112-76-5

Usage

Uses

Used in Pharmaceutical Industry:
Octadecanoyl chloride is used as a synthetic compound for the development of tumor-associated macrophages and antitumor agents. Its chemical properties allow it to be a key component in the creation of these pharmaceuticals, contributing to the fight against cancer.
Used in Chemical Synthesis:
In the field of chemical synthesis, Octadecanoyl chloride is used as a reagent for the preparation of various compounds, such as 4-fluoroceramide. It is also utilized in the synthesis of shimofuridin analogs, specifically 2′-O-(4-O-stearoyl-alpha-L-fucopyranosyl)thymidine and -uridine, which have potential applications in the medical field.
Overall, Octadecanoyl chloride is a versatile compound with applications in the pharmaceutical and chemical synthesis industries, primarily due to its role in the development and synthesis of antitumor agents and other important compounds.

InChI:InChI=1/C18H37Cl/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h2-18H2,1H3

Upstream product

• 75-44-5 phosgene 
• 57-11-4 stearic acid 
• 79-37-8 oxalyl dichloride 
• 6136-89-6 Stearinsaeure-isopropenyl-ester 
• 822-16-2 sodium stearate 

Downstream Products

• 4629-04-3 1-(piperidin-1-yl)octadecan-1-one 
• 4444-89-7 1-[2]furyl-octadecan-1-one 
• 4444-90-0 1-[2]thienyl-octadecan-1-one 
• 631-87-8 retinyl stearate 
• 63195-78-8 α-amyrin stearate 
• 6343-74-4 2-naphthyl octadecanoate 
• 77850-94-3 7-oxo-tetracosanoic acid 
• 54794-73-9 N-isobutyl-stearoyl amide 
• 638-08-4 stearic anhydride 
• 15430-36-1 N,N'-bis(octadecanoyl)-1,3-diaminobenzene 
• 102253-07-6 Stearinsaeure-(2-hydroxy-phenylester) 
• 113203-41-1 1,3-bis-stearoyloxy-benzene 
• 19165-27-6 2-(1-oxooctadecyl)aminobenzoic acid 
• 4445-04-9 stearoyl-(toluene-4-sulfonyl)-amine 

Relevant academic research and scientific papers

Three labdane-type diterpenes from the bark of Juniperus formosana HAY. var. concolor HAY.

Three new labdane-type diterpenes, (13S)-15-hydroxylabd-8(17)-en-19-oic acid, (13S)-15-acetoxylabd-8(17)-en-19-oic acid, and (13S)-15- octadecanoyloxylabd-8(17)-en-19-oic acid, together with one known compound, enantio-oliveric acid, were found from the hark of Juniperus formosana HAY. var. concolor HAY. Their structures were elucidated on the basis of spectral data and chemical transformation.

PHOTOLYSIS OF α-DIAZO CARBONYL COMPOUNDS IN THE PRESENCE OF IMIDAZOLE. A NEW METHOD FOR THE PREPARATION OF NOR OLEFINS AND ITS APPLICATION TO BILE ACID SIDE CHAIN DEGRADATION

α-Diazomethyl ketones derived from carboxylic acids are photolyzed in the presence of imidazole to give the corresponding nor olefins or, in the case of aryl diazo ketones, the corresponding, stable imidazolides.The application of the method to a novel degradation of bile acid side chain is reported.

Synthesis of 1-oxo-1-(3-pyridazinyl) derivatives - Potent inhibitors of Fatty Acid Amide Hydrolase (FAAH): An improved and optimized procedure

A greatly improved procedure for the preparation of long-chain α-ketopyridazines, a class of potent inhibitors of fatty acid amide hydrolase (FAAH), is described. This optimization study shows a great dependence of the yields of desired products on the pyrididazinyl lithium/Weinreb amide ratio and offers a general approach to this kind of compound. Georg Thieme Verlag Stuttgart.

Molecular assembly and photophysical properties of quaternary molecular hybrid materials with chemical bond

In this paper, two long chain aliphatic carboxylic acids (oleic acid [OLA] and stearic acid [STA]) are modified with cross-linking molecules (N-2-aminoethyl-3-aminopropyl-methyl-dimethoxylsiliane, (AEAPMMS, H 2N(CH2)2HN(CH2)3SiCH 3(OCH3)2 and 3-aminopropyl-methyl- diethoxylsiliane (APMES, H2N(CH2)3SiCH 3(OC2H5)2) resulting in four new kinds of structural molecular bridge OLA (STA)-AEAPMMS (APMES). Subsequently, ternary molecular complex systems with four molecular bridges OLA (STA)-AEAPMMS (APMES) and 2,2-bipyridyl (bipy) of lanthanides (terbium and europium) or zinc ions were assembled, which resulted in four novel kinds of quaternary molecular hybrid materials (named as bipy-Ln (Zn)-OLA (STA)-AEAPMMS (APMES) with strong chemical bonds (N-Ln(Zn)-O coordination bonds and Si-O covalent bonds) after a sol-gel (cohydrolysis and copolycondensation) process of the modified molecular bridges (as structural ligand) with inorganic precursor (tetraethoxysilane, TEOS). And especially bipy behaves as functional ligand to sensitize the luminescence of terbium or europium ions through the effective intramolecular energy transfer process, which gives rise to the characteristic emission of metal ions. The design and assembly from structural and functional ligands can help achieve a candidate technology for molecular hybrids.

