SML0480

Terreic Acid

from Aspergillus terreus, ≥98% (HPLC)

• Empirical Formula (Hill Notation): C₇H₆O₄
• CAS Number: 121-40-4
• Molecular Weight: 154.12
• UNSPSC Code: 12352106
• NACRES: NA.77

Properties

• biological source: Aspergillus terreus
• Quality Level: 200
• Assay: ≥98% (HPLC)
• form: solid
• solubility: DMSO: 10 mg/mL; H₂O: 2 mg/mL
• storage temp.: −20°C
• InChI: 1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1
• InChI key: ATFNSNUJZOYXFC-RQJHMYQMSA-N

Description

Application

Terreic Acid has been used to study its effect on alcohol intake and blood alcohol levels (BALs) in High Drinking in the Dark (HDID-1) mice. It has also been used as a supplement for culturing yeast progenitor cells to study its effect on yeast replicative lifespan.

Biochem/physiol Actions

Terreic acid (TA) is a covalent inhibitor of the bacterial cell wall biosynthetic enzyme MurA. The survival of most bacteria depends on the functionality of this cytosolic enzyme. The inactivation of MurA requires the presence of UDP-N-acetylglucosamine 1-Carboxyvinyl transferase, which catalyzes the first step in the biosynthesis of the bacterial cell wall. TA is more potent than the known MurA inhibitor Fosphomycin. TA was also found to severely inhibit the transcription of TNFα and IL-2. TA inhibits protein synthesis by blocking the formation of leucyl-tRNA in sensitive bacteria and inhibits the catalytic effect of Bruton′s tyrosine kinase (Btk), an important factor in B-cell and mast cell activation, by inducing conformational changes that prevent Protein Kinase C (PKC) from interacting with the Btk domain. Moreover, recent studies have demonstrated that TA exhibits a very high level of radical scavenging activity.

Features and Benefits

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Preparation Note

Store the product sealed at -20 °C. Under these conditions the product is stable for at least 2 years. Solution of the product in water is not stable and should be prepared immediately before use. Solution of the product in DMSO is stable for at least 2 months at 4 °C.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable