92285-01-3

Basic information

• Product Name: CIS-4,5,9-TRITHIADODECA-1,6,11-TRIENE-9-
• Synonyms: CIS-4,5,9-TRITHIADODECA-1,6,11-TRIENE-9-;Ajoene;(Z)-4,5,9-Trithiadodeca-1,6,11-triene-9-oxide;(2-Propenyl)[3-[(2-propenyl)sulfinyl]-1-propenyl] persulfide;2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl persulfide;2-Propenyl(4,5-dithia-2,7-octadiene-1-yl) sulfoxide;E/Z Ajoene;(Z)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene
• CAS NO: 92285-01-3
• Molecular Formula: C₉H₁₄OS₃
• Molecular Weight: 234.4
• Mol File: 92285-01-3.mol

Chemical Properties

• Boiling Point: 376°Cat760mmHg
• Flash Point: 181.2°C
• Appearance: /
• Density: 1.181g/cm³
• Vapor Pressure: 1.61E-05mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: −20°C
• CAS DataBase Reference: CIS-4,5,9-TRITHIADODECA-1,6,11-TRIENE-9-(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-4,5,9-TRITHIADODECA-1,6,11-TRIENE-9-(92285-01-3)
• EPA Substance Registry System: CIS-4,5,9-TRITHIADODECA-1,6,11-TRIENE-9-(92285-01-3)

Safety Data

• Hazardous Substances Data: 92285-01-3(Hazardous Substances Data)

Usage

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)

InChI:InChI=1/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5+

Upstream product

• 13702-10-8 S-(prop-2-yn-1-yl) ethanethioate 
• 928838-16-8 1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane 
• 2179-57-9 diallyl disulphide 
• 539-86-6 allicin 

Downstream Products

• 1380688-19-6 C₁₂H₁₄O₂S₃ 

Relevant articles and documents

Short Total Synthesis of Ajoene, (E,Z)-4,5,9-Trithiadodeca-1,6,11-triene 9-oxide, in Batch and (E,Z)-4,5,9-Trithiadodeca-1,7,11-triene in Continuous Flow

A short total synthesis of ajoene, (E,Z)-4,5,9-trithiadodeca-1,6,11-triene 9-oxide, has been achieved over six steps. In addition, a continuous flow synthesis under mild reaction conditions to (E,Z)-4,5,9-trithiadodeca-1,7,11-triene is described starting from simple and easily accessible starting materials. Over four steps including propargylation, radical addition of thioacetate, deprotection, and disulfide formation/ allylation, the target product can be obtained at a rate of 0.26 g h?1 in an overall yield of 12 %.

PROCESS FOR THE MANUFACTURE OF AJOENE DERIVATIVES

The present invention relates to the compound (E,Z)-ajoene of formula (1) for use in treatment of bacterial infections. Another aspect of the present invention is a composition comprising (E,Z)-ajoene of formula (1) and at least one antibiotic. Yet another aspect of the invention relates to a method for manufacturing (E,Z) ajoene of formula (1) wherein the conformation of the internal C=C- bond can be either E or Z or a mixture thereof, said method comprising reacting allicin of formula (3) with an acid in the presence of a solvent to provide (E,Z ajoene) of formula (1) as defined above. Yet another aspect of the invention is (E,Z)-ajoene of formula 1 obtainable by the method described above.