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

Description

(S)-Aseanostatin P5 is a chiral molecule belonging to the family of branched chain fatty acids (BCFA) known as Anteiso-fatty acids (aFA). It is characterized by an odd number of carbon atoms and a methyl-substituent at the antepenultimate carbon of the carboxyalkyl chain. The (S)-enantiomer is the primary form found in nature, and Anteiso 15:0 Fatty acid, a specific example of this molecule, can be found in both food and bacteria.

Uses

Used in Pharmaceutical Industry:
(S)-Aseanostatin P5 is used as a pharmaceutical compound for its potential therapeutic applications. Its unique molecular structure and chirality make it a promising candidate for the development of new drugs targeting various diseases.
Used in Food Industry:
In the food industry, (S)-Aseanostatin P5 is used as a component in the production of certain foods, where its presence contributes to the overall flavor and texture of the product.
Used in Biotechnology:
(S)-Aseanostatin P5 can be utilized in biotechnological applications, such as the development of novel bioactive compounds or the enhancement of existing ones, due to its unique molecular properties and potential for interaction with other biomolecules.
Used in Research and Development:
As a chiral molecule with potential applications in various fields, (S)-Aseanostatin P5 is used in research and development to explore its properties, understand its mechanisms of action, and identify new uses for this versatile compound.

Biochem/physiol Actions

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

Upstream product

• 1730-89-8 (S)-4-methylhexanoic acid 
• 818-88-2 sebacic acid mono methyl ester 
• 162610-49-3 (S)-12-methyltetradecanal 
• 162610-48-2 (S)-13-methyl-1-pentadecene 
• 41059-02-3 9-bromononanoic acid 
• 88462-46-8 (8-carboxyoctyl)triphenylphosphonium bromide 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 38261-81-3 (S)-2-methylbutyl tosylate 
• 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 

Downstream Products

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

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