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 with the molecular formula CH₃(CH₂)₁₂COOH. Its salts and

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

s are commonly referred to as myristates or tetradecanoates. It is named after the

binomial name In taxonomy, binomial nomenclature ("two-term naming system"), also called nomenclature ("two-name naming system") or binary nomenclature, is a formal system of naming species of living things by giving each a name composed of two parts, bo ...

for

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

(''

Myristica fragrans ''Myristica fragrans'' is an evergreen tree indigenous to the Maluku Islands of Indonesia. It is important as the main source of the spices nutmeg and mace. It is widely grown across the tropics including Guangdong and Yunnan in China, Taiwa ...

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

Occurrence

Nutmeg butter has 75% trimyristin, the

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

of myristic acid. 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 other two edible oils: ''palm oil'', extracted from the fruit pulp of the oil palm, and ''coconut oil'', extracted from ...

coconut oil frameless , right , alt = A cracked coconut and a bottle of coconut oil Coconut oil (or coconut butter) is an edible oil derived from the wick, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat; in warmer climates du ...

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. But ...

, 8–14% of bovine

milk Milk is a white liquid food produced by the mammary glands of mammals. It is the primary source of nutrition for young mammals (including breastfed human infants) before they are able to digest solid food. Immune factors and immune-modulat ...

, and 8.6% of

breast milk Breast milk (sometimes spelled as breastmilk) or mother's milk is milk produced by mammary glands located in the breast of a human female. Breast milk is the primary source of nutrition for newborns, containing fat, protein, carbohydrates ( la ...

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

spermaceti Spermaceti 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 contain as much as of ...

, 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 ''Physeter'' and one of three extant species in the sperm whale famil ...

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

Orris root Orris root (''rhizoma iridis'') is the root of '' Iris germanica'' and ''Iris pallida''. It had the common name of Queen Elizabeth Root. Constituent chemicals The most valued component of orris root is oil of orris (0.1–0.2%), a yellow-whi ...

Chemical behaviour

Myristic acid acts as a

lipid anchor Lipid-anchored proteins (also known as lipid-linked proteins) are proteins located on the surface of the cell membrane that are covalently attached to lipids embedded within the cell membrane. These proteins insert and assume a place in the bila ...

biomembrane A biological membrane, biomembrane or cell membrane is a selectively permeable membrane that separates the interior of a cell from the external environment or creates intracellular compartments by serving as a boundary between one part of the ...

s. Reduction of myristic acid yields myristyl aldehyde and

myristyl alcohol 1-Tetradecanol, or commonly myristyl alcohol (from ''Myristica fragrans'' – the nutmeg plant), is a straight-chain saturated fatty alcohol, with the molecular formula CH3(CH2)12CH2OH. It is a white waxy solid that is practically insoluble in wa ...

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 densi ...

(LDL) cholesterol.

References

{{Fatty acids Fatty acids Alkanoic acids