Retene, methyl isopropyl phenanthrene or 1-methyl-7-isopropyl phenanthrene, C₁₈H₁₈, is a

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. ...

present in the

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 psoriasi ...

fraction,

boiling Boiling is the rapid vaporization of a liquid, which occurs when a liquid is heated to its boiling point, the temperature at which the vapour pressure of the liquid is equal to the pressure exerted on the liquid by the surrounding atmosphere. Th ...

above 360 °C. It occurs naturally in the

tar Tar is a dark brown or black viscous liquid of hydrocarbons and free carbon, obtained from a wide variety of organic materials through destructive distillation. Tar can be produced from coal, wood, petroleum, or peat. "a dark brown or black bit ...

s obtained by the

distillation Distillation, or classical distillation, is the process of separation process, separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distilla ...

resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on natu ...

ous

wood Wood is a porous and fibrous structural tissue found in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulose fibers that are strong in tension and embedded in a matrix of lignin th ...

s. It crystallizes in large plates, which melt at 98.5 °C and boil at 390 °C. It is readily soluble in warm

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

and in hot

glacial acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...

Sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable iso ...

and boiling

amyl alcohol An amyl alcohol is any of eight alcohols with the formula C5H12O. A mixture of pentyl, amyl alcohols (also called amyl alcohol) can be obtained from fusel alcohol. Amyl alcohol is used as a solvent and in esterification, by which is produced amyl a ...

reduce it to a tetrahydroretene, but if it heated with

phosphorus Phosphorus is a chemical element with the symbol P and atomic number 15. Elemental phosphorus exists in two major forms, white phosphorus and red phosphorus, but because it is highly reactive, phosphorus is never found as a free element on Ear ...

and

hydriodic acid Hydroiodic acid (or hydriodic acid) is an aqueous solution of hydrogen iodide (HI). It is a strong acid, one that is ionized completely in an aqueous solution. It is colorless. Concentrated solutions are usually 48% to 57% HI. Reactions Hy ...

to 260 °C, a dodecahydride is formed.

Chromic acid The term chromic acid is usually used for a mixture made by adding concentrated sulfuric acid to a dichromate, which may contain a variety of compounds, including solid chromium trioxide. This kind of chromic acid may be used as a cleaning mixt ...

oxidizes it to retene quinone,

phthalic acid Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. Phthalic aci ...

and

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...

. It forms a

picrate A picrate is a salt containing the anion (O2N)3C6H2O− or an ester derivative of the picrate anion. These salts are often produced by reactions of picric acid (2,4,6-trinitrophenol). The picrate ion is intensely yellow, although many of its salt ...

that melts at 123-124 °C. Retene is derived by degradation of specific

diterpenoid Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...

s biologically produced by

conifer Conifers are a group of conifer cone, cone-bearing Spermatophyte, seed plants, a subset of gymnosperms. Scientifically, they make up the phylum, division Pinophyta (), also known as Coniferophyta () or Coniferae. The division contains a single ...

trees. The presence of traces of retene in the air is an indicator of

forest fire A wildfire, forest fire, bushfire, wildland fire or rural fire is an unplanned, uncontrolled and unpredictable fire in an area of Combustibility and flammability, combustible vegetation. Depending on the type of vegetation present, a wildfire ...

s; it is a major product of

pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...

trees. It is also present in

effluent Effluent is wastewater from sewers or industrial outfalls that flows directly into surface waters either untreated or after being treated at a facility. The term has slightly different meanings in certain contexts, and may contain various pollut ...

s from

wood pulp Pulp is a lignocellulosic fibrous material prepared by chemically or mechanically separating cellulose fibers from wood, fiber crops, waste paper, or rags. Mixed with water and other chemical or plant-based additives, pulp is the major raw mate ...

and

paper mill A paper mill is a factory devoted to making paper from vegetable fibres such as wood pulp, old rags, and other ingredients. Prior to the invention and adoption of the Fourdrinier machine and other types of paper machine that use an endless belt, ...

s. Retene, together with

cadalene Cadalene or cadalin (4-isopropyl-1,6-dimethylnaphthalene) is a polycyclic aromatic hydrocarbon with a chemical formula C15H18 and a cadinane skeleton. It is derived from generic sesquiterpenes, and ubiquitous in essential oils of many higher pla ...

simonellite Simonellite (1,1-dimethyl-1,2,3,4-tetrahydro-7-isopropyl phenanthrene) is a polycyclic aromatic hydrocarbon with a chemical formula C19H24. It is similar to retene. Simonellite occurs naturally as an organic mineral derived from diterpenes presen ...

and ip-iHMN, is a

biomarker In biomedical contexts, a biomarker, or biological marker, is a measurable indicator of some biological state or condition. Biomarkers are often measured and evaluated using blood, urine, or soft tissues to examine normal biological processes, ...

higher plant Vascular plants (), also called tracheophytes () or collectively Tracheophyta (), form a large group of land plants ( accepted known species) that have lignified tissues (the xylem) for conducting water and minerals throughout the plant. They a ...

s, which makes it useful for

paleobotanic Paleobotany, which is also spelled as palaeobotany, is the branch of botany dealing with the recovery and identification of plant remains from geological contexts, and their use for the biological reconstruction of past environments (paleogeogr ...

analysis of rock

sediment Sediment is a naturally occurring material that is broken down by processes of weathering and erosion, and is subsequently transported by the action of wind, water, or ice or by the force of gravity acting on the particles. For example, sand an ...

s. The ratio of retene/cadalene in sediments can reveal the ratio of the genus ''

Pinaceae The Pinaceae, or pine family, are conifer trees or shrubs, including many of the well-known conifers of commercial importance such as Cedrus, cedars, firs, Tsuga, hemlocks, larches, pines and spruces. The family is included in the order Pinales, ...

'' in the biosphere.

Health Effects

A recent study has shown retene, which is a component of the Amazonian organic

PM10 Particulates – also known as atmospheric aerosol particles, atmospheric particulate matter, particulate matter (PM) or suspended particulate matter (SPM) – are microscopic particles of solid or liquid matter suspended in the air. The te ...

, is cytotoxic to human lung cells.

References

{{1911, wstitle=Retene, volume=23, page=202 Petroleum products Phenanthrenes Biomarkers Isopropyl compounds Polycyclic aromatic hydrocarbons