764-85-2

Usage

Uses

1. Chitosan Modification:
Nonanoyl chloride is used as an acylating agent for the amine groups of chitosan, a biopolymer derived from chitin. The application reason is to simultaneously improve the material properties and adsorption capacity of chitosan, enhancing its performance in various applications such as water treatment, drug delivery, and tissue engineering.
2. Synthesis of N-nonanoyl Piperonylamide:
In the pharmaceutical industry, Nonanoyl chloride is used as a key intermediate in the synthesis of N-nonanoyl piperonylamide, a compound with potential applications in the treatment of various diseases.
3. Synthesis of Caged Vanilloid:
Nonanoyl chloride is also used in the synthesis of caged vanilloid, a compound that can be used to control the release of vanilloid receptors, which are involved in pain sensation and other physiological processes.
4. Synthesis of N-(4-hydroxy-3-methoxybenzyl)-N-(2-nitrobenzyl)-nonanoylamide:
Nonanoyl chloride, synthesized using Nonanoyl chloride, has potential applications in the development of new drugs targeting specific biological processes.
5. Synthesis of N-(2-Nitrobenzyl)-N-vanillyl-nonanoylamide:
Another compound synthesized using Nonanoyl chloride, this molecule may have potential applications in the pharmaceutical industry, particularly in the development of new therapeutic agents.
6. Synthesis of n-Benzylnonanamide:
Nonanoyl chloride is used in the synthesis of n-benzylnonanamide, a compound that may have potential applications in various industries, including pharmaceuticals and materials science.

Purification Methods

Reflux it with acetyl chloride (~ 3 volumes) for 1hour, then distil off AcCl followed by the nonanoyl chloride at ~12mm. It is moisture sensitive and should be stored in sealed ampoules. [Beilstein 2 IV 1023.]

InChI:InChI=1/C9H17ClO/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3

Upstream product

• 112-05-0 nonanoic acid 
• 79-37-8 oxalyl dichloride 
• 124-19-6 nonan-1-al 
• 7719-09-7 thionyl chloride 

Downstream Products

• 20308-70-7 1-(pyrrolidin-1-yl)nonan-1-one 
• 334-38-3 1-fluoro-decan-2-one 
• 20308-66-1 1-nonanoyl-hexahydro-azepine 
• 22913-02-6 tert-butylperoxy pelargonate 
• 7511-76-4 N-(4-amino-2-methyl-[6]quinolyl)-nonanamide 
• 102811-97-2 N-(4-benzyloxy-3-methoxy-benzyl)-nonanamide 
• 2444-46-4 Nonivamide 
• 1182-66-7 cholesteryl pelargonate 
• 139446-83-6 N-(3,4-dihydroxybenzyl)nonanamide 
• 57383-15-0 N,N-dipropyl-nonanamide 
• 10385-09-8 N,N-diethyl nonanamide 
• 168432-71-1 octyl p-tolyl ketone 
• 101741-11-1 1-(2,5-dimethoxy-phenyl)-nonan-1-one 
• 1551-41-3 nonanoic acid cyclohexyl ester 

Relevant academic research and scientific papers

Pseudotrienic acids A and B, two bioactive metabolites from Pseudomonas sp. MF381-IODS

Bioassay-guided fractionation of the liquid culture broth of Pseudomonas sp. MF381-IODS yielded two new antimicrobial substances, identified as (2E,4E,6E)-9-[((2S,3R)-3-hydroxy-4-{(3E,5E,7RS)-7-hydroxy-4-methylhexadeca-3, 5-dienoyl]amino}-2-methylbutanoyl)amino]nona-2,4,6-trienoic acid and the tetradeca equivalent, named pseudotrienic acids A (1) and B (2), respectively. The compounds are prone to lactone formation, and their structures suggest them to be derived from ring opening of a macrolide. Pseudotrienic acids A and B inhibited growth of Staphylococcus aureus (MIC 70 μg/mL) and Pseudomonas syringae pv. syringae (MIC 70 μg/mL). Two known antimicrobial compounds, the polyketide 2,3-deepoxy-2,3-didehydrorhizoxin (3) and the tryptophan-derived pyrrolnitrin (4), were also identified.

