A disulfide with antitumor and antiplatelet activities
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(E/Z)-Ajoene

Item No. 34881

Technical Information
Formal Name
2-propen-1-yl [3-(2-propen-1-ylsulfinyl)-1-propen-1-yl] disulfide
CAS Number
92285-01-3
Molecular Formula
C9H14OS3
Formula Weight
Purity
≥95%
A 5 mg/ml solution in ethyl acetate
Ethyl Acetate: 100 mg/ml
SMILES
C=CCS(C/C=C/SSCC=C)=O
InChi Code
InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5+
InChi Key
IXELFRRANAOWSF-FNORWQNLSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    (E/Z)-Ajoene is a disulfide that has been found in A. sativum and has antitumor and antiplatelet activities.1,2 It is cytotoxic to a variety of cancer cells, including B16-BL6 murine melanoma, and human HT-29 colon adenocarcinoma, MDA-MB-231 mammary, and PANC-1 pancreatic adenocarcinoma cells (IC50s = 18, 19, 7, and 38 µM, respectively).1 (E/Z)-Ajoene (25 mg/kg) reduces tumor growth and decreases the number of lung metastases in B16-BL6 murine models of melanoma. It also prevents thrombus formation in heparinized animals in a porcine model of severe vascular damage induced by intimal stripping and tunica media exposure when administered at a dose of 25 mg/kg.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Taylor, P., Noriega, R., Farah, C., et alAjoene inhibits both primary tumor growth and metastasis of B16/BL6 melanoma cells in C57BL/6 mice. Cancer Lett. 239(2), 298-304 (2006).

    2. Apitz-Castro, R., Badimon, J.J., and Badimon, L. A garlic derivative, ajoene, inhibits platelet deposition on severely damaged vessel wall in an in vivo porcine experimental model. Thromb. Res. 75(3), 243-249 (1994).