Gadoleic Acid

Base Information

• Chemical Name: Gadoleic Acid
• CAS No.: 29204-02-2
• Molecular Formula: C20H38 O2
• Molecular Weight: 310.521
• Hs Code.: 2916190090
• UNII: 474JWU0SQ6
• DSSTox Substance ID: DTXSID101045292
• Nikkaji Number: J17.206E
• Wikipedia: Gadoleic_acid
• Wikidata: Q5516412
• NCI Thesaurus Code: C68368
• Metabolomics Workbench ID: 517
• Mol file: 29204-02-2.mol

Synonyms:Gadoleic acid;cis-9-eicosenoic acid;29204-02-2;9Z-eicosenoic acid;9-Eicosenoic acid, (9Z)-;(Z)-icos-9-enoic acid;Gondoleic acid;9-Eicosenoic acid, (Z)-;9c-Eicosensaeure;(Z)-9-Eicosenoic acid;Eicos-9c-ensaeure;eicos-9c-enoic acid;(Z)-eicos-9-enoic acid;cis-gadoleic acid;UNII-474JWU0SQ6;cis-Delta(9)-eicosenoic acid;474JWU0SQ6;cis-9-icosenoic acid;C20:1C;(9Z)-icos-9-enoic acid;CHEBI:32419;eicos-9c-enoate;cis-9-eicosenoate;(Z)-eicos-9-enoate;C20:1n-11;9Z-Eicosenoate;9Z-eicosenic acid;9(Z)-Eicosenoic acid;starbld0000867;cis-delta(9)-Eicosenoate;Fatty Acid 20:1 n-11;SCHEMBL245176;DTXSID101045292;LMFA01030084;AKOS040756108;Q5516412;GADOLEIC ACID (CONSTITUENT OF BORAGE SEED OIL);20:1(N-11)

Chemical Property of Gadoleic Acid

Chemical Property:

• Vapor Pressure: 1.3E-07mmHg at 25°C
• Melting Point: 24.5°C
• Refractive Index: 1.4675 (estimate)
• Boiling Point: 402.7°C at 760 mmHg
• Flash Point: 299.5°C
• PSA: 37.30000
• Density: 0.895g/cm³
• LogP: 6.88870
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 17
• Exact Mass: 310.287180451
• Heavy Atom Count: 22
• Complexity: 258

Purity/Quality:

99%, ^*data from raw suppliers

9(Z)-EICOSENOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCCCCCC/C=C\CCCCCCCC(=O)O

Technology Process of Gadoleic Acid

There total 9 articles about Gadoleic 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: 100.0%

cis-Eicos-9-enoic acid methyl ester (67810-35-9) → gadoleic acid (29204-02-2,506-31-0)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/acs.jmedchem.9b01287

Reference yield:

borage oil → 6Z,8E,12Z-C18:3 (657403-47-9) + 7E,9Z,11E-C18:3 + cis-Δ9-docosenoic acid (25692-11-9,14134-53-3) + cis-Octadecenoic acid (112-80-1,2027-47-6) + cis-9,trans-11-octadecadienoic acid (544-70-7,544-71-8,872-23-1,1839-11-8,2540-56-9) + trans-10,cis-12-octadecadienoic acid (1072-36-2,2420-44-2,2420-56-6,7307-45-1,22880-03-1) + cis-vaccenic acid (506-17-2) + linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) + gadoleic acid (29204-02-2,506-31-0) + (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1,1955-33-5,21661-10-9,21661-09-6,21661-13-2,21661-11-0) + 1-hexadecylcarboxylic acid (57-10-3) + stearic acid (57-11-4) + (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid (109241-60-3)

Guidance literature:

With sodium hydroxide; In propylene glycol; at 160 ℃; for 2h;

Reference yield:

safflower oil (8001-23-8) → cis-9-hexadecenoic acid (373-49-9,2091-29-4) + cis-Octadecenoic acid (112-80-1,2027-47-6) + Elaidic acid (112-79-8,2027-47-6) + (9Z,12Z)-octadeca-9,11-dienoic acid (544-70-7) + cis-9,trans-11-octadecadienoic acid (544-70-7,544-71-8,872-23-1,1839-11-8,2540-56-9) + (10Z,12Z)-Octadeca-9,11-dienoic acid (7307-45-1) + trans-10,cis-12-octadecadienoic acid (1072-36-2,2420-44-2,2420-56-6,7307-45-1,22880-03-1) + linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) + (9E,12E)-Octadeca-9,12-dienoic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) + gadoleic acid (29204-02-2,506-31-0) + Arachidic acid (506-30-9) + n-docosanoic acid (112-85-6) + n-tetradecanoic acid (544-63-8) + 1-hexadecylcarboxylic acid (57-10-3) + stearic acid (57-11-4) + octadeca-11Z,13Z-dienoic acid (117624-52-9)

Guidance literature:

With sodium hydroxide; ethanol; water; at 150 - 215 ℃; for 0 - 6h; under 7500.75 - 24002.4 Torr; Product distribution / selectivity;

upstream raw materials:

eicos-9c-enoic acid ethyl ester

undecylaldehyde

safflower oil

methyl 8-bromooctanoate

Downstream raw materials:

linoleic acid

Arachidic acid

undecylaldehyde

undecylenic acid

Refernces

• 1、 -. "Process". Page/Page column 4-5. . Retrieved 2008/06/13.