5026-62-0

Basic information

• Product Name: Sodium methylparaben
• Synonyms: 4-hydroxybenzoic acid methyl ester sodium salt;methyl p-hydroxybenzoate sodium salt;METHYLPARABEN SODIUM;METHYLPARABEN, SODIUM SALT;METHYL 4-HYDROXYBENZOATE SODIUM;METHYL 4-HYDROXYBENZOATE SODIUM SALT;(p-carboxyphenoxy)-sodiumethylester;benzoicacid,4-hydroxy-,methylester,sodiumsalt
• CAS NO: 5026-62-0
• Molecular Formula: C₈H₇O₃*Na
• Molecular Weight: 174.13
• EINECS: 225-714-1
• Product Categories: Aromatic Esters;Benzoic acid Series;API;Cosmetics
• Mol File: 5026-62-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: >125°C
• Boiling Point: 265.5 °C at 760 mmHg
• Flash Point: 116.4 °C
• Appearance: White/Powder
• Density: 1.42 g/cm3 (20 °C)
• Vapor Pressure: 0.00555mmHg at 25°C
• Storage Temp.: Store at +15°C to +25°C.
• Solubility: Freely soluble in water, sparingly soluble in ethanol (96 per cent), practically insoluble in methylene chloride.
• PKA: 8.4[at 20 ℃]
• Water Solubility: 418g/L at 20℃
• BRN: 4165000
• CAS DataBase Reference: Sodium methylparaben(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium methylparaben(5026-62-0)
• EPA Substance Registry System: Sodium methylparaben(5026-62-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• WGK Germany: 1
• RTECS: DH2455000
• Hazardous Substances Data: 5026-62-0(Hazardous Substances Data)

Usage

Description

Sodium methylparaben, also known as sodium methyl 4-hydroxybenzoate, is a white powdery substance with antimicrobial properties. It is a derivative of methylparabens, which are widely used as additives in the pharmaceutical and cosmetic industries. Sodium methylparaben is particularly effective as a preservative due to its ability to inhibit the growth of microorganisms, ensuring the stability and safety of products.

Uses

Used in Pharmaceutical Industry:
Sodium methylparaben is used as a preservative in the pharmaceutical industry to prevent the growth of microorganisms in various formulations. Its antimicrobial characteristics make it an essential component in maintaining the quality and safety of medications, such as injectables, ointments, and oral dosage forms. Additionally, it can be combined with other parabens like propyl 4-hydroxybenzoate or ethyl 4-hydroxybenzoate to enhance the overall preservative effect.
Used in Cosmetic Industry:
In the cosmetic industry, sodium methylparaben is used as a preservative to maintain the freshness and safety of products. Its antimicrobial properties help prevent the growth of bacteria, fungi, and other microorganisms that can cause spoilage or contamination. This is particularly important for products that come into direct contact with the skin, such as creams, lotions, and makeup, ensuring that they remain safe for use over their intended shelf life.
Used as a Pharmaceutic Aid:
Sodium methylparaben is also used as a pharmaceutic aid, which refers to its role in enhancing the formulation and stability of pharmaceutical products. Its improved solubility in water compared to standard methyl 4-hydroxybenzoate makes it a preferred choice for various applications in the pharmaceutical industry. As a pharmaceutic aid, sodium methylparaben contributes to the overall quality, efficacy, and safety of medications, making it a valuable component in the development and production of pharmaceutical products.

Flammability and Explosibility

Nonflammable

Contact allergens

This substance is one of the parabens family. Parabens are esters formed by p-hydroxybenzoic acid and an alcohol. They are largely used as biocides in cosmetics and toiletries, medicaments, or food. They have synergistic power with other biocides. Parabens can induce allergic contact dermatitis, mainly in chronic dermatitis and wounded skin.

