Myristic acid (

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

name: tetradecanoic acid) is a common

saturated fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, ...

with the molecular formula . Its salts and

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s are commonly referred to as myristates or tetradecanoates. The name of the

acyl group In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group () or hydrogen in the case of formyl group ( ...

derived from myristic acid is myristoyl or tetradecanoyl. The acid is named after the

binomial name In taxonomy, binomial nomenclature ("two-term naming system"), also called binary nomenclature, is a formal system of naming species of living things by giving each a name composed of two parts, both of which use Latin grammatical forms, altho ...

for

nutmeg Nutmeg is the seed, or the ground spice derived from the seed, of several tree species of the genus '' Myristica''; fragrant nutmeg or true nutmeg ('' M. fragrans'') is a dark-leaved evergreen tree cultivated for two spices derived from its fru ...

(''

Myristica fragrans ''Myristica fragrans'', commonly known as the nutmeg tree, is an evergreen species Indigenous (ecology), indigenous to the Maluku Islands of Indonesia. This aromatic tree is economically significant as the primary source of two distinct spices: n ...

''), from which it was first isolated in 1841 by

Lyon Playfair Lyon Playfair, 1st Baron Playfair (1 May 1818 – 29 May 1898) was a British scientist and Liberal politician who was Postmaster-General from 1873 to 1874. Early life Playfair was born at Chunar, Bengal, the son of George Playfair (1781–1 ...

Occurrence

Nutmeg butter has 75%

trimyristin Trimyristin is a saturated fat and the triglyceride of myristic acid with the chemical formula C45H86O6. Trimyristin is a white to yellowish-gray solid that is insoluble in water, but soluble in ethanol, acetone, benzene, chloroform, dichlorometh ...

, the

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 ...

of myristic acid and a source from which it can be synthesised. Besides nutmeg, myristic acid is found in

palm kernel oil Palm kernel oil is an edible plant oil derived from the kernel of the oil palm tree ''Elaeis guineensis''. It is related to two other edible oils: ''palm oil'', extracted from the fruit pulp of the oil palm, and ''coconut oil'', extracted from ...

coconut oil Coconut oil (or coconut fat) is an edible oil derived from the kernels, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat below around , and a clear thin liquid oil at higher temperatures. Unrefined varieties have a disti ...

butterfat Butterfat or milkfat is the fatty portion of milk. Milk and cream are often sold according to the amount of butterfat they contain. Composition Butterfat is mainly composed of triglycerides. Each triglyceride contains three fatty acids. Butt ...

, 8–14% of bovine

milk Milk is a white liquid food produced by the mammary glands of lactating mammals. It is the primary source of nutrition for young mammals (including breastfeeding, breastfed human infants) before they are able to digestion, digest solid food. ...

, and 8.6% of

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 ...

as well as being a minor component of many other animal fats. It is found in

spermaceti Spermaceti (see also: Sperm oil) is a waxy substance found in the head cavities of the sperm whale (and, in smaller quantities, in the oils of other whales). Spermaceti is created in the spermaceti organ inside the whale's head. This organ may ...

, the crystallized fraction of oil from the

sperm whale The sperm whale or cachalot (''Physeter macrocephalus'') is the largest of the toothed whales and the largest toothed predator. It is the only living member of the Genus (biology), genus ''Physeter'' and one of three extant species in the s ...

. It is also found in the rhizomes of the Iris, including

Orris root Orris root (''Rhizoma iridis''; etymology possibly an alteration of ''iris (plant), iris'') is the root of ''Iris germanica'' and ''Iris pallida''. It had the common name of Queen Elizabeth Root. It is commonly used as a fixative (perfumery), fi ...

Chemical behaviour

Myristic acid acts as a lipid anchor in biomembranes. Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

Health effects

Myristic acid consumption raises

low-density lipoprotein Low-density lipoprotein (LDL) is one of the five major groups of lipoprotein that transport all fat molecules around the body in extracellular water. These groups, from least dense to most dense, are chylomicrons (aka ULDL by the overall density ...

(LDL) cholesterol.

References

{{Fatty acids Fatty acids Alkanoic acids

Occurrence

Chemical behaviour

Health effects

See also

References