2589-78-8

Usage

Uses

Used in Pesticide Production:
P-hexadecylphenol is used as an emulsifier and surfactant for the production of pesticides. Its capacity to lower surface tension enhances the spreading and wetting of the pesticide, improving its effectiveness in controlling pests.
Used in Personal Care Product Manufacturing:
In the personal care industry, p-hexadecylphenol is utilized as an emulsifier and surfactant in the formulation of various products. Its properties contribute to the stability and performance of these products, ensuring they spread and wet the skin effectively.
Used in Cleaning Agent Production:
P-hexadecylphenol is employed as an emulsifier and surfactant in the manufacturing of cleaning agents. It aids in the dispersion of dirt and grease, making the cleaning process more efficient.
It is crucial to handle and use p-hexadecylphenol with care due to potential health risks such as skin irritation and eye damage if proper safety measures are not adhered to.

InChI:InChI=1/C22H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-21-17-19-22(23)20-18-21/h17-20,23H,2-16H2,1H3

Upstream product

• 22165-11-3 4-hexadecyl-anisole 
• 2589-76-6 1-(4-hydroxyphenyl)hexadecane-1-one 
• 412319-06-3 4-hexadecyl-phenetole 
• 16693-91-7 4-hexadecyl-benzenesulfonic acid ; sodium-compound 
• 108-95-2 phenol 
• 112-67-4 n-hexadecanoyl chloride 
• 416846-26-9 1-(4-ethoxy-phenyl)-hexadecan-1-one 
• 1071581-75-3 C₂₂H₃₈N₂O 
• 24632-92-6 phenyl palmitate 
• 100-66-3 methoxybenzene 
• 102898-55-5 1-(4-methoxyphenyl)hexadecan-1-one 
• 194658-61-2 1-(4-benzyloxyphenyl)-1-hexadecanol 
• 78887-70-4 pentadecylmagnesium bromide 
• 4397-53-9 p-benzyloxybenzaldehyde 

Downstream Products

• 28294-58-8 5-hexadecylsalicylic acid 
• 412319-06-3 4-hexadecyl-phenetole 
• 611227-34-0 1-hexadecyl-4-methoxymethoxy-benzene 
• 1162025-36-6 bis(2-hydroxy-5-n-hexadecylphenyl)methane 
• 22165-11-3 4-hexadecyl-anisole 
• 611227-50-0 3-[5-n-hexadecyl-2-(methoxymethoxy)phenyl]-3-hydroxy-N,N-dimethylpropanamide 
• 611227-42-0 2-methoxymethoxy-5-n-hexadecylbenzaldehyde 

Relevant academic research and scientific papers

Alkylated phenol series in lacustrine black shales from the Noerdlinger Ries, southern Germany

Several series of alkylated phenols were detected for the first time in the extractable bitumens of organic matter-rich sediments from the Noerdlinger Ries (southern Germany). Most abundant and significant constituents comprise those with n-octadecyl, n-eicosanyl, phytanyl, and iso-pentadecyl and anteiso-pentadecyl substituents. The structures of these compounds are suggested from mass spectrometric and retention time data and coinjection with synthetic standards. Diagenetic alteration of phenolic algal lipids is suggested as a possible way to the formation of these compounds in the Noerdlinger Ries sediments. Copyright

Synthesis and critical micelle concentration of a series of gemini alkylphenol polyoxyethylene nonionic surfactants

A series of gemini n-alkylphenol polyoxyethylene surfactants (GAP) were successfully synthesized and their molecular structure were confirmed by NMR and FTIR spectrum. Using the same synthesis route, a Gemini nonylphenol polyoxyethylene surfactant (GNP) was synthesized using an industrial nonylphenol product and paraformaldehyde, and its molecular structure was also characterized by 1H-NMR and FTIR spectra. The optimal reaction conditions were established. The critical micelle concentration (CMC) values of GAP were determined by means of Wilhelmy plate method and steady-state fluorescence probe method. The experimental results show how the lengths of the hydrophilic polyoxyethylene chain and the hydrophobic tail alter the CMC values. The CMC values of the GAP are found to be much lower than those of corresponding conventional single tail nonionic surfactants of the polyethoxylated alkylphenol type, which indicates that the gemini species exhibit a better surface activity. AOCS 2011.

