51637-93-5

Basic information

• Product Name: Octadecyl chloroformate
• Synonyms: STEARYL CHLOROFORMATE;octadecyl chloroformate;Chloridocarbonic acid octadecyl ester;Chloroformic acid octadecyl ester;Carbonochloridic acid, octadecyl ester;Einecs 257-330-5;ChloroforMate octadecyl ester;Octadecyl carbonochloridate
• CAS NO: 51637-93-5
• Molecular Formula: C₁₉H₃₇ClO₂
• Molecular Weight: 332.94888
• EINECS: 257-330-5
• Mol File: 51637-93-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 396.9 °C at 760 mmHg
• Flash Point: 136.4 °C
• Appearance: /
• Density: 0.932 g/cm³
• Vapor Pressure: 1.65E-06mmHg at 25°C
• Refractive Index: 1.454
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Stability: Moisture Sensitive
• CAS DataBase Reference: Octadecyl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: Octadecyl chloroformate(51637-93-5)
• EPA Substance Registry System: Octadecyl chloroformate(51637-93-5)

Safety Data

• Hazardous Substances Data: 51637-93-5(Hazardous Substances Data)

Usage

Description

Octadecyl chloroformate, also known as Carbonochloridic Acid Octadecyl Ester, is a synthetic intermediate with various applications in the pharmaceutical and chemical industries. It is a chloroformate ester derived from octadecanol, characterized by its reactivity and ability to form esters with other compounds.

Uses

Used in Pharmaceutical Industry:
Octadecyl chloroformate is used as a synthetic intermediate for the development of novel kanamycin derivatives, which are being investigated for their antiviral activity against the influenza virus. Its reactivity allows for the creation of new compounds with potential therapeutic benefits.
Used in Antitumor Agent Synthesis:
In the field of cancer research, Octadecyl chloroformate is utilized as a reagent for the preparation of nucleoside derivatives. These derivatives have shown potential as antitumor agents, offering new avenues for cancer treatment and therapy development.

InChI:InChI=1/C19H37ClO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22-19(20)21/h2-18H2,1H3

Upstream product

• 75-44-5 phosgene 
• 112-92-5 1-octadecanol 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 53083-32-2 Carbonic acid octadecyl ester 3-oxo-2-(2,4,6-trimethyl-phenyl)-3H-inden-1-yl ester 
• 57717-05-2 Carbonic acid 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl ester octadecyl ester 
• 57717-44-9 [3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl]-carbamic acid octadecyl ester 
• 6325-77-5 Carbaminsaeure-octadecylester 
• 593-45-3 octadecane 
• 3386-33-2 1-chlorooctadecane 

Relevant articles and documents

Synthesis and in vitro activity of long-chain 5'-O- [(alkoxycarbonyl)phosphinyl]-3'axido-3'-azido-3'-deoxythymidines against wild-type and AZT- and foscarnet-resistant strains of HIV-1

