SML0480
Terreic Acid
from Aspergillus terreus, ≥98% (HPLC)
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About This Item
Empirical Formula (Hill Notation):
C7H6O4
CAS Number:
Molecular Weight:
154.12
UNSPSC Code:
12352106
NACRES:
NA.77
Recommended Products
biological source
Aspergillus terreus
Quality Level
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
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
This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
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.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Yuko Kawakami et al.
Allergology international : official journal of the Japanese Society of Allergology, 56(4), 403-409 (2007-08-24)
Atopic dermatitis is a chronic or chronically relapsing, pruritic inflammatory skin disease. The incidence of atopic dermatitis has dramatically increased during the past three decades in industrialized countries. We attempted to develop an improved method to induce an animal model
S Basu et al.
The Journal of applied bacteriology, 67(2), 191-200 (1989-08-01)
Studies on self-sensitivity of producer mutant vs. sensitivity of non-producer parent and unrelated organism showed that versilin inhibited spore germination and sporulation in the self-sensitive producer mutant, non-producer parent Aspergillus versicolor N5 and the unrelated sensitive Trichophyton rubrum. Sporulation appeared
T Subramanian et al.
Toxicology letters, 10(2-3), 249-253 (1982-02-01)
The binding of terreic acid to macromolecules such as nucleic acids and protein was examined. In vivo studies using [14C]terreic acid showed that radioactivity was incorporated into the protein and nucleic acid fractions of the liver mice. In vitro experiments
H Yamamoto et al.
The Japanese journal of antibiotics, 33(3), 320-328 (1980-03-01)
It was found that Aspergillus sp. No. Y-8980 which was isolated from a soil sample collected at Yoron Island in Kagoshima Prefecture belonged to Aspergillus terreus group by morphological observation. The active substance produced by the strain was obtained with
A high-throughput screen for yeast replicative lifespan identifies lifespan-extending compounds
Sarnoski EA, et al.
Cell Reports, 21(9), 2639-2646 (2017)
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