189506-61-4

Basic information

• Product Name: coronatine benzyl ester
• Synonyms: coronatine benzyl ester
• CAS NO: 189506-61-4
• Molecular Weight: 409.525
• Mol File: 189506-61-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: coronatine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: coronatine benzyl ester(189506-61-4)
• EPA Substance Registry System: coronatine benzyl ester(189506-61-4)

Safety Data

• Hazardous Substances Data: 189506-61-4(Hazardous Substances Data)

Upstream product

• 62251-98-3 (+/-)-(3a,6-trans; 3a,7a-cis)-6-ethyl-4-(hydroxymethyl)-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate 
• 193530-86-8 2-((R)-4-Oxo-cyclopent-2-enyl)-malonic acid allyl ester tert-butyl ester 
• 190073-22-4 (3aS,6R,7aS)-ethyl 6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate 
• 189506-60-3 (E)-4-Methylene-2-((S)-3-oxo-cyclopentyl)-hex-2-enoic acid ethyl ester 
• 189506-59-0 ethyl ((7S)-1,4-dioxaspiro[4.4]non-7-yl)acetate 
• 193530-88-0 (S)-2-(1,4-Dioxa-spiro[4.4]non-7-yl)-malonic acid diethyl ester 
• 193530-87-9 (S)-3-di(ethoxycarbonyl)methyl-1-cyclopentanone 
• 132665-05-5 ((1S)-4-oxocyclopent-2-enyl)acetic acid 
• 107932-04-7 (S)-(+)-ethyl 4-oxocyclopent-2-ene acetate 
• 62251-98-3 (+)-coronafacic acid 

Downstream Products

• 62251-96-1 (+)-coronatine 

Relevant articles and documents

Total syntheses of coronatines by exo-selective Diels-Alder reaction and their biological activities on stomatal opening

The natural phytotoxin coronatine, which is composed of two individual parts, coronafacic acid and coronamic acid, exhibits various promising biological activities similar to jasmonic acid. Interestingly, coronatine induces stomatal opening involving the swelling of guard cells in which jasmonic acid is not involved as an endogenous regulator. We established syntheses of four stereoisomers of coronatine employing the exo-selective Diels-Alder reaction as a key step. Remarkable differences in stomatal opening activity were observed between enantiomers of coronatine. This result strongly suggests that the stereo structure of coronatine is very important for its stomatal opening activity. In addition, SAR studies suggested that coronatine operates as a molecular mimic of jasmonyl-l-isoleucine in plant guard cells.

Asymmetric total syntheses of (+)-coronafacic acid and (+)-coronatine

An asymmetric total synthesis of (+)-coronafacic acid, starting from (R)-(+)-4-acetoxy-2-cyclopen-1-one as a chiral source, was accomplished. Construction of the 1-hydrindanone framework was carried out by using intramolecular 1,6-conjugate addition as the key step. Coupling between (+)-coronafacic acid and protected coronamic acid, and subsequent deprotection provided (+)-coronatine. This is the first asymmetric total synthesis of (+)-coronatine.