Lipophilic esters of 3'-azido-3'-deoxy-5'-O- (carboxyphosphinyl)thymidine (PFA-AZT) were synthesized and tested for antiretroviral activity in CD4+ HT4-6C cells infected with either wild-type HIV-1(LAI), a PFA-resistant strain encoding a single-point mutation in reverse transcriptase (E89K), or an AZT-resistant clinical isolate (A018- post). Arbuzov condensation of 1-octadecyl, 1-eicosanyl, and 1-docosanyl chloroformate with trimethyl phosphate yielded the corresponding dimethyl long-chain alkyl triesters of PFA. Selective removal of one methyl group from the triesters with sodium iodide yielded monosodium salts, whereas treatment with bromotrimethylsaline cleaved both methyl groups while leaving the long- chain alkyl group intact. Neutralization of the resulting I(alkyloxy)carbonylphosphonic acids with 2 equiv of sodium methoxide afforded disodium salts of the phosphonic acid moiety. Similar chemistry was used to obtain the mono- and disodium salts of the cholesterol ester of FPA. Reaction of the triesters with phosphorous pentachloride, followed by coupling with AZT and O-demethylation with sodium iodide, afforded 3'-azido-3'-deoxy-5'-O- [[(1-octadecyloxy)carboxyl]phosphinyl]thymidine (9a), 3'-azido-3'-deoxy-5'- O-[[1-eocosanyloxy)carbonyl]phosphinyl]thymidine (9b), 3'-azido-3'-deoxy-5'- O[[1-docosanyloxy)carbonyl[phosphinyl]thymidine (9c), and 3'-azido-3'-deoxy- 5'-O-[[3β-cholest-4-enyloxy)carbonyl]phosphinyl]thymidine (9d). Concentrations of the 9a-d found to inhibit replication of wild-type HIV- 1(LAI) by 50% (OC50 values) as measured in a plaque reduction assay were in the 0.1-0.3 μM range as compared with 0.013 μM for AZT and 133 μM for PFA. The concentration at which toxicity was observed in 50% of the host cells (TC50 values) as measured by a visual grading scale of cellular morphology was 10 μM for 9a and 93, 32 μM for 9b, and 320 μM for 9c. Thus, the TC50/EC50 ratio or selectivity index (SI) was 100 for 9a, 230 for 9b, and 1000 for 9c but only 33 for 9d, suggesting that the straight-chained fatty alcohol esters were more therapeutically selective. Similar TC50 and SI values were obtained for rapidly dividing CEM lymphoblasts as for HT4-8C cells. In assays against E89K, 9a-c had mean EC50 values of 0.13, 0.009, and 0.17 μM, whereas the EC50 of PFA was >1000 μM and that of AZT was 0.009 μM; thus E89K was highly resistant to PFA but not cross-resistant to either AZT or the lipophilic PFA-AZT conjugates. In viral replication assays against the A018C-post isolate, the mean EC50 values of 9a-c were 0.30, 0.53, and 0.77 μM as compared with 2.9 μM for AZT and 65 μM for PFA; thus, the virus recovered from a patient pretreated with AZT was not cross- resistant to either PFA or 9a-c. A notable feature of these results was that, in addition to being >1000-fold more potent than PFA against the PFA- resistant mutant, the lipophilic PFA-AZT conjugates were more potent than PFA, as well as AZT, against AZT-resistant HIV-1.

Synthesis, physicochemical properties and biological activities of novel alkylphosphocholines with foscarnet moiety

A series of alkylphosphocholines with foscarnet moiety was synthesized. The structure of these zwitterionic amphiphiles was modified in both polar and non-polar parts of surfactant molecule. Investigations of physicochemical properties are represented by the determination of critical micelle concentration, the surface tension value at the cmc and the surface area per surfactant head group utilising surface tension measurements. Hydrodynamic diameter of surfactant micelles was determined using the dynamic light scattering technique. Alkylphosphocholines exhibit significant cytotoxic, anticandidal (Candida albicans) and antiamoebal (Acanthamoeba spp. T4 genotype) activity. The relationship between the structure, physicochemical properties and biological activity of the tested compounds revealed that lipophilicity has a significant influence on biological activity of the investigated surfactants. More lipophilic alkylphosphocholines with octadecyl chains show cytotoxic activity against cancer cells which is higher than that of the compounds with shorter alkyl chains. The opposite situation was observed in case of anticandidal and antiamoebal activity of these surfactants. The most active compounds were found to have pentadecyl chains. The foscarnet analogue of miltefosine C15-PFA-C showed the highest anticandidal activity. The minimum value of anticandidal activity of this compound is 1,4 μM thus representing the highest anticandidal activity found within the group of alkylphosphocholines.

Antiviral compounds and methods of administration

The invention provides lipophilic phosphonoacid/nucleoside conjugates that exhibit exceptional antiviral activity, including activity against drug-resistant HIV strains. Compounds of the invention include phosphonoacid/nucleoside conjugates where the carboxyl group and phosphonyl groups of the phosphonacid are esterified whereby the compound contains at least one lipophilic group and at least one nucleoside group.