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W323705

Sigma-Aldrich

2,3,5,6-tétraméthylpyrazine

≥98%, FG

Synonyme(s) :

Chuanxingzine, Ligustrazine, Tetrapyrazine

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About This Item

Formule empirique (notation de Hill):
C8H12N2
Numéro CAS:
1124-11-4
Poids moléculaire :
136.19
Numéro FEMA:
3237
Numéro Beilstein :
113100
Numéro CE :
214-391-2
Conseil de l'Europe Nº :
734
Numéro MDL:
MFCD00006146
Code UNSPSC :
12164502
ID de substance PubChem :
24901575
Numéro Flavis :
14.018
Nomenclature NACRES :
NA.21

Source biologique

synthetic

Niveau de qualité

400

Qualité

FG
Fragrance grade
Halal
Kosher

Agence

follows IFRA guidelines
meets purity specifications of JECFA

Conformité réglementaire

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

Pureté

≥98%

Point d'ébullition

190 °C (lit.)

Pf

77-80 °C (lit.)

Application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

Allergène alimentaire

no known allergens

Allergène de parfum

no known allergens

Propriétés organoleptiques

chocolate; coffee; fatty; musty; nutty

Chaîne SMILES 

Cc1nc(C)c(C)nc1C

InChI

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

Clé InChI

FINHMKGKINIASC-UHFFFAOYSA-N

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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).

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
SHBQ8377
SHBQ5666
SHBP6908
SHBP0438
STBK2084

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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
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
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.
Penglong Wang et al.
Die Pharmazie, 68(9), 782-789 (2013-10-24)
A new anticancer ligustrazine derivative, 3beta-hydroxyolea-12-en-28-oic acid-3,5,6-trimethylpyrazin-2-methyl ester (T-OA, C38H58O3N2), was previously reported. It was synthesized via conjugating the effective antitumor ingredients of a classic traditional Chinese medicine (TCM) formulation. In the present study, anticancer efficacy of T-OA was evaluated
Yu-Fang Leng et al.
The American journal of Chinese medicine, 40(6), 1229-1239 (2012-12-12)
The Bennett and Xie (1988) model of chronic constriction injury (CCI) investigated the effects of tetramethylpyrazine (TMP) on neuropathic pain-associated behaviors and neuronal apoptosis in the spinal dorsal horn. Fifty-four male rats were randomly divided into sham (group S), CCI
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