Margaric acid

Last updated
Margaric acid [1]
Heptadecanoic acid.png
Heptadecanoic-acid-3D-balls.png
Names
Preferred IUPAC name
Heptadecanoic acid
Other names
Heptadecylic acid;
Daturic acid;
Margarinic acid;
17:0 (Lipid numbers)
Identifiers
3D model (JSmol)
1781004
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.298 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-027-1
253195
PubChem CID
UNII
  • InChI=1S/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19) Yes check.svgY
    Key: KEMQGTRYUADPNZ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)
    Key: KEMQGTRYUADPNZ-UHFFFAOYAT
  • O=C(O)CCCCCCCCCCCCCCCC
Properties
C17H34O2
Molar mass 270.45 g/mol
AppearanceWhite crystals
Density 0.853 g/cm3
Melting point 61.3 °C (142.3 °F; 334.4 K)
Boiling point 227 °C (441 °F; 500 K) 100 mmHg
insoluble
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related fatty acids
Palmitic acid
Stearic acid
Related compounds
Heptadecanol
Heptadecanal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Margaric acid, or heptadecanoic acid, is a saturated fatty acid. Its molecular formula is CH3(CH2)15CO2H. Classified as an odd-chain fatty acid, it occurs as a trace component of the fat and milkfat of ruminants. [2] Salts and esters of margaric acid are called heptadecanoates.

Contents

Its name is derived from the Ancient Greek μάργαρος (márgar(on)), meaning "pearl(y)", due to its appearance.

Semiochemistry

For many species, margaric acid plays a role as a semiochemical - specifically it possesses pheromonic and allomonic properties. Margaric acid has been identified in the subcaudal gland secretions of the European badger (Meles meles) [3] and in the occipital gland secretions of male Bactrian camels (Camelus bactrianus) where it is one of the many pheromonic chemicals responsible for aiding in the finding and selection of mates. [4]

Margaric acid is an attractant of the khapra beetle (Trogoderma granarium) [5] and the yellow fever mosquito (Aedes aegypti) but is a repellent of the common house mosquito (Culex pipiens). [6]

Margaric acid is also found in the precloacal gland secretions of many reptiles belonging to the order squamata, including the common leopard gecko (Eublepharis macularius) [7] and the European viper ( Vipera berus ), where it is used for the identification of sexual partners. [8]

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 fats [9] and some varieties of olive oils. [10] Minor amounts (< 1%) of C17:1 cis-10 and C17:2 cis-8,11 were detected in seed oil of Portia tree (Thespesia populnea). [11]

Rarity in vegetable and animal fats

Margaric acid is rare in animals and vegetables. [12] 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 of palmitic and stearic acids. [13]

See also

Related Research Articles

<span class="mw-page-title-main">Camel</span> Genus of mammals

A camel is an even-toed ungulate in the genus Camelus that bears distinctive fatty deposits known as "humps" on its back. Camels have long been domesticated and, as livestock, they provide food and textiles. Camels are working animals especially suited to their desert habitat and are a vital means of transport for passengers and cargo. There are three surviving species of camel. The one-humped dromedary makes up 94% of the world's camel population, and the two-humped Bactrian camel makes up 6%. The wild Bactrian camel is a separate species and is now critically endangered.

<span class="mw-page-title-main">Fatty acid</span> Carboxylic 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, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.

<span class="mw-page-title-main">Fat</span> Esters of fatty acid or triglycerides

In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food.

<span class="mw-page-title-main">Camelidae</span> Family of mammals belonging to even-toed ungulates

Camelids are members of the biological family Camelidae, the only currently living family in the suborder Tylopoda. The seven extant members of this group are: dromedary camels, Bactrian camels, wild Bactrian camels, llamas, alpacas, vicuñas, and guanacos. Camelids are even-toed ungulates classified in the order Artiodactyla, along with species including whales, pigs, deer, cattle, and antelopes.

<span class="mw-page-title-main">Dromedary</span> Largest living camelid in the world

The dromedary, also known as the dromedary camel, Arabian camel, or one-humped camel, is a large even-toed ungulate, of the genus Camelus, with one hump on its back.

<span class="mw-page-title-main">Bactrian camel</span> Central Asian mammal, beast of burden

The Bactrian camel, also known as the Mongolian camel, domestic Bactrian camel or two-humped 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 dromedary. Its population of 2 million exists mainly in the domesticated form. Their name comes from the ancient historical region of Bactria.

<span class="mw-page-title-main">Oleic acid</span> Monounsaturated omega-9 fatty acid

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is a common component of oils, and thus occurs in many types of food, as well as in soap.

The anal glands or anal sacs are small glands near the anus in many mammals. They are situated in between the external anal sphincter muscle and internal anal sphincter muscle. Their function in humans is unclear.

