coronafacic acid
(3aS,6R,7aS)-6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylic acid
Identification
| Name | coronafacic acid |
| IUPAC | (3aS,6R,7aS)-6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydroindene-4-carboxylic acid |
| CAS Number | 62251-98-3 |
| FDA UNII | Search |
| Molecular Formula | C12 H16 O3 |
| Molecular Weight | 208.25712000 |
| Nikkaji Number | J53.003D |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 375.40 °C. @ 760.00 mm Hg (est) |
| Flash Point | 383.00 °F. TCC ( 195.00 °C. ) (est) |
| logP (o/w) | 1.850 (est) |
| Soluble in | water, 1922 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| 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 | information only not used for fragrances or flavors |
| Recommendation for coronafacic acid usage levels up to | not for fragrance use. |
| Recommendation for coronafacic acid flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(3aS,6R,7aS)-6-
ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylic acid
(3aS,6R,7aS)-6-
ethyl-1-oxo-2,3,3a,6,7,7a-hexahydroindene-4-carboxylic acid
6-
ethyl-2,3,3as,6R,7,7as-hexahydro-1-oxo-1H-indene-4-carboxylic acid
1H-
indene-4-Carboxylic acid, 6-ethyl-2,3,3a,6,7,7a-hexahydro-1-oxo-, (3aS-(3alpha,6beta,7aalpha))-
1H-
indene-4-Carboxylic acid, 6-ethyl-2,3,3a,6,7,7a-hexahydro-1-oxo-, (3aS,6R,7aS)-
PubMed:
Pseudomonas syringae pv. tomato DC3000 CmaL (PSPTO4723), a DUF1330 family member, is needed to produce L-allo-isoleucine, a precursor for the phytotoxin coronatine.
PubMed:
Inactivation of PbTopo IIIβ causes hyper-excision of the Pathogenicity Island HAI2 resulting in reduced virulence of Pectobacterium atrosepticum.
PubMed:
Synthesis of coronafacic acid via TBAF-assisted elimination of the mesylate and its conversion to the isoleucine conjugate.
PubMed:
Azido-coronatine: a useful platform for "click chemistry"-mediated probe synthesis for bioorganic studies.
PubMed:
Streptomyces scabies 87-22 contains a coronafacic acid-like biosynthetic cluster that contributes to plant-microbe interactions.
PubMed:
Simple and rapid capillary zone electrophoresis method for the detection of coronamic acid, a precursor to the Pseudomonas syringae phytotoxin coronatine.
PubMed:
Synthesis of (+)-coronafacic acid.
PubMed:
Cascade reactions during coronafacic acid biosynthesis: elongation, cyclization, and functionalization during Cfa7-catalyzed condensation.
PubMed:
The phytotoxin coronatine contributes to pathogen fitness and is required for suppression of salicylic acid accumulation in tomato inoculated with Pseudomonas syringae pv. tomato DC3000.
PubMed:
Expedient stereoselective synthesis of coronafacic acid through intramolecular Diels-Alder cyclization.
PubMed:
The phytotoxin coronatine from Pseudomonas syringae pv. tomato DC3000 functions as a virulence factor and influences defence pathways in edible brassicas.
PubMed:
CorR regulates multiple components of virulence in Pseudomonas syringae pv. tomato DC3000.
PubMed:
The Pseudomonas syringae phytotoxin coronatine promotes virulence by overcoming salicylic acid-dependent defences in Arabidopsis thaliana.
PubMed:
The phytotoxin coronatine and methyl jasmonate impact multiple phytohormone pathways in tomato.
PubMed:
Characterization of Cfa1, a monofunctional acyl carrier protein involved in the biosynthesis of the phytotoxin coronatine.
PubMed:
Identification and characterization of a well-defined series of coronatine biosynthetic mutants of Pseudomonas syringae pv. tomato DC3000.
PubMed:
Characterization of CmaA, an adenylation-thiolation didomain enzyme involved in the biosynthesis of coronatine.
PubMed:
[6-endo-trig mode cyclization to a hydrindanone using samarium (II) iodide].
PubMed:
Control of temperature-responsive synthesis of the phytotoxin coronatine in Pseudomonas syringae by the unconventional two-component system CorRPS.
PubMed:
Analysis of the enzymatic domains in the modular portion of the coronafacic acid polyketide synthase.
PubMed:
Interactions of Pseudomonas syringae pv. glycinea with host and nonhost plants in relation to temperature and phytotoxin synthesis.
PubMed:
Biosynthesis of the Pseudomonas polyketide coronafacic acid requires monofunctional and multifunctional polyketide synthase proteins.
PubMed:
Characterization of CorR, a transcriptional activator which is required for biosynthesis of the phytotoxin coronatine.
PubMed:
Analysis of genes involved in biosynthesis of coronafacic acid, the polyketide component of the phytotoxin coronatine.
PubMed:
Growth phase and temperature influence promoter activity, transcript abundance, and protein stability during biosynthesis of the Pseudomonas syringae phytotoxin coronatine.
PubMed:
Expression and analysis of coronafacate ligase, a thermoregulated gene required for production of the phytotoxin coronatine in Pseudomonas syringae.
PubMed:
Use of Tn5-gusA5 to investigate environmental and nutritional effects on gene expression in the coronatine biosynthetic gene cluster of Pseudomonas syringae pv. glycinea.
PubMed:
Characterisation of genes involved in biosynthesis of coronafacic acid, the polyketide component of the phytotoxin coronatine.
PubMed:
Structure-activity relationships of cyclopentane analogs of jasmonic acid for induced responses of canola seedlings,Brassica napus L.
PubMed:
Characterization and transcriptional analysis of the gene cluster for coronafacic acid, the polyketide component of the phytotoxin coronatine.
PubMed:
Sequence, expression and transcriptional analysis of the coronafacate ligase-encoding gene required for coronatine biosynthesis by Pseudomonas syringae.
PubMed:
Cloning and expression of genes required for coronamic Acid (2-ethyl-1-aminocyclopropane 1-carboxylic Acid), an intermediate in the biosynthesis of the phytotoxin coronatine.
PubMed:
The Pseudomonas phytotoxin coronatine mimics octadecanoid signalling molecules of higher plants.
PubMed:
Characterization of the genes controlling the biosynthesis of the polyketide phytotoxin coronatine including conjugation between coronafacic and coronamic acid.
PubMed:
Physical and functional characterization of the gene cluster encoding the polyketide phytotoxin coronatine in Pseudomonas syringae pv. glycinea.
PubMed:
Plasmid-mediated production of the phytotoxin coronatine in Pseudomonas syringae pv. tomato.
PubMed:
Stimulation of ethylene production in bean leaf discs by the pseudomonad phytotoxin coronatine.