Skatole

Source: Wikipedia, the free encyclopedia.
Skatole
Names
Preferred IUPAC name
3-Methyl-1H-indole
Other names
3-Methylindole
4-Methyl-2,3-benzopyrrole
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
100.001.338 Edit this at Wikidata
UNII
  • InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3 checkY
    Key: ZFRKQXVRDFCRJG-UHFFFAOYSA-N checkY
  • InChI=1/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3
    Key: ZFRKQXVRDFCRJG-UHFFFAOYAZ
  • Cc1c[nH]c2ccccc12
  • c1cccc2c1c(c[nH]2)C
Properties
C9H9N
Molar mass 131.178 g·mol−1
Appearance White crystalline solid
Odor Fecal Matter (In low concentrations it can have a pleasant flowery aroma)
Melting point 93 to 95 °C (199 to 203 °F; 366 to 368 K)
Boiling point 265 °C (509 °F; 538 K)
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Skatole or 3-methylindole is an organic compound belonging to the indole family. It occurs naturally in the feces of mammals and birds and is the primary contributor to fecal odor. In low concentrations, it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. It has also been identified in certain cannabis varieties.[1]

It is used as a fragrance and fixative in many perfumes and as an aroma compound. Its name derives from the Greek root skato-, meaning feces. Skatole was discovered in 1877 by the German physician Ludwig Brieger (1849–1919).[2][3][4]

Original: "Ich habe mich zuerst mit der Untersuchung der flüchtigen Bestandtheile der Excremente aus sauerer Lösung beschäftigt. Es wurden dabei die flüchtigen Fettsäuren: Essigsäure, normale und Isobuttersäure, sowie die aromatischen Substanzen: Phenol, Indol und eine neue dem Indol verwandte Substanz, die ich Skatol nennen werde, erhalten."


Translation: "I was occupied initially with the investigation of the volatile components of excrement in acidic solution. One obtained thereby volatile fatty acids; acetic acid; normal and isobutyric acid; as well as the aromatic substances: phenol, indole and a new substance which is related to indole and which I will name 'skatole'." - Brieger (1878), page 130


Biosynthesis, chemical synthesis, and reactions

Skatole is derived from the amino acid

decarboxylates to give the methylindole.[5][6]

Skatole can be synthesized via the Fischer indole synthesis.[7]

It gives a violet color upon treatment with potassium ferrocyanide.[citation needed]

Skatole, along with the fecal odorant indole, can be neutralized by combining it with other scents, by producing perfumes or air fresheners that lack skatole and indole. In a manner similar to noise-cancelling headphones, the scent produced by the resultant concentrations of skatole and indole relative to other substances in the freshener is thus "in-phase" and perceived as pleasant.[8]

Insect attractant

Skatole is one of many compounds that are attractive to males of various species of

orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait for these bees for study.[9] It is also known for being an attractant for the Tasmanian grass grub beetle (Aphodius tasmaniae).[10]

Skatole has been shown to be an attractant to

combined sewage overflows (CSO), as streams and lakes containing CSO water have untreated human and industrial waste. CSO sites are thus of particular interest when studying mosquito-borne diseases such as West Nile virus.[11]

Animal studies

Skatole occurs naturally in the feces of all species of mammals and birds, and in the

Skatole has been shown to cause pulmonary edema in goats, sheep, rats, and some strains of mice. It appears to selectively target club cells, 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 adducts (see fog fever).[13]

With the testicular steroid androstenone, skatole is regarded as a principal determinant of boar taint.[14]

Skatole contributes to bad breath.[15]

Application

Skatole is the starting material in the synthesis of atiprosin.

See also

References

  1. PMID 37901519
    .
  2. . Retrieved 3 November 2020.
  3. . Retrieved 3 November 2020. Das Skatol ... (von το σχατος = faeces) ... (Skatole ... (from το σχατος = feces....)
  4. . Retrieved 3 November 2020.
  5. .
  6. .
  7. ^ Emil Fischer (1886) "Indole aus Phenylhydrazin" (Indole from phenylhydrazine), Annalen der Chemie, vol. 236, pages 126-151; for Fischer's synthesis of skatole, see page 137. (Fischer was not the first to prepare skatole. It was prepared, via other methods, in 1880 by von Baeyer, and in 1883 by Otto Fischer and German and by Fileti.)
  8. ^ Holusha, John (15 July 1990). "Technology; Making Bad Smell Good by Tricking the Nose". The New York Times.
  9. S2CID 2845587
    .
  10. .
  11. S2CID 23784247.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
  12. .
  13. .
  14. .
  15. . Retrieved 3 November 2020.