38713-56-3

Usage

Uses

Used in Cosmetics and Personal Care Industry:
4-Hydroxybenzoic Acid N-Nonyl Ester is used as a plasticizer and stabilizer for enhancing the flexibility and stability of various cosmetic and personal care products. Its incorporation into these products helps maintain their quality and performance over time.
Used as an Antimicrobial Agent:
In the cosmetics and personal care industry, 4-Hydroxybenzoic Acid N-Nonyl Ester is used as an antimicrobial agent to prevent the growth of harmful bacteria and fungi. This helps to maintain the safety and efficacy of the products, reducing the risk of contamination and spoilage.
Used as a Preservative:
Due to its antimicrobial properties, 4-Hydroxybenzoic Acid N-Nonyl Ester is used as a preservative in a variety of products. This helps to prolong the shelf life of these products, ensuring that they remain effective and safe for use over a longer period.
Environmental and Health Considerations:
While 4-Hydroxybenzoic Acid N-Nonyl Ester has numerous applications in the cosmetics and personal care industry, its potential environmental and health risks are a subject of ongoing research and debate. As such, the industry continues to evaluate the safety and sustainability of using 4-HYDROXYBENZOIC ACID N-NONYL ESTER in consumer products.

InChI:InChI=1/C16H24O3/c1-2-3-4-5-6-7-8-13-19-16(18)14-9-11-15(17)12-10-14/h9-12,17H,2-8,13H2,1H3

Synthetic route

4-Methoxycarbonyloxy-benzoic acid nonyl ester (134447-10-2) → n-nonyl 4-hydroxybenzoate (38713-56-3)

Conditions	Yield
With ammonium hydroxide In ethanol for 1h; Ambient temperature;	82.6%

p-(benzyloxy)benzoic acid (1486-51-7) → n-nonyl 4-hydroxybenzoate (38713-56-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 40℃; under 2585.7 Torr; for 2h;	82.5%
Multi-step reaction with 2 steps 1: Ph3P; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C 2: H2; AcOH / Pd(OH)2/C / ethyl acetate / 12 h View Scheme
Multi-step reaction with 2 steps 1: PPh3; diisopropyl azodicarboxylate / tetrahydrofuran / 20 °C 2: H2; AcOH / Pd(OH)2/C / ethyl acetate View Scheme
Multi-step reaction with 2 steps 1: 34 percent / benzene; dimethylformamide 2: 65.4 percent / H2 / hydrogenation catalyst View Scheme

Nonyl 4-benzyloxybenzoate (134447-07-7) → n-nonyl 4-hydroxybenzoate (38713-56-3)

Conditions	Yield
With hydrogen; hydrogenation catalyst	65.4%
With hydrogen; acetic acid; palladium dihydroxide In ethyl acetate
With hydrogen; acetic acid; palladium dihydroxide In ethyl acetate for 12h;

nonyl alcohol (143-08-8) + 4-hydroxy-benzoic acid (99-96-7) → n-nonyl 4-hydroxybenzoate (38713-56-3)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 20h;	64%
With sulfuric acid In toluene for 4h; Heating;	24.8%
With hydrogenchloride

nonyl alcohol (143-08-8) → n-nonyl 4-hydroxybenzoate (38713-56-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: Ph3P; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C 2: H2; AcOH / Pd(OH)2/C / ethyl acetate / 12 h View Scheme
Multi-step reaction with 2 steps 1: PPh3; diisopropyl azodicarboxylate / tetrahydrofuran / 20 °C 2: H2; AcOH / Pd(OH)2/C / ethyl acetate View Scheme
Multi-step reaction with 2 steps 1: 1) SOCl2, 2) Et3N / 2) CH2Cl2 2: 82.6 percent / conc. NH4OH / ethanol / 1 h / Ambient temperature View Scheme

4-benzyloxy-benzoic acid methyl ester (32122-11-5) → n-nonyl 4-hydroxybenzoate (38713-56-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: base / tetrahydrofuran; aq. ethanol / 24 h / Heating 2: 34 percent / benzene; dimethylformamide 3: 65.4 percent / H2 / hydrogenation catalyst View Scheme

methyl 4-hydroxylbenzoate (99-76-3) → n-nonyl 4-hydroxybenzoate (38713-56-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: benzene; dimethylformamide 2: base / tetrahydrofuran; aq. ethanol / 24 h / Heating 3: 34 percent / benzene; dimethylformamide 4: 65.4 percent / H2 / hydrogenation catalyst View Scheme

