4130-54-5

Usage

Uses

Used in Chemical Synthesis:
Stearic acid hydrazide is used as a precursor in the synthesis of other organic compounds, contributing to the development of new materials and products.
Used in Polymer and Plastic Production:
It plays a role in the production of certain polymers and plastics, enhancing their properties and expanding their applications.
Used in Metalworking Fluids:
Stearic acid hydrazide is used as a corrosion inhibitor in metalworking fluids, protecting metal surfaces from corrosion and extending the life of equipment.
Used in Cosmetic and Personal Care Products:
It serves as a stabilizer in some cosmetic and personal care products, ensuring the stability and effectiveness of these products over time.
Used in Pharmaceutical Industry:
Stearic acid hydrazide has been investigated for its potential use in drug delivery systems, offering a promising avenue for improving the efficacy and targeted delivery of pharmaceuticals.
Used in Antimicrobial Applications:
Its potential antimicrobial properties make stearic acid hydrazide a candidate for use in various applications where controlling the growth of microorganisms is essential.
Used in Antioxidant Applications:
STEARIC ACID HYDRAZIDE's potential antioxidant properties suggest its use in applications requiring protection against oxidative damage, such as in the food industry or in the development of new materials with enhanced durability.

InChI:InChI=1/C18H38N2O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(21)20-19/h2-17,19H2,1H3,(H,20,21)

Upstream product

• 555-43-1 glycerol tristearate 
• 122-32-7 trioleoylglycerol 
• 64-17-5 ethanol 
• 112-80-1 cis-Octadecenoic acid 
• 112-79-8 Elaidic acid 
• 112-62-9 Methyl oleate 
• 111-62-6 oleic acid ethyl ester 
• 112-61-8 Methyl stearate 
• 111-61-5 stearic acid ethyl ester 
• 124-26-5 stearamide 
• 7803-57-8 hydrazine hydrate 
• 57-11-4 stearic acid 
• 6915-08-8 octadec-9-enoic acid propane-1,2,3-triyl ester 
• 112-62-9 octadec-9-enoic acid methyl ester 

Downstream Products

• 112-10-7 isopropyl stearate 
• 93798-49-3 N-phenyl-2-stearoylhydrazinecarbothioamide 
• 1107003-73-5 3-(4',5'-dihydroxyphenyl)-5-heptadecyl-1H-1,2,4-triazole 
• 1107003-65-5 3-(4'-hydroxyphenyl)-5-heptadecyl-1H-1,2,4-triazole 
• 1107003-55-3 3-phenyl-5-heptadecyl-1H-1,2,4-triazole 
• 200505-63-1 N'-(2-chlorobenzylidene)stearohydrazide 
• 68181-04-4 N'-benzylidenestearohydrazide 
• 1273028-57-1 C₂₆H₄₄N₂OS 
• 186824-10-2 N'-(4-hydroxybenzylidene)stearohydrazide 
• 1394051-09-2 2-heptadecyl-5-phenyl-1,3,4-oxadiazole 
• 23455-87-0 4-amino-5-heptadecyl-2,4-dihydro-3H-1,2,4-triazole-3-thione 

Relevant academic research and scientific papers

Newly synthesized oxadiazole based mannich base derivatives of fatty acid: In silico study and in vivo anti-hyperglycaemic estimation

A receptor peroxisome proliferator activated receptor-gamma was targeted by series of new fatty acid chemical entities (M1-M22) which was designed, synthesized and characterized by spectral analysis. Metabolites molecular properties were calculated using Lipinski’s rule of five using molinspiration online software. Docking studies were done on co-crystallized protein structure of PPAR γ, PDB-1FM9 showing M15, M17 and M8 to be best located in the active sites with scores -10.43, -10.21 and -10.00 respectively. The free binding energy estimation was done using model of Maestro 9.0 (Schrodinger) and lies between -80.15 to -61.26 kcal/mol which is significant as compared to that of standard (-48.58 Kcal/mol). Nine best docked derivatives were evaluated in-vivo for oral glucose tolerance and antihyperglycemic activity by streptozotocin induced diabetes model and M15 exhibited most promising antidiabetic activity more than the standard glibenclamide. The promising results encourage future investigation on fatty acids for development of active compounds.