Synthesis, computational studies and enzyme inhibitory kinetics of benzothiazole-linked thioureas as mushroom tyrosinase inhibitors

Herein, we report synthesis of a set of benzothiazole-thiourea hybrids with aromatic and aliphatic side chains (BT1 to BT9) using an elegant synthetic strategy. The newly synthesized benzothiazole-thiourea conjugates were subjected to In-vitro tyrosinase inhibition and free radical scavenging activity. Majority of the compounds indicated inhibition considerably improved than the standard; compound (Kojic acid with IC50 = 16.8320 ± 1.1600 μM) BT2 with IC50 = 1.3431 ± 0.0254 μM was found to be the best inhibitor. A non-competitive mode of inhibition of BT2 was disclosed with Ki value of 2.8 μM. In order to study enzyme-inhibitor interactions SAR analysis molecular docking was carried out. The amino groups of thiourea were involved in hydrogen bonding with Glu322 showing the bond length of 1.74 and 2.70 ?, respectively. Moreover, the coupling of π-π was displayed between benzothiazole and benzene rings of His244 and His263, respectively. The outcome of this study might help to develop new inhibitors of melanogenesis, important for cosmetic and food products. Communicated by Ramaswamy H. Sarma.

Benzimidazole tethered thioureas as a new entry to elastase inhibition and free radical scavenging: Synthesis, molecular docking, and enzyme inhibitory kinetics

The porcine pancreatic elastase inhibition and free-radical scavenging play a crucial role in age progression. All the series of 10 newly synthesized benzimidazole thioureas (4a-j) were assessed for elastase inhibition and radical scavenging activity to identify the suitable anti-aging ingredient for cosmetics products. The compounds 4e, 4f, 4g, and 4h showed inhibition better than the standard, while compound 4f showed the most significant elastase inhibition with the IC50 value of 1.318 ± 0.025 μM compared with oleanic acid IC50 13.451 ± 0.014 used ±1.989 and 41.563 ± 0.824, respectively, as standard. Molecular docking studies were performed and the compound 4f showed binding energy of 7.2 kcal/mol. Kinetics studies revealed inhibition of the pancreatic elastase in a competitive manner. The relative binding energy and structure activity relationship (SAR) identified compound 4f as an effective inhibitor of porcine pancreatic elastase. Compounds 4e and 4i showed remarkable free-radical scavenging activity with SC50 values of 26.421.

L-ascorbyl 6-palmitate as lead compound targeting SphK1: an in silico and in vitro investigation

Sphingosine kinases (SphKs) are a class of lipid kinases, that have received extensive attention as important rate-limiting enzyme in tumor. Inhibition of the activity of SphK1 can lead to an anticancer effect. Herein, we describe the discovery process and biological characteristics of a new SphK1 inhibitor, ascorbyl palmitate, discovered through computer-aided drug design. Biochemical experiments show that ascorbyl palmitate has a strong inhibitory effect on SphK1, with an IC50 value of 6.4 μM. The MTT experiment showed that ascorbyl palmitate had anti-cancer effects toward the U87, A549, 22RV1, and A375 cell lines. Among them, ascorbyl palmitate has prominent inhibitory activity against the 22RV1 cell line, with an IC50 value of 41.57 μM. To explore the structure–activity relationship, four ascorbyl palmitate derivatives were synthesized and tested for kinase activity. The outstanding effect of ascorbyl palmitate toward SphK1 and its known non-toxicity suggest that ascorbyl palmitate may be a lead compound for the development of effective SphK1 anti-cancer inhibitors.

Neutrophil-Selective Fluorescent Probe Development through Metabolism-Oriented Live-Cell Distinction

Human neutrophils are the most abundant leukocytes and have been considered as the first line of defence in the innate immune system. Selective imaging of live neutrophils will facilitate the in situ study of neutrophils in infection or inflammation events as well as clinical diagnosis. However, small-molecule-based probes for the discrimination of live neutrophils among different granulocytes in human blood have yet to be reported. Herein, we report the first fluorescent probe NeutropG for the specific distinction and imaging of active neutrophils. The selective staining mechanism of NeutropG is elucidated as metabolism-oriented live-cell distinction (MOLD) through lipid droplet biogenesis with the help of ACSL and DGAT. Finally, NeutropG is applied to accurately quantify neutrophil levels in fresh blood samples by showing a high correlation with the current clinical method.

