9-Octadecenoic acid; (Z)-, methyl ester

9-Octadecenoic acid; (Z)-, methyl ester
Compound Structure:
Synonyms: METHYL OLEATE;112-62-9;Methyl cis-9-octadecenoate;Oleic acid methyl ester;Methyl (Z)-9-octadecenoate;Oleic acid, methyl ester;Edenor MeTiO5;Phytorob 926-67;methyl-cis-oleate;Exceparl M-OL;Emery, oleic acid ester;Esterol 112
Compound ID: NMPC-534
PubChem ID:

5364509

Molecular Formula: C19H36O2
Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OC
InChIKey: QYDYPVFESGNLHU-KHPPLWFESA-N
About the compound:

Methyl oleate is a fatty acid methyl ester formed by the formal condensation of the carboxyl group of oleic acid with methanol. It is functionally related to oleic acid. Methyl oleate, originating from oleic acid, is a monounsaturated fatty ester playing a crucial role in biodiesel production. Its attributes of renewability and biodegradability have made it a focal point of numerous research endeavors aimed at promoting sustainable and eco-friendly chemical methodologies. Recent studies have delved into activating methyl oleate and other vegetable oils for broader industrial use, highlighting the importance of adopting green chemical processes. A notable application of methyl oleate involves its modification with maleic anhydride to improve oil water dispersion capabilities, eliminating the necessity for external surfactants. This method capitalizes on the natural advantages of vegetable oils, like their biodegradable nature and renewability, positioning them as prime candidates for raw materials in chemical productions[1]. Additionally, the oxidative behavior of methyl oleate, in its pure form and when mixed with solketal, has been examined to assess its stability and aging patterns within biodiesel. Such studies are pivotal for enhancing biodiesel's durability by mitigating the oxidation process using antioxidants. Research indicates that incorporating substances such as tert-butylhydroquinone (TBHQ) and solketal can prevent the formation of oligomers, thereby improving the stability and efficacy of biodiesel fuels[2].

References

1. Semenzato, A., Tafuro, G., Sgarbossa, P., Bertani, R. (2022). Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence. Molecules, 27(23), 8142. https://doi.org/10.3390/molecules27238142.

2. Türck, J., Schmitt, F., Anthofer, L., Lichtinger, A., Türck, R., Ruck, W., & Krahl, J. (2023). Oxidation Kinetics of Neat Methyl Oleate and as a Blend with Solketal. Energies, 16(7), 3253.. https://www.mdpi.com/1996-1073/13/3/682.

GHS Hazard Statements

H319 (99.77%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

296.5 g/mol

XLogP3-AA

7.6

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

16

Exact Mass

296.271530387 g/mol

Monoisotopic Mass

296.271530387 g/mol

Topological Polar Surface Area

26.3Ų

Heavy Atom Count

21

Formal Charge

0

Complexity

246

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Clear colorless to amber liquid; [Hawley] Colorless or pale yellow liquid; [MSDSonline]

Boiling Point

425.3 °F at 20 mmHg (NTP, 1992)

Melting Point

-3.8 °F (NTP, 1992)

Density

0.8739 (NTP, 1992)

Solubility 

Insol in water; miscible with ethyl alcohol, ether; sol in chloroform

Vapor Pressure

0.00000629 [mmHg]

Source Species:
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