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Skatole or 3-methylindole is a mildly toxic white crystalline organic compound belonging to the indole family. It occurs naturally in feces (it is produced from tryptophan in the mammalian digestive tract) and coal tar and has a strong 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 is used as a fragrance and fixative in many perfumes and as an aroma compound. Its name is derived from the Greek root skato- meaning "dung". Skatole was discovered in 1877 by the German physician Ludwig Brieger (1849-1919).^[1] Skatole is also used by U.S. military in its non-lethal weaponry; specifically, malodorants.^[2]

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. It is soluble in alcohol and benzene, and it gives a violet color in potassium ferrocyanide (K₄Fe(CN)₆·3H₂O) and sulfuric acid (H₂SO₄). Skatole has a double ring system that displays aromaticity. It is continuous (all atoms in the ring are sp² hybridized), planar, and follows the 4n+2 rule because it has 10 π electrons. It can be synthesized through a Fischer indole synthesis, which was developed by Emil Fischer.^[3]

Insect attractant

Skatole 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.^[4]

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. Knowledge of this attractant makes CSO sites of particular interest when studying mosquito-borne diseases such as West Nile Virus.^[5]

Safety

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).^[6]

References

^ Brieger, Ludwig (1877) "Ueber die flüchtigen Bestandtheile der menschlichen Excremente" (On the volitile components of human excrement), Berichte der deutschen chemischen Gesellschaft, vol. 10, pages 1027-1032; reprinted in: "Ueber die flüchtigen Bestandtheile der menschlichen Excremente", Journal für Praktische Chemie, vol. 17, pages 124-138 (1878). See also: Brieger, Ludwig (1879) "Ueber Skatol" (On skatole), Berichte der deutschen chemischen Gesellschaft, vol. 12, pages 1985-1988.
Brieger named skatole in Brieger (1877), page 1028:

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 volitile components of excrement in acidic solution. One obtained thereby volitile 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 (1877), page 1030: Das Skatol ... (von το σχατος = faeces) ... (Skatole ... (from το σχατος = feces) ....)
^ U.S. Patent 6,386,113
^ 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. (It should be noted that 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.)
^ 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. PMID 12647866.
^ 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.
^ Miller, M; Kottler S, Ramos-Vara J, Johnson P, Ganjam V and 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.

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1. 口臭 bad breath

English Journal

Influence of fresh alfalfa supplementation on fat skatole and indole concentration and chop odour and flavour in lambs grazing a cocksfoot pasture.

Devincenzi T1, Prunier A2, Meteau K3, Nabinger C4, Prache S5.
Meat science.Meat Sci.2014 Dec;98(4):607-14. doi: 10.1016/j.meatsci.2014.06.008. Epub 2014 Jun 16.
We investigated the influence of the level of fresh alfalfa supplementation on fat skatole and indole concentration and chop sensory attributes in grazing lambs. Four groups of nine male Romane lambs grazing a cocksfoot pasture were supplemented with various levels of alfalfa for at least 60days bef
PMID 25089784

Measurement of boar taint in porcine fat using a high-throughput gas chromatography-mass spectrometry protocol.

Sørensen KM1, Engelsen SB.
Journal of agricultural and food chemistry.J Agric Food Chem.2014 Oct 1;62(39):9420-7. doi: 10.1021/jf5022785. Epub 2014 Sep 17.
This work outlines an optimized gas chromatrography-mass spectrometry (GC-MS) based protocol for screening of the presence of the three boar-taint-producing compounds indole, skatole (3-methylindole), and androstenone (5α-androst-16-en-3-one) in porcine fat. The study shows that an accuracy suitabl
PMID 25230360

How olfactory acuity affects the sensory assessment of boar fat: a proposal for quantification.

