Skatole

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Skatole

Skatole or 3-methylindole is a mildly toxic white

White

White is a color, the Color vision#Physiology of color perception which is evoked by light that stimulates all three types of color sensitive cone cells in the human eye in near equal amount and with high brightness compared to the surroundings....
crystal

Crystal

A crystal or crystalline solid is a solid material whose constituent atoms, molecules, or ions are arranged in an orderly repeating pattern extending in all three spatial dimensions....
line organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
belonging to the indole

Indole

Indole is an aromatic Heterocyclic compound organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring....
family. It occurs naturally in feces

Feces

Feces, faeces, or f?ces is a waste product from an animal's gastrointestinal tract expelled through the anus during defecation....
(it is produced from tryptophan

Tryptophan

Tryptophan is one of the 20 List of standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG....
in the mammalian digestive tract), beet

Beet

The beet is a plant in the Amaranthaceae. It is best known its numerous cultivated varieties, the most well known of which is probably the red root vegetable known as the garden beet....
s, and coal tar

Coal tar

Coal tar is a brown or black liquid of high viscosity, which smells of naphthalene and aromatic hydrocarbons. Coal tar is among the by-products when coal is...
, and has a strong fecal odor

Odor

An odor or odour is a volatilized chemical compound, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction....
. In low concentration

Concentration

In chemistry, concentration is the measure of how much of a given chemical substance there is mixed with another substance. This can apply to any sort of chemical mixture, but most frequently the concept is limited to homogeneous solutions, where it refers to the amount of solute in the solvent....
s it has a flower

Flower

A flower, sometimes known as a bloom or blossom, is the reproduction structure found in flowering plants . The biological function of a flower is to mediate the union of male sperm with female ovum in order to produce seeds....
y smell and is found in several flower

Flower

Essential oil

An essential oil is a concentrated, hydrophobic liquid containing volatile aroma compounds from plants. They are also known as volatile or ethereal oils, or simply as the "oil of" the plant material from which they were extracted, such as oil of clove....
s, including those of orange

Orange (fruit)

An orange?specifically, the sweet orange?is the citrus Citrus sinensis and its fruit. The orange is a Hybrid of ancient cultivated origin, possibly between pomelo and tangerine ....
blossom

Blossom

Blossom is a term given to the flowers of stone fruit fruit tree and of some other plants with a similar appearance that flower profusely but for a short period of time in the spring....
s, jasmine

Jasmine

Jasmine is a genus of shrubs and vines in the olive family ,with about 200 species, native to tropical and warm temperate regions of the Old World....
, and Ziziphus mauritiana
Ziziphus mauritiana

Ziziphus mauritiana is a tropical fruit tree species, belonging to the family Rhamnaceae. It is native to southern Asia though it is also cultivated and naturalisation elsewhere in the dry tropics, notably in Africa....
. It is used as a fragrance and fixative

Fixative

A fixative is a stabilizing or preservative agent:*Fixative *Fixation , a solution used to preserve or harden fresh tissue of cell specimens for microscopic examination....
in many perfume

Perfume

Perfume is a mixture of fragrant essential oils and aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces a pleasant smell....
s and as an aroma compound

Aroma compound

An aroma compound, also known as odorant, aroma, fragrance or flavor, is a chemical compound that has a smell or odor. A chemical compound has a smell or odor when two conditions are met: the compound needs to be volatile, so it can be transported to the olfactory system in the upper part of the nose, and it needs to b...
. Its name is derived from the Greek root skato- meaning "dung

Dung

Dung may refer to:* Dung, animal feces* Dung, Doubs, a commune in the Doubs department in France* Mundungus Fletcher , a character in Harry Potter...
".

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Chemical properties

Skatole can be found as a white crystalline or fine powder solid, and it browns upon aging. It is nitrogenous and one of the rings is a pyrrole

Pyrrole

Pyrrole, or pyrrol, is a heterocyclic aromatic organic compound, a five-membered ring with the chemical formula carbon4hydrogen4nitrogenH....
. It is soluble in alcohol and benzene

Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
and it gives a violet color in potassium ferrocyanide (K

Potassium

Potassium is a chemical element. It has the symbol K , atomic number 19, and atomic mass 39.0983. Potassium was first isolated from potash, hence the name....
₄Fe

Iron

Iron is a chemical element with the symbol Fe and atomic number 26. Iron is a Group 8 element and period 4 element. Iron is lustrous and silvery in color....
(CN

Cyanide

A cyanide is any chemical compound that contains the nitrile , which consists of a carbon atom chemical bond to a nitrogen atom. Inorganic cyanides are hydrogen cyanide salts in which cyanide is generally the anion CN-....
)₆·3H

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
₂O

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
) and sulfuric acid

Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
(H

Hydrogen

Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
O

Oxygen

Aromaticity

Aromaticity is a chemical property in which a conjugated system ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone....
. It is continuous (all atoms in the ring are sp² hybridized), planar, and follows the 4n+2 rule because it has 10 p electrons. It can be synthesized through a Fischer indole synthesis

Fischer indole synthesis

The Fischer indole synthesis is a chemical reaction that produces the aromatic Heterocyclic compound indole from a phenylhydrazine and an aldehyde or ketone under acidic conditions....
which was developed by Emil Fischer

Emil Fischer

Emil Fischer may refer to:* Emil Fischer , famous German dramatic basso* Franz Joseph Emil Fischer , German chemist* Hermann Emil Fischer , German chemist...
.

Insect attractant

It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.

3-Methylindole has been shown to be an attractant to gravid mosquitoes in both field and laboratory conditions. Because this compound is present in feces, it is found in combined sewage overflows (CSO) as streams and lakes containing CSO water have untreated human and industrial waste. Knowledge of this attractant makes CSO sites of particular interest when studying mosquito-borne diseases such as West Nile Virus

West Nile virus

West Nile virus is a virus of the family Flaviviridae. Part of the Japanese encephalitis antigenic complex of viruses, it is found in both tropics and temperate regions....
.

Safety

Skatole has been shown to cause pulmonary edema

Pulmonary edema

Pulmonary edema , or oedema , is swelling and/or fluid accumulation in the lungs. It leads to impaired gas exchange and may cause respiratory failure....
in goats, sheep, rats, and some strains of mice. It appears to selectively target Clara cell

Clara cell

Clara cells are non-mucous and non-ciliated secretion cell found in the primary bronchioles of the lungs.Clara cells are dome-shaped and have short microvilli....
s, which are the major site of cytochrome P450 enzymes in the lungs. These enzymes convert skatole to a reactive intermediate, 3-methyleneindolenine, which damages cells by forming protein adduct

Adduct

An adduct is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components, with formation of two chemical bonds and a net reduction in bond multiplicity in at least one of the reactants....
s.

In a 1994 report released by five top cigarette

Cigarette

A cigarette is a product consumed through smoking and manufactured out of curing and finely cut tobacco leaves and reconstituted tobacco, often combined with other List of additives in cigarettes, then rolled or stuffed into a paper-wrapped cylinder ....
companies, skatole was listed as one of the 599 additives to cigarettes. It is added as a flavoring ingredient.

Skatole

Chemical properties

Insect attractant

Safety

See also

External links