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Wikipedia

Skatole

October 21, 2023

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]

Skatole
Names
Preferred IUPAC name
3-Methyl-1H-indole
Other names
3-Methylindole
4-Methyl-2,3-benzopyrrole
Identifiers
  • 83-34-1 Y
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:9171 Y
ChemSpider
  • 6480 Y
ECHA InfoCard 100.001.338
  • 6736
UNII
  • 9W945B5H7R Y
  • DTXSID8021775
  • 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 ?)

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 Edit

Skatole is derived from the amino acid tryptophan in the digestive tract of mammals. Tryptophan is converted to indoleacetic acid, which 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 Edit

See also: Aphodius

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 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. CSO sites are thus of particular interest when studying mosquito-borne diseases such as West Nile virus.[11]

Animal studies Edit

Skatole occurs naturally in the feces of all species of mammals and birds, and in the bovine rumen.[12]

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 Edit

Skatole is the starting material in the synthesis of atiprosin.

See also Edit

References Edit

  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. doi:10.1021/acsomega.3c04496. ISSN 2470-1343.
  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.
  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.
  5. ^ Whitehead, T. R.; Price, N. P.; Drake, H. L.; Cotta, M. A. (25 January 2008). "Catabolic pathway for the production of skatole and indoleacetic acid by the acetogen Clostridium drakei, Clostridium scatologenes, and swine manure". Applied and Environmental Microbiology. 74 (6): 1950–3. Bibcode:2008ApEnM..74.1950W. doi:10.1128/AEM.02458-07. PMC 2268313. PMID 18223109.
  6. ^ Yokoyama, M. T.; Carlson, J. R. (1979). "Microbial metabolites of tryptophan in the intestinal tract with special reference to skatole". The American Journal of Clinical Nutrition. 32 (1): 173–178. doi:10.1093/ajcn/32.1.173. PMID 367144.
  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. ^ Schiestl, F.P. & Roubik, D.W. (2004). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology. 29 (1): 253–257. doi:10.1023/A:1021932131526. hdl:20.500.11850/57276. PMID 12647866. S2CID 2845587.
  10. ^ Osborne, G. O.; Penman, D. R.; Chapman, R. B. (1975). "Attraction of Aphodius tasmaniae Hope to skatole". Australian Journal of Agricultural Research. 26 (5): 839–841. doi:10.1071/AR9750839.
  11. ^ Beechler, J W., J G Miller, and M S Mulla (1994). "Field evaluation of synthetic compounds mediating oviposition in Culex mosquitoes (Diptera: Culicidae)". J Chem Ecol. 20 (2): 281–291. doi:10.1007/BF02064436. PMID 24242053. S2CID 23784247.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  12. ^ Yokoyama, M. T.; Carlson, J. R.; Holdeman, L. V. (1977). "Isolation and characteristics of a skatole-producing Lactobacillus sp. from the bovine rumen". Applied and Environmental Microbiology. 34 (6): 837–842. Bibcode:1977ApEnM..34..837Y. doi:10.1128/AEM.34.6.837-842.1977. PMC 242757. PMID 563703.
  13. ^ Miller, M; Kottler, S; Ramos-Vara, J; Johnson, P; Ganjam, V; Evans, T (2003). "3-Methylindole Induces Transient Olfactory Mucosal Injury in Ponies". Veterinary Pathology. 40 (4): 363–70. doi:10.1354/vp.40-4-363. PMID 12824507.
  14. ^ Wesoly, R.; Weiler, U. (2012). "Nutritional Influences on Skatole Formation and Skatole Metabolism in the Pig". Animals. 2 (2): 221–242. doi:10.3390/ani2020221. PMC 4494329. PMID 26486918.
  15. ^ Franklin, Deborah (1 May 2013). "To Beat Bad Breath, Keep the Bacteria in Your Mouth Happy". Scientific American. 308 (5): 30, 32. doi:10.1038/scientificamerican0513-30. PMID 23627212. Retrieved 3 November 2020.

