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SMB00577

Sigma-Aldrich

Diallyl trisulfide

≥97% (HPLC)

Synonyme(s) :

Allyl trisulfide, Di-2-propenyl trisulfide

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About This Item

Formule empirique (notation de Hill):
C6H10S3
Numéro CAS:
2050-87-5
Poids moléculaire :
178.34
Numéro CE :
218-107-8
Numéro MDL:
MFCD00040025
Code UNSPSC :
12352200
ID de substance PubChem :
329825066
Nomenclature NACRES :
NA.25

Source biologique

Allium sativum L.

Niveau de qualité

200

Pureté

≥97% (HPLC)

Forme

liquid

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

C=CCSSSCC=C

InChI

1S/C6H10S3/c1-3-5-7-9-8-6-4-2/h3-4H,1-2,5-6H2

Clé InChI

UBAXRAHSPKWNCX-UHFFFAOYSA-N

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Description générale

Diallyl trisulfide (DATS) is one of the stable naturally occurring bioactive polysulfide compounds found in Allium vegetables, especially in garlic.

Application

Diallyl trisulfide (DATS) has been used as an exogenous hydrogen sulfide (H2S)donor to study the effects on proliferation, apoptosis, and autophagy of human urothelial carcinoma (UC) cells in vitro.

Actions biochimiques/physiologiques

Diallyl trisulfide elicits cardioprotective and anti-metabolic syndrome (MetS) effects against ex vivo induced myocardial ischemia/reperfusion (I/R) injury in MetS rats (male Wistar albino). It is a potent anti-cancer agent and acts by modulating different cancer-related pathways, inducing cell cycle arrest, apoptosis, metastasis, and angiogenesis in in vitro studies. DATS is also an effective therapeutic agent against multidrug resistance in triple-negative breast cancer (TNBC). DATS and its nanoemulsions display high antifungal activity against wood-rotting fungi such as T. hirsuta and L. sulphureus. It also provides protection against brain damage induced by ischemia/reperfusion (I/R) by activating nuclear factor erythroid 2-related factor 2 (Nrf2) in rat brains.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Elisabetta Panza et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 151, 113137-113137 (2022-05-24)
The role of H2S in urothelial carcinoma (UC) is still unclear. Here we have evaluated the expression of H2S producing enzymes as well as the effect of endogenous and exogenous H2S on human bladder UC cells. In human UC cells
Diallyl Trisulfide, the Antifungal Component of Garlic Essential Oil and the Bioactivity of Its Nanoemulsions Formed by Spontaneous Emulsification.
Gong, et al.
Molecules (Basel), 26 (2022)
Garlic Derived Diallyl Trisulfide in Experimental Metabolic Syndrome: Metabolic Effects and Cardioprotective Role.
Jeremic, et al.
International Journal of Molecular Sciences, 21 (2021)
Carlos A Silva-Islas et al.
Antioxidants (Basel, Switzerland), 8(9) (2019-09-22)
Stroke is a public health problem due to its high mortality and disability rates; despite these, the pharmacological treatments are limited. Oxidative stress plays an important role in cerebral damage in stroke and the activation of the nuclear factor erythroid
Michael T Puccinelli et al.
International journal of molecular sciences, 18(8) (2017-08-10)
Bioactive dietary agents have been shown to regulate multiple cancer hallmark pathways. Epidemiologic studies have linked consumption of Allium vegetables, such as garlic and onions, to decreased incidence of cancer. Diallyl trisulfide (DATS), a bioactive compound derived from Allium vegetables
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