Pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) is a

terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes" ...

acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...

present at micromolar concentrations in the

blood plasma Blood plasma is a light amber-colored liquid component of blood in which blood cells are absent, but contains proteins and other constituents of whole blood in suspension. It makes up about 55% of the body's total blood volume. It is the intra ...

of healthy individuals. It is also found in the

lipids Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include ...

from many sources such as

freshwater Fresh water or freshwater is any naturally occurring liquid or frozen water containing low concentrations of dissolved salts and other total dissolved solids. Although the term specifically excludes seawater and brackish water, it does include ...

sponges Sponges, the members of the phylum Porifera (; meaning 'pore bearer'), are a basal animal clade as a sister of the diploblasts. They are multicellular organisms that have bodies full of pores and channels allowing water to circulate through ...

krill Krill are small crustaceans of the order Euphausiacea, and are found in all the world's oceans. The name "krill" comes from the Norwegian Norwegian, Norwayan, or Norsk may refer to: *Something of, from, or related to Norway, a country in n ...

earthworm An earthworm is a terrestrial invertebrate that belongs to the phylum Annelida. They exhibit a tube-within-a-tube body plan; they are externally segmented with corresponding internal segmentation; and they usually have setae on all segments. Th ...

whale Whales are a widely distributed and diverse group of fully aquatic placental marine mammals. As an informal and colloquial grouping, they correspond to large members of the infraorder Cetacea, i.e. all cetaceans apart from dolphins and ...

s, human milk fat, bovine depot fat, butterfat or

California California is a U.S. state, state in the Western United States, located along the West Coast of the United States, Pacific Coast. With nearly 39.2million residents across a total area of approximately , it is the List of states and territori ...

petroleum Petroleum, also known as crude oil, or simply oil, is a naturally occurring yellowish-black liquid mixture of mainly hydrocarbons, and is found in geological formations. The name ''petroleum'' covers both naturally occurring unprocessed crud ...

. It is usually present in combination with

phytanic acid Phytanic acid (or 3,7,11,15-tetramethyl hexadecanoic acid) is a branched chain fatty acid that humans can obtain through the consumption of dairy products, ruminant animal fats, and certain fish. Western diets are estimated to provide 50–100 ...

. In humans, pristanic acid is obtained from two sources: either directly from the diet or as the alpha oxidation product of

. At physiological concentrations pristanic acid is a natural ligand for

peroxisome proliferator-activated receptor alpha Peroxisome proliferator-activated receptor alpha (PPAR-α), also known as NR1C1 (nuclear receptor subfamily 1, group C, member 1), is a nuclear receptor protein functioning as a transcription factor that in humans is encoded by the ''PPARA'' gene ...

(PPARα). In liver, pristanic acid is degraded by

peroxisomal A peroxisome () is a membrane-bound organelle, a type of microbody, found in the cytoplasm of virtually all eukaryotic cells. Peroxisomes are oxidative organelles. Frequently, molecular oxygen serves as a co-substrate, from which hydrogen per ...

beta oxidation In biochemistry and metabolism, beta-oxidation is the catabolic process by which fatty acid molecules are broken down in the cytosol in prokaryotes and in the mitochondria in eukaryotes to generate acetyl-CoA, which enters the citric acid cycl ...

propionyl-CoA Propionyl-CoA is a coenzyme A derivative of propionic acid. It is composed of a 24 total carbon chain (without the coenzyme, it is a 3 carbon structure) and its production and metabolic fate depend on which organism it is present in. Several diffe ...

. Together with phytanic acid, pristanic acid accumulates in several inherited disorders such as

Zellweger syndrome Zellweger syndrome is a rare congenital disorder characterized by the reduction or absence of functional peroxisomes in the cells of an individual. It is one of a family of disorders called Zellweger spectrum disorders which are leukodystrophie ...

. The salts and esters of pristanic acid are called pristanates. Pristanic acid was first isolated from

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 ...

by R. P. Hansen and J. D. Morrison in 1964.R. P. Hansen, J. D. Morrison, The isolation and identification of 2,6,10,14-tetramethylpentadecanoic acid from butterfat, ''Biochemical Journal'' 1964 Nov;93(2):225-8. The name of the substance is derived from

pristane Pristane is a natural saturated terpenoid alkane obtained primarily from shark liver oil, from which its name is derived (Latin ''pristis'', "shark"). It is also found in the stomach oil of birds in the order Procellariiformes and in mineral oil ...

(2,6,10,14-tetramethylpentadecane), the corresponding

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...

. Pristane was isolated from

shark Sharks are a group of elasmobranch fish characterized by a cartilaginous skeleton, five to seven gill slits on the sides of the head, and pectoral fins that are not fused to the head. Modern sharks are classified within the clade Selachimo ...

liver and was named after

Latin Latin (, or , ) is a classical language belonging to the Italic branch of the Indo-European languages. Latin was originally a dialect spoken in the lower Tiber area (then known as Latium) around present-day Rome, but through the power of the ...

''pristis'', "shark".

References

{{Peroxisomal metabolism intermediates Carboxylic acids Diterpenes