cis-4,5,9-Trithiadodeca-1,6,11-triene-9-

Product Namecis-4,5,9-Trithiadodeca-1,6,11-triene-9-
CAS92285-01-3
MFC9H14OS3
MW234.4
EINECS
MOL File92285-01-3.mol

Chemical Properties

Boiling point	376.0±42.0 °C(Predicted)
Density	1.181±0.06 g/cm3(Predicted)
storage temp.	−20°C
solubility	Chloroform: slightly soluble,Ethyl Acetate: slightly soluble,Methanol: slightly soluble
form	Liquid
color	Colorless to light yellow
LogP	2.536 (est)

Usage And Synthesis

Uses

Ajoene, a garlic-derived compound, is an antithrombotic and antifungal agent. Ajoene inhibits proliferation and induces apoptosis of human leukaemia CD34-negative cells including HL-60, U937, HEL and OCIM-I. Anticancer activities[1][2].

Definition

ChEBI: (E)-Ajoene is a sulfoxide.

Anticancer Research

It is an organosulfur compound obtained from garlic and induces apoptosis in leukemiacells (Aggarwal and Shishodia 2004). Ajoene demonstrated a significantcytotoxic activity in different cancer cell lines including FS4 (human primaryfibroblast), BHK21 (a permanent and non-tumorigenic cell line derived from kidneycells of baby hamster), and BJA-B (tumorigenic lymphoid cell line derived fromBurkitt lymphoma) (Scharfenberg et al. 1990)

in vivo

Ajoene (25 μg/g body weight of Ajoene in 100 mL Intralipid; i.p.; every other day from the day of inoculation up to day 28) inhibits both primary tumor growth^[1].
Ajoene (25, 15 or 5 μg/g body weight of Ajoene in 100 μL Intralipid; i.p; every other day over 4 weeks) inhibits strongly metastasis to lung in the B16/BL6 melanoma tumor model in C57BL/6 mice^[1].

References

[1] Taylor P, et al. Ajoene inhibits both primary tumor growth and metastasis of B16/BL6 melanoma cells in C57BL/6 mice. Cancer Lett. 2006;239(2):298-304. DOI:10.1016/j.canlet.2005.08.022
[2] Ahmed N, et al. Ajoene, a garlic-derived natural compound, enhances chemotherapy-induced apoptosis in human myeloid leukaemia CD34-positive resistant cells. Anticancer Res. 2001;21(5):3519-3523. PMID:11848518