer cells with IC50 0.04-0.05 μM.

Chloroxime compound as well as preparation method and application thereof in pharmacy

The invention relates to a chloroxime compound, its preparation method and application in pharmacy. The chloroxime compound has a structure shown as the general formula I in the specification. The compounds has a very strong effect in synergistic regulation of heat shock protein activity, can be used for treating neurodegenerative diseases caused by injection of Abeta1-42 to rats, and aims to treat human neurodegenerative diseases. The compound also has a significant stress resistant effect, and can be used for preparation of new drugs treating diseases caused by protein misfolding and/or aggregation, and oxidative stress.

TRIFLUOROACETYL HYDRAZIDE COMPOUNDS AND MEDICAL USES THEREOF

The present invention relates to trifluoroacetyl hydrazide compounds and medical uses thereof. The compounds have a structure of the following formula: The compounds showed multifunctional mechanisms, including inhibition of glutamate excitotoxicity, activation of MEF2 transcriptional activity, clearance of free radicals, and promotion of nerve differentiation, and has a better protective effect on cells especially nerve cells. The compound can be used to prepare prophylactic or therapeutic medicaments with cytoprotective effects, for the prevention or treatment of diseases related to glutamate receptor activation, MEF2 disorders or excessive free radicals generation. The diseases include, for example, neurodegenerative diseases such as Alzheimer's disease, Parkinson and stroke, and the free radicals related diseases such as heart disease, myocardial ischemia, diabetes and other cardiovascular and cerebrovascular diseases.

Ligustrazine chalcone compound and preparation method and application thereof

The invention relates to a ligustrazine chalcone compound and a preparation method and application thereof. The ligustrazine chalcone compound is an antioxidant with a series of novel structure, and better antioxidation activities are shown by most of compounds, so that the ligustrazine chalcone compound has further studying and developing value, and the ligustrazine chalcone compound can be usedas a lead compound of the antioxidant. The invention further provides the application of preparing antioxidation medicines of the compound and a composition containing one or more compounds.

Novel Ligustrazine-Based Analogs of Piperlongumine Potently Suppress Proliferation and Metastasis of Colorectal Cancer Cells in Vitro and in Vivo

Piperlongumine 1 increases reactive oxygen species (ROS) levels and preferably induces cancer cell apoptosis by triggering different pathways. However, the poor solubility of 1 limits its intensive investigation and clinical application. Ligustrazine possesses a water-soluble pyrazine skeleton and can inhibit proliferation and metastasis of cancer cells. We synthesized compound 3 by replacement of the trimethoxyphenyl of 1 with ligustrazine moiety and further introduced 2-Cl, -Br, and -I to 3 for synthesis of 4-6, respectively. Compound 4 possessed 14-fold greater aqueous solubility than 1 and increased ROS levels in colorectal cancer HCT-116 cells. Additionally, 4 preferably inhibited proliferation, migration, invasion, and heteroadhesion of HCT-116 cells. Treatment with 4 suppressed tumor growth and lung metastasis in vivo and prolonged the survival of tumor-bearing mice. Furthermore, 4 mitigated TGF-β1-induced epithelial-mesenchymal transition and Wnt/β-catenin activation by inhibiting the Akt and GSK-3β phosphorylation in HCT-116 cells. Collectively, 4 displayed significant antiproliferation and antimetastasis activities, superior to 1.