173446-84-9

Basic information

• Product Name: ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate
• Synonyms: ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate
• CAS NO: 173446-84-9
• Molecular Weight: 370.532
• Mol File: 173446-84-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate(173446-84-9)
• EPA Substance Registry System: ethyl [8(Z),11(Z),14-pentadecatrienyl]salicylate(173446-84-9)

Safety Data

• Hazardous Substances Data: 173446-84-9(Hazardous Substances Data)

Upstream product

• 28598-82-5 1-bromo-8-chloro-octane 
• 50816-19-8 8-bromooctanol 
• 332011-48-0 ethyl 2-methoxy-6-[8(Z),11(Z),14-pentadecatrienyl]benzoate 
• 332011-45-7 ethyl 6-(8-iodooctyl)-2-methoxybenzoate 
• 332011-43-5 ethyl 6-(8-chlorooctyl)salicylate 
• 332011-44-6 ethyl 6-(8-chlorooctyl)-2-methoxybenzoate 
• 332011-40-2 11-chloro-1,1-diethoxy-2-undecyne 
• 332011-42-4 11-chloro-3-methoxy-2-undecenal 
• 332011-41-3 11-chloro-2-undecynal 
• 114802-11-8 ethyl 6-(7-formylheptyl)-2-methoxybenzoate 

Downstream Products

• 103904-73-0 6-(8(Z),11(Z),14-pentadecatrienyl)salicylic acid 

Relevant articles and documents

Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid

11-Chloro-3-methoxy-2-undecenal was synthesized from 8-bromooctanol, and an annelation reaction with this aldehyde and ethyl acetoacetate proceeded to give the ethyl 6-(8-chlorooctyl)salicylate. Ethyl 6-(8-chlorooctyl)salicylate was converted to ethyl 6-(7-formylheptyl)-2-methoxybenzoate through the iodide after protection of the phenolic hydroxyl group. Finally, the Wittig reaction with the aldehyde and triphenylphosphonium iodides in the presence of BuLi gave the methoxybenzoates, and then treatments of these methoxybenzoates with BBr3 in CH2Cl2 and 10% NaOH in ethanol gave 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid (anacardic acid 3) and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid (anacardic acid 4) which were isolated from plants of the anacardiaceae.