4-(methoxycarbonyloxy)benzoic acid (14180-11-1) → n-nonyl 4-hydroxybenzoate (38713-56-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) SOCl2, 2) Et3N / 2) CH2Cl2 2: 82.6 percent / conc. NH4OH / ethanol / 1 h / Ambient temperature View Scheme

4-hydroxybenzoyl chloride (28141-24-4) + nonyl alcohol (143-08-8) → n-nonyl 4-hydroxybenzoate (38713-56-3)

Conditions	Yield
With sulfuric acid In 1,1-dichloroethane

n-nonyl 4-hydroxybenzoate (38713-56-3) → nonyl 4-[(aminosulphonyl)oxy]benzoate

Conditions	Yield
With sulphamoyl chloride; sodium hydride In N,N-dimethyl-formamide; toluene for 10h; Heating;	10.7%
Stage #1: n-nonyl 4-hydroxybenzoate With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: With sulphamoyl chloride In N,N-dimethyl-formamide; toluene
Stage #1: n-nonyl 4-hydroxybenzoate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: With sulphamoyl chloride In N,N-dimethyl-formamide; toluene for 10h;

n-nonyl 4-hydroxybenzoate (38713-56-3) + 4-octanoyloxybenzoic acid (56670-31-6) → C31H42O6

Conditions	Yield
With dicyclohexyl-carbodiimide

n-nonyl 4-hydroxybenzoate (38713-56-3) + para-dodecanoyloxybenzoic acid (56670-30-5) → C35H50O6

Conditions	Yield
With dicyclohexyl-carbodiimide

n-nonyl 4-hydroxybenzoate (38713-56-3) + 4-n-decanoyloxybenzoic acid (86960-46-5) → C33H46O6

Conditions	Yield
With dicyclohexyl-carbodiimide

4-decyloxy-3-fluorobenzoic acid (451-94-5) + n-nonyl 4-hydroxybenzoate (38713-56-3) → 4-Decyloxy-3-fluoro-benzoic acid 4-nonyloxycarbonyl-phenyl ester

n-nonyl 4-hydroxybenzoate (38713-56-3) + 3-Chloro-4-decyloxybenzoic acid (106316-08-9) → 3-Chloro-4-decyloxy-benzoic acid 4-nonyloxycarbonyl-phenyl ester

n-nonyl 4-hydroxybenzoate (38713-56-3) + 3-methyl-4-decyloxybenzoic acid (161258-72-6) → 4-Decyloxy-3-methyl-benzoic acid 4-nonyloxycarbonyl-phenyl ester

n-nonyl 4-hydroxybenzoate (38713-56-3) + 4-Decyloxy-2-methylbenzoic acid (161258-73-7) → 4-Decyloxy-2-methyl-benzoic acid 4-nonyloxycarbonyl-phenyl ester

n-nonyl 4-hydroxybenzoate (38713-56-3) + 2-fluoro-4-n-decyloxybenzoic acid (106316-02-3) → 4-Decyloxy-2-fluoro-benzoic acid 4-nonyloxycarbonyl-phenyl ester

n-nonyl 4-hydroxybenzoate (38713-56-3) + 2-Chloro-4-decyloxybenzoic acid (106316-03-4) → 2-Chloro-4-decyloxy-benzoic acid 4-nonyloxycarbonyl-phenyl ester

1,2,4-tris(4-chloroformylphenyloxycarbonyl)benzene + n-nonyl 4-hydroxybenzoate (38713-56-3) → C78H84O18 (1194090-82-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 5h;
With triethylamine In dichloromethane at 20℃; for 5h;

Upstream product

• 143-08-8 nonyl alcohol 
• 99-96-7 4-hydroxy-benzoic acid 
• 134447-10-2 4-Methoxycarbonyloxy-benzoic acid nonyl ester 
• 134447-07-7 Nonyl 4-benzyloxybenzoate 
• 28141-24-4 4-hydroxybenzoyl chloride 
• 14180-11-1 4-(methoxycarbonyloxy)benzoic acid 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 32122-11-5 4-benzyloxy-benzoic acid methyl ester 
• 1486-51-7 p-(benzyloxy)benzoic acid 

Downstream Products

• 1194090-82-8 C₇₈H₈₄O₁₈ 

Relevant academic research and scientific papers

Dipole architecture of molecules and mesomorphic behavior of liquid crystals with rigid T-shaped mesogenic fragment

A number of liquid crystalline polyesters having a rigid T-shaped mesogenic fragment and differing in dipole architecture were synthesized and examined by polarizing optical microscopy, differential scanning calorimetry, and IR and 1H NMR spectroscopy. The thermal stability of the mesophase in the given series of compounds was shown to increase with extension of arms in the T-shaped mesogenic fragment, as well as on replacement of the terminal ester groups (COOAlk) therein by ether moieties (OAlk). Such replacement also enhances smectogenic properties.

