| Identification | More | [Name]
Diallyl trisulfide | [CAS]
2050-87-5 | [Synonyms]
ALLYL TRISULFIDE
DIALLYL TRISULFIDE
DIALLYL TRISULPHIDE
FEMA 3265
PROP-2-ENYL-TRITHIO PROP-2-ENE
1,3-Diallyltrisulfane
Trisulfide, di-2-propenyl
ALLYLTRISULPHIDE
1,1'-(Trithio)bis(2-propene)
Allitridin
Bis(2-propenyl) trisulfide
Diallyl pertrisulfide | [EINECS(EC#)]
218-107-8 | [Molecular Formula]
C6H10S3 | [MDL Number]
MFCD00040025 | [Molecular Weight]
178.34 | [MOL File]
2050-87-5.mol |
| Chemical Properties | Back Directory | [Boiling point ]
bp6 92°; bp0.0008 66-67° | [density ]
1.085 | [FEMA ]
3265 | [refractive index ]
nD20 1.5896 | [storage temp. ]
-20°C | [solubility ]
Soluble in acetone, Ethanol(~3 mg/ml), DMSO (~5 mg/ml), and DMF (~10 mg/ml). | [form ]
oil | [color ]
Colorless to light yellow | [Odor]
at 0.10 % in propylene glycol. garlic green onion metallic | [biological source]
Allium sativum L. | [Odor Type]
sulfurous | [Water Solubility ]
insoluble in water. | [JECFA Number]
587 | [InChI]
InChI=1S/C6H10S3/c1-3-5-7-9-8-6-4-2/h3-4H,1-2,5-6H2 | [InChIKey]
UBAXRAHSPKWNCX-UHFFFAOYSA-N | [SMILES]
S(SCC=C)SCC=C | [LogP]
4.59 | [CAS DataBase Reference]
2050-87-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Trisulfide, di-2-propenyl(2050-87-5) |
| Safety Data | Back Directory | [RIDADR ]
2810 | [WGK Germany ]
3 | [RTECS ]
BC6168000 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29309090 |
| Hazard Information | Back Directory | [Description]
Hydrogen sulfide (H2S) is an endogenously-produced gaseous second messenger that can regulate many physiological processes. Diallyl trisulfide (DATS) is an organic polysulfide compound found in garlic that acts as an H2S donor.1 It reduces the survival of prostate cancer PC-3 cells (IC50 = 22 μM)2 and inhibits the growth of human colon adenocarcinoma HCT15 cells (IC50 = 11.5 μM).3 DATS suppresses the growth of PC-3 xenografts in vivo in mice4 and induces vascular smooth muscle relaxation.1 Garlic extracts also lower cholesterol and there is evidence that DATS can alter the expression of genes and inhibit enzymes that are relevant to cholesterol synthesis.5,6 | [Chemical Properties]
Diallyl trisulfide is a yellow liquid with a disagreeable odor. It is a stable transformation product of allicin. Insoluble in water and ethanol, miscible in ether. Natural products are found in onions, garlic, etc. Diallyl trisulfide (DATS) and diallyl disulfide (DADS) are the two major organosulfides in garlic oil. | [Occurrence]
Reported found in garlic oil. | [Uses]
Diallyl Trisulfide, is an organosulfur garlic compound that induces neovasculogenesis and has preventive effects against ischemic injuries. Antiarrythmic effect. | [Definition]
ChEBI: An organic trisulfide that is trisulfane in which both of the hydrogens are replaced by allyl groups. A component of the essential oil of garlic and a major component of the traditional Chinese medicine allitridium, it exhibits antifungal, antitumour and a
tioxidant activity | [Preparation]
In nature, diallyl trisulfide is formed from alliin and allicin. | [General Description]
Diallyl trisulfide (DATS) is one of the organosulfur compounds found in garlic (Allium sativum), and other Allium genera such as onions. This sulfur-rich compound is produced by the rapid disintegration of its metabolic precursor Allicin. | [Biochem/physiol Actions]
Diallyl trisulfide (DATS) is a potent anti-cancer and chemopreventive agent that regulates apoptosis, metastasis, cell cycle, and angiogenesis in cancer pathways. It is also an excellent neuroprotective agent. DATS elicits antioxidant and anti-inflammatory activities against doxorubicin (DOX)-induced rats brains. It may improve glycemic control, muscle glucose utilization, and insulin secretion in streptozotocin-induced diabetic rats. | [storage]
Store at 2-8°C,stored under nitrogen | [References]
[1] GLORIA A BENAVIDES. Hydrogen sulfide mediates the vasoactivity of garlic.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2007: 17977-17982. DOI: 10.1073/pnas.0705710104
[2] DONG XIAO. Diallyl trisulfide-induced apoptosis in human prostate cancer cells involves c-Jun N-terminal kinase and extracellular-signal regulated kinase-mediated phosphorylation of Bcl-2[J]. Oncogene, 2004, 23 33: 5594-5606. DOI: 10.1038/sj.onc.1207747
[3] TAKASHI HOSONO. Diallyl trisulfide suppresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of beta-tubulin.[J]. The Journal of Biological Chemistry, 2005, 280 50: 41487-41493. DOI: 10.1074/jbc.m507127200
[4] DONG XIAO. Diallyl trisulfide suppresses growth of PC-3 human prostate cancer xenograft in vivo in association with Bax and Bak induction.[J]. Clinical Cancer Research, 2006, 12 22: 6836-6843. DOI: 10.1158/1078-0432.ccr-06-1273
[5] ZHE ZHOU. Microarray analysis of altered gene expression in diallyl trisulfide-treated HepG2 cells.[J]. Pharmacological Reports, 2005, 57 6: 818-823.
[6] GUPTA NISHA Porter T D. Garlic and Garlic-Derived Compounds Inhibit Human Squalene Monooxygenase[J]. Journal of Nutrition, 2001, 131 6: Pages 1662-1667. DOI: 10.1093/jn/131.6.1662 |
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