Skip to Content
MilliporeSigma
All Photos(3)

Documents

W323713

Sigma-Aldrich

2,3,5,6-Tetramethylpyrazine

greener alternative

natural, ≥98%, FG

Synonym(s):

Chuanxingzine, Ligustrazine, Tetrapyrazine

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C8H12N2
CAS Number:
1124-11-4
Molecular Weight:
136.19
FEMA Number:
3237
Beilstein/REAXYS Number:
113100
EC Number:
214-391-2
MDL number:
MFCD00006146
UNSPSC Code:
12164502
PubChem Substance ID:
24901576
Flavis number:
14.018

grade

FG
Fragrance grade
Halal
Kosher
natural

Quality Level

400

agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002

assay

≥98%

greener alternative product characteristics

Less Hazardous Chemical Syntheses
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

impurities

≤2.0% water (Karl Fischer)

bp

190 °C (lit.)

mp

77-80 °C (lit.)

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

greener alternative category

, Aligned

organoleptic

chocolate; coffee; fatty; musty; nutty

SMILES string

Cc1nc(C)c(C)nc1C

InChI

1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3

InChI key

FINHMKGKINIASC-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

2,3,5,6-Tetramethylpyrazine is one of the main volatile aroma compounds in roasted cocoa beans and maple syrup.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product is a Biobased products, showing key improvements in Green Chemistry Principles “Less Hazardous Chemical Syntheses” and “Use of Renewable Feedstock”.

Application


  • Booklice Liposcelis bostrychophila are efficiently attracted by the combination of 2,3,5,6-tetramethylpyrazine and ultraviolet light.: This study demonstrates that the combination of 2,3,5,6-tetramethylpyrazine and ultraviolet light effectively attracts booklice, suggesting a potential application for pest management in stored product environments (Tanaka et al., 2024).

  • 2,3,5,6-Tetramethylpyrazine protects retinal photoreceptors against endoplasmic reticulum stress by modulating ATF4-mediated inhibition of PRP aggregation.: The research highlights the neuroprotective effects of 2,3,5,6-tetramethylpyrazine, showing its potential in treating retinal diseases by protecting photoreceptors from stress-induced damage (Huang et al., 2021).

  • Tetramethylpyrazine-Inducible Promoter Region from Rhodococcus jostii TMP1.: The study identifies a promoter region in Rhodococcus jostii TMP1 that is inducible by tetramethylpyrazine, which could be utilized in genetic engineering and biotechnology applications (Stanislauskienė et al., 2018).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 7

1 of 7

2,3,5-Trimethylpyrazine ≥99%, FCC, FG

Sigma-Aldrich

W324418

2,3,5-Trimethylpyrazine

2,5-Dimethylpyrazine 98%

Sigma-Aldrich

175420

2,5-Dimethylpyrazine

2,5-Dimethylpyrazine ≥98%, FG

Sigma-Aldrich

W327204

2,5-Dimethylpyrazine

δ-Decalactone natural, ≥98%, FCC, FG

Sigma-Aldrich

W236128

δ-Decalactone

2-Ethyl-3-methylpyrazine ≥98%, FCC, FG

Sigma-Aldrich

W315508

2-Ethyl-3-methylpyrazine

γ-Nonanoic lactone ≥98%, FCC, FG

Sigma-Aldrich

W278106

γ-Nonanoic lactone

2,6-Dimethylpyrazine ≥98%, FG

Sigma-Aldrich

W327301

2,6-Dimethylpyrazine

Quantitation of alkylpyrazines in maple syrup, maple flavors and non-maple syrups.
Akochi-KE, et al.
Food Research International, 27(5), 451-457 (1994)
Donghui Xu et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 49(5), 2012-2021 (2018-09-24)
Ligustrazine (LSZ) has been identified as an antitumor agent against some types of cancers. Nevertheless, its ability to inhibit growth, migration and invasion of medulloblastoma cells is still unclear. This study aimed to explore the effect of LSZ on Daoy
Xian-Chao Cheng et al.
Bioorganic & medicinal chemistry, 17(8), 3018-3024 (2009-03-31)
A series of novel acylpiperazinyl Ligustrazine derivatives was designed, synthesized, and their protective effects on damaged ECV-304 cells and antiplatelet aggregation activities were evaluated. The results showed that compound E33 displayed most potential protective effects on the ECV-304 cells damaged
Hongfei Chen et al.
European journal of medicinal chemistry, 46(11), 5609-5615 (2011-10-14)
A series of novel ligustrazinyloxy-cinnamic acid derivatives were designed, synthesized and evaluated for their inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation in vitro, and also assayed for their protective effect against hydrogen peroxide (H(2)O(2))-induced oxidative damage on ECV-304 cells.
Xian-Chao Cheng et al.
Bioorganic & medicinal chemistry, 15(10), 3315-3320 (2007-03-27)
A series of novel Ligustrazine derivatives was designed, synthesized, and assayed for their protective effects on damaged ECV-304 cells and antiplatelet aggregation activities. The results showed that most Ligustrazine derivatives exhibited lower EC(50) values for protective effects on the ECV-304
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service