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Names | |
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IUPAC name 2,6,10,14-Tetramethylpentadecane [1] | |
Identifiers | |
3D model (JSmol) | |
1720538 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.016.047 |
EC Number |
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MeSH | pristane |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C19H40 | |
Molar mass | 268.529 g·mol−1 |
Appearance | Colorless liquid |
Odor | Odorless |
Density | 783 mg mL−1 |
Melting point | −100.0 °C; −147.9 °F; 173.2 K |
Boiling point | 296 °C (565 °F; 569 K) |
Refractive index (nD) | 1.438 |
Thermochemistry | |
Heat capacity (C) | 569.76 J K−1 mol−1 |
Hazards | |
GHS labelling: | |
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Warning | |
H315 | |
Flash point | >110 °C |
Related compounds | |
Related alkanes | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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 and some foods. [2] Pristane and phytane are used in the fields of geology and environmental science as biomarkers to characterize origins and evolution of petroleum hydrocarbons and coal. [3]
It is a transparent oily liquid that is immiscible with water, but soluble in diethyl ether, benzene, chloroform and carbon tetrachloride.
Pristane is known to induce autoimmune diseases in rodents. It is used in research to understand the pathogenesis of rheumatoid arthritis and lupus. [4] [5] [6]
It is used as a lubricant, a transformer oil, an immunologic adjuvant, and an anti-corrosion agent, biological marker, plasmocytomas inducer and in production of monoclonal antibodies.
Biosynthetically, pristane is derived from phytol and is used as a biomarker in petroleum studies. [7] Tocopherols represent an alternate sedimentary source of pristane in sediments and petroleum. [8]
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 with only weak odours. Because of their diverse molecular structures, it is difficult to generalize further. In the oil & gas industry, hydrocarbon is a generalised term, which combines petroleum and natural gas as the two naturally occurring phases of hydrocarbon commoditised by the sector. Most anthropogenic emissions of greenhouse gases are from the burning of fossil fuels including fuel production and combustion. Natural sources of hydrocarbons such as ethylene, isoprene, and monoterpenes come from the emissions of vegetation.
Kerogen is solid, insoluble organic matter in sedimentary rocks. Comprising an estimated 1016 tons of carbon, it is the most abundant source of organic compounds on earth, exceeding the total organic content of living matter 10,000-fold. It is insoluble in normal organic solvents and it does not have a specific chemical formula. Upon heating, kerogen converts in part to liquid and gaseous hydrocarbons. Petroleum and natural gas form from kerogen. Kerogen may be classified by its origin: lacustrine (e.g., algal), marine (e.g., planktonic), and terrestrial (e.g., pollen and spores). The name "kerogen" was introduced by the Scottish organic chemist Alexander Crum Brown in 1906, derived from the Greek for "wax birth" (Greek: κηρός "wax" and -gen, γένεση "birth").
A biogenic substance is a product made by or of life forms. While the term originally was specific to metabolite compounds that had toxic effects on other organisms, it has developed to encompass any constituents, secretions, and metabolites of plants or animals. In context of molecular biology, biogenic substances are referred to as biomolecules. They are generally isolated and measured through the use of chromatography and mass spectrometry techniques. Additionally, the transformation and exchange of biogenic substances can by modelled in the environment, particularly their transport in waterways.
Although the existence of hydrocarbons on extraterrestrial bodies like Saturn's moon Titan indicates that hydrocarbons are sometimes naturally produced by inorganic means, abiogenic petroleum origin is a largely discredited hypothesis which proposes that most of earth's petroleum and natural gas deposits were also formed inorganically. Mainstream theories about the formation of hydrocarbons on earth point to an origin from the decomposition of long-dead organisms. Theories explaining the origin of petroleum as abiotic are generally not well accepted by the scientific community, and are rejected by most researchers and scientific theories on the subject.
A polycyclic aromatic hydrocarbon (PAH) is a hydrocarbon—a chemical compound containing only carbon and hydrogen—that is composed of multiple aromatic rings. The group is a major subset of the aromatic hydrocarbons. The simplest of such chemicals is naphthalene, having two aromatic rings, and the three-ring compounds are anthracene and phenanthrene. The terms polyaromatic hydrocarbon or polynuclear aromatic hydrocarbon are also used for this concept.
Hopanoids are a diverse subclass of triterpenoids with the same hydrocarbon skeleton as the compound hopane. This group of pentacyclic molecules therefore refers to simple hopenes, hopanols and hopanes, but also to extensively functionalized derivatives such as bacteriohopanepolyols (BHPs) and hopanoids covalently attached to lipid A.
l-Kynurenine is a metabolite of the amino acid l-tryptophan used in the production of niacin.
In chemistry and geology, biomarkers are any suite of complex organic compounds composed of carbon, hydrogen and other elements or heteroatoms such as oxygen, nitrogen and sulfur, which are found in crude oils, bitumen, petroleum source rock and eventually show simplification in molecular structure from the parent organic molecules found in all living organisms. Essentially, they are complex carbon-based molecules derived from formerly living organisms. Each biomarker is quite distinctive when compared to its counterparts, as the time required for organic matter to convert to crude oil is discreet. Most biomarkers also usually have high molecular mass.