InChI:InChI=1/C8H8O3.Na/c1-11-8(10)6-2-4-7(9)5-3-6;/h2-5,9H,1H3;/q;+1/p-1

Synthetic route

methyl 4-hydroxylbenzoate (99-76-3) → sodium methylparaben (5026-62-0)

Conditions	Yield
With sodium hydroxide In methanol Inert atmosphere;	95%
In water
With sodium hydride In tetrahydrofuran; DMF (N,N-dimethyl-formamide) for 1.5h;
With sodium hydroxide In ethanol; water at 20℃; for 1.83333h;	32.4 g

4-(N-phenyl-benzimidoyloxy)-benzoic acid methyl ester (73823-12-8) + sodium methylate (124-41-4) → E-[2-methoxy-1-phenyl-methylene]-phenylamine (6780-39-8) + sodium methylparaben (5026-62-0)

Conditions	Yield
In methanol at 29.9℃; Mechanism; var. base concentrations;

4-[4'-(1-methoxy carbonyl-1-methylethyl)-phenyl]-1,2-epoxybutane (141969-79-1) + sodium methylparaben (5026-62-0) + methyl 4-hydroxylbenzoate (99-76-3) → 4-{4-[4'-(methoxy carbonyl-1-methylethyl)phenyl]-2-hydroxybutoxy}-benzoic acid methyl ester

Conditions	Yield
In N,N-dimethyl-formamide	98%

sodium methylparaben (5026-62-0) + pyrrole-1-carboxylic acid anhydride (107962-24-3) → Pyrrole-1-carboxylic acid 4-methoxycarbonyl-phenyl ester

Conditions	Yield
In tetrahydrofuran at 25℃; for 0.25h;	88%

sodium methylparaben (5026-62-0) + indole-1-carboxylic acid anhydride (109241-96-5) → Indole-1-carboxylic acid 4-methoxycarbonyl-phenyl ester (109242-03-7)

Conditions	Yield
In tetrahydrofuran at 25℃; for 0.25h;	78%

sodium methylparaben (5026-62-0) + prenyl bromide (870-63-3) → methyl 4-((3-methylbut-2-en-1-yl)oxy)benzoate (34593-50-5) + methyl 4-hydroxylbenzoate (99-76-3)

Conditions	Yield
In Hexafluorobenzene at 20℃; for 24h; Solvent; Temperature;	A 70% B 26%

2-(chloromethyl)thiirane (3221-15-6) + sodium methylparaben (5026-62-0) → methyl 4-(thietane-3-yloxy)benzoate

Conditions	Yield
In methanol; water at 45 - 55℃; for 2h;	68%

2-bromo-4-furan-2-yl-6-thiophen-2-yl-nicotinonitrile (956117-80-9) + sodium methylparaben (5026-62-0) → 4-(3-cyano-4-furan-3-yl-6-thiophen-2-yl-pyridin-2-yloxy)-benzoic acid methyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 18h;	68%

sodium methylparaben (5026-62-0) + 3-chloroprop-1-ene (107-05-1) → 2-allyloxybenzoic acid (59086-52-1)

Conditions	Yield
With hydrogenchloride; potassium hydroxide In methanol; water	65%

sodium methylparaben (5026-62-0) + prenyl bromide (870-63-3) → methyl 4-hydroxylbenzoate (99-76-3) + methyl 4-hydroxy-3-(3'-methyl-2'-butenyl)-5-(3''-methyl-2''-butenyl)benzoate (98969-33-6)

Conditions	Yield
at 80℃; for 24h;	A 56% B 39%

sodium methylparaben (5026-62-0) + prenyl bromide (870-63-3) → methyl 4-((3-methylbut-2-en-1-yl)oxy)benzoate (34593-50-5) + methyl 3-(3-methylbut-2-en-1-yl)-4-((3-methylbut-2-en-1-yl)oxy)benzoate + methyl-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate (101511-34-6) + methyl 4-hydroxylbenzoate (99-76-3)

Conditions	Yield
at 40℃; for 24h;	A 18% B 7% C 51% D 28%

trans-geranyl bromide (6138-90-5) + sodium methylparaben (5026-62-0) → methyl (2'E,2''E)-4-hydroxy-3-(3',7'-dimethylocta-2',6'-dienyl)-5-(3'',7''-dimethylocta-2'',6''-dienyl)benzoate (641614-05-3)

Conditions	Yield
at 20℃; for 24h;	45%

sodium methylparaben (5026-62-0) + prenyl bromide (870-63-3) → methyl 4-((3-methylbut-2-en-1-yl)oxy)benzoate (34593-50-5) + methyl 3,5-bis(3-methylbut-2-en-1-yl)-4-((3-methylbut-2-en-1-yl)oxy)benzoate + methyl-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate (101511-34-6) + methyl 4-hydroxylbenzoate (99-76-3) + methyl 4-hydroxy-3-(3'-methyl-2'-butenyl)-5-(3''-methyl-2''-butenyl)benzoate (98969-33-6)

