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99-76-3

Basic Information
CAS No.: 99-76-3
Name: Methylparaben
Article Data: 362
Cas Database
Molecular Structure:
Molecular Structure of 99-76-3 (Methylparaben)
Formula: C8H8O3
Molecular Weight: 152.15
Synonyms: Methyl parahydroxybenzoate (JP14);Methylester kyseliny p-hydroxybenzoove [Czech];Sodium 4-carbomethoxyphenolate;Sodium methyl p-hydroxybenzoate;Methyl p-oxybenzoate;Methyl ester of p-hydroxybenzoic acid;Methyl parahydroxybenzoate;p-Carbomethoxyphenol;Benzoic acid,4-hydroxy-,esters,methyl ester;Preserval M;Methylparaben (TN);Methylparaben sodium [USAN];Sodium, (p-carboxyphenoxy)-, methyl ester (7CI);p-Oxybenzoesauremethylester [German];Methyl-4-hydroxybenzoate;methylparaben;methyl paraben; methyl p-hydroxybenzoate;methyl para-hydroxybenzoate;Methyl p-Hydroxybenzoate(Methyl paraben);Methyl-p-hydroxybenzoate;p-Methoxycarbonylphenol;Methyl chemosept;4-Hydroxybenzoic acid, methyl ester;Methyl p-hydroxybenzoate, sodium salt;EPA Pesticide Chemical Code 061201;Methyl Butex;p-Hydroxybenzoic acid, methyl ester;component of Heb-Cort MC;Benzoic acid, p-hydroxy-, methyl ester;Methylparaben [USAN];Benzoic acid, 4-hydroxy-, methyl ester;sodium 4-methoxycarbonylphenolate;p-Hydroxybenzoic methyl ester;4-(Methoxycarbonyl)phenol;p-Hydroxybenzoic acid methyl ester;Methyl Paraben;
EINECS: 202-785-7
Density: 1.209 g/cm3
Melting Point: 125-128 °C(lit.)
Boiling Point: 265.5 °C at 760 mmHg
Flash Point: 116.4 °C
Solubility: Slightly soluble in water.
Appearance: white crystalline powder
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 36/37/38-20/21/22
Safety: 26-36-24/25
Transport Information: UN 2769
PSA: 46.53000
LogP: 1.17880
Synthetic route
67-56-1

methanol

99-96-7

4-hydroxy-benzoic acid

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With sulfuric acid for 8h; Heating;100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction; chemoselective reaction;100%
24262-66-6

methyl 4-acetoxybenzoate

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 6h;100%
With phosphate buffer In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder;100%
With ammonium acetate In methanol at 20℃; for 2.5h;100%
67-56-1

methanol

123-08-0

4-hydroxy-benzaldehyde

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With oxygen at 80℃; under 3750.38 Torr; for 4h; Temperature; Reagent/catalyst; Pressure; Sealed tube;99.3%
With perchloric acid; sodium percarbonate; vanadia for 1h; Cooling;98%
With perchloric acid; dihydrogen peroxide; vanadia In water at 5℃; for 2.5h; oxidative esterification;97%
74-88-4

methyl iodide

99-96-7

4-hydroxy-benzoic acid

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃;99%
Stage #1: 4-hydroxy-benzoic acid With sodium hydrogencarbonate In water at 20℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃;
95%
With potassium hydroxide at 220℃; im geschlossenen Rohr;
With N'',N'''''-1,8-naphthalenediyl bis[N,N,N',N'-tetramethyl]guanidine In N,N-dimethyl-formamide at 20℃; Kinetics;
137988-24-0

methyl 4-(cyanomethoxy)benzoate

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In ethanol99%
35750-24-4

methyl 4-allyloxybenzoate

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With aniline; (ϖ-allyl)palladium triflate based catalyst at 30℃; for 0.333333h;99%
With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); water; bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide at 30℃; for 24h; Schlenk technique;95%
With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide; water at 30℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;95%
133642-20-3

4-(tert-butyldimethylsilanyloxy)benzoic acid methyl ester

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; acetonitrile at 20℃; for 0.166667h;99%
With potassium hydroxide In ethanol at 20℃; for 0.7h;95%
With sodium phosphate dodecahydrate In N,N-dimethyl-formamide at 20℃; for 2h; chemoselective reaction;92%
67-56-1

methanol

201230-82-2

carbon monoxide

540-38-5

4-Iodophenol

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere;99%
With triethylamine at 80℃; under 3750.38 Torr; for 3h; Autoclave;75%
With triethylamine; G0-C2 PAMAM dendrimer*PPh2*PdMe2 at 105℃; under 5171.62 Torr; for 19h;100 % Chromat.
17763-71-2

