Methylparaben
- Iupac Name：methyl 4-hydroxybenzoate
- CAS No.: 99-76-3
- Molecular Weight：152.14732
- Modify Date.: 2022-10-31 06:21
- Introduction: It is used as preservative in foods, beverages and cosmetics.
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1. Names and Identifiers
- 1.1 Name
- Methylparaben
- 1.2 Synonyms
4-(Carbomethoxy)phenol 4-(Methoxycarbonyl)phenol 4-Hydroxybenzoic Acid Methyl Ester 4-Hydroxy-benzoic acid methyl ester 4-Hydroxybenzoic acid methylester 4-Hydroxybenzoic acid, methyl ester 4-HYDROXYBENZOICACIDMETHYLESTER(METHYLPARABEN) 4-HYDROXYLMETHYLBENZOATE Benzoic acid, 4-hydroxy-, methyl ester Benzoic acid, p-hydroxy-, methyl ester EINECS 202-785-7 Killitol Mekkings M Metagin Methyl 4-hydroxybenzoate Methyl chemosept Methyl Paraben Methyl parahydroxybenzoate methyl para-hydroxybenzoate Methyl parasept methyl p-hydroxybenzoate Methyl-4-hydroxybenzoate METHYLPARABEN,FCC METHYLPARABEN,NF MFCD00002352 NIPAGIN NIPAGIN PLAIN P-HYDROXYBENZOIC ACID METHYL ESTER p-Hydroxybenzoic acid, methyl ester p-Hydroxybenzoic methyl ester RARECHEM AL BF 0098 Tegosept M
- 1.3 CAS No.
- 99-76-3
- 1.4 CID
- 7456
- 1.5 EINECS(EC#)
- 202-785-7
- 1.6 Molecular Formula
- C8H8O3 (isomer)
- 1.7 Inchi
- InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
- 1.8 InChkey
- LXCFILQKKLGQFO-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- COC(=O)C1=CC=C(C=C1)O
- 1.10 Isomers Smiles
- COC(=O)C1=CC=C(C=C1)O
2. Properties
- 2.1 Density
- 1.209
- 2.1 Melting point
- 125-128℃
- 2.1 Boiling point
- 265.5 °C at 760 mmHg
- 2.1 Refractive index
- 1.5204 (137 C)
- 2.1 Flash Point
- 116.4 °C
- 2.1 Precise Quality
- 152.04700
- 2.1 PSA
- 46.53000
- 2.1 logP
- 1.17880
- 2.1 Solubility
- ethanol: soluble0.1M, clear, colorless
- 2.2 Appearance
- white crystalline powder
- 2.3 Storage
- Ventilated , low temperature and dry warehouse.
- 2.4 Carcinogenicity
- The carcinogenic potential ofmethyl paraben has been studied in rodents. Several studiesare available, but none that expose animals via oral or dermalroutes. No evidence of a carcinogenic effect was observedfollowing intravenous or subcutaneous injection .
- 2.5 Chemical Properties
- White needle crystal; Slightly soluble in water, easily soluble in ethanol, ether, acetone and other organic solvents.
- 2.6 Color/Form
- Powder
- 2.7 Contact Allergens
- This substance is one of the parabens family. Parabens are esters formed by p-hydroxybenzoic acidand an alcohol. They are largely used as biocides incosmetics and toiletries, medicaments, or food. Theyhave synergistic power with other biocides. Parabenscan induce allergic contact dermatitis, mainly inchronic dermatitis and wounded skin.
- 2.8 Decomposition
- When heated to decomp it emits acrid smoke and fumes.
- 2.9 Odor
- Odorless or has faint characteristic odor
- 2.10 PH
- 5.8 (H2O, 20°C) (saturated solution)
- 2.11 pKa
- pKa 8.15(H2O,t =20.0) (Uncertain)
- 2.12 Water Solubility
- Slightly soluble
- 2.13 Spectral Properties
- MAX ABSORPTION (ALCOHOL): 258 NM (LOG E= 4.22); SADTLER REFERENCE NUMBER: 18045 (IR, PRISM); 369 (IR, GRATING)
Intense mass spectral peaks: 121 m/z (100%), 152 m/z (80%), 93 m/z (70%), 65 m/z (63%)
IR: 6245 (Coblentz Society Spectral Collection)
UV: 969 (Sadtler Research Laboratories Spectral Collection)
NMR: 1191 (Sadtler Research Laboratories Spectral Collection)
MASS: 68125 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version); 175 (Aldermaston, Eight Peak Index of Mass)
- 2.14 Stability
- Stable. Incompatible with strong oxidizing agents, strong bases.
- 2.15 StorageTemp
- room temp
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in bluberries.