Conditions	Yield
at 40℃; for 24h;	A 9% B 8% C 29% D 40% E 11%

sodium methylparaben (5026-62-0) → 3,4-dihydroxybenzoic acid methyl ester (2150-43-8)

Conditions	Yield
With α,α'-bisamino>m-xylene - Cu(MeCN)4ClO4 (1:2 complex); oxygen In acetonitrile	37%
With N,N,N',N'-tetra-(2-(N-methylbenzimidazol-2-yl)ethyl)-m-xylylenediamine Cu(I)2; oxygen 1.) CH3CN; Yield given. Multistep reaction;
With α,α'-bisamino>-m-xylene - Cu(MeCN)4ClO4; oxygen In acetonitrile Mechanism; other phenol-deriv. sodium salts;
With oxygen; [Cu2(L-66)](2+) In acetone at -80 - -60℃; Oxidation;
With [((2-pyridyl)bis(3-tert-butylpyrazol-2-yl)methane)Cu2O2](SbF6)2 In dichloromethane at -78.16℃; Kinetics; Inert atmosphere;

sodium methylparaben (5026-62-0) + 2-bromoethanol (540-51-2) → 4-(2-hydroxyethoxy)benzoic acid methyl ester (3204-73-7)

Conditions	Yield
With sodium iodide In methanol at 60℃; for 18h;	35%

2,2-dimethylpent-4-enoic acid (16386-93-9) + 4-(2-aminoacetyl)phenyl ethylacetate hydrochloride + sodium methylparaben (5026-62-0) → C23H27NO6

Conditions	Yield
Stage #1: 2,2-dimethylpent-4-enoic acid With hydrogen bromide; dibenzoyl peroxide In toluene Cooling with ice; Stage #2: With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: 4-(2-aminoacetyl)phenyl ethylacetate hydrochloride; sodium methylparaben Further stages;	13.9%

carbon disulfide (75-15-0) + sodium methylparaben (5026-62-0) → C17H14O6S (116858-42-5)

Conditions	Yield
Yield given. Multistep reaction;

2-ethoxy-6-carbethoxytetrahydropyran (3612-48-4) + sodium methylparaben (5026-62-0) → trans-2-(p-carbomethoxyphenoxy)-6-carbethoxytetrahydropyran (133754-29-7)

Conditions	Yield
With hydrogenchloride 1.) diethyl ether, 30 min, 2.) DMF; Multistep reaction;

sodium methylparaben (5026-62-0) + 2-chlorotetrahydro-2H-pyran (3136-02-5) → 4-methoxycarbonylphenyl 2-tetrahydropyranyl ether (106342-09-0)

Conditions	Yield
With hydrogenchloride 1.) diethyl ether, 30 min, 2.) DMF; Multistep reaction;

methyl 2,2-dichloropropionate (17640-02-7) + sodium methylparaben (5026-62-0) → α-<4-Methoxycarbonyl-phenoxy>-acrylsaeure-methylester (16929-34-3)

Conditions	Yield
(i) cyclohexanone, (ii) TsOH; Multistep reaction;

sodium methylparaben (5026-62-0) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(4-carbomethoxyphenyl) N,N-dimethylthiocarbamate (13492-59-6)

sodium methylparaben (5026-62-0) → 4-hydroxy-benzoic acid (99-96-7)

Conditions	Yield
With phosphate buffer; Sucrose at 60℃; pH=8.0; Kinetics; Further Variations:; Reagents;

sodium methylparaben (5026-62-0) + sodium salt of dimethyl methylmalonate + 2-bromoallyl bromide (513-31-5) → methyl 4-bromo-2-(methylcarboxy)-2-methylpent-4-enoate (199923-58-5) + 2-[2-(4-methoxycarbonyl-phenoxy)-allyl]-2-methyl-malonic acid dimethyl ester + 2-[1-(4-methoxycarbonyl-phenoxymethyl)-vinyl]-2-methyl-malonic acid dimethyl ester + C19H18O6

