Myristoleic acid: structure, properties, sources

Structure of myristoleic acid

Myristoleic acid (14 carbon atoms) is an uncommon monounsaturated (the cis double bond from the methyl end is omega-5 (ω-5) so in shorthand 14:1n-5) fatty acid member of the sub-group called long chain fatty acids (LCFA) (from 14 to 18 carbon atoms).

Properties of myristoleic acid

Myristoleic Acid
Fig. 1 – (Z)-tetradec-9-enoic Acid

Molecular weight: 226.35504 g/mol
Molecular formula: C14H26O2
IUPAC name: (Z)-tetradec-9-enoic acid
PubChem: 5281119

In purified form its melting point is at -4 °C (24.8 °F; 269.15 K).

Other names of myristoleic acid

  • 9-tetradecenoic acid
  • (9Z)-tetradecenoic acid
  • cis-delta(9)-tetradecenoic acid
  • 14:1n-5

Food sources of myristoleic acid

It occurs as glycerol ester in animal fats.
It is also found in some non-edible vegetable oils; in fact, as the corresponding saturated fatty acid, myristic acid, is one of the main components of seed oils derived from plants of the genus Myristicaceae (in some species up to 30% of the oil; however, myristic acid is present in larger amounts).
It is found in a few foods, and in most cases, in very low quantities.
It is present in small amounts in meat from cattle, horse, chicken and turkey, with a highest value in the brisket of adult cattle, 0.32 g/100 g of edible portion. It is absent in pork. It is also found in whale’s blubber, and turtle fat.
It is absent in almost all processed and preserved meats, such as cold cuts  and sausages. Small amounts are present in the cured raw beef (Bresaola), 0.01 g/100 g of edible portion, and in some types of salami, 0.02 g/100 g of edible portion, while the highest value is found in suet, 0.5 g/100 g of edible portion. It is absent in lard.
In dairy products, it is present:

  • in very small amounts in milk and yogurt;
  • in larger amounts in cream, 0.31 g/100 g of edible portion;
  • but, butter is the food which contains the highest amount in absolute terms, 1.14 g / 100 g of edible portion;
  • it is absent in most of seasoned

It is absent in eggs.
It is virtually absent in all fishes, excluding sturgeon where it is present in very small amounts, 0.01 g/100 g of edible portion, eel fillet, 0.18 g/100 g of edible portion, and shark liver.
It is absent in edible vegetable fats and oils, including margarine.
It is not found in cereals and derived flours, legumes, and fruit.

References

Akoh C.C. and Min D.B. “Food lipids: chemistry, nutrition, and biotechnology” 3th ed. 2008

Chow Ching K. “Fatty acids in foods and their health implication” 3th ed. 2008

 

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