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W301912

Sigma-Aldrich

Skatole

≥98%

Synonyme(s) :

3-Methylindole, Skatole

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About This Item

Formule empirique (notation de Hill):
C9H9N
Numéro CAS:
83-34-1
Poids moléculaire :
131.17
Numéro FEMA:
3019
Numéro Beilstein :
111296
Numéro CE :
201-471-7
Numéro MDL:
MFCD00005627
Code UNSPSC :
12164502
ID de substance PubChem :
329830553
Numéro Flavis :
14.004
Nomenclature NACRES :
NA.21

Source biologique

synthetic

Agence

meets purity specifications of JECFA

Pureté

≥98%

Point d'ébullition

265-266 °C (lit.)

Pf

92-97 °C (lit.)

Application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

Allergène alimentaire

no known allergens

Propriétés organoleptiques

animalic

Chaîne SMILES 

Cc1c[nH]c2ccccc12

InChI

1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3

Clé InChI

ZFRKQXVRDFCRJG-UHFFFAOYSA-N

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Description générale

Skatole is an indole derivative with a strong fecal odor that occurs naturally in feces formed due to the degradation of tryptophan. It is found in several flowers such as jasmine owing to its flowery smell when present in low concentration. Skatole is also one of the key contributors to the development of boar taint in fat samples.

Application


  • Microbiome-metabolomics analysis reveals abatement effects of itaconic acid on odorous compound production in Arbor Acre broilers.: Investigates the impact of itaconic acid on the microbiome and metabolomics profiles of broilers, significantly reducing skatole production, which is a key contributor to odors in poultry (Zhu et al., 2023).

  • Postmortomics: The Potential of Untargeted Metabolomics to Highlight Markers for Time Since Death.: Discusses the potential of untargeted metabolomics in forensic science to identify time-since-death markers, including skatole, which is relevant in decomposition studies (Pesko et al., 2020).
  • A versatile method for producing labeled or unlabeled Aß55, Aß40, and other ß-amyloid family peptides.: This article describes methods for producing peptides in biochemistry, including skatole, used in research contexts related to protein misfolding diseases (Zerweck et al., 2019).

  • Chemical-Mediated Digestion: An Alternative Realm for Middle-down Proteomics: Explores alternative methods for protein digestion in proteomics, using chemical mediators including skatole to facilitate the process, offering new avenues for the study of protein structures and functions (Srzentic et al., 2018).

Clause de non-responsabilité

For R&D or non-EU Food use. Not for retail sale.

Pictogrammes

Environment
GHS09

Mentions de danger

H411

Conseils de prudence

P273 - P391 - P501

Classification des risques

Aquatic Chronic 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

269.6 °F

Point d'éclair (°C)

132 °C

Certificats d'analyse (COA)

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Skatole (2010)
Role of 4-phenyl-3-buten-2-one in boar taint: identification of new compounds related to sensorial descriptors in pig fat.
Rius Sole MA & Garcia Regueiro JA.
Journal of Agricultural and Food Chemistry, 49(11), 5303-5309 (2001)
Walter S Leal et al.
PloS one, 3(8), e3045-e3045 (2008-08-30)
Synthetic mosquito oviposition attractants are sorely needed for surveillance and control programs for Culex species, which are major vectors of pathogens causing various human diseases, including filariasis, encephalitis, and West Nile encephalomyelitis. We employed novel and conventional chemical ecology approaches
Mechanisms of 3-methylindole pneumotoxicity.
G S Yost
Chemical research in toxicology, 2(5), 273-279 (1989-09-01)
James B Y H Behrendorff et al.
Chemical research in toxicology, 25(9), 1964-1974 (2012-08-21)
Cytochrome P450 2F1 (P450 2F1) is expressed exclusively in the human respiratory tract and is implicated in 3-methylindole (3MI)-induced pneumotoxicity via dehydrogenation of 3MI to a reactive electrophilic intermediate, 3-methyleneindolenine (3-MEI). Studies of P450 2F1 to date have been limited
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