2485-71-4

Usage

Uses

Used in Pharmaceutical Industry:
13-METHYLTETRADECANOIC ACID is used as a pharmaceutical compound for its potential therapeutic applications. The branched-chain structure of this fatty acid may contribute to its unique properties, making it a valuable candidate for the development of new drugs and therapies.
Used in Nutritional Supplements:
In the nutritional supplement industry, 13-METHYLTETRADECANOIC ACID is used as an ingredient in various health and wellness products. Its presence in natural sources like milk and fish suggests potential benefits for human health, and it may be incorporated into supplements to support overall well-being.
Used in Food Industry:
13-METHYLTETRADECANOIC ACID is used as an additive in the food industry, where it may be utilized to enhance the flavor, texture, or nutritional profile of certain products. Its natural occurrence in various food sources indicates its potential for safe use in the culinary world.
Used in Cosmetics Industry:
In the cosmetics industry, 13-METHYLTETRADECANOIC ACID is used as an ingredient in skincare and personal care products. Its unique properties may contribute to the development of innovative formulations that address specific skin concerns or provide targeted benefits.
Used in Research and Development:
13-METHYLTETRADECANOIC ACID is used as a research compound for the study of its chemical properties, biological activities, and potential applications in various fields. This may include investigations into its role in cellular processes, interactions with other molecules, and its potential for use in the development of new technologies or products.

Biochem/physiol Actions

Iso 15:0 fatty acid possesses anti-cancer activity in various human cancer cells.

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

Upstream product

• 186581-53-3 diazomethane 
• 2724-57-4 isomyristic acid 
• 95799-79-4 10-Keto-13-methyltetradecansaeuremethylester 
• 179095-19-3 (3R)-N-<3-(13'-methyltetradecanoyloxy)-15-methylhexadecanoyl>glycyl-L-serine 
• 75853-51-9 13-methyl-1-tetradecanal 
• 5129-59-9 methyl 13-methyltetradecanoate 
• 929-33-9 methyl 11-iodoundecanoate 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 78-77-3 Isobutyl bromide 
• 2834-05-1 11-bromoundecanoic acid 
• 68532-63-8 (11-methoxy-11-oxoundecyl)(triphenyl)phosphonium bromide 
• 6287-90-7 11-bromo-undecanoic acid methyl ester 
• 112-47-0 1,10-Decanediol 
• 95331-19-4 10-(benzyloxy)decane-1-ol 

Downstream Products

• 5129-59-9 methyl 13-methyltetradecanoate 
• 179869-82-0 (R)-15-Methyl-3-(13-methyl-tetradecanoyloxy)-hexadecanoic acid benzhydryl ester 
• 179869-86-4 (S)-15-Methyl-3-(13-methyl-tetradecanoyloxy)-hexadecanoic acid benzhydryl ester 
• 213197-35-4 (S)-2-Amino-hexanedioic acid 6-benzyl ester 1-((S)-1-carbamoylmethyl-13-methyl-tetradecyl) ester 
• 171272-37-0 (3S)-3-{(2S)-5-benzyloxycarbonyl-2-(tert-butoxycarbonyl)aminopentanoyl}oxy-15-methylhexadecanamide 
• 1456898-57-9 C₈₅H₁₂₂O₁₈ 
• 96095-04-4 (15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-L-serine 

Relevant academic research and scientific papers

Lipid length and iso-branching of trehalose diesters influences Mincle agonist activity

We report on the efficient synthesis of linear trehalose diesters (TDEs) and iso-branched TDEs (maradolipids or iso-TDEs) and their ability to activate bone marrow-derived macrophages (BMDMs) as determined by cytokine (IL-1β IL-12, IL-6, IL-10) and chemokine (MIP-2) production. Both classes of TDEs were found to activate BMDMs in a Mincle-dependent manner, with longer-chain (≥C18) lipids leading to a robust inflammatory response. On the whole, the iso-branched TDEs led to greater cytokine production and a faster immune response when compared to their linear counterparts. Moreover, C12-TDE and iso-C12-TDE elicited the production of MIP-2 by BMDMs, thereby providing the first example of TDEs with a chain length of ≤ C12 leading to a Mincle-dependent immune response and one that is less inflammatory in nature.

Synthesis of sulfobacin A and B, new sulfonolipids isolated from Chryseobacterium sp.

Sulfobacin A (1) and B (2), new sulfonolipids isolated from Chryseobacterium sp. as von Willebrand factor antagonists, were synthesized stereoselectively by starting from L-cysteine.

Synthesis of sphingosine relatives. Part 22. Synthesis of sulfobacin A, B and flavocristamide A, new sulfonolipids isolated from Chryseobacterium sp.

Sulfobacin A (1), B (2), and flavocristamide A (3), new sulfonolipids isolated from Chryseobacterium sp. were synthesized stereoselectively by starting from L-cysteine.

Expansion of the structure-activity relationship of branched chain fatty acids: Effect of unsaturation and branching group size on anticancer activity

Branched chain fatty acids (BCFAs) are a class of fatty acid with promising anticancer activity. The BCFA 13-methyltetradecanoic acid (13-MTD) inhibits tumour growth in vivo without toxicity but efficacy is limited by moderate potency, a property shared b

SYNTHETIC INNATE IMMUNE RECEPTOR LIGANDS AND USES THEREOF

An adjuvant formulation includes a monophosphoryl Lipid A (MPLA) analogue, a Pam3CSK4 analogue, or a muramyldipeptide (MDP) analogue, or combinations thereof. The adjuvant may be formulated in soluble form or in a nanoparticle, such as polylactic glycolic acid nanoparticles. A vaccine formulation comprises the adjuvant formulation and an immunogen. Methods of vaccinating an animal include delivering the vaccine formulation to the animal.

