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Technology Process of Coronatine

Coronatine

Base Information
  • Chemical Name:Coronatine
  • CAS No.:62251-96-1
  • Molecular Formula:C18H25NO4
  • Molecular Weight:319.3954
  • Hs Code.:
  • UNII:WCR4XUE8VB
  • DSSTox Substance ID:DTXSID20977826
  • Nikkaji Number:J57.969F
  • Wikipedia:Coronatine
  • Wikidata:Q5172198
Coronatine

Synonyms:coronatine

Suppliers and Price of Coronatine
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
Total 21 raw suppliers
Chemical Property of Coronatine
Chemical Property:
  • Vapor Pressure:2.97E-14mmHg at 25°C 
  • Boiling Point:565.2°Cat760mmHg 
  • Flash Point:295.6°C 
  • Density:1.22g/cm3 
  • XLogP3:2
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:4
  • Rotatable Bond Count:5
  • Exact Mass:319.17835828
  • Heavy Atom Count:23
  • Complexity:582
Purity/Quality:

99%, *data from raw suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:CCC1CC2C(CCC2=O)C(=C1)C(=O)NC3(CC3CC)C(=O)O
  • Isomeric SMILES:CC[C@@H]1C[C@H]2[C@H](CCC2=O)C(=C1)C(=O)N[C@]3(C[C@@H]3CC)C(=O)O
Technology Process of Coronatine

There total 18 articles about Coronatine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

coronatine benzyl ester
189506-61-4

coronatine benzyl ester

(+)-coronatine
62251-96-1

(+)-coronatine

Guidance literature:
With hydrogen; palladium on activated charcoal; In ethyl acetate; for 0.333333h; Ambient temperature;
DOI:10.1016/S0040-4020(97)00614-5

Reference yield:

(+)-coronafacic acid
62251-98-3

(+)-coronafacic acid

(+)-coronatine
62251-96-1

(+)-coronatine

Guidance literature:
Multi-step reaction with 2 steps
1: 89 percent / Et3N, DMAP, EtN=C=N(CH2)3NMe2*HCl / CH2Cl2 / 24 h / Ambient temperature
2: 80 percent / H2 / Pd-C / ethyl acetate / 0.33 h / Ambient temperature
With dmap; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(97)00614-5

Reference yield:

(E)-4-Methylene-2-((S)-3-oxo-cyclopentyl)-hex-2-enoic acid ethyl ester
189506-60-3

(E)-4-Methylene-2-((S)-3-oxo-cyclopentyl)-hex-2-enoic acid ethyl ester

(+)-coronatine
62251-96-1

(+)-coronatine

Guidance literature:
Multi-step reaction with 4 steps
1: NaH / ethanol / 0 deg C to rt
2: 70 percent / aq. HCl / Heating
3: 89 percent / Et3N, DMAP, EtN=C=N(CH2)3NMe2*HCl / CH2Cl2 / 24 h / Ambient temperature
4: 80 percent / H2 / Pd-C / ethyl acetate / 0.33 h / Ambient temperature
With hydrogenchloride; dmap; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(97)00614-5
upstream raw materials:

coronatine benzyl ester

(+)-coronafacic acid

(S)-(+)-ethyl 4-oxocyclopent-2-ene acetate

((1S)-4-oxocyclopent-2-enyl)acetic acid

Downstream raw materials:

(+)-coronafacic acid

(1S,2S)-(+)-1-Amino-2-ethyl-1-cyclopropanecarboxylic Acid

C49H73F3N6O11Si

(+/-)-(3a,6-trans; 3a,7a-cis)-6-ethyl-4-(hydroxymethyl)-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate

Refernces

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

10.1039/b905159g

The research primarily focuses on the total synthesis of coronatines, a group of natural phytotoxins produced by Pseudomonas syringae, and their biological activities, specifically their impact on stomatal opening in plants. The study employs the exo-selective Diels–Alder reaction as a key step to synthesize four stereoisomers of coronatine, highlighting the significant differences in stomatal opening activity between the enantiomers. The research uses a variety of analytical techniques, including NMR, HPLC, ESI-MS, HRMS, IR spectroscopy, and optical rotation measurements, to monitor the progress of the synthesis and to characterize the synthesized compounds. The synthetic route also enables the preparation of various derivatives of coronatine for further structural and biological studies. Additionally, the study examines the biological activities of these synthetic derivatives on stomatal opening in Ipomoea tricolor (morning glory), comparing their effects with those of naturally occurring compounds like jasmonic acid and jasmonyl-L-isoleucine. The results indicate that the stereochemistry of coronatine is crucial for its activity, suggesting it acts as a molecular mimic of jasmonyl-L-isoleucine in plant guard cells.

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