A disulfide with diverse biological activities
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(E)-Ajoene

Item No. 26242

Technical Information
Formal Name
2-propen-1-yl (1E)-3-(2-propen-1-ylsulfinyl)-1-propen-1-yl, disulfide
CAS Number
92284-99-6
Synonyms
  • NSC 614554
Molecular Formula
C9H14OS3
Formula Weight
Purity
≥95%
A 10 mg/ml solution in ethyl acetate
Chloroform: slightly solubleEthyl Acetate: slightly solubleMethanol: slightly soluble
λmax
246 nm
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)-Ajoene is a disulfide that has been found in A. sativum and has diverse biological activities.1,2,3,4 It is active against Gram-positive and Gram-negative bacteria (MICs = 10-250 and 150->500 µg/ml, respectively) and fungi (MICs = 15-50 µg/ml).1 (E)-Ajoene inhibits proliferation of a variety of cancer cells, including MDA-MB-231 breast, HeLa cervical, and WHCO1 esophageal cancer cells (IC50s = 18.6, 61, and 39.2 µM, respectively).2 It also inhibits human glutathione reductase and T. cruzi trypanothione reductase when used at a concentration of 200 µM.3 (E)-Ajoene (25 mg/kg) is neuroprotective in a gerbil model of ischemia-reperfusion injury, reducing reactive astrocytosis and microgliosis in the hippocampal CA1 region.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yoshida, H., Iwata, N., Katsuzaki, H., et alAntimicrobial activity of a compound isolated from an oil-macerated garlic extract. Biosci. Biotechnol. Biochem. 62(5), 1014-1017 (1998).

    2. Kaschula, C.H., Hunter, R., Hassan, H.T., et alAnti-proliferation activity of synthetic ajoene analogues on cancer cell-lines. Anticancer Agents Med. Chem. 11(3), 260-266 (2011).

    3. Gallwitz, H., Bonse, S., Martinez-Cruz, A., et alAjoene is an inhibitor and subversive substrate of human glutathione reductase and Trypanosoma cruzi trypanothione reductase: Crystallographic, kinetic, and spectroscopic studies. J. Med. Chem. 42(3), 364-372 (1999).

    4. Yoo, D.Y., Kim, W., Nam, S.M., et alNeuroprotective effects of Z-ajoene, an organosulfur compound derived from oil-macerated garlic, in the gerbil hippocampal CA1 region after transient forebrain ischemia. Food Chem. Toxicol. 72, 1-7 (2014).