October 21, 2023
skatole, methylindole, organic, compound, belonging, indole, family, occurs, naturally, feces, mammals, birds, primary, contributor, fecal, odor, concentrations, flowery, smell, found, several, flowers, essential, oils, including, those, orange, blossoms, jasm. 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 Skatole NamesPreferred IUPAC name 3 Methyl 1H indoleOther names 3 Methylindole4 Methyl 2 3 benzopyrroleIdentifiersCAS Number 83 34 1 Y3D model JSmol Interactive imageInteractive imageChEBI CHEBI 9171 YChemSpider 6480 YECHA InfoCard 100 001 338PubChem CID 6736UNII 9W945B5H7R YCompTox Dashboard EPA DTXSID8021775InChI InChI 1S C9H9N c1 7 6 10 9 5 3 2 4 8 7 9 h2 6 10H 1H3 YKey ZFRKQXVRDFCRJG UHFFFAOYSA N YInChI 1 C9H9N c1 7 6 10 9 5 3 2 4 8 7 9 h2 6 10H 1H3Key ZFRKQXVRDFCRJG UHFFFAOYAZSMILES Cc1c nH c2ccccc12c1cccc2c1c c nH 2 CPropertiesChemical formula C 9H 9NMolar mass 131 178 g mol 1Appearance White crystalline solidOdor 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 InsolubleExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N 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 2 3 4 Original Ich habe mich zuerst mit der Untersuchung der fluchtigen Bestandtheile der Excremente aus sauerer Losung beschaftigt Es wurden dabei die fluchtigen Fettsauren Essigsaure normale und Isobuttersaure 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 Contents 1 Biosynthesis chemical synthesis and reactions 2 Insect attractant 3 Animal studies 4 Application 5 See also 6 ReferencesBiosynthesis chemical synthesis and reactions EditSkatole is derived from the amino acid tryptophan in the digestive tract of mammals Tryptophan is converted to indoleacetic acid which 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 EditSee also Aphodius 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 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 CSO sites are thus of particular interest when studying mosquito borne diseases such as West Nile virus 11 Animal studies EditSkatole occurs naturally in the feces of all species of mammals and birds and in the bovine rumen 12 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 EditSkatole is the starting material in the synthesis of atiprosin See also Edit1 Methylindole 2 Methylindole methylketol 5 Methylindole 7 Methylindole CadaverineReferences Edit 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 doi 10 1021 acsomega 3c04496 ISSN 2470 1343 Brieger Ludwig 1877 Uber die fluchtigen 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 Uber die fluchtigen Bestandtheile der menschlichen Excremente Journal fur Praktische Chemie 17 124 138 doi 10 1002 prac 18780170111 Retrieved 3 November 2020 Das Skatol von to sxatos faeces Skatole from to sxatos feces Brieger Ludwig 1879 Uber Skatol On skatole Berichte der Deutschen Chemischen Gesellschaft 12 2 1985 1988 doi 10 1002 cber 187901202206 Retrieved 3 November 2020 Whitehead T R Price N P Drake H L Cotta M A 25 January 2008 Catabolic pathway for the production of skatole and indoleacetic acid by the acetogen Clostridium drakei Clostridium scatologenes and swine manure Applied and Environmental Microbiology 74 6 1950 3 Bibcode 2008ApEnM 74 1950W doi 10 1128 AEM 02458 07 PMC 2268313 PMID 18223109 Yokoyama M T Carlson J R 1979 Microbial metabolites of tryptophan in the intestinal tract with special reference to skatole The American Journal of Clinical Nutrition 32 1 173 178 doi 10 1093 ajcn 32 1 173 PMID 367144 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 Holusha John 15 July 1990 Technology Making Bad Smell Good by Tricking the Nose The New York Times Schiestl F P amp Roubik D W 2004 Odor Compound Detection in Male Euglossine Bees Journal of Chemical Ecology 29 1 253 257 doi 10 1023 A 1021932131526 hdl 20 500 11850 57276 PMID 12647866 S2CID 2845587 Osborne G O Penman D R Chapman R B 1975 Attraction of Aphodius tasmaniae Hope to skatole Australian Journal of Agricultural Research 26 5 839 841 doi 10 1071 AR9750839 Beechler J W J G Miller and M S Mulla 1994 Field evaluation of synthetic compounds mediating oviposition in Culex mosquitoes Diptera Culicidae J Chem Ecol 20 2 281 291 doi 10 1007 BF02064436 PMID 24242053 S2CID 23784247 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Yokoyama M T Carlson J R Holdeman L V 1977 Isolation and characteristics of a skatole producing Lactobacillus sp from the bovine rumen Applied and Environmental Microbiology 34 6 837 842 Bibcode 1977ApEnM 34 837Y doi 10 1128 AEM 34 6 837 842 1977 PMC 242757 PMID 563703 Miller M Kottler S Ramos Vara J Johnson P Ganjam V Evans T 2003 3 Methylindole Induces Transient Olfactory Mucosal Injury in Ponies Veterinary Pathology 40 4 363 70 doi 10 1354 vp 40 4 363 PMID 12824507 Wesoly R Weiler U 2012 Nutritional Influences on Skatole Formation and Skatole Metabolism in the Pig Animals 2 2 221 242 doi 10 3390 ani2020221 PMC 4494329 PMID 26486918 Franklin Deborah 1 May 2013 To Beat Bad Breath Keep the Bacteria in Your Mouth Happy Scientific American 308 5 30 32 doi 10 1038 scientificamerican0513 30 PMID 23627212 Retrieved 3 November 2020 Retrieved from https en wikipedia org w index php title Skatole amp oldid 1180915149, wikipedia, wiki, book, books, library,

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