U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
The effect of unsaturated fatty acids in benzyl alcohol on the percutaneous permeation of three model penetrants.
2005-09-14
High performance liquid chromatographic determination of oxeladin citrate and oxybutynin hydrochloride and their degradation products.
2005-08
Oestrogenic activity of p-hydroxybenzoic acid (common metabolite of paraben esters) and methylparaben in human breast cancer cell lines.
2005-07-16
A novel gradient HPLC method for simultaneous determination of ranitidine, methylparaben and propylparaben in oral liquid pharmaceutical formulation.
2005-07-15
Safety assessment of esters of p-hydroxybenzoic acid (parabens).
2005-07
Parabens: a review of epidemiology, structure, allergenicity, and hormonal properties.
2005-06
Propyl paraben induces potassium efflux in Escherichia coli.
2005-06
Simultaneous determination of preservatives (benzoic acid, sorbic acid, methylparaben and propylparaben) in foodstuffs using high-performance liquid chromatography.
2005-05-06
Novel solid-phase extraction protocol for 11-nor-9-carboxy-delta9-tetrahydrocannabinol from urine samples employing a polymeric mixed-mode cation-exchange resin, Strata-X-C, suitable for gas chromatography-mass spectrometry or liquid chromatography-mass spectrometry analysis.
2005-05-06
Effect of homocysteine-lowering nutrients on blood lipids: results from four randomised, placebo-controlled studies in healthy humans.
2005-05
Phenolic compounds and flavonoids as plant growth regulators from fruit and leaf of Vitex rotundifolia.
2005-04-09
Preventing sexual transmission of HIV: anti-HIV bioregulatory and homeostatic components of commercial sexual lubricants.
2005-03-25
The use of colloidal microgels as a (trans)dermal drug delivery system.
2005-03-23
Stability assessment of pharmaceuticals by isothermal calorimetry: two component systems.
2005-03-23
Development and validation of a stability indicating HPLC method for determination of lisinopril, lisinopril degradation product and parabens in the lisinopril extemporaneous formulation.
2005-03-09
Decrease in skin permeation and antibacterial effect of parabens by a polymeric additive, poly(2-methacryloyloxyethyl phosphorylcholine-co-butylmetacrylate).
2005-03
Inter- and intralaboratory variation of in vitro diffusion cell measurements: an international multicenter study using quasi-standardized methods and materials.
2005-03
Estrogenic activity of cosmetic components in reporter cell lines: parabens, UV screens, and musks.
2005-02-27
[Synthesis of 2,3,4-trihydroxyacetophenone hydrazones and study on their spectral properties].
2005-02
Partition of antimicrobial additives in an intravenous emulsion and their effect on emulsion physical stability.
2005-01-20
Thermodynamics of solubility, sublimation and solvation processes of parabens.
2005-01
Separation of preservatives in cosmetic products by micellar electrokinetic chromatography.
2004-12
Simultaneous HPLC determination of ketoprofen and its degradation products in the presence of preservatives in pharmaceuticals.
2004-11-15
Characterization of three glycosyltransferases involved in the biosynthesis of the phenolic glycolipid antigens from the Mycobacterium tuberculosis complex.
2004-10-08
Morphometric analysis of mice uteri treated with the preservatives methyl, ethyl, propyl, and butylparaben.
2004-09
Prevalence and relevance of contact dermatitis allergens: a meta-analysis of 15 years of published T.R.U.E. test data.
2004-09
Allergic contact dermatitis to condoms: description of a clinical case and analytical review of current literature.
2004-08
Single crystal EPR studies of an organic NLO material: methyl-p-hydroxy benzoate.
2004-07
HPLC determination of estradiol, its degradation product, and preservatives in new topical formulation Estrogel HBF.
2004-07
Allergic contact sensitivity in elderly patients.
2004-06
Solvent effects on infrared spectra of methyl 4-hydroxybenzoate in pure organic solvents and in ethanol/CCl4 binary solvents.
2004-06
Burkholderia cepacia infections associated with intrinsically contaminated ultrasound gel: the role of microbial degradation of parabens.
2004-04
Comparison of equations describing band broadening in high-performance liquid chromatography.
2004-03-19
Measurement of anti-HIV activity of marketed vaginal products and excipients using a PBMC-based in vitro assay.
2004-03
Simultaneous determination of metformin in combination with rosiglitazone by reversed-phase liquid chromatography.
2004-02
Effect of heat on the percutaneous absorption and skin retention of three model penetrants.
2004-02
Concentrations of parabens in human breast tumours.
2004-01-28
Determination of combined p-hydroxy benzoic acid preservatives in a liquid pharmaceutical formulation by HPLC.
2004-01-27
Release of simulated anthrax particles from disposable respirators.
2004-01
Simultaneous high-performance liquid chromatographic determination of pioglitazone and metformin in pharmaceutical-dosage form.
2004-01
Solvent effects in permeation assessed in vivo by skin surface biopsy.
2003-12-18
The physical stability of thermally-stressed phospholipid-based emulsions containing methyl, propyl and heptyl parabens as model drugs.
2003-10-20
Reversed-phase porous silica rods, an alternative approach to high-performance liquid chromatographic separation using the sequential injection chromatography technique.
2003-10-10
Antiprotozoal activities of symmetrical bishydroxamic acids.
2003-10-01
Determination of bifonazole in creams containing methyl- and propyl p-hydroxybenzoate by derivative spectrophotometric method.
2003-09-15
[Evaluation of interaction between drugs and ordered phospholipid membrane by immobilized artificial membrane chromatography].
2003-09
Crystallization of two forms of a cyclodextrin inclusion complex containing a common organic guest.
2003-08-21
In vivo and in vitro estrogen bioactivities of alkyl parabens.
2003-07
[Studies for analyzing phenoxyethanol and parabens in commercial lotions].
2003
Alkaloids of Thalictrum angustifolium.
2002
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
NIH
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