23377-40-4

Usage

Uses

Used in Personal Care and Cosmetic Industry:
1-O-Hexadecyl-propanediol-(1,3) is used as an emollient for its moisturizing properties, helping to maintain skin and hair hydration.
1-O-Hexadecyl-propanediol-(1,3) is used as an emulsifier to blend oil and water components in formulations, ensuring a stable and uniform mixture.
1-O-Hexadecyl-propanediol-(1,3) is used as a thickening agent to enhance the viscosity and texture of skincare and haircare products, creating a smooth and creamy consistency.

Upstream product

• 112-82-3 hexadecanyl bromide 
• 504-63-2 trimethyleneglycol 
• 6068-28-6 tosylate de n-hexadecyle 
• 20779-14-0 methanesulfonic acid hexadecyl ester 
• 36653-82-4 1-Hexadecanol 

Downstream Products

• 268729-67-5 N²-(p-anisyldiphenylmethyl)-9-[(2-hydroxyethoxy)methyl]guanine 2-chlorophenyl (3-hexadecyloxypropyl) phosphate 
• 864068-45-1 {[3-(hexadecyloxy)propoxy](hydroxy)phosphoryl}methyl tosylate 
• 1258789-57-9 Bn/HDP H-phosphonate 
• 1258789-59-1 HDP/Bn methylphosphonate 
• 1362039-08-4 phosphonic acid [[(S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)-2-(triphenylmethoxy)ethyl]methyl]mono[3-(hexadecyloxy)propyl]ester 
• 4673-33-0 3-hexadecyloxy-1-propanamine 
• 911208-73-6 hexadecyloxypropyl tenofovir 
• 1404216-55-2 benzyl N-(3-{ethoxy[3-(hexadecyloxy)propoxy]phosphoryl}propyl)carbamate 
• 1404216-57-4 ethyl 3-(hexadecyloxy)propyl [3-({[4-(benzyloxy)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl}amino)propyl]phosphonate 
• 1344121-73-8 3-(hexadecyloxy)propyl 4-N-benzoyl-2',3'-isopropylidenecytidin-5'-yl vinylphosphonate 
• 1256339-63-5 (S)-3-(hexadecyloxy)propyl 2-aminopropanoate tosylate 

Relevant academic research and scientific papers

Locked Nucleic Acid Gapmers and Conjugates Potently Silence ADAM33, an Asthma-Associated Metalloprotease with Nuclear-Localized mRNA

Two mechanisms dominate the clinical pipeline for oligonucleotide-based gene silencing, namely, the antisense approach that recruits RNase H to cleave target RNA and the RNAi approach that recruits the RISC complex to cleave target RNA. Multiple chemical designs can be used to elicit each pathway. We compare the silencing of the asthma susceptibility gene ADAM33 in MRC-5 lung fibroblasts using four classes of gene silencing agents, two that use each mechanism: traditional duplex small interfering RNAs (siRNAs), single-stranded small interfering RNAs (ss-siRNAs), locked nucleic acid (LNA) gapmer antisense oligonucleotides (ASOs), and novel hexadecyloxypropyl conjugates of the ASOs. Of these designs, the gapmer ASOs emerged as lead compounds for silencing ADAM33 expression: several gapmer ASOs showed subnanomolar potency when transfected with cationic lipid and low micromolar potency with no toxicity when delivered gymnotically. The preferential susceptibility of ADAM33 mRNA to silencing by RNase H may be related to the high degree of nuclear retention observed for this mRNA. Dynamic light scattering data showed that the hexadecyloxypropyl ASO conjugates self-assemble into clusters. These conjugates showed reduced potency relative to unconjugated ASOs unless the lipophilic tail was conjugated to the ASO using a biocleavable linkage. Finally, based on the lead ASOs from (human) MRC-5 cells, we developed a series of homologous ASOs targeting mouse Adam33 with excellent activity. Our work confirms that ASO-based gene silencing of ADAM33 is a useful tool for asthma research and therapy.

