(-)-jasmonoyl-L-isoleucine

Base Information

• Chemical Name: (-)-jasmonoyl-L-isoleucine
• CAS No.: 120330-93-0
• Molecular Formula: C₁₈H₂₉NO₄
• Molecular Weight: 323.433
• DSSTox Substance ID: DTXSID50420572
• Nikkaji Number: J272.686F
• Wikidata: Q27155650
• Metabolomics Workbench ID: 199773

Synonyms:(-)-jasmonoyl-L-isoleucine;120330-93-0;(-)-JA-L-Ile;jasmonic acid-isoleucine;(2S,3S)-3-methyl-2-[[2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetyl]amino]pentanoic acid;N-[(3R,7R)-(?)-Jasmonoyl]-(S)-isoleucine;N-Jasmonoylisoleucine;N-({(1r,2r)-3-Oxo-2-[(2z)-Pent-2-En-1-Yl]cyclopentyl}acetyl)-L-Isoleucine;N-[2-[(1R,2R)-3-oxo-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-L-isoleucine,N-[2-[(1S,2S)-3-oxo-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-L-isoleucine;CMC_7385;N-Jasmonoyl-L-isoleucine;Jasmonate-isoleucine conjugate;SCHEMBL16597077;CHEBI:81897;(+/-)-Jasmonic Acid-Isoleucine;DTXSID50420572;CMC_13966;HY-142006;CS-0311652;C18699;Q27155650;N-[[3-Oxo-2-(2-pentenyl)cyclopentyl]acetyl]isoleucine, 9CI;L-Isoleucine, N-[[(1R,2R)-3-oxo-2-(2Z)-2-pentenylcyclopentyl]acetyl]- (9CI);L-isoleucine, N-[[(1R,2R)-3-oxo-2-[(2Z)-2-pentenyl]cyclopentyl]acetyl]-;L-Isoleucine, N-[[3-oxo-2-(2-pentenyl)cyclopentyl]acetyl]-, [1R-[1alpha,2beta(Z)]]-;JAI

Chemical Property of (-)-jasmonoyl-L-isoleucine

Chemical Property:

• Vapor Pressure: 1.54E-12mmHg at 25°C
• Boiling Point: 527.5°C at 760 mmHg
• Flash Point: 272.8°C
• Density: 1.064g/cm³
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 323.20965841
• Heavy Atom Count: 23
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC1C(CCC1=O)CC(=O)NC(C(C)CC)C(=O)O
• Isomeric SMILES: CC/C=C\C[C@@H]1[C@H](CCC1=O)CC(=O)N[C@@H]([C@@H](C)CC)C(=O)O

Technology Process of (-)-jasmonoyl-L-isoleucine

There total 2 articles about (-)-jasmonoyl-L-isoleucine 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:

jasmonic acid (3572-65-4,3572-66-5,6894-38-8,42536-96-9,62653-85-4,69978-77-4,77026-92-7,109959-41-3,126372-33-6,136845-15-3) → N-<(+)-jasmonoyl>-S-isoleucine (28838-58-6,120330-92-9,120330-93-0,145414-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 1 h / -10 °C

2: 1.) Amberlite IRC-50 (1+)-form> / 2.) aqueous THF, 4 deg C, 5 h

With Amberlite IRC-50 ; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)81437-X

Reference yield:

jasmonic acid (3572-65-4,3572-66-5,6894-38-8,42536-96-9,62653-85-4,69978-77-4,77026-92-7,109959-41-3,126372-33-6,136845-15-3) → N-<(-)-jasmonoyl>-(S)-isoleucine (28838-58-6,120330-92-9,120330-93-0,145414-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 1 h / -10 °C

2: 1.) Amberlite IRC-50 (1+)-form> / 2.) aqueous THF, 4 deg C, 5 h

With Amberlite IRC-50 ; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)81437-X

upstream raw materials:

jasmonic acid

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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