Skatole

Skatole
Names
	Preferred IUPAC name 3-Methyl-1H-indole
	Other names 3-Methylindole; 4-Methyl-2,3-benzopyrrole
Identifiers
CAS Number	83-34-1 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:9171 ;
ChemSpider	6480 ;
ECHA InfoCard	100.001.338
PubChem CID	6736;
UNII	9W945B5H7R ;
CompTox Dashboard (EPA)	DTXSID8021775 ;
	InChI InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3 Key: ZFRKQXVRDFCRJG-UHFFFAOYSA-N ; InChI=1/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3 Key: ZFRKQXVRDFCRJG-UHFFFAOYAZ;
	SMILES Cc1c[nH]c2ccccc12; c1cccc2c1c(c[nH]2)C;
Properties
Chemical formula	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)
Solubility in water	Insoluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

^ Oswald, Iain W. H.; Paryani, Twinkle R.; Sosa, Manuel E.; Ojeda, Marcos A.; Altenbernd, Mark R.; Grandy, Jonathan J.; Shafer, Nathan S.; Ngo, Kim; Peat, Jack R.; Melshenker, Bradley G.; Skelly, Ian; Koby, Kevin A.; Page, Michael F. Z.; Martin, Thomas J. (2023-10-12). "Minor, Nonterpenoid Volatile Compounds Drive the Aroma Differences of Exotic Cannabis". ACS Omega. 8 (42): 39203–39216. doi:10.1021/acsomega.3c04496. ISSN 2470-1343. PMC 10601067. PMID 37901519.
^ Brieger, Ludwig (1877). "Über die flüchtigen Bestandtheile der menschlichen Excremente" [On the volatile components of human excrement]. Berichte der Deutschen Chemischen Gesellschaft. 10: 1027–1032. doi:10.1002/cber.187701001288. Retrieved 3 November 2020.
^ Brieger, Ludwig (1878). "Über die flüchtigen Bestandtheile der menschlichen Excremente". Journal für Praktische Chemie. 17: 124–138. doi:10.1002/prac.18780170111. Retrieved 3 November 2020. Das Skatol ... (von το σχατος = faeces) ... (Skatole ... (from το σχατος = feces....)
^ Brieger, Ludwig (1879). "Über Skatol" [On skatole]. Berichte der Deutschen Chemischen Gesellschaft. 12 (2): 1985–1988. doi:10.1002/cber.187901202206. Retrieved 3 November 2020.

[1] Oswald, Iain W. H.; Paryani, Twinkle R.; Sosa, Manuel E.; Ojeda, Marcos A.; Altenbernd, Mark R.; Grandy, Jonathan J.; Shafer, Nathan S.; Ngo, Kim; Peat, Jack R.; Melshenker, Bradley G.; Skelly, Ian; Koby, Kevin A.; Page, Michael F. Z.; Martin, Thomas J. (2023-10-12). "Minor, Nonterpenoid Volatile Compounds Drive the Aroma Differences of Exotic Cannabis". ACS Omega. 8 (42): 39203–39216. doi:10.1021/acsomega.3c04496. ISSN 2470-1343. PMC 10601067. PMID 37901519.

[2] Brieger, Ludwig (1877). "Über die flüchtigen Bestandtheile der menschlichen Excremente" [On the volatile components of human excrement]. Berichte der Deutschen Chemischen Gesellschaft. 10: 1027–1032. doi:10.1002/cber.187701001288. Retrieved 3 November 2020.

[Brieger-1878-3] Brieger, Ludwig (1878). "Über die flüchtigen Bestandtheile der menschlichen Excremente". Journal für Praktische Chemie. 17: 124–138. doi:10.1002/prac.18780170111. Retrieved 3 November 2020. Das Skatol ... (von το σχατος = faeces) ... (Skatole ... (from το σχατος = feces....)

[4] Brieger, Ludwig (1879). "Über Skatol" [On skatole]. Berichte der Deutschen Chemischen Gesellschaft. 12 (2): 1985–1988. doi:10.1002/cber.187901202206. Retrieved 3 November 2020.

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