4-carbomethoxyphenyl triflate

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h;99%
With caesium carbonate In toluene at 80℃; for 15h;87%
With ammonium acetate; methanol; magnesium; palladium on activated charcoal at 20℃; for 24h;51%
With (1,2-dimethoxyethane)dichloronickel(II); N-isopropyl-N-tert-butylamine; N-tert-butoxycarbonyl-proline; 4,4'-di-tert-butyl-2,2'-bipyridine In dimethyl sulfoxide at 40℃; for 14h; Irradiation; Sealed tube;27 %Spectr.
32122-11-5

4-benzyloxy-benzoic acid methyl ester

99-76-3

methyl 4-hydroxylbenzoate

Conditions
ConditionsYield
With cyclohexa-1,4-diene; 3,6-bis(dimethylamino)-9H-carbazole; caesium carbonate In dimethyl sulfoxide at 23℃; for 44h; Inert atmosphere; Schlenk technique; Irradiation;99%
With pentamethylbenzene,; boron trichloride In dichloromethane at -78℃; for 0.333333h;97%
With thiophene; sodium hydrogen sulfate; silica gel for 6h; Heating;96%
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  • Methylparaben      CAS: 99-76-3

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    Chemical Name: MethylParaben CAS No.: 99-76-3 Molecular Fomula: C8H8O3 Molecular weight: 152.15 g/mol Appearance:white powder Assay: 98-102 Appearance:White powder Storage: Room Temperature Package: 25kg/drum or 20kg/bag Application: P

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    Product Name: Methylparaben CAS: 99-76-3 MF: C8H8O3 MW: 152.15 EINECS: 202-785-7 Mol File: 99-76-3.mol Methylparaben Structure Methylparaben Chemical Properties Melting point 125-128 °C (lit.) Boiling point 298.6 °

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Specification

The Methylparaben, with the CAS registry number 99-76-3, is also known as Methyl p-hydroxybenzoate; 4-(Methoxycarbonyl)phenol.It belongs to the product categories of Developer;Functional Materials;Aromatics.Its EINECS number is 202-785-7.This chemical's molecular formula is C8H8O3 and molecular weight is 152.15. What's more,Its systematic name is Benzoic acid,4-hydroxy-,methyl ester.Methylparaben 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.

Physical properties about Methylparaben are: (1)ACD/LogP: 1.882; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.88; (4)ACD/LogD (pH 7.4): 1.83; (5)ACD/BCF (pH 5.5): 15.83; (6)ACD/BCF (pH 7.4): 14.11; (7)ACD/KOC (pH 5.5): 251.25; (8)ACD/KOC (pH 7.4): 223.85; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.547; (13)Molar Refractivity: 39.908 cm3; (14)Molar Volume: 125.756 cm3; (15)Surface Tension: 45.7929992675781 dyne/cm; (16)Density: 1.21 g/cm3; (17)Flash Point: 116.398 °C; (18)Enthalpy of Vaporization: 52.377 kJ/mol; (19)Boiling Point: 265.536 °C at 760 mmHg; (20)Vapour Pressure: 0.00600000005215406 mmHg at 25°C;

Uses of Methylparaben: Methylparaben is known to slow Drosophila growth rate in the larval and pupal stages. It is an antifungal that is widely used as a preservative for food, drugs, and cosmetics. Mycocten, and is commonly used as an anti-fungal agent in Drosophila food media.Methylparaben is an anti-fungal agent often used in hair gels. The compound is often found in carpules of local anaesthetic, acting as a bacteriostatic agent and preservative. Methylparaben (also called Nipigin M, Tegosept, and Mycocten) is commonly used as a fungicide in Drosophila food media. Usage of methylparaben is known to slow Drosophila growth rate in the larval and pupal stages.
The Methylparaben is harmful by inhalation, in contact with skin and if swallowed. It is Irritating to eyes,respiratory system and skin .when you use it ,wear suitable protective clothing,avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES:COC(=O)c1ccc(cc1)O;
(2)Std. InChI:InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3;
(3)Std. InChIKey:LXCFILQKKLGQFO-UHFFFAOYSA-N.

The toxicity data of Methylparaben as follows:

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) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 45, Pg. 260, 1956.
mouse LD50 oral > 8gm/kg (8000mg/kg) BEHAVIORAL: ATAXIA

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
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.