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W301912

Sigma-Aldrich

Skatole

≥98%

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Synonym(s):
3-Methylindole, Skatole
Empirical Formula (Hill Notation):
C9H9N
CAS Number:
Molecular Weight:
131.17
FEMA Number:
3019
Beilstein/REAXYS Number:
111296
EC Number:
MDL number:
UNSPSC Code:
12164502
PubChem Substance ID:
Flavis number:
14.004
NACRES:
NA.21

biological source

synthetic

Quality Level

agency

meets purity specifications of JECFA

assay

≥98%

bp

265-266 °C (lit.)

mp

92-97 °C (lit.)

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

organoleptic

animalic

SMILES string

Cc1c[nH]c2ccccc12

InChI

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

InChI key

ZFRKQXVRDFCRJG-UHFFFAOYSA-N

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General description

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).

Disclaimer

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

pictograms

Environment

hcodes

Hazard Classifications

Aquatic Chronic 2

wgk_germany

WGK 2

flash_point_f

269.6 °F

flash_point_c

132 °C


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
P K Mathur et al.
Meat science, 91(4), 414-422 (2012-03-23)
A system for sensory evaluation of boar taint was used to evaluate boar taint in fat samples from 6574 entire males. The term "human nose scoring" has been used to describe this system. The samples from each boar were heated
Putative mechanisms of toxicity of 3-methylindole: from free radical to pneumotoxicosis.
T M Bray et al.
Annual review of pharmacology and toxicology, 34, 91-115 (1994-01-01)

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