Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route

Brenna, Elisabetta; Colombo, Danilo; Lecce, Giuseppe Di; Gatti, Francesco G.; Ghezzi, Maria Chiara; Tentori, Francesca; Tessaro, Davide; Viola, Mariacristina

doi:10.3390/molecules25081882

Cited by 28 publications

(32 citation statements)

References 40 publications

(62 reference statements)

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“…Chemical oxidation is industrially feasible (Bieser et al, 2018) but a possible alternative is the biological oxidation, which can become economically and environmentally convenient (see e.g. Brenna et al, 2020). Our group has been involved in a project for the exploitation of oleic acid from natural sources for the synthesis of dicarboxylic acids as building blocks toward biodegradable polyesters.…”

Section: Resultsmentioning

confidence: 99%

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A Short Method for the Synthesis of Hydroxyoleic Acids

Imperio

Morelli

Panza

2020

J Americ Oil Chem Soc

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Enzymatic or microbiological oxidation of oleic acid can afford azelaic acid as a building block for bioplastics. However, during the oxidation, the formation of hydroxylated byproducts is observed. To better follow the oxidation reaction, the availability of reference compounds is of great importance. To this aim, the synthesis of a series of oleic acids hydroxylated at ω ‐ 1, ω ‐ 2, ω ‐ 3 positions is described without the use of protecting groups. The final products are obtained by partial lactone reduction to hydroxyaldehyde followed by Grignard addition, selective oxidation of the primary hydroxyl group, and Wittig reaction.

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Section: Resultsmentioning

confidence: 99%

“…To the best of our knowledge, mainly enzymatic or microbiological production of these compounds is described (Brenna et al, 2020), although an example of the synthesis of 16‐hydroxyoleic (paleic) acid appeared in the literature (Watanabe et al, 2010).…”

Section: Resultsmentioning

confidence: 99%

A Short Method for the Synthesis of Hydroxyoleic Acids

Imperio

Morelli

Panza

2020

J Americ Oil Chem Soc

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“…In the case of monoenoic fatty acids, Di9:0 was found to be formed from 18:1n-9 (oleic acid) and 16:1n-7 (palmitoleic acid) [23][24][25]. However, the amounts of 18:1n-9 would barely be changed by losses corresponding to the amount of Di9:0 in the head samples.…”

Section: Concentrations Of Dicarboxylated Fatty Acids (Difa-dimes) In Tilapia Head Tissuementioning

confidence: 93%

Identification and quantification of dicarboxylic fatty acids in head tissue of farmed Nile tilapia (Oreochromis niloticus)

Lehnert

Rashid

Barman

et al. 2021

Eur Food Res Technol

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Nile tilapia (Oreochromis niloticus) was grown in Bangladesh with four different feeding treatments as part of a project that aims to produce fish in a cost-effective way for low-income consumers in developing countries. Fillet and head tissue was analysed because both tissues were destined for human consumption. Gas chromatography with mass spectrometry (GC/MS) analyses of transesterified fatty acid methyl ester extracts indicated the presence of ~ 50 fatty acids. Major fatty acids in fillet and head tissue were palmitic acid and oleic acid. Both linoleic acid and polyunsaturated fatty acids with three or more double bonds were presented in quantities > 10% of total fatty acids in fillet, but lower in head tissue. Erucic acid levels were below the newly proposed tolerable daily intake in the European Union, based on the consumption of 200 g fillet per day. Moreover, further analysis produced evidence for the presence of the dicarboxylic fatty acid azelaic acid (nonanedioic acid, Di9:0) in head tissue. To verify this uncommon finding, countercurrent chromatography was used to isolate Di9:0 and other dicarboxylic acids from a technical standard followed by its quantification. Di9:0 contributed to 0.4–1.3% of the fatty acid profile in head tissue, but was not detected in fillet. Fish fed with increasing quantities of flaxseed indicated that linoleic acid was the likely precursor of Di9:0 in the head tissue samples.

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“…Very recently, we employed this enzyme-promoted epoxidation to convert commercial oleic acid into 9,10-dihydroxystearic acid by intermediate oxirane opening. The diol derivative was then submitted to chemical oxidative cleavage to afford azelaic and pelargonic acid [70].…”

Section: Fine Chemicals Production From Soapstockmentioning

confidence: 99%

Enzymatic Methods for the Manipulation and Valorization of Soapstock from Vegetable Oil Refining Processes

Casali

Brenna

Parmeggiani

et al. 2021

Sustainable Chemistry

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The review will discuss the methods that have been optimized so far for the enzymatic hydrolysis of soapstock into enriched mixtures of free fatty acids, in order to offer a sustainable alternative to the procedure which is currently employed at the industrial level for converting soapstock into the by-product known as acid oil (or olein, i.e., free fatty acids removed from raw vegetable oil, dissolved in residual triglycerides). The further biocatalyzed manipulation of soapstock or of the corresponding acid oil for the production of biodiesel and fine chemicals (surfactants, plasticizers, and additives) will be described, with specific attention given to processes performed in continuous flow mode. The valorization of soapstock as carbon source in industrial lipase production will be also considered.

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Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route

Cited by 28 publications

References 40 publications

A Short Method for the Synthesis of Hydroxyoleic Acids

A Short Method for the Synthesis of Hydroxyoleic Acids

Identification and quantification of dicarboxylic fatty acids in head tissue of farmed Nile tilapia (Oreochromis niloticus)

Enzymatic Methods for the Manipulation and Valorization of Soapstock from Vegetable Oil Refining Processes

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