Palmitoleic acid, or (9''Z'')-hexadec-9-enoic acid, is an omega-7

monounsaturated In biochemistry and nutrition, a monounsaturated fat is a fat that contains a monounsaturated fatty acid (MUFA), a subclass of fatty acid characterized by having a double bond in the fatty acid chain with all of the remaining carbon atoms being s ...

fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...

(16:1n-7) with the formula CH₃(CH₂)₅CH=CH(CH₂)₇COOH. It is a rare component of fats. It is a common constituent of the

glyceride Glycerides, also known as acylglycerols, are esters formed from glycerol and fatty acids, and are generally very hydrophobic. Glycerol has three hydroxyl functional groups, which can be esterified with one, two, or three fatty acids to form mo ...

s of human

adipose tissue Adipose tissue (also known as body fat or simply fat) is a loose connective tissue composed mostly of adipocytes. It also contains the stromal vascular fraction (SVF) of cells including preadipocytes, fibroblasts, Blood vessel, vascular endothel ...

. It is present in all tissues but, in general, found in higher concentrations in the

liver The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...

. It is biosynthesized from

palmitic acid Palmitic acid (hexadecanoic acid in IUPAC nomenclature) is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms.Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra. The ...

by the action of the enzyme

Stearoyl-CoA desaturase-1 Stearoyl-CoA desaturase (Δ-9-desaturase or SCD-1) is an endoplasmic reticulum enzyme that catalyzes the rate-limiting step in the formation of Monounsaturated fat, monounsaturated fatty acids (MUFAs), specifically Oleic acid, oleate and Palmito ...

. Animal and cell culture studies indicate that palmitoleic acid is anti-inflammatory, and improves

insulin sensitivity Insulin resistance (IR) is a pathological response in which cells in insulin-sensitive tissues in the body fail to respond normally to the hormone insulin or downregulate insulin receptors in response to hyperinsulinemia. Insulin is a hormone ...

in liver and skeletal muscles, but more studies are required to establish its actions in humans. Many of the effects of palmitoleic acid are due to its activation of PPAR-alpha.

Dietary sources

Palmitoleic acid is found in trace amounts in most foods except for

sardine Sardine and pilchard are common names for various species of small, oily forage fish in the herring suborder Clupeoidei. The term "sardine" was first used in English during the early 15th century; a somewhat dubious etymology says it com ...

oil, which contains 15% of this acid as a component of

triglyceride A triglyceride (from '' tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates ...

s. Other dietary sources of palmitoleic acid include

breast milk Breast milk (sometimes spelled as breastmilk) or mother's milk is milk produced by the mammary glands in the breasts of women. Breast milk is the primary source of nutrition for newborn infants, comprising fats, proteins, carbohydrates, and a var ...

, a variety of

animal fat Animal fats are lipids derived from animals which are used by the animal for a multitude of functions, or can be used by humans for dietary, sanitary, and cosmetic purposes. Depending on the temperature of the fat, it can change between a solid s ...

vegetable oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of edible plants. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed ...

s, and

marine oil Fish oil is oil derived from the tissues of oily fish. Fish oils contain the omega−3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), precursors of certain eicosanoids that are known to reduce inflammation in the body ...

Macadamia oil Macadamia oil, also known as macadamia nut oil, is a non-volatile oil extracted from the nuts of the macadamia tree (''Macadamia integrifolia''), indigenous to Australia. This oil is used in culinary applications as a frying or salad oil, and in c ...

(''

Macadamia integrifolia ''Macadamia integrifolia'' is a small to medium-sized tree native to Australian rainforests. Common names include macadamia, smooth-shelled macadamia, bush nut, Queensland nut, Bauple nut and nut oak. Description ''Macadamia integrifolia'' tree ...

'') and

sea buckthorn oil Sea buckthorn oil is a red-orange oil derived from sea buckthorn plants. The most commonly used species for this purpose is ''Hippophae rhamnoides''. Species belonging to this genus accumulate lipids in the mesocarp (the fruit pulp), so the oil ...

(''

Hippophae rhamnoides ''Hippophae rhamnoides'', also known as sea buckthorn, sandthorn, sallowthorn or seaberry, is a species of flowering plant in the family Elaeagnaceae, native to cold-temperate regions of Eurasia. It is a spiny deciduous shrub. The plant is used ...

'') are botanical sources with high concentrations, containing 17% and 19-29% palmitoleic acid, respectively.

References

{{Fatty acids Alkenoic acids Fatty acids