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 5h; Further byproducts given. Title compound not separated from byproducts;
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 2h; Further byproducts given. Title compound not separated from byproducts;

sodium methylparaben (5026-62-0) → 4-(thietane-3-yloxy)benzoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 68 percent / methanol; H2O / 2 h / 45 - 55 °C 2: 93 percent / HCl / methanol; H2O View Scheme

sodium methylparaben (5026-62-0) → 4-[2-(tetrahydropyran-2-yloxy)ethoxy]benzoic acid methyl ester (182358-82-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / NaI / methanol / 18 h / 60 °C 2: 90 percent / ISiMe3 / CH2Cl2 / 0.5 h / 25 °C View Scheme

sodium methylparaben (5026-62-0) → 4-<(dimethylcarbamoyl)thio>benzoic acid (13511-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 2: aq. HCl 3: tetrahydrothiophene 1,1-dioxide / 220 °C View Scheme

sodium methylparaben (5026-62-0) → 4--benzoesaeure (13522-57-1)

Conditions	Yield
Multi-step reaction with 2 steps 2: aq. HCl View Scheme

sodium methylparaben (5026-62-0) → α-(4-Carboxy-phenoxy)-acrylsaeure (16929-38-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) cyclohexanone, (ii) TsOH 2: aq. NaOH / Ambient temperature View Scheme

Upstream product

• 73823-12-8 4-(N-phenyl-benzimidoyloxy)-benzoic acid methyl ester 
• 124-41-4 sodium methylate 
• 99-76-3 methyl 4-hydroxylbenzoate 

Downstream Products

• 116858-42-5 C₁₇H₁₄O₆S 
• 3204-73-7 4-(2-hydroxyethoxy)benzoic acid methyl ester 
• 99-96-7 4-hydroxy-benzoic acid 
• 13511-91-6 4-<(dimethylcarbamoyl)thio>benzoic acid 
• 13522-57-1 4--benzoesaeure 
• 279239-17-7 N-[(4-carboxyphenoxy)acetyl]-4-[(2,6-dichlorobenzoyl)amino]-L-phenylalanine 
• 21120-78-5 methyl 4-(4-nitrophenoxy)benzoate 
• 92501-87-6 methyl 4-(2-morpholinoethoxy)benzoate 
• 34593-50-5 methyl 4-((3-methylbut-2-en-1-yl)oxy)benzoate 
• 101511-34-6 methyl-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate 
• 99-76-3 methyl 4-hydroxylbenzoate 

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Skin aging inhibitor

PROBLEM TO BE SOLVED: To provide a skin aging inhibitor. SOLUTION: A skin aging inhibitor contains, as an active ingredient, at least one compound selected from a hydroxy benzoic acid represented by formula (1) and a derivative thereof [in the formula R1 is hydrogen, a methyl group or a glucosyl group; in the formula R2 is a group selected from the group consisting of hydrogen, a C1-8 linear or branched hydrocarbon group, an aromatic hydrocarbon group, and a sugar residue of glucose or sorbitol] and a salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

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Process for the preparation of alkali metal salts of hydroxybenzoates, which are substantially anhydrous and free from hydroxybenzoic acid

Alkali metal salts of hydroxybenzoates are claimed which are substantially anhydrous and free from hydrobenzoic acid and have the formula STR1 in which R1 denotes alkyl, alkenyl, cycloalkyl or aralkyl, R2 and R3 are identical or different and represent hydrogen, halogen, hydroxyl, amino, alkylamino, alkyl, alkoxy, aralkyl or aryl and Me denotes an alkali metal. Furthermore a process for the preparation of the said alkali metal salts of hydroxybenzoates, which are substantially anhydrous and free from hydrobenzoic acid, characterized in that a solution or suspension of a hydroxybenzoate of the formula STR2 in which R1, R2 and R3 have the abovementioned meaning, is neutralized with an alkali metal hydroxide at -10° to +50° C. until the degree of neutralization is 0.95 to 1.05, a degree of neutralization of 1.00 denoting the end point of the neutralization of the phenolic OH group by the alkali metal hydroxide, and the resulting solution or suspension of the alkali metal salt of the hydroxybenzoate is passed to a mild drying operation which does not damage the product and is in itself known, after a time such that the content of hydroxybenzoic acid or the alkali metal salt thereof in this solution or suspension does not reach the value of 1% by weight, relative to the amount of alkali metal salt of hydroxybenzoate contained in this solution or suspension.