Synthesis of various nitrogen heterocycles as antimicrobial surface agents

A number of novel, thiazole 5, oxadiazole 6, thiadiazole 7, triazole 8, 9, and fused triazole derivatives 10, 11, 12 were obtained from a valuable and inexpensive fatty acids (stearic acid). Propoxylation of these compounds using 5 moles of propylene oxide produced nonionic surface active agents (13, 14,15 16, 17,18,19,20). The surface properties and the biodegradability of the latter compounds were evaluated. Some of the synthesized compounds were investigated for their antimicrobial activities.

Synthesis of 5-heptadecyl- and 5-heptadec-8-enyl substituted 4-amino-1,2,4-triazole-3-thiol and 1,3,4-oxadiazole-2-thione from (Z)-octadec-9-enoic acid: preparation of Palladium(II) complexes and evaluation of their antimicrobial activity

Abstract: Two 4-amino-1,2,4-triazoles and two 1,3,4-oxadiazoles are obtained in a common synthetic route including hydrogenation-hydrazidation of (Z)-methyl octadec-9-enoate to octadecanoic hydrazide under atmospheric air. Preservation of olefinic bond in heptadec-8-enyl group is achieved by carrying out hydrazidation reaction under the presence of an argon atmosphere. The disappearance of the olefinic bond is detected by physical data, IR, 1H, and13C NMR spectroscopy. New palladium complexes derived from 4-amino-5-heptadecyl-1,2,4-triazole-3-thiol and 5-heptadecyl-1,3,4-oxadiazole-2(3H)-thione are obtained and characterized by elemental analysis (solid state), IR, 1H, 13C NMR spectroscopy, XRD, and XPS. These resulting metallic entities are also identified in solution based in mass spectrometry (MS-ESI) experiments. Most compounds and their palladium(II) complexes are tested in vitro against Gram-positive, Gram-negative bacteria, and fungi, some of them showed variable activity. Graphic abstract: [Figure not available: see fulltext.].

Synthesis, ADME, docking studies and in vivo anti-hyperglycaemic potential estimation of novel Schiff base derivatives from octadec-9-enoic acid

A new series of octadec-9-enoic acid schiff base entities (S1-S30) were designed and synthesized targeting peroxisome proliferator activated receptor-gamma for agonist action. Molinspiration software (online) was used to estimate drug like molecular properties of the metabolites. Docking disquisition on co-crystallized protein of PPAR-γ (PDB ID 1FM9) was carried out which showed S21, S10 and S7 as best situated in the vital sites of receptor having docking scores ?9.19, ?8.68 and ?8.64 respectively. Free binding energy measured using model of Maestro 9.0 and was in range of from ?40.01 and ?80.54 kcal/mol, significant when compared with pioglitazone (?51.58 Kcal/mol). Seven best docked derivatives were assessed for in-vivo oral glucose tolerance on normal rats and anti-hyperglycaemic activity by streptozotocin induced diabetes model. S21 unveiled to be the best measured analogue among all the synthesized entities. Encouraging outcomes motivates fatty acids for further development of more effective and safer compounds.

A new class of human fatty acid synthase inhibitors: Synthesis and their anticancer evaluation

A series of 3-pentadecyl/heptadecyl-6-subsituted phenyl[l,2,4]triazolo[3,4-&][l,3,4]thiadiazoles have been designed, synthesized and screened for their in vitro antitumour activity against breast cancer cell Jines. Three compounds namely, 3- pentadecyl-6-phenyl[l,2,4]triazolo[3,4-b][l,3,4]thiadiazole (6e), 3-heptadecyl-6-phenyl[l,2,4]triazolo[3,4-i][l,3,4]thiadiazole (6j) and 3-heptadecyl-6(3-nitrophenyl)[l,2,4]triazolo[3,4b][l,3,4]-thiadiazole (6g) have displayed comparable activities towards human breast cancer lines. Molecular docking studies have been carried out on the crystal structure of human fatty acid synthase thioesterase domain (2PX6) by using GLIDE integrated Maestro 9.3 version. The designed compounds have shown good binding interactions with the active site residues present in the enzyme and have given very good G-scores when compared to the known inhibitor orlistat.

