A benzopyrene is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula C₂₀H₁₂. Structurally speaking, the colorless isomers of benzopyrene are pentacyclic hydrocarbons and are fusion products of

pyrene Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is . This yellow solid is the smallest peri-fused PAH (one where the rings are fused through mo ...

and a phenylene group. Two

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Is ...

ic species of benzopyrene are benzo 'a''yrene and the less common benzo 'e''yrene. They belong to the chemical class of

polycyclic aromatic hydrocarbon A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. ...

Overview

Related compounds include cyclopentapyrenes,

dibenzopyrenes Dibenzopyrenes are a group of high molecular weight polycyclic aromatic hydrocarbons with the molecular formula C24H14. There are five isomers of dibenzopyrene which differ by the arrangement of aromatic rings: dibenzo 'a'',''e''yrene, dibenzo ' ...

, indenopyrenes and naphthopyrenes. Benzopyrene is a component of pitch and occurs together with other related pentacyclic

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

species such as

picene Picene is a hydrocarbon found in the Pitch (resin), pitchy residue obtained in the distillation of peat tar and of petroleum. This is distilled to dryness and the distillate repeatedly Recrystallization (chemistry), recrystallized from cymene. It ...

, benzo

fluoranthene Fluoranthene is a polycyclic aromatic hydrocarbon (PAH). The molecule can be viewed as the fusion of naphthalene and benzene unit connected by a five-membered ring. Although samples are often pale yellow, the compound is colorless. It is soluble ...

s, and

perylene Perylene or perilene is a polycyclic aromatic hydrocarbon with the chemical formula C20H12, occurring as a brown solid. It or its derivatives may be carcinogenic, and it is considered to be a hazardous pollutant. In cell membrane cytochemistry, ...

. It is naturally emitted by

forest fire A wildfire, forest fire, bushfire, wildland fire or rural fire is an unplanned, uncontrolled and unpredictable fire in an area of combustible vegetation. Depending on the type of vegetation present, a wildfire may be more specifically identi ...

s and

volcanic eruptions Several types of volcanic eruptions—during which lava, tephra (ash, lapilli, volcanic bombs and volcanic blocks), and assorted gases are expelled from a volcanic vent or fissure—have been distinguished by volcanologists. These are often ...

and can also be found in

coal tar Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat pso ...

cigarette smoke Tobacco smoke is a sooty aerosol produced by the incomplete combustion of tobacco during the smoking of cigarettes and other tobacco products. Temperatures in burning cigarettes range from about 400 °C between puffs to about 900 °C ...

, wood smoke, and burnt foods such as

coffee Coffee is a drink prepared from roasted coffee beans. Darkly colored, bitter, and slightly acidic, coffee has a stimulating effect on humans, primarily due to its caffeine content. It is the most popular hot drink in the world. Seeds of ...

. Fumes that develop from fat dripping on blistering charcoal are rich in benzopyrene, which can condense on grilled goods. Benzopyrenes are harmful because they form carcinogenic and mutagenic

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, ...

s (such as (+)-benzo 'a''yrene-7,8-dihydrodiol-9,10-epoxide from benzo 'a''yrene) which

intercalate Intercalation may refer to: *Intercalation (chemistry), insertion of a molecule (or ion) into layered solids such as graphite * Intercalation (timekeeping), insertion of a leap day, week or month into some calendar years to make the calendar foll ...

into DNA, interfering with transcription. They are considered

pollutants A pollutant or novel entity is a substance or energy introduced into the environment that has undesired effects, or adversely affects the usefulness of a resource. These can be both naturally forming (i.e. minerals or extracted compounds like o ...

and carcinogens. The mechanism of action of benzo yrene-related DNA modification has been investigated extensively and relates to the activity of cytochrome P450 subclass 1A1 (

CYP1A1 Cytochrome P450, family 1, subfamily A, polypeptide 1 is a protein that in humans is encoded by the ''CYP1A1'' gene. The protein is a member of the cytochrome P450 superfamily of enzymes. Function Metabolism of xenobiotics and drugs CYP1A ...

). Seemingly, the high activity of CYP1A1 in the intestinal mucosa prevents major amounts of ingested benzo yrene from entering portal blood and systemic circulation. The intestinal (but not hepatic) detoxification mechanism seems to depend on receptors that recognize bacterial surface components (

TLR2 Toll-like receptor 2 also known as TLR2 is a protein that in humans is encoded by the ''TLR2'' gene. TLR2 has also been designated as CD282 (cluster of differentiation 282). TLR2 is one of the toll-like receptors and plays a role in the immune sys ...

). Evidence exists to link benzo 'a''yrene to the formation of

lung cancer Lung cancer, also known as lung carcinoma (since about 98–99% of all lung cancers are carcinomas), is a malignant lung tumor characterized by uncontrolled cell growth in tissues of the lung. Lung carcinomas derive from transformed, mali ...

. In February 2014,

NASA The National Aeronautics and Space Administration (NASA ) is an independent agency of the US federal government responsible for the civil space program, aeronautics research, and space research. NASA was established in 1958, succeedin ...

announced
greatly upgraded database
for tracking polycyclic aromatic hydrocarbons (PAHs), including benzopyrene, in the

universe The universe is all of space and time and their contents, including planets, stars, galaxies, and all other forms of matter and energy. The Big Bang theory is the prevailing cosmological description of the development of the univers ...

. According to scientists, more than 20% of the

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon ma ...

in the universe may be associated with PAHs, possible starting materials for the

formation Formation may refer to: Linguistics * Back-formation, the process of creating a new lexeme by removing or affixes * Word formation, the creation of a new word by adding affixes Mathematics and science * Cave formation or speleothem, a secondar ...

life Life is a quality that distinguishes matter that has biological processes, such as signaling and self-sustaining processes, from that which does not, and is defined by the capacity for growth, reaction to stimuli, metabolism, energy ...

. PAHs seem to have been formed several billion years after the

Big Bang The Big Bang event is a physical theory that describes how the universe expanded from an initial state of high density and temperature. Various cosmological models of the Big Bang explain the evolution of the observable universe from the ...

, are widespread throughout the universe, and are associated with new stars and

exoplanets An exoplanet or extrasolar planet is a planet outside the Solar System. The first possible evidence of an exoplanet was noted in 1917 but was not recognized as such. The first confirmation of detection occurred in 1992. A different planet, init ...

References

External links

{{PAHs Endocrine disruptors Carcinogens Polycyclic aromatic hydrocarbons

Overview

See also

References

External links