Selectivity in the photodimerization of 6-alkylcoumarins

Coumarin and 6-alkylcoumarins (alkyl = C1 to C16) were photodimerized in homogeneous solvents differing in polarity and in aqueous micellar solutions. The four possible photodimers, syn head-to-head (hh), anti head-to-head, syn head-to-tail (ht), and anti head-to-tail, were identified through a combination of X-ray analysis and NMR spectroscopy. In 6-methylcoumarin the concentration-corrected dimerization (quantum) yield increases with decreasing concentration of the educt; anti- hh was formed exclusively in nonpolar solvents and upon triplet sensitization and was the main product under all conditions except for ionic micellar systems, which direct to preferred syn-hh dimerization. Long alkyl substituents, however, lead to anti-hh in polar solvents and in micelles, too. Predominating ht dimer formation was observed for nonsubstituted coumarin in polar solvents only. Thus, syn/anti and hh/ht selectivity can be steered by varying the 6-alkyl substituent. Syn- hh photodimers of 6-methylcoumarin can be photochemically split into the monomers; they partly proved thermally unstable against acids, bases, methanol, and on SiO2 surfaces.

Structure-activity relationship studies of the amide functionality in (p-O-sulfamoyl)-N-alkanoyl tyramines as estrone sulfatase inhibitors

Recently, we reported the synthesis and biochemical studies of a series of (p-O-sulfamoyl)-N-alkanoyl tyramines as nonsteroidal estrone sulfatase inhibitors. One of the most potent inhibitors in this series is (p-O- sulfamoyl)-N-tridecanoyl tyramine 1 with an IC50 value of 61.3 nM. In this study, we synthesized four analogs of 1 (compounds 2-5) to investigate the structure-activity relationships of the amide functionality in (p-O- sulfamoyl)-N-tridecanoyl tyramine. Replacement of the amide functionality in 1 with an ethylene moiety to form the alkyl analog 5 resulted in complete loss of sulfatase inhibitory activity (IC50 of 61.3 nM vs. >20 μM). The keto, hydroxy, and ester analogs (inhibitors 2-4) are 8-15 times less in affinity to the sulfatase than inhibitor 1. However, their inhibitory activities are significantly higher than the alkyl analog 5. The results suggest that the amide functionality is favorable for sulfatase inhibitory activity and that there may be a hydrogen bonding component to the enzyme interaction in this region.

Tilt Angle Variation as a Function of Chain Length and Temperature in the Smectic C Phases of p,Alkoxyphenyl-p,Alkoxybenzoates

The variation of the tilt angle with temperature in the smectic C phase has generally been shown to be non-existent or very slow for compounds or mixtures with the nematic-smectic C transition, while in the case of systems with the smectic A-smectic C transition, a relation between the steepness of this variation, near the transition, and the width of the smectic A domain has been observed.In this work, the variation of tilt angle in the smectic C phase is described for p-alkoxyphenyl-p-alkoxybenzoate homologous series, for which the evolution of polymorphism can be controlled systematically, by varying stepwise the length of the aliphatic chains, and for which large domains can be obtained for each type of phase sequence, nematic-, smectic A- and isotropic-smectic C.After completing the discussion made previously on the incidence of chain length on polymorphism, we confirm that the variation of tilt angle with temperature is slowest for compounds with intermediate chain lengths corresponding to the largest smectic A temperature range; this variation becomes continuously steeper when the smectic A domain becomes narrow.In addition, we show that the same description can be extended to the other types of phase sequences, by using the hypothesis of a virtual smectic A-smectic C transition above the observed nematic- or isotropic-smectic C transition.In fact, short chain lengths for homologues with a nematic/smectic C transition, or long chain lengths for homologues with an isotropic/smectic C transition, lead to an increase of the tilt angle at the phase transition and to a decrease of the amplitude of its variation with temperature; in our description, this behaviour corresponds to an increase of the temperature range between the real and virtual transitions.As a consequence, the homologues with very short and very long chain lengths show a quasi temperature-independent tilt angle, while the other homologues present a tilt angle variation similar to that observed for compounds exhibiting a smectic C/smectic A transition.This feature indicates that there is no need to distinguish between different types of smectic C phase.