Stereoselective synthesis of unnatural (2S, 3S)-6-hydroxy-4-sphingenine-containing sphingolipids

6-Hydroxy-(4E)-sphingenine-containing sphingolipids are found in mammalian and bacterial membranes and have multiple intra- and intercellular functions. Most sphingolipids contain a (2S,3R)-2-amino-1,3-diol core structure, but only limited examples of unnatural (2S,3S)-2-amino-1,3-diol derivates have so far been reported. Using an underexplored hydrozirconation-transmetalation reaction and an unusual three-step-one-pot deprotection sequence, we were able to synthesize several unnatural (2S,3S)-6-hydroxy-(4E)-sphingenine-containing sphingolipids in only three (protected) or four (deprotected) consecutive steps, respectively, including a fluoresence-labeled derivative suitable for future biological studies.

COMPOSITIONS SOUS FORME D'UNE SOLUTION AQUEUSE INJECTABLE COMPRENANT DU GLUCAGON HUMAIN ET UN CO-POLYAMINOACIDE

Physically stable compositions in the form of an injectable aqueous solution, wherein the pH is from 6.0 to 8.0, includes at least: a) human glucagon andb) a co-polyamino acid bearing carboxylate charges and hydrophobic radicals Hy. In one embodiment, the compositions further comprise a gut hormone.

INJECTABLE SOLUTION AT PH 7 COMPRISING AT LEAST ONE BASAL INSULIN WHEREIN THE PI IS COMPRISED FORM 5.8 TO 8.5 AND A CO-POLYAMINO ACID BEARING CARBOXYLATE CHARGES AND HYDROPHOBIC RADICALS

In one embodiment, the composition according to the invention is characterized in that the co-polyamino acid bearing carboxylate charges and at least one hydrophobic radical -Hy is chosen among the co-polyamino acids according to formula XXXb hereinafter: wherein, D represents, independently, either a group —CH2— (aspartic acid) or a group —CH2—CH2— (glutamic acid),X represents a cationic entity chosen in the group comprising alkali cations,Rb and Rb′, identical or different, are either a hydrophobic radical -Hy, or a radical chosen in the group consisting of an H, a C2 to C10 linear acyl group, a C3 to C10 branched acyl group, a benzyl, a terminal “amino acid” unit and a pyroglutamate, at least one of Rb and R′b is a hydrophobic radical -Hy,Q and Hy are as defined above.n+m represents the degree of polymerization DP of the co-polyamino acid, namely the mean number of monomeric units per co-polyamino acid chain and 5≤n+m≤250.

N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

Bacteria of the Roseobacter group (Rhodobacteraceae) are important members of many marine ecosystems. Similar to other Gram-negative bacteria many roseobacters produce N-acylhomoserine lactones (AHLs) for communication by quorum sensing systems. AHLs regulate different traits like cell differentiation or antibiotic production. Related N-acylalanine methyl esters (NAMEs) have been reported as well, but so far only from Roseovarius tolerans EL-164. While screening various roseobacters isolated from macroalgae we encountered four strains, Roseovarius sp. D12_1.68, Loktanella sp. F13, F14 and D3 that produced new derivatives and analogs of NAMEs, namely N-acyl-2-aminobutyric acid methyl esters (NABME), N-acylglycine methyl esters (NAGME), N-acylvaline methyl esters (NAVME), as well as for the first time a methyl-branched NAME, N-(13-methyltetradecanoyl)alanine methyl ester. These compounds were detected by GC–MS analysis, and structural proposals were derived from the mass spectra and by derivatization. Verification of compound structures was performed by synthesis. NABMEs, NAVMEs and NAGMEs are produced in low amounts only, making mass spectrometry the method of choice for their detection. The analysis of both EI and ESI mass spectra revealed fragmentation patterns helpful for the detection of similar compounds derived from other amino acids. Some of these compounds showed antimicrobial activity. The structural similarity of N-acylated amino acid methyl esters and similar lipophilicity to AHLs might indicate a yet unknown function as signalling compounds in the ecology of these bacteria, although their singular occurrence is in strong contrast to the common occurrence of AHLs. Obviously the structural motif is not restricted to Roseovarius spp. and occurs also in other genera.

Structural verification via convergent total synthesis of dipeptide–lipids isolated from Porphyromonas gingivalis

A periodontal pathogen, Porphyromonas gingivalis, produces two serine dipeptide lipid classes that we labeled lipid 654 and lipid 430, and both contain L-serine as the terminal amino acid. The lipid 654 and lipid 430 classes are each comprised of three species with differing fatty acid substitutions, but the most abundant species demonstrate unit masses of either 654 or 430, respectively. Recently we observed that the lipid 654 can be hydrolyzed by specific lipases to lipid 430. However, a substantial percentage of the naturally occurring lipid 654 cannot be enzymatically hydrolyzed to lipid 430. The observed partial hydrolysis could be due to the presence of a mixture of stereoisomers. Testing this theory requires structural verification of our so-called 654 and 430 by total synthesis. We present herein details of the convergent synthesis of lipids 430 and 654, which confirm the proposed structure of P. gingivalis lipid 654 to be (3R and 3S)-L-serine-2. The bis(fatty acid) (3R)-L-serine-2 was prepared as well as the synthetic precursor, serine dipeptide mono-fatty acid (3R)-L-serine-1, which is the structure of lipid 430. We also synthesized the (3S)-L-serine-2 diastereomer as well as (3S)-L-serine-1. Using these synthetic standards, we confirmed that PLA2-mediated hydrolysis of lipid 654 is enantioselective in that only the (3R)-L-serine-2, but not (3S)-L-serine 2 is enzymatically hydrolyzed.