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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C8H8O3
Molecular Weight 152.1473
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLPARABEN

SMILES

COC(=O)C1=CC=C(O)C=C1

InChI

InChIKey=LXCFILQKKLGQFO-UHFFFAOYSA-N
InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3

HIDE SMILES / InChI
Molecular Formula C8H8O3
Molecular Weight 152.1473
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.fda.gov/Food/IngredientsPackagingLabeling/GRAS/SCOGS/ucm260472.htm

Methylparaben (E number E218) is preservative in the food, cosmetic, and pharmaceutical industries. It is completely absorbed through the skin or after ingestion and and it is hydrolyzed to para-hydroxybenzoic acid, and metabolites are rapidly excreted in the urine. Methylparaben is on the FDA generally regarded as safe list.

Originator

University of Budapest
2
Sources: Condensation of Dimethyl-a-resorcylyl Chlorides with Phenol Ethers. Journal fuer Praktische Chemie (Leipzig), 1913, 87:403-9

Approval Year

1987
121
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
Approved
8583
Olanzapine

Approved Use

Olanzapine is used to treat the symptoms of psychotic conditions such as schizophrenia and bipolar disorder (manic depression) in adults and children who are at least 13 years old.

Launch Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
57 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/36220432/
62.4 mg single, transdermal
dose: 62.4 mg
route of administration: Transdermal
experiment type: SINGLE
co-administered: PROPYLPARABEN
PROPYLPARABEN
 METHYLPARABEN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.4 μM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/36220432/
62.4 mg single, transdermal
dose: 62.4 mg
route of administration: Transdermal
experiment type: SINGLE
co-administered: PROPYLPARABEN
PROPYLPARABEN
 METHYLPARABEN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/36220432/
62.4 mg single, transdermal
dose: 62.4 mg
route of administration: Transdermal
experiment type: SINGLE
co-administered: PROPYLPARABEN
PROPYLPARABEN
 METHYLPARABEN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2A6
879

