544-74-1

Basic information

• Product Name: tariric acid
• Synonyms: tariric acid;6-Octadecynoic acid
• CAS NO: 544-74-1
• Molecular Formula: C₁₈H₃₂O₂
• Molecular Weight: 280.45
• Mol File: 544-74-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 60.25°C (estimate)
• Boiling Point: 433.28°C (rough estimate)
• Flash Point: 196.3°C
• Appearance: /
• Density: 0.9365 (rough estimate)
• Vapor Pressure: 1.07E-07mmHg at 25°C
• Refractive Index: 1.4283 (estimate)
• CAS DataBase Reference: tariric acid(CAS DataBase Reference)
• NIST Chemistry Reference: tariric acid(544-74-1)
• EPA Substance Registry System: tariric acid(544-74-1)

Safety Data

• Hazardous Substances Data: 544-74-1(Hazardous Substances Data)

Usage

Definition

ChEBI: An octadecynoic acid having its triple bond at position 6.

InChI:InChI=1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-11,14-17H2,1H3,(H,19,20)

Upstream product

• 124-07-2 Octanoic acid 
• 408536-68-5 dodec-6-ynedioic acid monomethyl ester 
• 96497-68-6 6,7-dibromo-octadecanoic acid 
• 533-86-8 6,7-diiodo-octadec-6-enoic acid 
• 875250-06-9 hexadec-4-ynyl-malonic acid 
• 4712-34-9 6-octadecenoic acid 
• 14093-35-7 1,10‐dichlorodec‐5‐yne 
• 100253-19-8 dodec-6-ynedinitrile 
• 61621-71-4 dodec-6-ynedioic acid 
• 26186-02-7 tridec-1-yne 
• 2861-50-9 6-octadecyn-1-ol 
• 408536-80-1 dodec-6-ynedioic acid dimethyl ester 
• 855905-38-3 1-iodo-hexadec-4-yne 
• 2067-33-6 5-bromopentanoic acid 

Downstream Products

• 2777-64-2 methyl 6-octadecynoxylate 
• 143-07-7 lauric acid 
• 110-94-1 1,5-pentanedioic acid 
• 593-39-5 Petroselinic acid 
• 593-40-8 Petroselaidic acid 
• 112-37-8 undecylenic acid 
• 16694-32-9 7-oxooctadecanoic acid 
• 533-86-8 6,7-diiodo-octadec-6-enoic acid 
• 57-11-4 stearic acid 
• 19220-35-0 octadec-7-ynoic acid 
• 2861-50-9 6-octadecyn-1-ol 
• 124-04-9 Adipic acid 

Relevant articles and documents

2-Methoxylated FA Display Unusual Antibacterial Activity Towards Clinical Isolates of Methicillin-Resistant Staphylococcus aureus (CIMRSA) and Escherichia coli

The naturally occurring (6Z)-(±)-2-methoxy-6-hexadecenoic acid (1) and (6Z)-(±)-2-methoxy-6-octadecenoic acid (2) were synthesized in 7–8 steps with 38 and 13% overall yields, respectively, by using an acetylide coupling approach, which made it possible to obtain a 100% cis-stereochemistry for the double bonds. In a similar fashion, the acetylenic analogs (±)-2-methoxy-6-hexadecynoic acid (3) and (±)-2-methoxy-6-octadecynoic acid (4) were also synthesized in 6–7 steps with 48 and 16% overall yields, respectively. The antibacterial activity of acids 1–4 was determined against clinical isolates of methicillin-resistant Staphylococcus aureus (ClMRSA) and Escherichia coli. Among the series of compounds, acid 4 was the most active bactericide towards CIMRSA displaying IC50s (half maximal inhibitory concentrations) between 17 and 37?μg/mL, in sharp contrast to the 6-octadecynoic acid, which was not bactericidal at all. On the other hand, acids 1 and 3 were the only acids that displayed antibacterial activity towards E. coli., but 1 stood out as the best candidate with an IC50 of 21?μg/mL. The critical micelle concentrations (CMCs) of acids 1–4 were also determined. The C18 acids 2 and 4 displayed a five-fold lower CMC (15–20?μg/mL) than the C16 analogs 1 and 3 (70–100?μg/mL), indicating that 4 exerts its antibacterial activity in a micellar state. None of the studied acids were inhibitory towards S. aureus DNA gyrase discounting this type of enzyme inhibition as a possible antibacterial mechanism. It was concluded that the combination of α-methoxylation and C-6 unsaturation increases the bactericidal activity of the C16 and C18 FA towards the studied bacterial strains. Acids 1 and 4 stand out as viable candidates to be used against E. coli and CIMRSA, respectively.