5502-94-3

Usage

Uses

Used in Chemical and Pharmaceutical Research:
12-METHYLTETRADECANOIC ACID is used as a research compound for studying the properties and functions of medium-chain anteiso-fatty acids. Its unique structure and characteristics contribute to a better understanding of the behavior and potential applications of similar compounds in the chemical and pharmaceutical industries.
Used in Biomedical Applications:
In the biomedical field, 12-METHYLTETRADECANOIC ACID may be utilized as a component in the development of novel drugs or therapies targeting specific health conditions. Its unique properties could potentially be harnessed to improve drug delivery, bioavailability, and therapeutic outcomes.
Used in Industrial Applications:
12-METHYLTETRADECANOIC ACID may also find applications in various industrial processes, such as the production of specialty chemicals, lubricants, or additives, where its unique properties can provide advantages over traditional materials.

InChI:InChI=1/C15H30O2/c1-3-14(2)12-10-8-6-4-5-7-9-11-13-15(16)17/h14H,3-13H2,1-2H3,(H,16,17)

Upstream product

• 62691-05-8 methyl 12-methyltetradecanoate 
• 92857-54-0 6-Oxo-12-methyl-tetradecansaeure 
• 83855-21-4 Neopeptin B 
• 111045-01-3 10-Keto-12-methyltetradecansaeuremethylester 
• 112-38-9 10-undecenoic acid 
• 543-27-1 isobutyl chloroformate 
• 592-34-7 carbonochloridic acid, butyl ester 
• 41059-02-3 9-bromononanoic acid 
• 88462-46-8 (8-carboxyoctyl)triphenylphosphonium bromide 
• 14065-32-8 methyl 10-chloro-10-oxodecanoate 
• 818-88-2 sebacic acid mono methyl ester 
• 106-79-6 dimethyl sebacate 
• 70794-53-5 <1-(ethoxycarbonyl)decyl>triphenylphosphonium iodide 
• 92730-55-7 6-[5-(2-methyl-butyl)-thiophen-2-yl]-6-oxo-hexanoic acid 

Downstream Products

• 62691-05-8 methyl 12-methyltetradecanoate 
• 19207-26-2 12-Methyl-tetradecanoic acid 2,3-dihydroxy-propyl ester 

Relevant academic research and scientific papers

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.

Alkylation of alkenes: Ethylaluminum sesquichloride-mediated hydro-alkyl additions with alkyl chloroformates and di-tert-butylpyrocarbonate

A general method for the hydro-alkyl addition to the nonactivated C=C double bond of alkenes using alkyl chloroformates (primary, secondary), 12, and di-tert-butylpyrocarbonate, 52, mediated by ethylaluminum sesquichloride (Et3Al2Cl3) has been developed. Reaction of 12 and 52, respectively, with Et3Al2Cl3 gives an alkyl cation which is added to the alkene; hydride transfer to the adduct carbenium ion or, if applicable, 1,2-H shift followed by hydride transfer from Et3Al2Cl3 to the rearranged adduct carbenium ion gives the saturated addition product. The reaction has been applied to 1-alkenes, 2-methyl-1-alkenes, internal double bonds, and to three cyclic alkenes. Special interest has been focused on alkylations of unsaturated fatty compounds, such as oleic acid (2), which are important renewable feedstocks. 2-Methylalkanes, 3-methylalkanes, 2,4-dimethylalkanes, 2,3-dimethylalkanes, 2,2,4-trimethylalkanes, cyclohexylalkanes, and carboxylic acids and esters with the respective branched alkyl chain have been synthesized with good to moderate yields.

Anticancer effects of specific branched-chain fatty acids and related production process

A group of specific branched-chain fatty acids, with significant anticancer effects on human and animals; methods of making using either chemical synthesis or biosynthesis methods; and methods of treating cancer.

Friedel-Crafts alkylation of alkenes: Ethylaluminum sesquichloride induced alkylations with alkyl chloroformates

The formal addition of propane to nonactivated double bonds can be achieved with isopropyl chloroformate (2) in the presence of Et3Al2Cl3. Thus, a 1:1 mixture of 10-isopropyloctadecanoic acid (3) and the 9- regioisomer is formed from oleic acid (1). The reaction may also be carried out with 1-alkenes by the addition of triethylsilane as a hydride donor.

1-O-(13-Methyl-1-Z-tetradecenyl)-2-O-(13-methyltetradecanoyl)-glycero-3-phospho-ethanolamine, a Plasmalogen from Myxococcus stipitatus

The structure of 1-O-(13-methyl-1-Z-tetradecenyl)-2-O-(13-methyltetradecanoyl)-glycero-3-phospho-ethanolamine isolated from Myxococcus stipitatus has been elucidated. 1H and 13C NMR as well as mass spectral data have been accumulated which allow a ready identification and structure elucidation of compounds of this type. - Keywords: Myxobacteria, Myxococcus stipitatus, Phospholipids, Plasmalogen, Structure Elucidation