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Margaric acid, or heptadecanoic acid, is a saturated
fatty acid In chemistry, particularly 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, f ...
. Its molecular formula is CH3(CH2)15CO2H. Classified as an
odd-chain fatty acid Odd-chain fatty acids are those fatty acids that contain an odd number of carbon atoms. In addition to being classified according to their saturation or unsaturation, fatty acids are also classified according to their odd or even numbers of consti ...
, it occurs as a trace component of the fat and milkfat of
ruminant Ruminants (suborder Ruminantia) are hoofed herbivorous grazing or browsing mammals that are able to acquire nutrients from plant-based food by fermenting it in a specialized stomach prior to digestion, principally through microbial actions. The ...
s.
Salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively c ...
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 of margaric acid are called heptadecanoates. Its name is derived from the
Ancient Greek Ancient Greek includes the forms of the Greek language used in ancient Greece and the ancient world from around 1500 BC to 300 BC. It is often roughly divided into the following periods: Mycenaean Greek (), Dark Ages (), the Archaic pe ...
μάργαρος (''márgar(on)''), meaning "pearl(y)", due to its appearance.


Semiochemistry

For many species, margaric acid plays a role as a
semiochemical A semiochemical, from the Greek wiktionary:σημεῖον, σημεῖον (''semeion''), meaning "signal", is a chemical substance or mixture released by an organism that affects the behaviors of other individuals. Semiochemical communication c ...
- specifically it possesses pheromonic and allomonic properties. Margaric acid has been identified in the subcaudal gland secretions of the
European badger The European badger (''Meles meles''), also known as the Eurasian badger, is a badger species in the family Mustelidae native to almost all of Europe. It is classified as least concern on the IUCN Red List as it has a wide range and a large stab ...
(''Meles meles'') and in the occipital gland secretions of male
Bactrian camel The Bactrian camel (''Camelus bactrianus''), also known as the Mongolian camel or domestic Bactrian camel, is a large even-toed ungulate native to the steppes of Central Asia. It has two humps on its back, in contrast to the single-humped dro ...
s (''Camelus bactrianus'') where it is one of the many pheromonic chemicals responsible for aiding in the finding and selection of mates. Margaric acid is an attractant of the
khapra beetle The khapra beetle (''Trogoderma granarium''), also called cabinet beetle, which originated in South Asia, is one of the world's most destructive pests of grain products and seeds.
(''Trogoderma granarium'') and the
yellow fever mosquito ''Aedes aegypti'', the yellow fever mosquito, is a mosquito that can spread dengue fever, chikungunya, Zika fever, Mayaro and yellow fever viruses, and other disease agents. The mosquito can be recognized by black and white markings on its legs ...
(''Aedes aegypti'') but is a repellent of the common house mosquito (''Culex pipiens''). Margaric acid is also found in the precloacal gland secretions of many reptiles belonging to the order
squamata Squamata (, Latin ''squamatus'', 'scaly, having scales') is the largest order of reptiles, comprising lizards, snakes, and amphisbaenians (worm lizards), which are collectively known as squamates or scaled reptiles. With over 10,900 species, ...
, including the
common leopard gecko The leopard gecko or common leopard gecko (''Eublepharis macularius'') is a ground-dwelling lizard native to the rocky dry grassland and desert regions of Afghanistan, Iran, Pakistan, India, and Nepal. The leopard gecko has become a popular pet, ...
(''Eublepharis macularius'') and the European viper ('' Vipera berus''), where it is used for the identification of sexual partners.


Unsaturated forms

Unsaturated derivatives of margaric acid are found in nature, although rarely. Unsaturation occurs at position 9 or both at 9 and 12 positions of the fatty chain giving heptadecenoic (C17:1) and heptadecadienoic (C17:2) acids, respectively. C17:1 cis-9 (ω-8) is found at trace amounts in
ruminant Ruminants (suborder Ruminantia) are hoofed herbivorous grazing or browsing mammals that are able to acquire nutrients from plant-based food by fermenting it in a specialized stomach prior to digestion, principally through microbial actions. The ...
fats and some varieties of olive oils. Minor amounts (< 1%) of C17:1 cis-10 and C17:2 cis-8,11 were detected in seed oil of Portia tree (''Thespesia populnea'').


Rarity in vegetable and animal fats

Margaric acid is rare in animals and vegetables. In the 19th and early 20th centuries, however, the acid was often identified as a significant component of natural fats. Most likely, these were cases of misidentifying a
eutectic mixture A eutectic system or eutectic mixture ( ) is a homogeneous mixture that has a melting point lower than those of the constituents. The lowest possible melting point over all of the mixing ratios of the constituents is called the ''eutectic tempe ...
of palmitic and stearic acids.Чёт или нечет? Занимательные очерки по химии
pages 116-120


See also

*
List of saturated fatty acids See also * List of unsaturated fatty acids *Carboxylic acid **List of carboxylic acids *Dicarboxylic acid {{DEFAULTSORT:List Of Saturated Fatty Acids Saturated Fatty Acids A saturated fat is a type of fat in which the fatty acid chains ...
*
List of carboxylic acids Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature, which ensures systematic and consistent naming of chemicals. Numerous organic compounds have o ...
* Pentadecylic acid


References


External links

* {{Fatty acids Fatty acids Alkanoic acids Semiochemicals