Molecular design of multifunctional food additives: Antioxidative antifungal agents

A series of alkyl 3,4-dihydroxybenzoates (protocatechuates) was synthesized, and their fungicidal activity against Saccharomyces cerevisiae was assayed using a 2-fold serial broth dilution method. Nonyl and octyl 3,4-dihydroxybenzoate were noted to be the most effective against this yeast with the minimum fungicidal concentration of 12.5 μg/mL each. The activity was found to correlate with the hydrophobic alkyl chain length. The time-kill curve study showed that nonyl 3,4-dihydroxybenzoate was fungicidal against S. cerevisiae at any growth stage and this activity was not influenced by pH values. The fungicidal activity of alkyl 3,4-dihydroxybenzoates was noted in combination with their ability to disrupt the native membrane-associated function nonspecifically as surface-active agents (surfactants) and to inhibit the respiratory electron transport. However, the primary fungicidal activity of nonyl 3,4-dihydroxybenzoate likely comes from its ability to act as a surfactant.

Inhibition of estrone sulfatase (ES) by alkyl and cycloalkyl ester derivatives of 4-[(aminosulfonyl)oxy] benzoic acid

In our search for potent inhibitors of the enzyme estrone sulfatase (ES), we have undertaken the synthesis and biochemical evaluation of a range of esters of 4-[(aminosulfonyl)oxy] benzoic acid. The results of the study show that the synthesised compounds possess potent inhibitory activity, indeed the cyclooctyl derivative was found to be more potent than 667-COUMATE, which is currently undergoing clinical trials.

Rational design of antimicrobial agents: Antifungal activity of alk(en)yl dihydroxybenzoates and dihydroxyphenyl alkanoates

A homologous series (C3-C14) of each alkyl 3,4- and 3,5-dihydroxybenzoates, and 3,4- and 3,5-dihydroxyphenyl alkanoates exhibit similar antifungal activity against Saccharomyces cerevisiae. Their nonyl derivatives exhibit the most potent antifungal activity against this yeast with the minimum fungicidal concentration (MFC) in the range between 12.5 and 50 μg/mL. In addition, various 3,4-dihydroxybenzoates, possessing different side chains, namely unsaturated, branched and alicyclic were synthesized and their activity was compared.

Synthesis and biochemical evaluation of some novel benzoic acid based esters as potential inhibitors of oestrone sulphatase

Oestrone sulphatase is an important target in the fight against hormone-dependent breast cancer. In an effort to investigate the reported definitive pharmacophore for oestrone sulphatase and continue our search for potent inhibitors of this enzyme, we have undertaken extensive synthesis, biochemical evaluation and physicochemical property determination of a range of benzoic acid based esters. Here, we report the initial results of our study into a series of straight chain alkyl esters of 4-sulphonylbenzoic acid. Using these compounds, we have investigated the involvement of two physicochemical properties, namely logP and pKa. The results of this study show that there was a strong correlation between the inhibitory activity and the logP of the parent compound. Within the series of compounds studied, hydrophobicity appears to be a more important factor than pKa in determining the overall inhibitory activity. In a previous report, we showed that pKa plays an important role in stabilizing the phenoxide ion resulting from the hydrolysis of the sulphamate group. Here, we propose that although pKa is an important factor in determining the overall inhibitory activity when a wide range of compounds are considered, both hydrophobicity and pKa need to be considered in the design of potential inhibitors of oestrone sulphatase.

Molecular design of antifungal agents

In a rational approach to the design of antifungal agents against Saccharomyces cerevisiae, a series of alkyl gallates (3,4,5-trihydroxybenzoates) were synthesized and assayed. Nonyl gallate (1) was found to be the most effective with a minimum fungicidal concentration (MFC) of 12.5 μg/mL (42 μM), followed by octyl gallate (2) with an MFC of 25 μg/mL (89 μM). These MFCs are little influenced by pH values. A time-kill curve study indicates that nonyl gallate exhibits fungicidal activity against S. cerevisiae at any growing stage. The antifungal activity of nonyl gallate is due primarily to its ability to act as a nonionic surface-active agent (surfactant). The length of the alkyl group is not a major contributor but plays a role in eliciting the activity to a large extent. As far as alkyl gallates are concerned, their antimicrobial spectra and potency depend largely on the hydrophobic portion of the molecules.