CYP2E1
1060

CYP1A2
2153

CYP2C19
2057
UGT1A6
343

UGT1A1
479

UGT1A9
423

UGT2B7
456

UGT2B15
236

UGT1A3
470

UGT1A4
399

UGT1A7
249

UGT1A8
323

UGT1A10
331

UGT2B17
237
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no [IC50 >10 uM]
CYP2A6
911
 no [IC50 >10 uM]
CYP2C19
2141
 no [IC50 >10 uM]
CYP2C9
2497
 no [IC50 >10 uM]
CYP2D6
2546
 no [IC50 >10 uM]
CYP2E1
1146
 no [IC50 >10 uM]
CYP3A4
2633
 no [IC50 >10 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
UGT1A3
470
 likely
UGT1A4
399
 likely
UGT1A10
331
 weak
UGT1A7
249
 weak
UGT1A8
323
 weak
UGT2B15
236
 weak
UGT2B17
237
 weak
UGT2B7
456
 weak
UGT1A9
423
 yes [Km 1.28 uM]
UGT1A1
479
 yes
UGT1A6
343
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Sorption of parabens by flexible tubings.
2001 Aug
Antibacterial effect of parabens against planktonic and biofilm Streptococcus sobrinus.
2001 Dec
Alkaloids of Thalictrum angustifolium.
2002
Sorption of benzoic acid, sorbic acid, benzyl alcohol, and benzalkonium chloride by flexible tubing.
2002 Jan
Interaction of methylparaben preservative with selected sugars and sugar alcohols.
2002 Jul
HPLC and LC-MS studies of the transesterification reaction of methylparaben with twelve 3- to 6-carbon sugar alcohols and propylene glycol and the isomerization of the reaction products by acyl migration.
2002 Mar
[Studies for analyzing phenoxyethanol and parabens in commercial lotions].
2003
Allergy and toxic reactions to local anesthetics.
2003 Apr
Metabolic profiling of root exudates of Arabidopsis thaliana.
2003 Apr 23
Simultaneous determination of methylparaben, propylparaben, hydrocortisone acetate and its degradation products in a topical cream by RP-HPLC.
2003 Aug 8
Solvent effects in permeation assessed in vivo by skin surface biopsy.
2003 Dec 18
Antioxidant properties and phytochemical characteristics of extracts from Lactuca indica.
2003 Feb 26
Determination of methylparaben in o/w emulsions by solid-phase extraction and high-performance liquid chromatography.
2003 Jan-Feb
Influence of methylparaben as a solid-state plasticizer on the physicochemical properties of Eudragit RS PO hot-melt extrudates.
2003 Jul
Determination of methylparaben, propylparaben, triamcinolone acetonide and its degradation product in a topical cream by RP-HPLC.
2003 Jun
Effects of methyl p-hydroxybenzoate (methyl paraben) on Ca2+ concentration and histamine release in rat peritoneal mast cells.
2003 May
Reversed-phase porous silica rods, an alternative approach to high-performance liquid chromatographic separation using the sequential injection chromatography technique.
2003 Oct 10
[Evaluation of interaction between drugs and ordered phospholipid membrane by immobilized artificial membrane chromatography].
2003 Sep
Burkholderia cepacia infections associated with intrinsically contaminated ultrasound gel: the role of microbial degradation of parabens.
2004 Apr
Allergic contact dermatitis to condoms: description of a clinical case and analytical review of current literature.
2004 Aug
Simultaneous determination of metformin in combination with rosiglitazone by reversed-phase liquid chromatography.
2004 Feb
Effect of heat on the percutaneous absorption and skin retention of three model penetrants.
2004 Feb
Release of simulated anthrax particles from disposable respirators.
2004 Jan
Simultaneous high-performance liquid chromatographic determination of pioglitazone and metformin in pharmaceutical-dosage form.
2004 Jan
Determination of combined p-hydroxy benzoic acid preservatives in a liquid pharmaceutical formulation by HPLC.
2004 Jan 27
Concentrations of parabens in human breast tumours.
2004 Jan-Feb
Single crystal EPR studies of an organic NLO material: methyl-p-hydroxy benzoate.
2004 Jul
HPLC determination of estradiol, its degradation product, and preservatives in new topical formulation Estrogel HBF.
2004 Jul
Allergic contact sensitivity in elderly patients.
2004 Jun
Solvent effects on infrared spectra of methyl 4-hydroxybenzoate in pure organic solvents and in ethanol/CCl4 binary solvents.
2004 Jun
Measurement of anti-HIV activity of marketed vaginal products and excipients using a PBMC-based in vitro assay.
2004 Mar
Comparison of equations describing band broadening in high-performance liquid chromatography.
2004 Mar 19
Simultaneous HPLC determination of ketoprofen and its degradation products in the presence of preservatives in pharmaceuticals.
2004 Nov 15
Characterization of three glycosyltransferases involved in the biosynthesis of the phenolic glycolipid antigens from the Mycobacterium tuberculosis complex.
2004 Oct 8
Morphometric analysis of mice uteri treated with the preservatives methyl, ethyl, propyl, and butylparaben.
2004 Sep
Prevalence and relevance of contact dermatitis allergens: a meta-analysis of 15 years of published T.R.U.E. test data.
2004 Sep
High performance liquid chromatographic determination of oxeladin citrate and oxybutynin hydrochloride and their degradation products.
2005 Aug
Estrogenic activity of cosmetic components in reporter cell lines: parabens, UV screens, and musks.
2005 Feb 27
Partition of antimicrobial additives in an intravenous emulsion and their effect on emulsion physical stability.
2005 Jan 20
Parabens: a review of epidemiology, structure, allergenicity, and hormonal properties.
2005 Jun
Development and validation of a stability indicating HPLC method for determination of lisinopril, lisinopril degradation product and parabens in the lisinopril extemporaneous formulation.
2005 Mar 9
The effect of unsaturated fatty acids in benzyl alcohol on the percutaneous permeation of three model penetrants.
2005 Sep 14
Patents

Patents

04006123
3
04289692
2
04293484
3
04293486
2
04293489
2
04297277
2
04373953
2
04607053
2
04713474
2
04753962
2
05225425
2
05240938
4
JP2000204017A
2
JP2000204039A
2
JP2000256583A
2
JP2000327591A
2
JP2001026542A
2
JP2002533379A
53
JP2003002810A
2
JP2003012420A
2
JP2003342146A
2
JP2003512415A
2
JP2004231895A
2
JP2004520358A
16
JP2005535711A
5
JP2007031394A
2
JP2007161641A
2
JP2007169242A
2
JP2007507419A
4
JP2008295837A
2
JP2009227649A
2
JP2010209116A
2
JP2011006454A
3
JP2011162519A
2
JP2011524901A
14
JP3844491B2
8
JP5302239B2
2
JPH01275501A
2
JPH01287018A
2
JPH02200611A
2
JPH0273014A
2
JPH03184539A
2
JPH04120011A
2
JPH05194257A
2
JPH06122618A
2
JPH0710752A
8
JPH07238086A
2
JPH07278251A
2
JPH08310928A
2
JPH0838196A
2
JPH09176029A
2
JPH09249534A
2
JPH11508482A
2
JPS57183780A
2
JPS5929614A
2
JPS608202A
2

