terreic acid
7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, stereoisomer
Identification
| Name | terreic acid |
| IUPAC | (1R,6S)-3-hydroxy-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione |
| CAS Number | 121-40-4 |
| FDA UNII | XM2Y0DRJ7D |
| Molecular Formula | C7 H6 O4 |
| Molecular Weight | 154.12162000 |
| Nikkaji Number | J5.338D |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 127.00 °C. @ 760.00 mm Hg |
| Boiling Point | 333.60 °C. @ 760.00 mm Hg (est) |
| Flash Point | 297.00 °F. TCC ( 147.40 °C. ) (est) |
| logP (o/w) | -0.210 (est) |
| Soluble in | water, 1764 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 75 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for terreic acid usage levels up to | not for fragrance use. |
| Recommendation for terreic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
5,6-
epoxy-3-hydroxy-p-toluquinone
(1R,6S)-3-
hydroxy-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
3-
hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
7-
oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, stereoisomer
PubMed:
Molecular Genetic Characterization of Terreic Acid Pathway in Aspergillus terreus.
PubMed:
Culture-based and sequence-based insights into biosynthesis of secondary metabolites by Aspergillus terreus ATCC 20542.
PubMed:
Differential antibacterial properties of the MurA inhibitors terreic acid and fosfomycin.
PubMed:
New species in Aspergillus section Terrei.
PubMed:
The fungal product terreic acid is a covalent inhibitor of the bacterial cell wall biosynthetic enzyme UDP-N-acetylglucosamine 1-carboxyvinyltransferase (MurA) .
PubMed:
An improved mouse model of atopic dermatitis and suppression of skin lesions by an inhibitor of Tec family kinases.
PubMed:
Ca2+-independent activation of Bruton's tyrosine kinase is required for store-mediated Ca2+ entry in human platelets.
PubMed:
Modulation of the Fcepsilon receptor I signaling by tyrosine kinase inhibitors: search for therapeutic targets of inflammatory and allergy diseases.
PubMed:
Terreic acid, a quinone epoxide inhibitor of Bruton's tyrosine kinase.
PubMed:
Characterization of versilin-sensitive sites in self-sensitive producer and sensitive non-producer or unrelated organism.
PubMed:
The structure of manumycin. III. Absolute configuration and conformational studies.
PubMed:
Stereochemistry of the epoxydon group antibiotic G7063-2 isolated from a Streptomyces species HPL Y-25711.
PubMed:
In vivo and in vitro studies on the binding nature of terreic acid with macromolecules such as protein and nucleic acids.
PubMed:
Studies on terreic acid.
PubMed:
G7063-2, a new nitrogen-containing antibiotic of the epoxydon group, isolated from the fermentation broth of a species of Streptomyces.
PubMed:
Total synthesis and resolution of terreic acid.
PubMed:
Gas chromatographic analysis of the mycotoxins kojic acid, terreic acid, and terrein.
PubMed:
Quinone epoxides. V. The biosynthesis of terreic acid.