Eleostearic acid

Base Information

• Chemical Name: Eleostearic acid
• CAS No.: 544-72-9
• Molecular Formula: C18H30O2
• Molecular Weight: 278.435
• Hs Code.: 2916190090
• Metabolomics Workbench ID: 75576
• Wikidata: Q27117716
• Mol file: 544-72-9.mol

Synonyms:9,11,13-CLN;9,11,13-conjugated linolenic acid;9,11,13-octadecatrienoic acid;9c,11t,13t-CLN;9cis,11trans,13trans-conjugated linolenic acid;eleostearic acid;eleostearic acid, (E,E,E)-isomer;eleostearic acid, (E,Z,E)-isomer;eleostearic acid, (Z,E,E)-isomer;eleostearic acid, (Z,Z,E)-isomer;trichosanic acid

Chemical Property of Eleostearic acid

Chemical Property:

• Melting Point: 62°C
• Refractive Index: 1.5114
• Boiling Point: 361.24°C (rough estimate)
• PKA: 4.78±0.10(Predicted)
• PSA: 37.30000
• Density: 0.9027
• LogP: 5.66050
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 278.224580195
• Heavy Atom Count: 20
• Complexity: 301

Purity/Quality:

99%, ^*data from raw suppliers

9(Z),11(E),13(Z)-Octadecatrienoic Acid ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CC=CC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCC/C=C/C=C\C=C\CCCCCCCC(=O)O

Technology Process of Eleostearic acid

There total 20 articles about Eleostearic acid 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: 54.0%

(+/-)-t-butyl coriolate (111699-15-1) → eleostearic acid (506-23-0,544-72-9,544-73-0,3884-88-6,4337-71-7,13296-76-9,24022-76-2,146525-62-4)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 25 ℃; for 3h;

DOI:10.1246/bcsj.60.1103

Reference yield:

octadeca-11t,13t-dien-9-ynoic acid (95168-90-4) → eleostearic acid (506-23-0,544-72-9,544-73-0,3884-88-6,4337-71-7,13296-76-9,24022-76-2,146525-62-4)

Guidance literature:

With quinoline; Lindlar's catalyst; Ethyl propionate; Hydrogenation;

DOI:10.1039/jr9570001622

Reference yield:

methyl α-eleostearate (4175-47-7) → eleostearic acid (506-23-0,544-72-9,544-73-0,3884-88-6,4337-71-7,13296-76-9,24022-76-2,146525-62-4)

Guidance literature:

DOI:10.1016/S0040-4039(01)81743-3

upstream raw materials:

octadeca-11t,13t-dien-9-ynoic acid

methyl α-eleostearate

(+/-)-t-butyl coriolate

(Z)-9-octadecenoyl chloride

Downstream raw materials:

(9E,11E,13E)-9,11,13-octadecatrienoic acid

azelaic acid

oxalic acid

valeric acid

Refernces

• 1、 Ratovelomanana, Victorin,Linstrumelle, Gerard. "STEREOSELECTIVE PREPARATION OF 1-CHLORO-(E,E)-1,3-DIENES. APPLICATION TO THE SYNTHESIS OF METHYL ELEOSTEARATE.". . p. 6001 - 6004. Retrieved 2007/10/02.