Deoxyribonuclease I, is an endonuclease of the DNase family coded by the human gene DNASE1. DNase I is a nuclease that cleaves DNA preferentially at phosphodiester linkages adjacent to a pyrimidine nucleotide, yielding 5'-phosphate-terminated polynucleotides with a free hydroxyl group on position 3', on average producing tetranucleotides. It acts on single-stranded DNA, double-stranded DNA, and chromatin. In addition to its role as a waste-management endonuclease, it has been suggested to be one of the deoxyribonucleases responsible for DNA fragmentation during apoptosis.
Cholestane is a saturated tetracyclic triterpene. This 27-carbon biomarker is produced by diagenesis of cholesterol and is one of the most abundant biomarkers in the rock record. Presence of cholestane, its derivatives and related chemical compounds in environmental samples is commonly interpreted as an indicator of animal life and/or traces of O2, as animals are known for exclusively producing cholesterol, and thus has been used to draw evolutionary relationships between ancient organisms of unknown phylogenetic origin and modern metazoan taxa. Cholesterol is made in low abundance by other organisms (e.g., rhodophytes, land plants), but because these other organisms produce a variety of sterols it cannot be used as a conclusive indicator of any one taxon. It is often found in analysis of organic compounds in petroleum.
Phytane is the isoprenoid alkane formed when phytol, a constituent of chlorophyll, loses its hydroxyl group. When phytol loses one carbon atom, it yields pristane. Other sources of phytane and pristane have also been proposed than phytol.
Lupus erythematosus is a collection of autoimmune diseases in which the human immune system becomes hyperactive and attacks healthy tissues. Symptoms of these diseases can affect many different body systems, including joints, skin, kidneys, blood cells, heart, and lungs. The most common and most severe form is systemic lupus erythematosus.
Unresolved complex mixture (UCM), or hump, is a feature frequently observed in gas chromatographic (GC) data of crude oils and extracts from organisms exposed to oil.
Blisibimod is a selective antagonist of B-cell activating factor, being developed by Anthera Pharmaceuticals as a treatment for systemic lupus erythematosus. It is currently under active investigation in clinical trials.
Dinosterane is a steroidal alkane, also known as 4α,23,24-trimethylcholestane. It is used in geochemistry as a biomarker, interpreted as an indication of dinoflagellate presence due to its derivative dinosterol high occurrence in extant dinoflagellate species and its rarity in other taxa, although it has been shown to be produced by a single species of marine diatom as well.
Bisnorhopanes (BNH) are a group of demethylated hopanes found in oil shales across the globe and can be used for understanding depositional conditions of the source rock. The most common member, 28,30-bisnorhopane, can be found in high concentrations in petroleum source rocks, most notably the Monterey Shale, as well as in oil and tar samples. 28,30-Bisnorhopane was first identified in samples from the Monterey Shale Formation in 1985. It occurs in abundance throughout the formation and appears in stratigraphically analogous locations along the California coast. Since its identification and analysis, 28,30-bisnorhopane has been discovered in oil shales around the globe, including lacustrine and offshore deposits of Brazil, silicified shales of the Eocene in Gabon, the Kimmeridge Clay Formation in the North Sea, and in Western Australian oil shales.
Crenarchaeol is a glycerol biphytanes glycerol tetraether (GDGT) biological membrane lipid. It has a distinctive cyclohexane moiety and has been proposed as a specific biomarker for pelagic ammonia-oxidizing archaea (AOA). Structurally, the molecule consists of two long hydrocarbon chains that extend through the cell membrane and are bound on each to glycerol through ether linkage. Crenarchaeol can be preserved for hundreds of millions of years in the environment and is part of the TEX86 paleothermometer, a temperature proxy for sea surface temperatures that has been used to reconstruct paleoclimate through to the middle Jurassic (~160 Ma).
Highly branched isoprenoids (HBIs) are long-chain alkenes produced by a small number of marine diatoms. There are a variety of highly branched isoprenoid structures, but C25 Highly branched isoprenoids containing 1 to 3 double bonds are the most common in the sedimentary record. Highly branched isoprenoids have been used as environmental proxies for sea ice conditions in the Arctic and Antarctic throughout the Holocene, and more recently, are being used to reconstruct more ancient ice records.
Lycopane (C40H82; 2,6,10,14,19,23,27,31-octamethyldotriacontane), a 40 carbon alkane isoprenoid, is a widely present biomarker that is often found in anoxic settings. It has been identified in anoxically deposited lacustrine sediments (such as the Messel formation and the Condor oil shale deposit). It has been found in sulfidic and anoxic hypersaline environments (such as the Sdom Formation). It has been widely identified in modern marine sediments, including the Peru upwelling zone, the Black Sea, and the Cariaco Trench. It has been found only rarely in crude oils.
Elizabeth A. Canuel is a chemical oceanographer known for her work on organic carbon cycling in aquatic environments. She is the Chancellor Professor of Marine Science at the College of William & Mary and is an elected fellow of the Geochemical Society and the European Association of Geochemistry.