Inhibitory effect of novel 5-O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response

We previously found that vitamin K3 (menadione, 2-methyl-1,4-naphthoquinone) inhibits the activity of human mitochondrial DNA polymerase γ (pol γ). In this study, we focused on juglone (5-hydroxy-1,4-naphthoquinone), which is a 1,4-naphthoquinone derivative, and chemically synthesized novel juglones conjugated with C2:0 to C22:6 fatty acid (5-O-acyl juglones). The chemically modified juglones enhanced mammalian pol inhibition and their cytotoxic and anti-inflammatory activities. The juglone conjugated with oleic acid (C18:1-acyl juglone) showed the strongest inhibition of DNA replicative pol α activity and human colon carcinoma (HCT116) cell growth in 10 synthesized 5-O-acyl juglones. C12:0-Acyl juglone was the strongest inhibitor of DNA repair-related pol λ, as well as the strongest suppression of the production of tumor necrosis factor (TNF)-α production induced by lipopolysaccharide (LPS) in the compounds tested. Moreover, this compound caused the greatest reduction in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced acute inflammation in mouse ears. C12:0- and C18:1-Acyl juglones selectively inhibited the activities of mammalian pol species, but did not influence the activities of other pols and DNA metabolic enzymes tested. These data indicate that the novel 5-O-acyl juglones target anti-cancer and/or anti-inflammatory agents based on mammalian pol inhibition. Moreover, the results suggest that acylation of juglone is an effective chemical modification to improve the anti-cancer and anti-inflammation of vitamin K3 derivatives, such as juglone.

Synthesis and self-assembly of Salen type Schiff based on o-phenylenediamine organogels in response to Zn2+

Two Salen type Schiff based on o-phenylenediamine were synthesized. The prepared organogelators demonstrated excellent gel properties in some selected solvents, such as n-pentanol, chloroform, and 1,2-dichloroethane. The results for thermal stability showed that under concentrations increasing of the gel molecules and then the gel-to-sol transition temperature value is increased. Through various techniques found that the hydrogen bonding between molecules, the van der Waals force, and the π-π stacking provide multiple driving forces for gel self-assembly. The morphology of the xerogel was investigated by Scanning Electron Microscope (SEM). The metal ions responsiveness experiment is completed by adding the metal ions solution dropwise to the gel surface and confirmed by the UV spectrum.

Catalyst for synthesizing acyl chloride compounds and application thereof

The invention relates to a catalyst for synthesizing an acyl chloride compound and application of the catalyst. The structural formula is as shown in the specification, and in the formula, R is alkali of which the carbon atom number is 1-12. The catalyst is capable of effectively increasing the product yield, improving the production efficiency and lowering the production cost of acyl chloride, and has wide application prospects. The invention further provides a method for synthesizing acyl chloride with the catalyst.

ABUSE-RESISTANT LONG-ACTING RELEASE OPIOID PRODRUGS

There are provided, prodrugs of opioid such as levorphanol or morphine, having enhanced physical and chemical stability to resist tampering and to make long- acting release formulations, and pharmaceutically accepted salts and solvates thereof. There are also provided methods of using the disclosed compounds as abuse deterrent products.

Sialic acid lipid derivative and preparation method and application thereof

The invention belongs to the technical field of medicines, and provides a sialic acid lipid derivative which can be used for modifying a particle preparation and a preparation method and application thereof. The structural general formula of the sialic acid lipid derivative is as shown in the specification, wherein R1 is an H atom or C1-C6 alkyl; R2 is H, (CH2) m or C2-C6 alkenyl, and m =1-17; when X is an H atom or an O atom, R3 is (CH2) n or cholesteryl, and n = 1-17; when X is a carbonyl group, R3 is a C12-C24 alkoxy group, a C12-C24 alkyl substituted amino group or cholesteryl; and R4 is -OH, -NHCOCH3 or -NHCOCH2OH. The sialic acid lipid derivative disclosed by the invention can be used for modifying a particle preparation and realizing different treatment or diagnosis purposes according to the properties of the medicine. Especially in the anti-tumor aspect, the sialic acid lipid derivative can endow a particle preparation with excellent tumor targeting ability to improve the tumorinhibition effect.

A new class of pure estrogen alpha receptor antagonists; design, synthesis and in-vitro screening

Background: In view of the estrogenic receptor inhibitory properties of coumarin nucleus, long chain nature of fatty acid and anti-breast cancer activity of fatty acids, it was proposed to attach long chain fatty acids at 3rd,4th and 7th position of coumarin nucleus and evaluate for their anti-breast cancer activity through suitable in-vitro methods. Methods: The present study focuses a library of fatty acid coumarin conjugates as ligands to the ligand-binding domain of the human estrogen receptor α (PDB ID 2IOG) and their binding affinities using GLIDE module of Schrodinger after ascertaining their drug-likeness with QIKPROP. The compounds LNAC 8, SAC 1 and OAC 5 are the best hits based on their docking scores as well as the Prime MM-GBSA free energy of binding. Based on the in-silico results and synthetic feasibility the compounds SAC 1 PAC 1 and OAC 1 are synthesized, characterized and investigated for their time interval growth inhibitory effect on MCF-7 which is an ER positive breast cancer cell lines. Results: SAC 1, showed better in vitro growth inhibitory effect in sub micromolar range as compared to Tamoxifen, a standard estrogen receptor modulator. Conclusion: Conclusively, in silico molecular docking studies have been very useful in predicting the pharmacokinetic profiles and the binding affinities of new hits before a detailed preclinical and clinical evaluation.