- 3.2 Produe Method
- Methylparaben is prepared by the esterification of p-hydroxybenzoicacid with methanol.
- 3.3 Purification Methods
- Fractionally crystallise the ester from its melt, and recrystallise it from *benzene, then from *benzene/MeOH and dry it over CaCl2 in a vacuum desiccator. [Beilstein 10 IV 360.]
- 3.4 Usage
- It is used as preservative in foods, beverages and cosmetics.
4. Safety and Handling
- 4.1 Symbol
- ;
- 4.1 Hazard Codes
- Xi,Xn
- 4.1 Risk Statements
- R36/37/38
- 4.1 Safety Statements
- S24/25
- 4.1 Exposure Standards and Regulations
- Methylparaben is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.
- 4.2 Packing Group
- Z01
- 4.2 Octanol/Water Partition Coefficient
- log Kow = 1.96
- 4.3 Other Preventative Measures
- SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
- 4.4 Hazard Declaration
- H412
- 4.4 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.5 RIDADR
- UN 2769
- 4.5 Caution Statement
- P273
- 4.5 Formulations/Preparations
- Topical antibiotic or corticosteroid preparations usually contain 0.3% parabens; however, ointments of tetracyclines contain 3% and some surgical powders of tetracyclines contain as much as 20% parabens. /Parabens/
Methylparaben USP ... Methylparaben and propylparaben solution (preserved water)
Grade: United States Pharmacopeia, "Food Chemical Codex"
The esters are usually dissolved in boiling water and then added to prepn, but when no water is present in formula they may be dissolved in alcohol, acetone, triethanolamine, glycerin, perfume oils, or melted fats. /Parabens/
A combination of 0.18% methylparaben and 0.02% propylparaben is approved for use as preservative for certain parenteral solutions, eg, aq procaine penicillin suspensions.
Trade Names: Abiol, Aseptoform, Maseptol, Metaben, Methaben, Methyl butex, Methyl chemosept, Methyl parasept, Methylben, Metoxyde, Moldex, Nipagin, Nipagin M, Paridol, Preserval, Septos, Solbrol, Solbrol M, and Tegosept M.
- 4.6 Incompatibilities
- The antimicrobial activity of methylparaben and other parabens isconsiderably reduced in the presence of nonionic surfactants, suchas polysorbate 80, as a result of micellization.However,propylene glycol (10%) has been shown to potentiate theantimicrobial activity of the parabens in the presence of nonionicsurfactants and prevents the interaction between methylparabenand polysorbate 80. Incompatibilities with other substances, such as bentonite,magnesium trisilicate,talc,tragacanth,sodium alginate,essential oils,sorbitol,and atropine,have been reported. Italso reacts with various sugars and related sugar alcohols.Absorption of methylparaben by plastics has also been reported;the amount absorbed is dependent upon the type of plastic and thevehicle. It has been claimed that low-density and high-densitypolyethylene bottles do not absorb methylparaben. Methylparaben is discolored in the presence of iron and issubject to hydrolysis by weak alkalis and strong acids.
- 4.7 WGK Germany
- 1
- 4.7 RTECS
- DH2450000
- 4.7 Protective Equipment and Clothing
- METHYL PARABEN ... AS SATURATED AQ SOLN ... NOTED TO BE MODERATELY IRRITATING TO EYE ... .
- 4.8 Skin, Eye, and Respiratory Irritations
- METHYL PARABEN ... AS SATURATED AQ SOLN ... NOTED TO BE MODERATELY IRRITATING TO EYE ... .
- 4.9 Safety
-
Hazard Codes:?
Xi,
Xn
Risk Statements: 36/37/38-20/21/22?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25?
S24/25:Avoid contact with skin and eyes.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
RTECS: DH2450000
- 4.10 Specification
-
?Methylparaben , its cas register number is 99-76-3. It also can be called Methyl paraben ; Methyl p-hydroxybenzoate ; 4-(Methoxycarbonyl)phenol ; 4-(Carbomethoxy)phenol ; Methyl Parasept ; Methyl Butex ; Methaben; Metaben ; Methyl 4-hydroxybenzoate ; and 4-Hydroxybenzoic acid methyl ester .?Methylparaben (CAS NO.99-76-3) is readily absorbed from the gastrointestinal tract or through the skin. It is hydrolyzed to p-hydroxybenzoic acid and rapidly excreted without accumulation in the body. In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported. It?can be found in many of the leading skin/face products.
