Ajoene

Names

[ Name ]:
Ajoene

[Synonym ]:
(E,Z)-ajoene
2E,4Z-Heptadienal
(E/Z)-4,5,9-trithiadodeca-1,6,11-triene-9-oxide
(E,Z)-2,4-heptadienal
4,5,9-trithiadodeca-1,6,11-triene-9-oxide
(Z,E)-4,5,9-trithiadodeca-1,6,11-triene-9-oxide
(2E,4Z)-2,4-heptadienal
hepta-2t,4c-dienal
2,4-Heptadienal,(E,Z)

Biological Activity

[Description]:

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].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[In Vitro]

Ajoene shows cytotoxicity with IC50s in the 7-41 uM range for B16/BL6, HT-29, A549, MDA-MB231, PANC-1, and SKBR-3 cells[1].

[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.

[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.

Chemical & Physical Properties

[ Density]:
1.181g/cm3

[ Boiling Point ]:
376ºC at 760mmHg

[ Molecular Formula ]:
C₉H₁₄OS₃

[ Molecular Weight ]:
234.40200

[ Flash Point ]:
181.2ºC

[ Exact Mass ]:
234.02100

[ PSA ]:
86.88000

[ LogP ]:
3.86790

[ Index of Refraction ]:
1.602

Safety Information

[ HS Code ]:
2930909090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%