coronafacic acid

(3aS,6R,7aS)-6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylic acid

CAS: 62251-98-3 C12 H16 O3 MW: 208.25712000

Identification

Namecoronafacic acid
IUPAC(3aS,6R,7aS)-6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydroindene-4-carboxylic acid
CAS Number62251-98-3
FDA UNIISearch
Molecular FormulaC12 H16 O3
Molecular Weight208.25712000
Nikkaji NumberJ53.003D

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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryinformation only not used for fragrances or flavors
Recommendation for coronafacic acid usage levels up tonot for fragrance use.
Recommendation for coronafacic acid flavor usage levels up tonot for flavor use.

No supplier data available

Potential Uses

None Found

Natural Occurrence

not found in nature

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.