- 4.11 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| guinea pig |
LD50 |
oral |
3gm/kg (3000mg/kg) |
? |
FAO Nutrition Meetings Report Series. Vol. 53A, Pg. 81, 1974. |
| mouse |
LD50 |
intraperitoneal |
960mg/kg (960mg/kg) |
PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ATAXIA |
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 45, Pg. 260, 1956. |
| mouse |
LD50 |
oral |
> 8gm/kg (8000mg/kg) |
PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
BEHAVIORAL: ATAXIA |
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 45, Pg. 260, 1956. |
| mouse |
LD50 |
subcutaneous |
1200mg/kg (1200mg/kg) |
? |
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 128, Pg. 135, 1960. |
| rabbit |
LD50 |
oral |
6gm/kg (6000mg/kg) |
? |
FAO Nutrition Meetings Report Series. Vol. 53A, Pg. 81, 1974. |
| rat |
LD50 |
subcutaneous |
> 500mg/kg (500mg/kg) |
? |
Clinical Toxicology. Vol. 4(2), Pg. 185, 1971. |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | H412 Harmful to aquatic life with long lasting effects |
| Precautionary statement(s) | |
| Prevention | P273 Avoid release to the environment. |
| Response | none |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
99-76-3Total: 86 Synthesis Route
9. Other Information
- 9.0 Merck
- 14,6107
- 9.1 BRN
- 509801
- 9.2 Chemical properties
- Methylparaben is a colourless crystalline powder that is odourless or has a faint characteristic odour and a slight burning taste. Slightly soluble in water, easily soluble in ethanol, ether, acetone and other organic solvents.One gram dissolves in 2.5 ml ethanol, in about 4 ml of propylene glycol, and in 400 ml of water at 25°C or about 50 ml of water at 80 a C. It is permissible at levels up to 0.1 % in soft drinks, non-leavened bakery products, and other products where it is generally used as a fungistat. From 1000 to 4000 ppm are required to inhibit Gram-positive bacteria. Like the benzoates, its effectiveness increases with decreasing pH.
Methylparaben can by assayed by placing 2 g in a flask and adding 40.0 ml of I N NaOH (with rinsing of sides of flask with water). With a watch glass cover in place, boil gently for I h and cool. Add five drops of bromthymol blue T.S., and titrate the excess NaOH with 1 N H2S04 to pH 6.5 by matching the colour of pH 6.5 phosphate buffer containing the same proportion of indicator. Each ml of 1 N NaOH = 152.2 mg of methylparaben (National Academy of Sciences, 1963).
- 9.3 Uses
- Methylparaben is the ester of methyl alcohol and p-hydroxybenzoic acid, It is a bacteriostatic agent and preservative that was added to local anesthetic agents without vasoconstrictors before 1984 to prevent bacterial growth.Allergic reactions developed from repeated exposures to parabens led to the removal of this agent from dental anesthetic solutions.
Similar products produced by similar production methods, like ethyl p-hydroxybenzoate (paraben B) and propyl p-hydroxybenzoate (Nepalese c), are also disinfectant preservatives.The products are irritating to the skin.
- 9.4 Content analysis
- Method one: determinate according to the content analysis method in "butyl p-hydroxybenzoate (07002)". Per mL 1 mol/L sodium hydroxide is equivalent to the product (C8H8O3) 152.2mg.
Method two: Take 0.1 g (accurate to 1 mg) of the sample previously dried on silica gel for 5 h and move into a 300 ml flask with a glass plug. Plus l mol/L sodium hydroxide 10ml, heated in the water bath for 15min. After cooling, add 0.1mol/L potassium bromate 0.00ml, potassium bromide 5.0g and l mol/L hydrochloric acid 30ml. Put 15min in the dark room after sealing. Add potassium iodide 1 g, shake the flask vigorously, with 0.1mol/L sodium thiosulfate titration, with starch test solution (TS-235) as an indicator. Per ml 0.1mol/L potassium bromate is equivalent to the product (C8H8O3) 25.36mg.
- 9.5 Toxicity
- ADI 0～10mg/kg(FAO/WHO,2001).
GRAS(FDA,§184．1490，2000).
LD503000mg/kg(Dog, mouth)
- 9.6 Utilization limitation
- FAO/WHO (1984): Jam, jelly, 1000mg/kg (single or with benzoate, sorbic acid and potassium sorbate).
EEC(1990,mg/kg): For use in pigment solutions, flavor syrups, coffee extracts, frozen drinks, fruit, glucose and soft drinks, pickled fish, salad, sauce, snack food, concentrated soup and so on, limited to GMP; Beer 70; Snack cereals and soup concentrate 175, the same as "07018 p-hydroxybenzoate".
HACSG is listed as a restricted list.
FDA,§184.1490(2000):0.1%.
