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

Base Information

• Chemical Name: (+/-)-JASMONIC ACID-9,10-D2
• CAS No.: 183948-71-2
• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 212.257
• Mol file: 183948-71-2.mol

Synonyms:(+/-)-JASMONIC ACID-9,10-D2;(+/-)-jasmonic acid-9,10-d2, ca. 96atom%d;(+/-)-Jasmonic Acid-9,10-d2 ca. 96atom%D (containing ca. 5% of (+/-)-7-epi-Jasmonic Acid-9,10-d2) (200micro g/ml in Acetonitrile) [Internal standard for qualitative analysis of endogenous Jasmonic Acid]

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

Chemical Property:

• PSA: 54.37000
• LogP: 2.41270
• Storage Temp.: Freezer

Purity/Quality:

99% ^*data from raw suppliers

(+/-)-JASMONIC ACID-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

There total 6 articles about (+/-)-JASMONIC ACID-9,10-D2 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: 91.0%

methyl (+/-)-2-(2,3-2H2)jasmonate (183948-77-8) → (+/-)-2-(2,3-2H2)jasmonic acid (183948-71-2)

Guidance literature:

With potassium hydroxide; In methanol; water; for 5h; Ambient temperature;

DOI:10.1271/bbb.60.1709

Reference yield: 69.0%

(2R*,3S*)-3-carboxymethyl-2-(2-pentynyl)cyclopentanone (29119-46-8) → (+/-)-2-(2,3-2H2)jasmonic acid (183948-71-2)

Guidance literature:

With deuterium; palladium on barium sulfate; In pyridine; for 1h; Ambient temperature;

DOI:10.1271/bbb.60.1709

Reference yield:

2-(pent-2-ynyl)-cyclopent-2-enone (29119-44-6) → (+/-)-2-(2,3-2H2)jasmonic acid (183948-71-2)

Guidance literature:

Multi-step reaction with 4 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: 82 percent / KOH / methanol; H₂O / 5 h / Ambient temperature

4: 69 percent / D₂ / Pd-BaSO₄ / pyridine / 1 h / Ambient temperature

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

DOI:10.1271/bbb.60.1709

upstream raw materials:

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

methyl (+/-)-2-(2,3-2H2)jasmonate

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

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

Downstream raw materials:

[3,4α,7,9,10-(2)H5]-iso-jasmonic acid methyl ester

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.