Boosting the efficacy of anti-MRSA β-lactam antibiotics via an easily accessible, non-cytotoxic and orally bioavailable FtsZ inhibitor

The rapid emergence of methicillin-resistant Staphylococcus aureus (MRSA) strains has undermined the therapeutic efficacy of existing β-lactam antibiotics (BLAs), prompting an urgent need to discover novel BLAs adjuvants that can potentiate their anti-MRSA activities. In this study, cytotoxicity and antibacterial screening of a focused compound library enabled us to identify a compound, namely 28, which exhibited low cytotoxicity against normal cells and robust in vitro bactericidal synergy with different classes of BLAs against a panel of multidrug-resistant clinical MRSA isolates. A series of biochemical assays and microscopic studies have revealed that compound 28 is likely to interact with the S. aureus FtsZ protein at the T7-loop binding pocket and inhibit polymerization of FtsZ protein without interfering with its GTPase activity, resulting in extensive delocalization of Z-ring and morphological changes characterized by significant enlargement of the bacterial cell. Animal studies demonstrated that compound 28 had a favorable pharmacokinetic profile and exhibited potent synergistic efficacy with cefuroxime antibiotic in a murine systemic infection model of MRSA. Overall, compound 28 represents a promising lead of FtsZ inhibitor for further development of efficacious BLAs adjuvants to treat the staphylococcal infection.

Utilization of hexabromoacetone for protection of alcohols and aldehydes and deprotection of acetals, ketals, and oximes under UV irradiation

Hexabromoacetone (HBA) was efficiently used for the protection of alcohols and aldehydes and deprotection of benzaldehyde dimethyl acetal, solketal, and other acetals and ketals. In only 10?min, the protection of glycerol yielded 90% of solketal and protection of benzaldehyde gave 95% of benzaldehyde dimethyl acetal. The deprotection of benzaldehyde dimethyl acetal under UV irradiation gave over 90% yield of benzaldehyde within 15?s using only 2.5?mol% of HBA. HBA was also successfully used for deoximation. Solvent was found to play an important role in the efficiency of HBA for these reactions.

IONIZABLE CATIONIC LIPID FOR RNA DELIVERY

What is described is a compound of formula I consisting of a compound in which R1 is a branched chain alkyl consisting of 10 to 31 carbons; R2 is a linear alkyl, alkenyl, or alkynyl consisting of 2 to 20 carbons; L1 and L2 are the same or different, each a linear alkylene of 1 to 20 carbons or a linear alkenylene of 2 to 20 carbons; X1 is S or O; R3 is a linear or branched alkylene consisting of 1 to 6 carbons; and R4 and R5 are the same or different, each a hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.

Synthesis, Physicochemical Properties, and Thermo-Oxidative Stability of Diesters of 5,7-Dimethyl-1,3-Adamantanediol and 5,7-Dimethyl-1,3-bis(Hydroxymethyl)adamantane

A series of diesters on the basis of 5,7-dimethyl-1,3-adamantanediol and 5,7-dimethyl-1,3- bis(hydroxymethyl)adamantane and C3–C10 aliphatic acids have been synthesized and their physicochemical and thermo-oxidative properties have been studied. The properties of the esters obtained have been compared to those of trimethylolpropane and neopentyl glycol esters.

Janus particles self-assembled from a small organic atypical asymmetric gemini surfactant

A series of atypical asymmetric gemini surfactants with an amphiphilic carbonate group (-O-CO-O-) have been prepared. Some of these compounds could self-assemble in water into gourd-shaped Janus particles (JPs). Initial results suggested that the formation of JPs was highly likely to be related to their atypical gemini surfactant structure. To our knowledge, this is the first report on JPs that are self-assembled from a single kind of small organic molecule. We believe that our results will be utilized in many fields.