- 9.7 Preparation
- The drug is esterified with p-hydroxybenzoic acid and methanol. The p-hydroxybenzoic acid was added to excess methanol to dissolve, stirring and adding concentrated sulfuric acid slowly. After heating and refluxing 10h, pour into the water to precipitate crystallization, then washed with water, sodium carbonate solution and water, finally obtain the crude product. Recrystallize from water or 25% ethanol to obtain finished product. The yield was 85%. Raw material consumption (kg/t): p-hydroxybenzoic acid 1200, methanol 1000.
- 9.8 Category
- Toxic Chemicals
- 9.9 Toxic grading
- Moderate toxicity
- 9.10 Acute toxicity
- Abdomen-mouse LD50: 960 mg/kg
- 9.11 Flammability hazard characteristics
- Combustible, excretes spicy smoke from fireground
- 9.12 Storage
- Ventilated , low temperature and dry warehouse.
- 9.13 Extinguishing agent
- Water, carbon dioxide, dry powder, sand.
- 9.14 Chemical Properties
- Methylparaben occurs as colorless crystals or a white crystalline powder. It is odorless or almost odorless and has a slight burning taste. Soluble in alcohol,ether; slightly soluble in water, benzene, and carbontetrachloride.
- 9.15 Chemical Properties
- Methyl p-hydroxybenzoate is odorless or has a faint characteristic odor and a slight burning taste. Methyl p-hydroxybenzoate is more commonly known as methyl paraben and is an ester of p-hydroxybenzoic acid.
- 9.16 Occurrence
- Reported present in cloudberry, yellow passion fruit juice, white wine, botrytised wine and Bourbon vanilla.
- 9.17 Uses
- parabens is one of the most commonly used group of preservatives in the cosmetic, pharmaceutical, and food industries. Parabens provide bacteriostatic and fungistatic activity against a diverse number of organisms, and are considered safe for use in cosmetics, particularly in light of their low sensitizing potential. An evaluation of preservatives for use in leave-on cosmetic preparations lists parabens among the least sensitizing. The range of concentrations used in cosmetics varies between 0.03 and 0.30 percent, depending on the conditions for use and the product to which the paraben is added.
Methylparaben is one of the most popular preservatives in beauty products and food items. According to the National Library of Medicine, the ingredient occurs naturally in a handful of fruits—like blueberries—though it can also be created synthetically.It's found in everything from cream cleansers and moisturizers to primers and foundations and helps these products maintain their effectiveness. Rabach says that it's chock-full of anti-fungal and antibacterial properties, which work wonders to extend the shelf life of skincare, haircare, and cosmetic products.
https://www.byrdie.com/methylparaben-for-skin-4779820
- 9.18 Uses
- Methylparaben is an antimicrobial agent which is a white free-flowing powder. it is active against yeast and molds over a wide ph range. see parabens.
- 9.19 Definition
- ChEBI: A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blu berries.
- 9.20 Preparation
- Produced by the methanol esterification of p-hydroxybenzoic acid in the presence of sulfuric acid. The materials are heated for distillation in a glass-lined reactor under reflux. The acid is then neutralized with caustic soda and the product is crystallized by cooling. The crystallized product is centrifuged, washed, dried under vacuum, milled and blended, all in corrosion-resistant equipment to avoid metallic contamination.
- 9.21 Production Methods
- Methylparaben is prepared by the esterification of p-hydroxybenzoic acid with methanol.
- 9.22 Aroma threshold values
- Detection: 2.6 ppm.
- 9.23 General Description
-
Methyl paraben is basically a methyl ester of p-hydroxybenzoic acid. It is non-toxic, and non-carcinogenic in nature. It is a stable, non-volatile compound and finds application as an anti-microbial preservative in foods, drugs and cosmetics. It is readily absorbed through the skin and gastrointestinal tract. Upon hydrolyzation, it is hydrolyzed to p-hydroxybenzoic acid, and the conjugates formed get rapidly excreted in the urine.
- 9.24 Usage
- Methyl 4-hydroxybenzoate is used as an anti-fungal agent. It is also used as a preservative in foods, beverages and cosmetics. It acts as an inhibitor of growth of molds and to lesser extent bacteria and as a vehicle for ophthalmic solution.
10. Computational chemical data
- Molecular Weight: 152.14732g/mol
- Molecular Formula: C8H8O3
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 152.047344113
- Monoisotopic Mass: 152.047344113
- Complexity: 136
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 46.5
- Heavy Atom Count: 11
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADASAmAIyDoAABgCIAiDSCAACAAAkIAAIiAEGCMgIJjKCNRqAcQAkwBEIuYeI7CzOIAAAAAAAAABAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
Methylparaben has been used as a preservative in the food, cosmetic, and pharmaceutical industries for over 50 years. The chemical formula for methyl paraben is C 8 H 8 O 3 . It is also found naturally in fruits like blueberries where it has antimicrobial activity. Uses Methylparaben is commonly us...
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