38713-56-3

Basic information

• Product Name: 4-HYDROXYBENZOIC ACID N-NONYL ESTER
• Synonyms: N-NONYLPARABEN;N-NONYL 4-HYDROXYBENZOATE;NONYL 4-HYDROXYBENZOATE;NONYL P-HYDROXYBENZOATE;4-HYDROXYBENZOIC ACID N-NONYL ESTER;4-hydroxybenzoic acid nonyl ester;nonylparaben;4-HYDROXYBENZOIC ACID N-NONYL ESTER 98+%
• CAS NO: 38713-56-3
• Molecular Formula: C₁₆H₂₄O₃
• Molecular Weight: 264.36
• Product Categories: Aromatic Esters
• Mol File: 38713-56-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 44°C
• Boiling Point: 367.59°C (rough estimate)
• Flash Point: 152°C
• Appearance: /
• Density: 1.0468 (rough estimate)
• Vapor Pressure: 2.15E-06mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: 1.275g/L(25 oC)
• CAS DataBase Reference: 4-HYDROXYBENZOIC ACID N-NONYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXYBENZOIC ACID N-NONYL ESTER(38713-56-3)
• EPA Substance Registry System: 4-HYDROXYBENZOIC ACID N-NONYL ESTER(38713-56-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 38713-56-3(Hazardous Substances Data)

Usage

General Description

4-Hydroxybenzoic Acid N-Nonyl Ester is a chemical compound commonly used as a plasticizer and stabilizer in the manufacturing of cosmetics and personal care products. It has a role as an antimicrobial agent and is an aryl ester and a member of monohydroxybenzoic acids. The substance often serves as a preservative due to its antimicrobial properties, preventing the growth of harmful bacteria and fungi, to prolong the shelf life of products. Despite its wide usage, its potential environmental and health risks are a subject of ongoing research and debate.

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

Downstream Products

• 1194090-82-8 C₇₈H₈₄O₁₈ 

Relevant articles and documents

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.

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.

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.