Palmitoleic acid: structure, properties, food sources, and lipokine

Palmitoleic acid (16 carbon atoms) was noticed first in 1854 by Hofstädter P.G. in sperm whale oil and named physetoleic acid.
In 1906 Bull H. discovered its molecular composition, at the time when Lewkowitsch gave the present name.
The structure was established in 1925 by Armstrong E.F. et al.
It is a monounsaturated fatty acid (one cis double bond, from the methyl end is in omega-7 (ω-7) or n-7, so in shorthand 16:1n-7) member of the sub-group called long chain fatty acids (LCFA) (from 14 to 18 carbon atoms).
Both in plants and animals it is produced de novo by the Δ9 desaturation of palmitic acid.

Fig. 1 - Synthesis of Palmitoleic Acid
Fig. 1 – Synthesis of (Z)-hexadec-9-enoic Acid


Palmitoleic Acid
Fig. 2 – (Z)-hexadec-9-enoic Acid

Molecular weight: 254.4082 g/mol
Molecular formula: C16H30O2
IUPAC name: (Z)-hexadec-9-enoic acid
CAS registry number: 373-49-9
PubChem: 445638

In purified form its melting point is from -0.5 to +0.5 °C (31.1-32.9 °F; 272.65-273.65 K) and boiling point at 140-141 °C (284-285.8 °F; 413.15-414.15 K) at 5 mm Hg.

Other names
zoomaric acid
cis-9-hexadecenoic acid
palmitolinoleic acid
(9Z)-hexadecenoic acid
(Z)-hexadec-9-enoic acid
(9Z)-hexadec-9-enoic acid
cis-delta(9)-hexadecenoic acid

Food sources of palmitoleic acid

It occurs as glycerol ester mainly in animal fats, particularly in fish and marine mammals, but also in vegetable oils; in the latter sources it is abundant in Roureopsis obliquifoliata, Macadamia ternifolia, Hippophae rhamnoides, Asclepis syriaca seed oils, respectively 32, 20, 16-22, 10 % of the total fatty acids.
In humans is a common component of triglycerides in adipose tissues and is present in higher concentrations in the liver.

A new lipokine

A work of Cao H. et al. (2008) pointed out that adipose tissue communicates with other organs also by palmitoleic acid (so it is a lipokine); in particular researchers demonstrated that this fatty acid strongly stimulates muscle and liver insulin action. This further underscore the highly interconnection between fat metabolism and glucose homeostasis.


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

Cao H., Gerhold K., Mayers J.R., Wiest M.M., Watkins S.M., Hotamisligil G.S. Identification of a lipokine, a lipid hormone linking adipose tissue to systemic metabolism. Cell 2008; 134:933-44 doi:10.1016/j.cell.2008.07.048

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

Olefsky J.M. Fat Talks, Liver and Muscle Listen. Cell 2008; 134:914-16 doi:10.1016/j.cell.2008.09.001

3 thoughts on “Palmitoleic acid: structure, properties, food sources, and lipokine”

  1. I am 55 years old and I have never had a problem with weight I can loose weight easily and have problems with putting it on since I was a child, I don’t eat meat except for fish (I don’t like meat). Your presentation is very informative and true, we are born with certain amount of fat cells and they don’t disappear they simply shrink or inflate they are our subcutaneous tissue, but most people don’t know this. I take and have taking high amount of vitamins and other nutrients since I was in my twenties following a book I read ” ……….” by researchers …….. and ……….. and their great formula and I still do to this day, it works!, and after all these years they have been proven right. What I mean to say is that what you are saying makes total sense as well, RMarie Ruiz

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