(+/-)-JASMONIC ACID-9,10-D2 METHYL ESTER

Base Information

• Chemical Name: (+/-)-JASMONIC ACID-9,10-D2 METHYL ESTER
• CAS No.: 183948-77-8
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 229.26
• Mol file: 183948-77-8.mol

Synonyms:(+/-)-JASMONIC ACID-9,10-D2 METHYL ESTER;METHYL (+/-)-JASMONATE-9,10-D2;(+/-)-jasmonic acid-9,10-d2 methyl ester, ca. 97atom%d;methyl (+/-)-jasmonate-9,10-d2, ca. 97atom%d;Methyl (+/-)-Jasmonate-9,10-d2 ca. 97atom%D (containing ca. 5% of Methyl (+/-)-7-epi-Jasmonate-9,10-d2) (200micro g/ml in Acetonitrile) [Internal standard for qualitative analysis of endogenous Methyl Jasmonate]

Chemical Property of (+/-)-JASMONIC ACID-9,10-D2 METHYL ESTER

Chemical Property:

• PSA: 43.37000
• LogP: 2.50110
• Storage Temp.: Freezer

Purity/Quality:

97% ^*data from raw suppliers

METHYL (+/-)-JASMONATE-9,10-D2 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+/-)-JASMONIC ACID-9,10-D2 METHYL ESTER

There total 4 articles about (+/-)-JASMONIC ACID-9,10-D2 METHYL ESTER 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: 86.0%

(2R*,3S*)-3-methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanone (29119-47-9,114029-37-7,37435-88-4,82423-75-4,83648-24-2,131063-53-1) → C13H19(2)HO3 + C13H19(2)HO3 + methyl (+/-)-2-(2,3-2H2)jasmonate (183948-77-8)

Guidance literature:

With deuterium; palladium on barium sulfate; In pyridine; for 20h; Yields of byproduct given; Ambient temperature;

DOI:10.1271/bbb.60.1709

Reference yield:

2-(pent-2-ynyl)-cyclopent-2-enone (29119-44-6) → methyl (+/-)-2-(2,3-2H2)jasmonate (183948-77-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / methanol / 1.) 40 deg C, 1.5 h, .2 ) -10 deg C, 1 h

2: 71 percent / H₂O / dimethylsulfoxide / 48 h / 165 °C

3: 86 percent / D₂ / Pd-BaSO₄ / pyridine / 20 h / Ambient temperature

With water; deuterium; palladium on barium sulfate; In pyridine; methanol; dimethyl sulfoxide;

DOI:10.1271/bbb.60.1709

Reference yield:

2-((1R,2S)-3-Oxo-2-pent-2-ynyl-cyclopentyl)-malonic acid dimethyl ester → methyl (+/-)-2-(2,3-2H2)jasmonate (183948-77-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / H₂O / dimethylsulfoxide / 48 h / 165 °C

2: 86 percent / D₂ / Pd-BaSO₄ / pyridine / 20 h / Ambient temperature

With water; deuterium; palladium on barium sulfate; In pyridine; dimethyl sulfoxide;

DOI:10.1271/bbb.60.1709

upstream raw materials:

(2R*,3S*)-3-methoxycarbonylmethyl-2-(2-pentynyl)cyclopentanone

2-(pent-2-ynyl)-cyclopent-2-enone

diazomethane

[3,4α,7,9,10-(2)H5]-iso-jasmonic acid

Downstream raw materials:

(+/-)-2-(2,3-2H2)jasmonic acid

Refernces

• 1、 Seto,Fujioka,Fujisawa,Goto,Nojiri,Yamane,Yoshida. "Preparation of (±)-2-(2,3-2H2) jasmonic acid and its methyl ester, methyl (±)-2-(2,3-2H2)jasmonate". . p. 1709 - 1711. Retrieved 2007/10/03.