Lipids

thumb|Structures of some common lipids. At the top are cholesterol and [[oleic acid. The middle structure is a triglyceride composed of oleoyl, stearoyl, and palmitoyl chains attached to a glycerol backbone. At the bottom is the common phospholipid phosphatidylcholine.]]

thumb|right|Cetyl palmitate, a typical [[wax ester]] thumb|Commercial honeycomb foundation, made by pressing beeswax between patterned metal rollers

type of unsaturated fat that occurs in small amounts in nature, but is also produced industrially from vegetable fats for use in foods

thumb|250px|Structure of a chylomicron (the largest lipoprotein). ApoA, ApoB, ApoC, ApoE are [[apolipoproteins; green particles are phospholipids; T is triglyceride; C is cholesterol ester.]]

thumb|Glycerol thumb|Triacetin, the simplest possible fat (triglyceride) after [[triformin]] Glycerides, also known as acylglycerols, are esters formed from glycerol and fatty acids, and are generally very hydrophobic.

fat in which the fatty acid chains have all or predominantly single bonds

thumb|500px|class=skin-invert|General structures of sphingolipids

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 (particularly 1,3-DAG) has been investigated extensively as a fat substitute due to its ability to suppress the accumulation of body fat; with total annual sales of approximate

thumb|Ceramide. R represents the alkyl portion of a fatty acid. thumb|class=skin-invert|upright=2|General structures of sphingolipids Ceramides are a family of waxy lipid molecules. A ceramide is composed of sphingosine and a fatty acid joined by an amide bond. Ceramides are found in high concentrations within the cell membrane of eukaryotic cells, since they are component lipids that make up sphingomyelin, one of the major lipids in the lipid bilayer. Contrary to previous assumptions that ceramides and other sphingolipids found in cell membrane were purely supporting structural elements, cera

fat or fatty acid in which there is at least one double bond within the fatty acid chain

mass of potassium hydroxide (in mg) necessary to neutralise the free fatty acids contained in 1 g of fat

thumb|Molecular structure of 1-monoacylglycerols thumb|Molecular structure of 2-monoacylglycerols

thumb | right | alt=Light brown corpse on a black background | Reconstruction of Ötzi's mummy: the corpse was immersed in water before its mummification, which "dissolved" its epidermis and initiated the process of adipocere formation. Adipocere (), also known as corpse wax, grave wax or mortuary wax, is a wax-like organic substance formed by the anaerobic bacterial hydrolysis of fat in tissue, such as body fat in corpses. In its formation, putrefaction is replaced by a permanent firm cast of fatty tissues, internal organs, and the face.

small sterol- and sphingolipid-enriched membrane domains that compartmentalize cellular processes

class of chemical compounds

panel of blood tests

Oleamide is an organic compound with the formula . It is the amide derived from the fatty acid oleic acid. It is a colorless waxy solid and occurs in nature. Sometimes labeled as a fatty acid primary amide (FAPA), it is biosynthesized from N-oleoylglycine.

chemical compound

class of chemical compounds

Monolaurin (also called glycerol monolaurate, glyceryl laurate, and 1-lauroyl-glycerol) is a monoglyceride. It is the mono-ester formed from glycerol and lauric acid. Its chemical formula is .

oil made from 4 parts glycerol trioleate and 1 part glycerol trierucate

Palmitoylethanolamide (PEA) is an endogenous fatty acid amide, and lipid modulator.

any fatty acid having only one double or triple bond within the carbon chain

ALC-0315 ([(4-hydroxybutyl)azanediyl]di(hexane-6,1-diyl) bis(2-hexyldecanoate)) is a synthetic lipid. A colorless oily material, it has attracted attention as a component of the SARS-CoV-2 vaccine, BNT162b2, from BioNTech and Pfizer. Specifically, it is one of four components that form lipid nanoparticles (LNPs), which encapsulate and protect the otherwise fragile mRNA that is the active ingredient in these drugs. These nanoparticles promote the uptake of therapeutically effective nucleic acids such as oligonucleotides or mRNA both in vitro and in vivo.

chemical compound

thumb|150px|Chemical structure of sulfoquinovosyl distearoylglycerol, a type of sulfoquinovosyl diacylglycerol Sulfolipids are a class of lipids which possess a sulfur-containing functional group. An abundant sulfolipid is sulfoquinovosyl diacylglycerol, which is composed of a glycoside of sulfoquinovose and diacylglycerol. In plants, sulfoquinovosyl diacylglycerides (SQDG) are important members of the sulfur cycle. Other important sulfolipids include sulfatide and seminolipid, each of which are sulfated glycolipids. Sulfolipids have been implicated in the functions of two of the core componen

lipid found in membranes

thumb|right|General chemical structure of lysophosphatidylcholines, where R is a variable fatty acid chain

2-Oleoylglycerol (2OG) is a monoacylglycerol that is found in biologic tissues. Its synthesis is derived from diacylglycerol precursors. It is metabolized to oleic acid and glycerol primarily by the enzyme monoacylglycerol lipase (MAGL). In 2011, 2OG was found to be an endogenous ligand to GPR119. 2OG has been shown to increase glucagon-like peptide-1 (GLP-1) and gastric inhibitory polypeptide (GIP) levels following administration to the small intestine. 2OG has also been discovered to potentiate G protein and not β-arrestin signaling via allosteric binding of the 5-HT2A receptor.

pharmaceutical product

chemical compound

thumb|400px|Examples of various lipid species.

Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is soap, approximately 8.9 million tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfate

γ-Oryzanol is a mixture of lipids derived from rice (Oryza sativa). γ-Oryzanol occurs mainly in the fat fraction of rice bran and rice bran oil.

drug delivery system

ALC-0159 is a PEG/lipid conjugate (i.e. PEGylated lipid), specifically, it is the N,N-dimyristylamide of 2-hydroxyacetic acid, O-pegylated to a PEG chain mass of about 2 kilodaltons (corresponding to about 45-46 ethylene oxide units per molecule of N,N-dimyristyl hydroxyacetamide). It is a non-ionic surfactant by its nature. It has been deployed in the Pfizer-BioNTech SARS-CoV-2 mRNA vaccine (0.05 mg per dose) that contains the active ingredient tozinameran.

Archaeol is a diether composed of two phytanyl chains linked to the sn-2 and sn-3 positions of glycerol. As its phosphate ester, it is a common component of the membranes of archaea.

Siponimod, sold under the brand name Mayzent, is a selective sphingosine-1-phosphate receptor modulator for oral use that is used for multiple sclerosis (MS). It is intended for once-daily oral administration.

lipids in the blood, either free or bound to other molecules

Palmitoylcarnitine is an ester derivative of carnitine involved in the metabolism of fatty acids. During the tricarboxylic acid cycle (TCA), fatty acids undergo a process known as β-oxidation to produce energy in the form of ATP. β-oxidation occurs primarily within mitochondria, however the mitochondrial membrane prevents the entry of long chain fatty acids (>C10), so the conversion of fatty acids such as palmitic acid is key. Palmitic acid is brought to the cell and once inside the cytoplasm is first converted to Palmitoyl-CoA. Palmitoyl-CoA has the ability to freely pass the outer mitochondr

thumb|right|The structural formulae of selected oxylipins Oxylipins constitute a family of oxygenated natural products which are formed from fatty acids by pathways involving at least one step of dioxygen-dependent oxidation. These small polar lipid compounds are metabolites of polyunsaturated fatty acids (PUFAs) including omega-3 fatty acids and omega-6 fatty acids. Oxylipins are formed by enzymatic or non-enzymatic oxidation of PUFAs.

chemical compound

thumb|350px|The lipidome (in yellow) as a part of the metabolome and the total [[interactome of a cell.]] thumb|350px|The quantitative lipidome (on the level of lipid classes) of yeast [[Saccharomyces cerevisiae in different phases of growth.]] The lipidome refers to the totality of lipids in cells. Lipids are one of the four major molecular components of biological organisms, along with proteins, sugars and nucleic acids. Lipidome is a term coined in the context of omics in modern biology, within the field of lipidomics. It can be studied using mass spectrometry and bioinformatics as well as

thumb|Molecular structures of iGDGTs containing 0 to 4 cyclopentane rings (GDGT-0 to GDGT-4). Caldarchaeol is a membrane-spanning lipid of the isoprenoid glycerol dialkyl glycerol tetraether (iGDGT) class, produced and used by archaea. Membranes made up of caldarchaeol are more stable since the hydrophobic chains are linked together (as compared to lipid bilayer structures in eukaryotes and bacteria), allowing archaea to withstand extreme conditions.

Salatrim is the abbreviation for "Short- and long-chain acyl triglyceride molecule". It is a novel food additive, accepted as a reduced-calorie fat substitute according to the 2003 Novel food Regulation (EC) No 258/97 of the European Parliament. In 1999, Danisco, formerly Cultor Food Science, applied for approval of salatrims in the United Kingdom. In 2001, the Scientific Committee on Food delivered its opinion that salatrims were safe for human consumption.

A lysochrome is a soluble dye used for histochemical staining of lipids, which include triglycerides, fatty acids, and lipoproteins. Lysochromes such as Sudan IV dissolve in the lipid and show up as colored regions. The dye does not stick to any other substrates, so a quantification or qualification of lipid presence can be obtained.

number of milligrams of potassium hydroxide required to neutralize the acetic acid taken up on acetylation of one gram of a chemical substance that contains free hydroxyl groups

'''N,N-Dimethylsphingosine (also known as DMS''') is an inhibitor of sphingosine kinase.

thumb|The surface of a curved lipid bilayer Lipidology is the scientific study of lipids. Lipids are a group of biological macromolecules that have a multitude of functions in the body. Clinical studies on lipid metabolism in the body have led to developments in therapeutic lipidology for disorders such as cardiovascular disease.

thumb|400px|right|Diagram showing glycerol (1) and all the possible acetate esters of glycerol (2-6)

class of enzymes

SM-102 is a synthetic amino lipid which is used in combination with other lipids to form lipid nanoparticles. These are used for the delivery of mRNA-based vaccines, and in particular SM-102 forms part of the drug delivery system for the Moderna COVID-19 vaccine.