5746-58-7

Basic information

• Product Name: (S)-Aseanostatin P5
• Synonyms: (S)-12-Methyltetradecanoic acid;(S)-Aseanostatin P5;[S,(+)]-12-Methyltetradecanoic acid
• CAS NO: 5746-58-7
• Molecular Formula: C₁₅H₃₀O₂
• Molecular Weight: 242.4
• Mol File: 5746-58-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C
• CAS DataBase Reference: (S)-Aseanostatin P5(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Aseanostatin P5(5746-58-7)
• EPA Substance Registry System: (S)-Aseanostatin P5(5746-58-7)

Safety Data

• Hazardous Substances Data: 5746-58-7(Hazardous Substances Data)

Usage

General Description

Anteiso-fatty acids (aFA) contain odd number of carbon atoms. It belongs to a family of branched chain fatty acids (BCFA). aFA is a chiral molecule and the (S)-enantiomers are the primary form. A methyl-substituent is present at the antepenultimate carbon of the carboxyalkyl chain. Anteiso 15:0 Fatty acid is found in food and bacteria.

Biochem/physiol Actions

Anteiso 15:0 fatty acid plays a major role in the growth of Listeria monocytogenes even at low temperatures.

Upstream product

• 862463-97-6 (E)-thiopent-2-ene-oic acid (S)-ethyl ester 
• 79010-63-2 S-ethyl (S)-3-methylpentanethioate 
• 15877-57-3 3-methylpentanal 
• 13991-37-2 trans-2-pentenoic acid 
• 38261-81-3 (S)-2-methylbutyl tosylate 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 88462-46-8 (8-carboxyoctyl)triphenylphosphonium bromide 
• 41059-02-3 9-bromononanoic acid 
• 162610-48-2 (S)-13-methyl-1-pentadecene 
• 162610-49-3 (S)-12-methyltetradecanal 
• 1730-89-8 (S)-4-methylhexanoic acid 
• 818-88-2 sebacic acid mono methyl ester 

Downstream Products

• 162610-57-3 (S)-3-benzyloxy-2-hydroxypropyl (S)-12-methyltetradecanoate 
• 62691-05-8 (S)-(+)-12-methyltetradecanoic acid methyl ester 

Relevant articles and documents

Lenzimycins A and B, Metabolites With Antibacterial Properties From Brevibacillus sp. Associated With the Dung Beetle Onthophagus lenzii

Symbiotic microorganisms associated with insects can produce a wide array of metabolic products, which provide an opportunity for the discovery of useful natural products. Selective isolation of bacterial strains associated with the dung beetle, Onthophagus lenzii, identified two strains, of which the antibiotic-producing Brevibacillus sp. PTH23 inhibited the growth of Bacillus sp. CCARM 9248, which is most closely related to the well-known entomopathogen, Bacillus thuringiensis. A comprehensive chemical investigation based on antibiotic activity discovered two new antibiotics, named lenzimycins A and B (1-2), which inhibited growth of Bacillus sp. CCARM 9248. The 1H and 13C NMR, MS, MS/MS, and IR analyses elucidated the structures of 1 and 2, which comprised a novel combination of fatty acid (12-methyltetradecanoic acid), glycerol, sulfate, and N-methyl ethanolamine. Furthermore, the acid hydrolysis of 1 revealed the absolute configuration of 12-methyltetradecanoic acid as 12S by comparing its optical rotation value with authentic (R)- and (S)-12-methyltetradecanoic acid. In addition to inhibition of Bacillus sp. CCARM 9248, lenzimycins A and B were found to inhibit the growth of some human pathogenic bacteria, including Enterococcus faecium and certain strains of Enterococcus faecalis. Furthermore, the present study elucidated that lenzimycins A and B activated a reporter system designed to detect the bacterial cell envelope stress, thereby indicating an activity against the integrity of the bacterial cell wall.

Synthesis of (S)-(+)-enantiomers of food-relevant (n-5)-monoenoic and saturated anteiso-fatty acids by a Wittig reaction

We developed an enantioselective synthesis for the food-relevant anteiso-fatty acids a15:0, a16:0, and a17:0. Different (carboxyalkyl)triphenylphosphonium bromide salts were coupled with (S)-3-methylpentanal in a Wittig reaction. Mixtures of the obtained cis-/trans-isomers were separated by Ag+-HPLC to give the novel cis-isomers of (S)-(+)-a15:1n-5, (S)-(+)-a16:1n-5, and (S)-(+)-a17:1n-5. Hydrogenation of the monoenoic products led to (S)-(+)-a15:0, (S)-(+)-a16:0, and (S)-(+)-a17:0, which are essential for the assessment of the bioactivity of tests with standards of anteiso-fatty acids.

Synthesis of both the enantiomers of aseanostatin P5 (sarcinic acid), an inhibitor of myeloperoxidase release, and four diastereomers of aggreceride A, a platelet aggregation inhibitor.

Both the enantiomers of aseanostatin P5 (sarcinic acid), an inhibitor of myeloperoxidase (MPO) release from human polymorphonuclear leukocytes (PMN), with high optical purity were synthesized by starting from (S)-2-methylbutanol and methyl (S)-3-hydroxy-2