Trautmann J1, Gertheiss J2, Wicke M1, Mörlein D3.
Meat science.Meat Sci.2014 Oct;98(2):255-62. doi: 10.1016/j.meatsci.2014.05.037. Epub 2014 Jun 7.
Due to animal welfare concerns the production of entire male pigs is one viable alternative to surgical castration. Elevated levels of boar taint may, however, impair consumer acceptance. Due to the lack of technical methods, control of boar taint is currently done using sensory quality control. Whi
PMID 24976560

Japanese Journal

におい識別装置及びGC/MSによる腐敗臭豚腸の簡易判定について

升井洋至,長尾綾子
武庫川女子大学紀要. 自然科学編 60, 35-40, 2013
… In this study, we examined the simplified method for estimating the quality of porcine bowels with FragranceAnalyzer（ FF-1） and GC/MS. In the experiment with FF-1, we examined for skatole as the ingredientof excrement smell. … In GC/MS analysis,skatole and hexanal were detected in all samples. … It is possible to use the FF-1 to estimating the quality of porcine bowels by thecombination with GC/MS analysis identifying the unpleasant odor except for skatole as the standard for qualityestimation. …
NAID 110009574660

室内の温湿度がにおいに対する嗅覚閾値,臭気強度,快・不快度に与える影響

長谷博子,光田恵
人間と生活環境 19(1), 35-43, 2012-05
本研究では,室内の温湿度がにおいに対する嗅覚閾値,臭気強度と快・不快度に及ぼす影響を官能評価により検討することを目的とした.パネルは,若年者の男性7名を対象とした.におい物質は,スカトール,イソ吉草酸,β-フェニルエチルアルコールを用いた.測定項目は,嗅覚閾値,臭気強度と快・不快度とした.嗅覚閾値は,におい物質間や温湿度条件間において,有意な差は認められなかった.スカトールは,嗅覚閾値の平均が最も …
NAID 110009444625

豚脂肪中のスカトール含量と官能評価への影響

西岡輝美,石塚譲,因野要一 [他],入江正和
日本畜産學會報 = The Japanese journal of zootechnical science 82(2), 147-153, 2011-05-25
豚肉の嗜好性に影響を与えるにおい物質の現状を把握するとともに，におい物質含量の違いをどの程度識別できるのかを明らかにするため，市場出荷豚128頭の脂肪中のスカトール，インドール各含量を測定し，さらに官能評価に基づくスカトール識別濃度を調査した．市場出荷された去勢豚と雌豚の背脂肪中スカトール含量は，0.00 μg/gから0.20 μg/gに達するものまで個体により大きく異なっていたが，中央値は0.0 …
NAID 10029741644

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リンク元

「スカトール」

Skatole
Names
	IUPAC name 3-methylindole
	Other names 4-Methyl-2,3-benzopyrrole
Identifiers
CAS Registry Number	83-34-1
ChEBI	CHEBI:9171
ChemSpider	6480
	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 ;
Jmol-3D images	Image; Image
PubChem	6736
	SMILES C1=C2C(=CC=C1)C(=C[N]2C)C ; c1cccc2c1c(cn2)C ;
UNII	9W945B5H7R
Properties
Chemical formula	C9H9N
Molar mass	131.18 g·mol−1
Appearance	White crystalline solid
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).
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	Infobox references

　　[★]

英: skatole
同: 3-メチルインドール、β-メチルインドール β-methylindole
関: トリプトファン

[1] Brieger, Ludwig (1877) "Ueber die flüchtigen Bestandtheile der menschlichen Excremente" (On the volitile components of human excrement), Berichte der deutschen chemischen Gesellschaft, vol. 10, pages 1027-1032; reprinted in: "Ueber die flüchtigen Bestandtheile der menschlichen Excremente", Journal für Praktische Chemie, vol. 17, pages 124-138 (1878). See also: Brieger, Ludwig (1879) "Ueber Skatol" (On skatole), Berichte der deutschen chemischen Gesellschaft, vol. 12, pages 1985-1988.
Brieger named skatole in Brieger (1877), page 1028:

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 volitile components of excrement in acidic solution. One obtained thereby volitile 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 (1877), page 1030: Das Skatol ... (von το σχατος = faeces) ... (Skatole ... (from το σχατος = feces) ....)

[2] U.S. Patent 6,386,113

[3] 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. (It should be noted that 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.)

[4] 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. PMID 12647866.

[5] 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.

[6] Miller, M; Kottler S, Ramos-Vara J, Johnson P, Ganjam V and 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.

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skatole