Synthesis and antimicrobial studies of 5-n-alkyl-1,3,4-oxadiazole-2-thiol derivatives from fatty acids

The novel 5-N-alkyl-1,3,4-oxadiazole-2-thiol derivatives have been synthesized by esterification of fatty acid followed by reaction the ester with hydrazine hydrate. The acid hydrazide was converted to 1,3,4-oxadiazole by ring closure mechanism. The synthesized compounds have been characterized by physical (melting point and TLC) and spectral (IR, 1H NMR and mass) data. All the compounds were screened for their antimicrobial activity. The compounds 3F1 & 3F4 showed good inhibition activity against all four types of bacteria; while compound 3F2 & 3F3 shown moderate activity.

Cyclocondensation between fatty acid hydrazides and 1,1,1-trifluoro-4-alkoxy-3-alken-2-ones: Introducing a trifluoromethylated head onto fatty acid moieties

This paper reports the regioselective synthesis of new trifluoromethylated lipid derivatives, namely, 1-(5-hydroxy-5-trifluoromethyl-3-alkyl-4,5-dihydro-1H-pyrazol-1-yl)alkan-1-ones, through cyclocondensation reactions between a series of fatty hydrazides (palmitoyl, stearoyl, and oleoyl hydrazides) obtained from fatty acids from renewable resources (1,1,1-trifluoro-4-alkoxy-3-alken-2-ones [F3CC(O)CH?C(R1)OR, where R1 = H and R?Et; R1 = –(CH2)6CH3, –(CH2)6CH3, –(CH2)8CH3, –(CH2)9CH3, –(CH2)10CH3, –(CH2)12CH3, –(CH2)2Ph], and R?Me). Experimental observations showed that the lipophilic characteristic of 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazoles (5–7) prevent the acid catalyzed dehydration to aromatization of 1H-pyrazole ring, although in some cyclocondensations a proportion of the aromatic derivative 1-(5-trifluoromethyl-3-alkyl-1H-pyrazol-1-yl)alkan-1-one was obtained. All products were characterized using multinuclear (1H, 13C, 19F) NMR spectroscopy.

Novel fatty acid analogues as human fatty acid synthase thioesterase domain inhibitors: Synthesis and their cytotoxicity screening

A new class of 1, 3, 4-oxadiazoles substituted stearic/palmitic acid analogues were prepared. In-silico docking studies have been done into the crystal structure of thioesterase domain of human fatty acid synthase (2PX6) that gave some important structural information on the ligand binding interactions. The residues His 2481, Tyr 2462 & Ala 2448 formed hydrogen bonds with 1, 3, 4-oxadiazole ring. All the target compounds exhibited good binding interactions with the active site residues. Cytotoxicity has been done for some selected compounds against human lung carcinoma cell lines (A-549) by SRB method. The compounds showed strong cytotoxicity.

Synthesis and Surface Characterization Studies of Polyether-Linked Symmetric Higher Sulfanyl-1,3,4-Oxadiazoles

The synthesis and the characterization of a series of novel symmetric double length alkyl-chained sulfanyl-1,3,4-oxadiazoles functionalized with a polyether head group are reported. In addition, surface characterization studies were conducted on the metal surface of these synthesized compounds. The metal surfaces were characterized by contact angle measurements via the sessile-drop method, and 3D images of the metal surface were obtained using an optical profilometer. The surface studies showed that the inhibitor molecule increases the hydrophobic character and decreases the wettability of the metal surface.

Improved protocol toward 1,3,4-oxadiazole-2(3H)-thiones and scale-up synthesis in the presence of SDS as a micelle promoted catalyst

Convenient procedure for in situ cyclization of hydrazinecarbodithioate potassium salts to 1,3,4-oxadiazole-2(3H)-thiones under normal phase micellar media catalysis promoted by sodium dodecyl sulfate (SDS) as an anionic surfactant is reported. The main advantage of this procedure is to provide shorter reaction time for the completion of cyclization; scale-up synthesis is possible and the oxadiazoles were obtained in high to excellent yields (87-100%), making the protocol an attractive alternative to the available methods.