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terreic acid
7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, stereoisomer

Supplier Sponsors

Name:(1R,6S)-3-hydroxy-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
CAS Number: 121-40-4Picture of molecule3D/inchi
FDA UNII: XM2Y0DRJ7D
Nikkaji Web:J5.338D
XlogP3-AA:-0.20 (est)
Molecular Weight:154.12162000
Formula:C7 H6 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
(-)-Terreic acid ≥99%
Odor: characteristic
Use: (-)-Terreic acid is a selective inhibitor of Bruton's tyrosine kinase (BTK) wi
EMD Millipore
For experimental / research use only.
(-)-Terreic Acid, Synthetic
sds
Santa Cruz Biotechnology
For experimental / research use only.
Terreic Acid 99%
Sigma-Aldrich: Sigma
For experimental / research use only.
Terreic Acid from Aspergillus terreus, ≥98% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 75 mg/kg
Japanese Journal of Antibiotics. Vol. 33, Pg. 320, 1980.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :91437
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(1R,6S)-3-hydroxy-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Chemidplus:0000121404
RTECS:RN8925000 for cas# 121-40-4
 
References:
 (1R,6S)-3-hydroxy-3-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):91437
Pubchem (sid):135048130
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
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
 

Articles:

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.
 
Notes:
antibiotic metabolite of mold aspergillus terreus.
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