<span class="mw-page-title-main">Uropygial gland</span> Gland

The uropygial gland, informally known as the preen gland or the oil gland, is a bilobed sebaceous gland possessed by the majority of birds used to distribute the gland's oil through the plumage by means of preening. It is located dorsally at the base of the tail and is greatly variable in both shape and size. In some species, the opening of the gland has a small tuft of feathers to provide a wick for the preen oil. It is a holocrine gland enclosed in a connective tissue capsule made up of glandular acini that deposit their oil secretion into a common collector tube ending in a variable number of pores (openings), most typically two. Each lobe has a central cavity that collects the secretion from tubules arranged radially around the cavity. The gland secretion is conveyed to the surface via ducts that, in most species, open at the top of a papilla.

Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food.

<span class="mw-page-title-main">Rumenic acid</span> Chemical compound

Rumenic acid, also known as bovinic acid, is a conjugated linoleic acid (CLA) found in the fat of ruminants and in dairy products. It is an omega-7 trans fatty acid. Its lipid shorthand name is cis-9, trans-11 18:2 acid. The name was proposed by Kramer et al. in 1998. It can be considered as the principal dietary form, accounting for as much as 85-90% of the total CLA content in dairy products.

<span class="mw-page-title-main">Femoral pore</span> Gland found in certain reptiles

Femoral pores are a part of a holocrine secretory gland found on the inside of the thighs of certain lizards and amphisbaenians which releases pheromones to attract mates or mark territory. In certain species only the male has these pores and in other species, both sexes have them, with the male's being larger. Femoral pores appear as a series of pits or holes within a row of scales on the ventral portion of the animal's thigh.

Pentadecylic acid, also known as pentadecanoic acid or C15:0, is an odd-chain saturated fatty acid. Its molecular formula is CH3(CH2)13CO2H. It is a colorless solid.

<span class="mw-page-title-main">Diglyceride</span> Type of fat derived from glycerol and two fatty acids

A diglyceride, or diacylglycerol (DAG), is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Two possible forms exist, 1,2-diacylglycerols and 1,3-diacylglycerols. Diglycerides are natural components of food fats, though minor in comparison to triglycerides. DAGs can act as surfactants and are commonly used as emulsifiers in processed foods. DAG-enriched oil has been investigated extensively as a fat substitute due to its ability to suppress the accumulation of body fat; with total annual sales of approximately USD 200 million in Japan since its introduction in the late 1990s till 2009.

<span class="mw-page-title-main">Hybrid camel</span> Hybrid between a Bactrian camel and dromedary

A hybrid camel is a hybrid between a Bactrian camel and dromedary.

<span class="mw-page-title-main">Wild Bactrian camel</span> Species of camel

The wild Bactrian camel is a critically endangered species of camel living in parts of northwestern China and southwestern Mongolia. It is closely related to the domestic Bactrian camel. Both are large, double-humped even-toed ungulates native to the steppes of central Asia. Until recently, wild Bactrian camels were thought to have descended from domesticated Bactrian camels that became feral after being released into the wild. However, genetic studies have established it as a separate species which diverged from the Bactrian camel about 1.1 million years ago.

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<span class="mw-page-title-main">Phagomimicry</span>

Phagomimicry is a defensive behaviour of sea hares, in which the animal ejects a mixture of chemicals, which mimic food, and overwhelm the senses of their predator, giving the sea hare a chance to escape. The typical defence response of the sea hare to a predator is to release two chemicals - ink from the ink gland and opaline from the opaline gland. While ink creates a dark, diffuse cloud in the water which disrupts the sensory perception of the predator by acting as a smokescreen and as a decoy, the opaline, which affects the senses dealing with feeding, causes the predator to instinctively attack the cloud of chemicals as if it were indeed food. This ink is able to mimic food by having a high concentration of amino acids and other compounds that are normally found in food, and the attack behaviour of the predator allows the sea-hares the opportunity to escape.

<i>Coridius janus</i> Species of true bug

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References

  1. Merck Index , 13th Edition, 5775
  2. R. P. Hansen, F. B. Shorland and N. June Cooke (1957). "Occurrence in Butterfat of n-Heptadecanoic Acid (Margaric Acid)". Nature. 179 (98): 98. Bibcode:1957Natur.179...98H. doi: 10.1038/179098a0 . PMID   13400103. S2CID   4144443.
  3. Sin, Yung Wa; Buesching, Christina D.; Burke, Terry; Macdonald, David W. (2012-05-30). "Molecular characterization of the microbial communities in the subcaudal gland secretion of the European badger (Meles meles)". FEMS Microbiology Ecology. 81 (3): 648–659. doi: 10.1111/j.1574-6941.2012.01396.x . ISSN   0168-6496. PMID   22530962.
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