Structure-Activity Relationships of Glucosamine-Derived Glycerolipids: The Role of the Anomeric Linkage, the Cationic Charge and the Glycero Moiety on the Antitumor Activity

The potent antitumor activity of 1-O-hexadecyl-2-O-methyl-3-O-(2′-amino-2′-deoxy-β-D-glucopyranosyl)-sn-glycerol (1) was previously shown to arise through an apoptosis-independent pathway. Here, a systematic structure-activity study in which the effects o

Synthesis and antiproliferative activity of cytidine-5'-alkylphosphonophosphates and structurally related compounds

The chemical synthesis of cytidine-5'-alkyl- and cytidine-5'-alkyl(acyl)deoxyglycerophosphonophosphates is reported. The compounds obtained represent a novel class of cytostatically active agents based on phospholipids, which inhibit the growth of various tumor cell lines in vitro. They are phosphono analogs of the cytidine-5'-diphosphale-diacylglycerol (CDP-DAG) possessing a structurally modified lipid moiety and a phospholipase C-resistant P-C bond. The antiproliferative efficacy of the cytidine-5'-alkylphosphonophosphates strongly depends on the alkyl chain length. The cytidine-5'-hexadecylphosphonophosphate was found to be the most effective compound tested in this study. Its cytostatic effect was distinctly higher than that of the alkyl(acyl)deoxyglycero derivatives and of the corresponding diphosphates. The structures of the new compounds were confirmed by fast atom bombardment mass spectrometry (FAB). The FAB fragmentation pattern is discussed.

ANTIVIRAL COMPOUNDS

The present disclosure provides compounds for treating a variety of diseases, such as respiratory syncytial virus (RSV), HRV, hMPV, ebola, Zika, West Nile, Dengue, and HCV.

ω-Functionalized Lipid Prodrugs of HIV NtRTI Tenofovir with Enhanced Pharmacokinetic Properties

Tenofovir (TFV) is the cornerstone nucleotide reverse transcriptase inhibitor (NtRTI) in many combination antiretroviral therapies prescribed to patients living with HIV/AIDS. Due to poor cell permeability and oral bioavailability, TFV is administered as one of two FDA-approved prodrugs, both of which metabolize prematurely in the liver and/or plasma. This premature prodrug processing depletes significant fractions of each oral dose and causes toxicity in kidney, bone, and liver with chronic administration. Although TFV exalidex (TXL), a phospholipid-derived prodrug of TFV, was designed to address this issue, clinical pharmacokinetic studies indicated substantial hepatic extraction, redirecting clinical development of TXL toward HBV. To circumvent this metabolic liability, we synthesized and evaluated ω-functionalized TXL analogues with dramatically improved hepatic stability. This effort led to the identification of compounds 21 and 23, which exhibited substantially longer t1/2 values than TXL in human liver microsomes, potent anti-HIV activity in vitro, and enhanced pharmacokinetic properties in vivo.

Novel antiviral nucleoside reverse transcriptase inhibitor

The invention relates to a novel antiviral nucleoside reverse transcriptase inhibitor compound, a pharmaceutical composition comprising the same and preparation and application thereof. Particularly,the invention discloses a condensed pyrimidine compound

NEW ANTIVIRAL ACYCLONUCLEOSIDE ANALOGUES

The present invention concerns a compound having the following formula (I): as well as its use as a medicament, especially for its use for treating viral infections.

Improved method for synthesis technology of n-hexadecyloxypropyl tenofovir disoproxil

The invention discloses an improved method for a synthesis technology of n-hexadecyloxypropyl tenofovir disoproxil, and belongs to the technical field of organic synthesis. The method comprises the following steps: 1, reacting n-hexadecyl bromide (2) with 1,3-propylene glycol (3) to obtain 3-n-hexadecyloxypropanol (4); 2, chlorinating PMPA (5) to obtain an acyl chloride intermediate (6); 3, esterifying the acyl chloride intermediate (6) and the 3-n-hexadecyloxypropanol (4) to obtain an intermediate (7); and 4, hydrolyzing and re-crystallizing the intermediate (7) to obtain the n-hexadecyloxypropyl tenofovir disoproxil (1), wherein the total yield is about 62%, and the purity is more than 99%. The method mainly has the advantages of easily available materials, simplicity in operation, low cost, and facilitation of industrial production.

Lipophilic amines as potent inhibitors of N-acylethanolamine-hydrolyzing acid amidase

N-Acylethanolamines (NAEs) including N-arachidonoylethanolamine (anandamide) and N-palmitoylethanolamine are endogenous lipid mediators. These molecules are degraded to the corresponding fatty acids and ethanolamine by fatty acid amide hydrolase (FAAH) or NAE-hydrolyzing acid amidase (NAAA). Lipophilic amines, especially pentadecylamine (2c) and tridecyl 2-aminoacetate (11b), were found to exhibit potent NAAA inhibitory activities (IC50 = 5.7 and 11.8 μM), with much weaker effects on FAAH. These simple structures would provide a scaffold for further improvement in NAAA inhibitory activity.

Phosphonate Ester Derivatives and Methods of Synthesis Thereof

The disclosure describes methods of synthesis of phosphonate ester derivatives. Preferred methods according to the disclosure allow for large-scale preparation of phosphonate ester compounds having high purity. In some embodiments, preferred methods accor