29204-02-2

Basic information

• Product Name: GADOLEICACID
• Synonyms: (9Z)-9-Icosenoic acid;(Z)-9-Icosenoic acid;Z-9-Eicosenoic acid;cis-9-Icosenoic acid;(Z)-icos-9-enoic acid
• CAS NO: 29204-02-2
• Molecular Formula: C₂₀H₃₈O₂
• Molecular Weight: 310.51
• Mol File: 29204-02-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 24.5°C
• Boiling Point: 419.84°C (estimate)
• Flash Point: 299.5°C
• Appearance: /
• Density: 0.8882
• Vapor Pressure: 1.3E-07mmHg at 25°C
• Refractive Index: 1.4675 (estimate)
• CAS DataBase Reference: GADOLEICACID(CAS DataBase Reference)
• NIST Chemistry Reference: GADOLEICACID(29204-02-2)
• EPA Substance Registry System: GADOLEICACID(29204-02-2)

Safety Data

• Hazardous Substances Data: 29204-02-2(Hazardous Substances Data)

Usage

General Description

Gadoleic acid, also known as 13-docosenoic acid, is a monounsaturated omega-9 fatty acid with 20 carbon atoms. It is found in small amounts in various plant and animal sources, including fish oils, vegetable oils, and marine oils. Gadoleic acid is known to have potential health benefits, such as reducing inflammation and improving heart health. Additionally, it has been shown to have antimicrobial properties and may have potential applications in the pharmaceutical and cosmetic industries. However, further research is needed to fully understand the extent of its therapeutic benefits and potential uses.

InChI:InChI=1/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-

Synthetic route

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

Conditions	Yield
With water; lithium hydroxide In tetrahydrofuran at 20℃;	100%

eicos-9c-enoic acid ethyl ester (116557-14-3) → gadoleic acid (29204-02-2)

Conditions	Yield
With sodium hydroxide

undecylaldehyde (112-44-7) + ω-carbethoxyoctyl triphenylphosphonium iodide → gadoleic acid (29204-02-2)

Conditions	Yield
(i) NaOEt, (ii) /BRN= 1753213/, (iii) aq. NaOH; Multistep reaction;

borage oil → 6Z,8E,12Z-C18:3 (657403-47-9) + 7E,9Z,11E-C18:3 + cis-Δ9-docosenoic acid (25692-11-9) + cis-Octadecenoic acid (112-80-1) + 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) + gadoleic acid (29204-02-2) + (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1) + 1-hexadecylcarboxylic acid (57-10-3) + stearic acid (57-11-4) + (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid (109241-60-3)

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

...Expand

Upstream product

• 116557-14-3 eicos-9c-enoic acid ethyl ester 
• 17696-11-6 8-bromooctanoic acid 
• 67810-35-9 cis-Eicos-9-enoic acid methyl ester 
• 1309764-97-3 methyl icos-9-ynoate 
• 26825-92-3 methyl 8-bromooctanoate 
• 8001-23-8 safflower oil 
• 112-44-7 undecylaldehyde 

Downstream Products

• 123-99-9 azelaic acid 
• 62133-71-5 eicos-9t-enoic acid 
• 112-44-7 undecylaldehyde 
• 112-37-8 undecylenic acid 
• 506-30-9 Arachidic acid 
• 60-33-3 linoleic acid 

Relevant articles and documents

A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA1) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA1 agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA1 receptor agonist described so far (Emax = 118%, EC50 = 0.24 μM, KD = 19.6 nM; inactive at autotaxin and LPA2-6 receptors). This compound induces characteristic LPA1-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

NEW CONJUGATED LINOLENIC ACIDS AND METHODS FOR COMMERCIAL PREPARATION AND PURIFICATION

A method for the preparation and purification of conjugated linolenic acids is described. The method comprises blending a mixture of vegetable oils and or fats including various concentrations of alpha or gamma and or both linolenic acids with a base. The method transforms approximately over two thirds of α-linolenic acid (9Z,12Z,15Z-octadecatrienoic acid) into 9Z,11E,15Z-octadecatrienoic acid and 9Z,13E,15Z-octadecatrienoic acid. The method also transforms gamma-linolenic acid (6Z,9Z,12Z-octadecatrienoic acid) into 6Z,8E,15Z-octadeccatrienoic acid and 6Z,10E,12Z-octadecatrienoic acid. In all cases, geometrical isomers and fully conjugated isomers are also produced.