73367-75-6

Upstream product

• 505-95-3 12-hydroxydodecanoic acid 
• 5675-51-4 1,12-dodecandiol 
• 60633-18-3 (3-carboxy-propyl)triphenylphosphonium chloride 
• 73367-80-3 12-bromododecanoic acid 
• 603-35-0 triphenylphosphine 

Downstream Products

• 622842-33-5 13-(2-[5-(tetrahydropyran-2-yloxy)pent-1-ynyl]phenyl)tridec-12-enoic acid 
• 711597-33-0 13-phenyl-12-tridecenoic acid 
• 1380444-53-0 C₃₂H₄₁F₅O₂ 
• 247063-08-7 18-(dibenzylamino)-12-octadecenoic acid 
• 247063-04-3 24-(dibenzylamino)-12-tetracosenoic acid 
• 75912-18-4 24-hydroxytetracosanoic acid 
• 109135-39-9 Sodium; 12-(triphenyl-λ⁵-phosphanylidene)-dodecanoate 
• 73367-79-0 ο-(diphenylphosphinyl)-dodecansaeure 

Relevant academic research and scientific papers

Synthesis of vitamin E-carnosine (VECAR): New antioxidant molecule with potential application in atherosclerosis

Natural antioxidants such as carnosine and α-tocopherol (vitamin E) provide protection against several oxidative stress-related diseases such as atherosclerosis and Alzheimer's. The synthetic combination of α-tocopherol and carnosine can take advantage of the cellular transport mechanism of α-tocopherol by α-tocopherol transfer protein (α-TTP) to colocate α-tocopherol and carnosine at the interface between a lipophilic and a hydrophilic domain and protect both from oxidation. Successful synthesis of a novel heterodimer of α-tocopherol (vitamin E) and carnosine, VECAR was carried out in a total of nine steps. The VECAR design uses a 13-carbon phytyl-chain mimic to link carnosine to Trolox at the C2 carbon position. This design feature is anticipated to maintain binding to α-TTP, while maintaining the antioxidant activity of the two heterodimer components. Our results confirmed that there was no loss in antioxidant activity in VECAR using an in-vitro DPPH assay, versus α-tocopherol and Trolox. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental.

Alicyclic Claisen rearrangement with a two-atom ring contraction. A new synthetic approach to cembranoids

Methylenation of certain olefinic lactones with dimethyl titanocene, followed by thermal or triisobutylaluminium-mediated Claisen rearrangement leads to cembrane-like 11-15-membered ring ketones bearing an isopropenyl side chain.

A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA1) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA1 agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA1 receptor agonist described so far (Emax = 118%, EC50 = 0.24 μM, KD = 19.6 nM; inactive at autotaxin and LPA2-6 receptors). This compound induces characteristic LPA1-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

Synthesis of antifungal alatanone and trineurone polyketides

The antifungal polyketides alatanones A and B and trineurones A–E have been synthesized using a one-pot C-acylation reaction coupling 1,3-cyclohexanediones with the appropriate carboxylic acids. This key transformation is believed to proceed via initial carbodiimide-mediated O-acylation followed by a DMAP-catalyzed Claisen–Haase rearrangement, resulting in O to C acyl migration.

Development of an enzyme-linked immunosorbent assay for the determination of the linear alkylbenzene sulfonates and long-chain sulfophenyl carboxylates using antibodies generated by pseudoheterologous immunization

ELISA methods have been developed for screening contamination of water resources by linear alkyl benzene sulfonates (LAS) or the most immediate degradation products, the long chain sulfophenyl carboxylates, SPCs. The assay uses antibodies raised through pseudoheterologous immunization strategies using an equimolar mixture of two immunogens (SFA-KLH and 13C13-SPC-KLH) prepared by coupling N-(4-alkylpnenyl)sulfonyl-3-aminopropanoic acid (SFA) andp-(1-carboxy-13-tridecyl)-phenylsulfonic acid (13C13-SPC) to keyhole limpet hemocyanin (KLH). The immunizing haptens have been designed to address recognition versus two different epitopes of the molecule. The SFA hapten maximizes recognition of the alkyl moiety while preserving the complexity of the different alkyl chains present in the LAS technical mixture. The 13C13-SPC hapten addresses recognition of the common and highly antigenic phenylsulfonic group. The antisera raised using this strategy have been shown to be superior to those obtained through homologous immunization procedures using a single substance. By using an indirect ELISA format, LAS and long-chain SPCs can be detected down to 1.8 and 0.2 μg L-1, respectively. Coefficients of variation of 6 and 12% within and between assays, respectively, demonstrate immunoassay reproducibility. The assay can be used in media with a wide range of pH and ionic strength values. Preliminary experiments performed to assess matrix effects have demonstrated the potential applicability of the method as a screening tool to assess contamination by these types of surfactants in natural water samples.

ALBUMIN-BINDING COMPOUNDS

The present invention provides an albumin-binding compound essentially of the following elements: a spacer group, a water-soluble bridging group, a fatty acid chain and an acidic group characterised in that the acidic group is attached to the distal end of the fatty acid chain. The invention also provides an albumin-binding compound to which one or more biologically active moieties are attached.

Novel Synthesis of ω-(Diphenylphosphinyl)alkylcarboxylic Acids from Triphenyl-ω-carboxyalkylphosphonium Salts

A novel method for the synthesis of triphenylphosphonium salts of the type (C6H5)3P+(CH2)nCO2H,X- (1: n=2,3; X=Cl; n=5,10,11; X=Br) from the corresponding ω-haloalkylcarboxylic acids and triphenylphosphine has been described.When members of 1 were treated with NaH/Me2SO/THF at room temperature under N2, the corresponding ω-(diphenylphosphinyl)alkylcarboxylic acids 2 (n=3,5,10,11) were isolated.The yields were good (62-75percent) for compounds with longer side chains (n=10,11).In one case (n=3), (C6H5)3P was isolated as a side product (yield 20percent).Attempts to prepare the Wittig reagents from 1 and the subsequent reaction with aldehydes (benzaldehyde and 9-anthraldehyde) failed to yield the expected alkenes.However, members of 2 were produced, and it was possible to recover >90percent of the unreacted 9-anthraldehyde.The structures of the compounds in the series 1 and 2 have been established via the spectral properties and elemental analyses.The 31P and 13C chemical shifts as well as C-P coupling constants have been evaluated and analyzed.A tentative mechanism has been proposed for the formation of 2 from 1.