Skatole

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.

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
UNII
  • InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3 Y
    Key: ZFRKQXVRDFCRJG-UHFFFAOYSA-N Y
  • 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).
Y verify (what is YN ?)
Infobox references

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).

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

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.