Sample Use Guides

In Vivo Use Guide
Methylparaben is used as a preservative in the food, cosmetic, and pharmaceutical industries. It is administered orally with food or applied topically with cosmetic products.
Route of Administration: Other
In Vitro Use Guide
The fungistatic activity of methyl parahydroxybenzoate was determined against Candida albicans, Trichophyton rubrum, T. mentagrophytes, Microsporum audouini, Geotrichum asteroides, and Cryptococcus neoformans. Methylparaben was effective at concentrations of 150 to 350 mg/ml.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:55:42 GMT 2025
Edited
by admin
on Mon Mar 31 17:55:42 GMT 2025
Record UNII
A2I8C7HI9T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYL HYDROXYBENZOATE
MART.   WHO-IP  
Preferred Name English
METHYLPARABEN
FCC   HSDB   II   INCI   MI   USAN   USP-RS   VANDF   WHO-DD  
INCI   USAN  
Official Name English
FEMA NO. 2710
Code English
INS NO.218
Code English
Methylparaben [WHO-DD]
Common Name English
METHYL P-OXYBENZOATE
Common Name English
PRESERVAL M
Common Name English
METHYL P-HYDROXYBENZOATE [FHFI]
Common Name English
NSC-3827
Code English
KILLITOL
Common Name English
INS-218
Code English
METHYLPARABEN [II]
Common Name English
METHYLPARABEN [USP-RS]
Common Name English
METHYL PARABEN [VANDF]
Common Name English
P-HYDROXYBENZOIC METHYL ESTER
Common Name English
Methyl 4-hydroxybenzoate
Systematic Name English
METHYLPARABEN [HSDB]
Common Name English
NSC-406127
Code English
MOLDEX
Common Name English
METHYLPARABEN [USAN]
Common Name English
METHYL PARAHYDROXYBENZOATE [JAN]
Common Name English
METHYLPARABEN [FCC]
Common Name English
METHYLPARABEN [MI]
Common Name English
METHYL PARABEN (E218)
Common Name English
METHYL PARAHYDROXYBENZOATE [EP MONOGRAPH]
Common Name English
BENZOIC ACID, 4-HYDROXY-, METHYL ESTER
Common Name English
PROPYL HYDROXYBENZOATE IMPURITY B [EP IMPURITY]
Common Name English
METHYLPARABEN [VANDF]
Common Name English
METHYL PARABEN
VANDF  
Common Name English
METHYLPARABEN E218
Common Name English
TEGOSEPT M
Common Name English
METHYLIS HYDROXYBENZOAS [WHO-IP LATIN]
Common Name English
METHYL SALICYLATE IMPURITY C [EP IMPURITY]
Common Name English
METHYL HYDROXYBENZOATE [MART.]
Common Name English
E-218
Code English
METHYL PARAHYDROXYBENZOATE
EP  
Systematic Name English
METHYL HYDROXYBENZOATE [WHO-IP]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
CODEX ALIMENTARIUS (GSFA) INS-218
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
JECFA EVALUATION INS-218
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
NDF-RT N0000185508
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
DSLD 1906 (Number of products:2)
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
NCI_THESAURUS C92608
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
EPA PESTICIDE CODE 61201
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
CFR 21 CFR 184.1490
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
Code System Code Type Description
NSC
3827
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
NCI_THESAURUS
C76720
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
NDF-RT
N0000171131
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY Allergens [Chemical/Ingredient]
CHEBI
31835
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
NDF-RT
N0000184306
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY Cell-mediated Immunity [PE]
RXCUI
29903
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY RxNorm
CAS
99-76-3
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
WIKIPEDIA
METHYLPARABEN
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
DRUG CENTRAL
1766
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
SMS_ID
100000088519
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
MESH
C015358
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
RS_ITEM_NUM
1432005
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
MERCK INDEX
m7450
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY Merck Index
PUBCHEM
7456
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
USAN
Y-26
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
DRUG BANK
DB14212
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
EVMPD
SUB12154MIG
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
NDF-RT
N0000175629
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY Increased Histamine Release [PE]
ChEMBL
CHEMBL325372
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METHYLPARABEN
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water; soluble in boiling water; freely soluble in ethanol (~750 g/l) TS and ether R. Category: Antimicrobial preservative. Storage: Methyl hydroxybenzoate should be kept in a well-closed container.Additional information: Methyl hydroxybenzoate is normally used in combination with other hydroxybenzoates. Requirements: Methyl hydroxybenzoate contains not less than 99.0% and not more than the equivalent of 101.0% of C8H8O3, calculated with reference to the dried substance.
FDA UNII
A2I8C7HI9T
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
NSC
406127
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID4022529
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
HSDB
1184
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
DAILYMED
A2I8C7HI9T
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-785-7
Created by admin on Mon Mar 31 17:55:42 GMT 2025 , Edited by admin on Mon Mar 31 17:55:42 GMT 2025
PRIMARY
Related Record Type Details
Structure of METHYLPARABEN SODIUM
SALT/SOLVATE -> PARENT
Structure of POTASSIUM METHYLPARABEN
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of PROPYLPARABEN
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Methyl salicylate
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
EP
Structure of BUTYLPARABEN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of PROPYLPARABEN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ETHYLPARABEN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-Hydroxybenzoic Acid
IMPURITY -> PARENT
correction factor: for the calculation of content, multiply the peak area of impurity A by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of METHYLPARABEN
ACTIVE MOIETY
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