22800-25-5

Usage

Uses

Used in Surfactant Applications:
(S)-2-tridecyl-2,5-dihydro-4-methyl-5-oxo-3-furoic acid is used as a surfactant in the chemical industry for its potential to lower surface tension between two liquids or a liquid and a solid. Its long hydrophobic tail and hydrophilic head contribute to its effectiveness in stabilizing mixtures and emulsions.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, (S)-2-tridecyl-2,5-dihydro-4-methyl-5-oxo-3-furoic acid is used as a potential therapeutic agent due to the biological activity often associated with furoic acid derivatives. Its specific (S)-configuration might offer unique advantages in drug design and development.
Used in Organic Chemistry:
(S)-2-tridecyl-2,5-dihydro-4-methyl-5-oxo-3-furoic acid is used as a reagent or intermediate in organic synthesis because of its interesting reactivity, particularly the presence of a methyl and keto group in the furoic acid portion of the molecule, which may facilitate various chemical reactions and the creation of new compounds.

InChI:InChI=1/C19H32O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-16-17(18(20)21)15(2)19(22)23-16/h16H,3-14H2,1-2H3,(H,20,21)/t16-/m0/s1

Upstream product

• 22800-27-7 (-)-allo-protolichesterinic acid 
• 93711-21-8 (+)-(S)-5-tridecylfuran-2(5H)-one 
• 897657-64-6 (4S,5S)-4-hydroxy-5-tridecyl-4,5-dihydro-3H-furan-2-one 
• 152612-37-8 (2S,3R)-(-)-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid 
• 493-46-9 (+)-protolichesterinic acid 
• 493-46-9 (2S,3R)-tetrahydro-4-methylene-5-oxo-2-n-tridecyl-3-furancarboxylic acid 
• 108-24-7 acetic anhydride 
• 17002-28-7 4-methylene-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid 

Downstream Products

• 493-47-0 (+/-)-lichesterinic acid 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of potential antibacterial butyrolactones

Novel butyrolactone analogues were designed and synthesized based on the known lichen antibacterial compounds, lichesterinic acids (B-10 and B-11), by substituting different functional groups on the butyrolactone ring trying to enhance its activity. All synthesized butyrolactone analogues were evaluated for their in vitro antibacterial activity against Streptococcus gordonii. Among the derivatives, B-12 and B-13 had the lowest MIC of 9.38 μg/mL where they have shown to be stronger bactericidals, by 2–3 times, than the reference antibiotic, doxycycline. These two compounds were then checked for their cytotoxicity against human gingival epithelial cell lines, Ca9–22, and macrophages, THP-1, by MTT and LDH assays which confirmed their safety against the tested cell lines. A preliminary study of the structure–activity relationships unveiled that the functional groups at the C4position had an important influence on the antibacterial activity. An optimum length of the alkyl chain at the C5position registered the best antibacterial inhibitory activity however as its length increased the bactericidal effect increased as well. This efficiency was attained by a carboxyl group substitution at the C4position indicating the important dual role contributed by these two substituents which might be involved in their mechanism of action.

Contribution to the Chemistry of Proto- and allo-Proto-lichesterinic Acids

The isolation and spectroscopic characterization of (-)-allo-proto-lichesterinic acid from Cetraria komarovii is described.Proto-lichesterinic and allo-proto-lichesterinic acids are transformed into numerous nitrogen-containing derivatives and the isomerization of the dihydro acids is investigated. Key words: Proto-lichesterinic Acid, allo-Proto-lichesterinic Acid, Lichen Substances