Lignoceric acid

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Lignoceric acid
Lignocerinskabe.svg
Names
Preferred IUPAC name
Tetracosanoic acid
Other names
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.347 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26) Yes check.svgY
    Key: QZZGJDVWLFXDLK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)
    Key: QZZGJDVWLFXDLK-UHFFFAOYAH
  • O=C(O)CCCCCCCCCCCCCCCCCCCCCCC
Properties
C24H48O2
Molar mass 368.63 g/mol
Melting point 84.2 °C (183.6 °F; 357.3 K) [1]
Related compounds
Related Fatty acids
Behenic acid (C22:0)
Cerotic acid (C26:0)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoceric acid (1.1% – 2.2%). [1] This fatty acid is also a byproduct of lignin production.

Reduction of lignoceric acid yields lignoceryl alcohol.

See also

Related Research Articles

<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">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

A saturated fat is a type of fat in which the fatty acid chains have all single bonds. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched chain of carbon (C) atoms. Along the chain, some carbon atoms are linked by single bonds (-C-C-) and others are linked by double bonds (-C=C-). A double bond along the carbon chain can react with a pair of hydrogen atoms to change into a single -C-C- bond, with each H atom now bonded to one of the two C atoms. Glyceride fats without any carbon chain double bonds are called saturated because they are "saturated with" hydrogen atoms, having no double bonds available to react with more hydrogen.

An unsaturated fat is a fat or fatty acid in which there is at least one double bond within the fatty acid chain. A fatty acid chain is monounsaturated if it contains one double bond, and polyunsaturated if it contains more than one double bond.

<span class="mw-page-title-main">Stearic acid</span> Eighteen-carbon straight-chain fatty acid

Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a waxy solid with the formula CH3(CH2)16CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin.

Palmitic acid is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. It is a major component of the oil from the fruit of oil palms, making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats. Palmitates are the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4).

<span class="mw-page-title-main">Peanut oil</span> Mild-tasting vegetable oil derived from peanuts

Peanut oil, also known as groundnut oil or arachis oil, is a vegetable oil derived from peanuts. The oil usually has a mild or neutral flavor but, if made with roasted peanuts, has a stronger peanut flavor and aroma. It is often used in American, Chinese, Indian, African and Southeast Asian cuisine, both for general cooking, and in the case of roasted oil, for added flavor. Peanut oil has a high smoke point relative to many other cooking oils, so it is commonly used for frying foods.

In chemistry, a saturated compound is a chemical compound that resists the addition reactions, such as hydrogenation, oxidative addition, and binding of a Lewis base. The term is used in many contexts and for many classes of chemical compounds. Overall, saturated compounds are less reactive than unsaturated compounds. Saturation is derived from the Latin word saturare, meaning 'to fill'.

Polyunsaturated fatty acids (PUFAs) are fatty acids that contain more than one double bond in their backbone. This class includes many important compounds, such as essential fatty acids and those that give drying oils their characteristic property.

The wax acids are a subgroup of saturated unbranched alkanoic acids. The frontier between fatty acids and wax acids is fluid. It often begins at 22 carbon atoms.

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

Pecan oil is an edible pressed oil extracted from the pecan nut. Pecan oil is neutral in flavor and takes on the flavor of whatever seasoning is being used with it. Pecan oil contains 9.5% saturated fat, which is less than in olive oil (13.5%), peanut oil (16.90%) or corn oil (12.70%). It is also used as a massage oil and in aromatherapy applications.

A wax ester (WE) is an ester of a fatty acid and a fatty alcohol. Wax esters comprise the main components of three commercially important waxes: carnauba wax, candelilla wax, and beeswax.

<span class="mw-page-title-main">Low-fat diet</span> Diet that contains limited amounts of fat

A low-fat diet is one that restricts fat, and often saturated fat and cholesterol as well. Low-fat diets are intended to reduce the occurrence of conditions such as heart disease and obesity. For weight loss, they perform similarly to a low-carbohydrate diet, since macronutrient composition does not determine weight loss success. Fat provides nine calories per gram while carbohydrates and protein each provide four calories per gram. The Institute of Medicine recommends limiting fat intake to 35% of total calories to control saturated fat intake.

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

Nervonic acid is a fatty acid. It is a monounsaturated analog of lignoceric acid (24:0). It is also known as selacholeic acid and cis-15-tetracosenoic acid. Its name derives from the Latin word nervus, meaning nerve or sinew.

1-Tetracosanol is a fatty alcohol containing 24 carbon atoms, usually derived from the fatty acid lignoceric acid.

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. Salts and esters of margaric acid are called heptadecanoates.

A very-long-chain fatty acid (VLCFA) is a fatty acid with 22 or more carbons. Their biosynthesis occurs in the endoplasmic reticulum. VLCFA's can represent up to a few percent of the total fatty acid content of a cell.

Tricosylic acid, or tricosanoic acid, is a 23-carbon long-chain saturated fatty acid with the chemical formula CH3(CH2)21COOH.

<span class="mw-page-title-main">Trans fat</span> Type of unsaturated fat

Trans fat, also called trans-unsaturated fatty acids, or trans fatty acids, is a type of unsaturated fat that occurs in foods. Trace concentrations of trans fats occur naturally, but large amounts are found in some processed foods. Since consumption of trans fats is unhealthy, artificial trans fats are highly regulated or banned in many nations. However, they are still widely consumed in developing nations, resulting in hundreds of thousands of deaths each year. Serious interest has been given to determining their sources, to better avoid them.

References

  1. 1 2 Beare-Rogers, J. L.; Dieffenbacher, A.; Holm, J. V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685. S2CID   84492006.