organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...

, polyenes are poly- unsaturated,

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. The ...

s that contain at least three alternating

double A double is a look-alike or doppelgänger; one person or being that resembles another. Double, The Double or Dubble may also refer to: Film and television * Double (filmmaking), someone who substitutes for the credited actor of a character * Th ...

() and

single Single may refer to: Arts, entertainment, and media * Single (music), a song release Songs * "Single" (Natasha Bedingfield song), 2004 * "Single" (New Kids on the Block and Ne-Yo song), 2008 * "Single" (William Wei song), 2016 * "Single", by ...

()

carbon–carbon bond A carbon–carbon bond is a covalent bond between two carbon atoms. The most common form is the single bond: a bond composed of two electrons, one from each of the two atoms. The carbon–carbon single bond is a sigma bond and is formed b ...

s. These carbon–carbon double bonds interact in a process known as

conjugation Conjugation or conjugate may refer to: Linguistics * Grammatical conjugation, the modification of a verb from its basic form * Emotive conjugation or Russell's conjugation, the use of loaded language Mathematics * Complex conjugation, the chang ...

, resulting in some unusual

optical properties The optical properties of a material define how it interacts with light. The optical properties of matter are studied in optical physics, a subfield of optics. The optical properties of matter include: *Refractive index *Dispersion *Transmittance an ...

. Related to polyenes are

diene In organic chemistry a diene ( ) (diolefin ( ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nomenclature. ...

s, where there are only two alternating double and single bonds. The following polyenes are used as

antibiotics An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention o ...

for humans:

amphotericin B Amphotericin B is an antifungal medication used for serious fungal infections and leishmaniasis. The fungal infections it is used to treat include mucormycosis, aspergillosis, blastomycosis, candidiasis, coccidioidomycosis, and cryptococcosis. Fo ...

nystatin Nystatin, sold under the brandname Mycostatin among others, is an antifungal medication. It is used to treat '' Candida'' infections of the skin including diaper rash, thrush, esophageal candidiasis, and vaginal yeast infections. It may also be ...

candicidin Candicidin is an antifungal compound obtained from ''Streptomyces griseus''. It is active against some fungi including ''Candida albicans''. Candicidin is administered intravaginally in the treatment of vulvovaginal candidiasis. This bioactive c ...

pimaricin Natamycin, also known as pimaricin, is an antifungal medication used to treat fungal infections around the eye. This includes infections of the eyelids, conjunctiva, and cornea. It is used as eyedrops. Natamycin is also used in the food industr ...

, methyl partricin, and

trichomycin Hachimycin, also known as trichomycin, is a polyene macrolide antibiotic, antiprotozoal, and antifungal derived from streptomyces ''Streptomyces'' is the largest genus of Actinomycetota and the type genus of the family Streptomycetaceae. Over ...

Optical properties

Some polyenes are brightly colored, an otherwise rare property for a hydrocarbon. Normally alkenes absorb in the

ultraviolet Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nanometer, nm (with a corresponding frequency around 30 Hertz, PHz) to 400 nm (750 Hertz, THz), shorter than that of visible light, but longer than ...

region of a

spectrum A spectrum (plural ''spectra'' or ''spectrums'') is a condition that is not limited to a specific set of values but can vary, without gaps, across a continuum. The word was first used scientifically in optics to describe the rainbow of colors i ...

, but the absorption energy state of polyenes with numerous conjugated double bonds can be lowered such that they enter the visible region of the spectrum, resulting in compounds which are coloured (because they contain a

chromophore A chromophore is the part of a molecule responsible for its color. The color that is seen by our eyes is the one not absorbed by the reflecting object within a certain wavelength spectrum of visible light. The chromophore is a region in the molec ...

). Thus many natural

dye A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution an ...

s contain linear polyenes.

Chemical and electrical properties

Polyenes tend to be more reactive than simpler alkenes. For example, polyene-containing

triglycerides A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''tri-'' and ''glyceride''). Triglycerides are the main constituents of body fat in humans and other vertebrates, as we ...

are reactive towards atmospheric oxygen.

Polyacetylene Polyacetylene (IUPAC name: polyethyne) usually refers to an organic polymer with the repeating unit . The name refers to its conceptual construction from polymerization of acetylene to give a chain with repeating olefin groups. This compound i ...

, which partially oxidized or reduced, exhibits high electrical conductivity. Most

conductive polymer Conductive polymers or, more precisely, intrinsically conducting polymers (ICPs) are organic polymers that conduct electricity. Such compounds may have metallic conductivity or can be semiconductors. The biggest advantage of conductive polymer ...

s are polyenes, and many have conjugated structures. Poly(aza)acetylenes are readily prepared from

pyridine Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...

precursors without the necessity of a controlled atmosphere, simply by

irradiation of a mixture of pyridine and poly(4-vinyl) pyridine. Recent research at the

Weizmann Institute The Weizmann Institute of Science ( he, מכון ויצמן למדע ''Machon Vaitzman LeMada'') is a public research university in Rehovot, Israel, established in 1934, 14 years before the State of Israel. It differs from other Israeli univ ...

and

Aix-Marseille University Aix-Marseille University (AMU; french: Aix-Marseille Université; formally incorporated as ''Université d'Aix-Marseille'') is a public research university located in the Provence region of southern France. It was founded in 1409 when Louis II o ...

showed a clear transition between ionic and electronic conductivity with increasing UV dose over 30 hours.

Occurrence

A few

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...

s are polyenes. Another class of important polyenes are

polyene antimycotic Polyene antimycotics, sometimes referred to as polyene antibiotics, are a class of antimicrobial polyene compounds that target fungi. These polyene antimycotics are typically obtained from some species of ''Streptomyces'' bacteria. Previously, pol ...

s, File:Amphotericin B new.svg,

Amphotericin B Amphotericin B is an antifungal medication used for serious fungal infections and leishmaniasis. The fungal infections it is used to treat include mucormycosis, aspergillosis, blastomycosis, candidiasis, coccidioidomycosis, and cryptococcosis. Fo ...

is an example of a polyene antifungal (antimycotic) agent. File:Leukotriene A4.svg,

Leukotriene Leukotrienes are a family of eicosanoid inflammatory mediators produced in leukocytes by the oxidation of arachidonic acid (AA) and the essential fatty acid eicosapentaenoic acid (EPA) by the enzyme arachidonate 5-lipoxygenase. Leukotrienes ...

A4 is a regulator of the immune response. File:Trans-Polyacetylene.svg,

s are a synthetic polymer of theoretical interest because they exhibit metallic properties upon oxidation.Lam, Jacky W. Y.; Tang, Ben Zhong "Functional Polyacetylenes" Accounts of Chemical Research 2005, volume 38, pp. 745-754.

References

{{reflist Polyenes Conjugated hydrocarbons