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SMB00577

Sigma-Aldrich

Diallyl trisulfide

≥97% (HPLC)

Synonym(s):

Allyl trisulfide, Di-2-propenyl trisulfide

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About This Item

Empirical Formula (Hill Notation):
C6H10S3
CAS Number:
2050-87-5
Molecular Weight:
178.34
EC Number:
218-107-8
MDL number:
MFCD00040025
UNSPSC Code:
12352200
PubChem Substance ID:
329825066
NACRES:
NA.25

biological source

Allium sativum L.

Quality Level

200

assay

≥97% (HPLC)

form

liquid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

C=CCSSSCC=C

InChI

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

InChI key

UBAXRAHSPKWNCX-UHFFFAOYSA-N

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General description

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.

Biochem/physiol Actions

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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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
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
Garlic Derived Diallyl Trisulfide in Experimental Metabolic Syndrome: Metabolic Effects and Cardioprotective Role.
Jeremic, et al.
International Journal of Molecular Sciences, 21 (2021)
RamaRao Malla et al.
Journal of pharmaceutical analysis, 12(2), 221-231 (2022-05-19)
Breast cancer is one of the leading causes of cancer-related deaths in women worldwide. It is a cancer that originates from the mammary ducts and involves mutations in multiple genes. Recently, the treatment of breast cancer has become increasingly challenging
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)
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