3004-93-1

Basic information

• Product Name: 2-METHYLOCTANOIC ACID
• Synonyms: 2-methyl-octanoicaci;a-methylcaprylicacid;Octanoicacid,2-methyl-;α-Methylcaprylicacid;2-METHYLOCTANOIC ACID;2-Methyloctansaure;2-methylcaprylic acid
• CAS NO: 3004-93-1
• Molecular Formula: C₉H₁₈O₂
• Molecular Weight: 158.24
• EINECS: 221-104-4
• Mol File: 3004-93-1.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 246.47°C (estimate)
• Flash Point: 129.7 °C
• Appearance: /
• Density: 0.9113 (rough estimate)
• Vapor Pressure: 0.0057mmHg at 25°C
• Refractive Index: 1.4159 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-METHYLOCTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLOCTANOIC ACID(3004-93-1)
• EPA Substance Registry System: 2-METHYLOCTANOIC ACID(3004-93-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 3004-93-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 4550, 1950 DOI: 10.1021/ja01166a060

InChI:InChI=1/C9H18O2/c1-3-4-5-6-7-8(2)9(10)11/h8H,3-7H2,1-2H3,(H,10,11)

Upstream product

• 39999-00-3 o-2-Octylphenol 
• 818-81-5 2-methyloctan-1-ol 
• 1116-73-0 trihexylaluminium 
• 91327-69-4 (4R,5R)-((E)-2-Propenyl)-[1,3]dioxolane-4,5-dicarboxylic acid bis-dimethylamide 
• 60-29-7 diethyl ether 
• 29117-48-4 (R)-(-)-2-iodooctane 
• 111-66-0 oct-1-ene 
• 201230-82-2 carbon monoxide 
• 4360-86-5 2-hexyl-2-methylmalonic acid 
• 592-41-6 1-hexene 
• 802294-64-0 propionic acid 
• 14593-46-5 sodium tert-pentoxide 
• 628-61-5 2-chlorooctane 
• 557-35-7 2-bromooctane 

Downstream Products

• 49642-49-1 2-methyl-1-octanal 
• 818-81-5 2-methyloctan-1-ol 
• 3004-93-1 (R)-(-)-2-methyloctanoic acid 
• 3004-93-1 (2S)-2-Methyl-octanoic acid 
• 7786-29-0 (R)-α-methyloctanal 
• 117184-53-9 Aranorosin 
• 131033-26-6 (+)-4-(2-methyloctanoyl)-phenol 
• 128342-67-6 (2R)-2-methyl-N-((S)-1-phenylethyl)octanamide 
• 128342-66-5 (2S)-2-methyl-N-((S)-1-phenylethyl)octanamide 
• 105453-00-7 2-methyl-N-phenyloctanamide 
• 1610613-93-8 3,3′-O,O-(dotriacontane-1,32-diyl)bis{2-O-[(10RS)-10-methylhexadecyl]-sn-glycerol} 
• 1610613-90-5 1-O-benzyl-3-O-[(10RS)-10-methylheptadec-16-en-1-yl]-2-O-[(10RS)-methylhexadecyl]-sn-glycerol 

Relevant articles and documents

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A direct synthesis of carboxylic acidsviaplatinum-catalysed hydroxycarbonylation of olefins

The platinum-catalysed hydroxycarbonylation of olefins is reported for the first time. Using a combination of PtCl2/2,2′-bis(tert-butyl(pyridin-2-yl)phosphanyl)-1,1′-binaphthalene (Neolephos) in the presence of sulfuric acid [0.6 M] in acetic acid selective carbonylation of terminal aliphatic olefins proceeds to good yields and selectivities to the corresponding carboxylic acids. Comparing the reactivity of different butenes (iso- andn-butenes), the terminal olefin can be selectively carbonylated.

Bifunctional Doscadenamides Activate Quorum Sensing in Gram-Negative Bacteria and Synergize with TRAIL to Induce Apoptosis in Cancer Cells

New cyanobacteria-derived bifunctional analogues of doscadenamide A, a LasR-dependent quorum sensing (QS) activator in Pseudomonas aeruginosa, characterized by dual acylation of the pyrrolinone core structure and the pendant side chain primary amine to form an imide/amide hybrid are reported. The identities of doscadenamides B-J were confirmed through total synthesis and a strategic focused library with different acylation and unsaturation patterns was created. Key molecular interactions for binding with LasR and a functional response through mutation studies coupled with molecular docking were identified. The structure-activity relationships (SARs) were probed in various Gram-negative bacteria, including P. aeruginosa and Vibrio harveyi, indicating that the pyrrolinone-N acyl chain is critical for full agonist activity, while the other acyl chain is dispensable or can result in antagonist activity, depending on the bacterial system. Since homoserine lactone (HSL) quorum sensing activators have been shown to act in synergy with TRAIL to induce apoptosis in cancer cells, selected doscadenamides were tested in orthogonal eukaryotic screening systems. The most potent QS agonists, doscadenamides S10-S12, along with doscadenamides F and S4 with partial or complete saturation of the acyl side chains, exhibited the most pronounced synergistic effects with TRAIL in triple negative MDA-MB-231 breast cancer cells. The overall correlation of the SAR with respect to prokaryotic and eukaryotic targets may hint at coevolutionary processes and intriguing host-bacteria relationships. The doscadenamide scaffold represents a non-HSL template for combination therapy with TRAIL pathway stimulators.