Inhibition of estrone sulfatase (ES) by derivatives of 4-[(aminosulfonyl)oxy] benzoic acid

In our search for potent inhibitors of the enzyme estrone sulfatase (ES), we have undertaken the synthesis and biochemical evaluation of a range of straight chain alkyl esters of 4-[(aminosulfonyl)oxy] benzoic acid. The results of the study show that the synthesised compounds possess greater inhibitory activity when compared to COUMATE, although they were all found to possess lower inhibitory activity with respect to EMATE. Furthermore, the data suggest a strong correlation between logP and IC50 and therefore adds further support to our previous report where we suggested a link between inhibitory activity and hydrophobicity.

The Effect of Carbonyl Containing Terminal Chains on Mesomorphic Properties in 4,4'-Disubstituted Phenylbenzoates and Thiobenzoates 8. Phenylbenzoates Containing Two Carbonyl Containing Terminal Chains

A variety of phenylbenzoates of the type (1) with both X and Y being the carbonyl containing chains (CH2)nCOR (n = 0 - 1), (CH2)nCO2R and (CH2)nOCOR (R = alkyl chain) in various combinations were synthesized and their mesomorphic properties studied to determine if an additive effect occurs when these chains are incorporated into the same molecule.No reliable additive effect could be found.Instead, clearing temperatures often seemed to be closer to the clearing temperature of the parent single carbonyl containing chain ester with the higher clearing temperature.An attempt was also made to improve the properties of the esters 1 with X or Y being I, F, CN or NO2 by using a carbonyl containing chain as the second substituent and assuming an additive effect.However, such an effect was also not observed in these esters.Smectic C phases were found in some of the esters with X = CN which is rare for compounds containing this substituent. - Keywords: liquid crystals, phenylbenzoates, synthesis, NMR, esters, ketones

Liquid crystal compositions

A liquid crystal compound represented by the following formula; wherein R1 and R2 each represents an alkyl group having 3 - 20 carbon atoms, and X represents a group or -O-, or a single bond, and a liquid crystal composition exhibiting optically tristable states comprising the liquid crystal compound represented by the above formula and a liquid crystal compound containing asymmetric carbon as chiral center which are responsible to exhibit the tristable states.

The Effect of Carbonyl Containing Terminal Chains on Mesomorphic Properties in 4,4'-Disubstituted Phenylbenzoates and Phenylthiobenzoates. 4. Phenylbenzoates Containing A (CH2)nCO2R' Group (n = 0-2) on the Phenolic End

The effect of a (CH2)nCO2R' group on the mesomorphic properties of the esters where X = alkyl or alkoxy, Y = (CH2)nCO2R'(R' = C7 and C9) and n = 0-2 has been studied by synthesizing these esters and determining their mesomorphic properties by hot-stage polarizing microscopy.The starting phenols were prepared by esterification of 4-hydroxybenzoic, phenylacetic or phenylpropionic acids.Both the benzyl and methoxycarbonyl protecting groups were tried with the latter giving higher yields when n = 0 because of better solubility of the protected acid.No mesophases were observed in the esters when n = 1, nematic and smectic A phases occurred when n = 2 and smectic A and C phases when n = 0.A few 1,4-cyclohexane diesters were also prepared using these phenols.The mesomorphic properties of these esters followed the same trend observed in the phenylbenzoates escept no C phases were observed.Comparisons of the transition temperatures for these esters with those for Y = R' showed that both small increases or decreases were observed for Y = CO2R'.However, the addition of a spacer methylene group (n = 1 and 2) always gave lower temperatures with the amount of lowering being much greater for n = 2 than n = 1.A comparison of transition temperatures for Y = CO2R', OCOR', COR' and OR' indicated that these temperatures were higher when Y = COR' as expected from dipole moment considerations but were lower when Y = CO2R' than when Y = OCOR', the opposite expected from these considerations.This trend was also observed in the cyclohexane diesters.Transition temperatures were always higher for the esters when Y has an oxygen atom adjacent to the benzene ring.Therefore, esters with Y = O(CH2)nCO2R', n = 1 and 2 were also synthesized.The phenols were prepared by alkylation of 4-benzyloxyphenol with the bromo esters followed by hydrogenolysis.However, these esters showed no mesophases except the cyclohexane diester with n = 2.