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

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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
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

8.4404162E11
PubMed

PubMed

TitleDatePubMed
Antibacterial effect of parabens against planktonic and biofilm Streptococcus sobrinus.
2001 Dec
ER-dependent estrogenic activity of parabens assessed by proliferation of human breast cancer MCF-7 cells and expression of ERalpha and PR.
2001 Dec
Determination of ethyl-p-hydroxybenzoate in sow pancreatic juice by reversed-phase high-performance liquid chromatography.
2001 Feb 25
The first example of a paraben-dependent antibody to an Rh protein.
2001 Mar
Shellac formulations to reduce epiphytic survival of coliform bacteria on citrus fruit postharvest.
2001 Nov
Alkaloids of Thalictrum angustifolium.
2002
An evaporation study for phthalic acids--a rapid method for pharmaceutical characterization.
2002 Apr
Larvicidal effects of mineral turpentine, low aromatic white spirits, aqueous extracts of Cassia alata, and aqueous extracts, ethanolic extracts and essential oil of betel leaf (Piper betle) on Chrysomya megacephala.
2002 Dec
Identification of methyl salicylate as the principal volatile component in the methanol extract of root bark of Securidaca longepedunculata Fers.
2002 Jun
Evaluation of the health aspects of methyl paraben: a review of the published literature.
2002 Oct
[Studies for analyzing phenoxyethanol and parabens in commercial lotions].
2003
Metabolic profiling of root exudates of Arabidopsis thaliana.
2003 Apr 23
Oestrogenic activity of benzylparaben.
2003 Jan-Feb
In vivo and in vitro estrogen bioactivities of alkyl parabens.
2003 Jul
Effects of methyl p-hydroxybenzoate (methyl paraben) on Ca2+ concentration and histamine release in rat peritoneal mast cells.
2003 May
Separation of preservatives in cosmetic products by micellar electrokinetic chromatography.
2004 Dec
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
Phenolic compounds and flavonoids as plant growth regulators from fruit and leaf of Vitex rotundifolia.
2004 Jul-Aug
Allergic contact sensitivity in elderly patients.
2004 Jun
Comparison of equations describing band broadening in high-performance liquid chromatography.
2004 Mar 19
Morphometric analysis of mice uteri treated with the preservatives methyl, ethyl, propyl, and butylparaben.
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
Thermodynamics of solubility, sublimation and solvation processes of parabens.
2005 Jan
Partition of antimicrobial additives in an intravenous emulsion and their effect on emulsion physical stability.
2005 Jan 20
A novel gradient HPLC method for simultaneous determination of ranitidine, methylparaben and propylparaben in oral liquid pharmaceutical formulation.
2005 Jul 15
Oestrogenic activity of p-hydroxybenzoic acid (common metabolite of paraben esters) and methylparaben in human breast cancer cell lines.
2005 Jul-Aug
Parabens: a review of epidemiology, structure, allergenicity, and hormonal properties.
2005 Jun
Propyl paraben induces potassium efflux in Escherichia coli.
2005 Jun
Inter- and intralaboratory variation of in vitro diffusion cell measurements: an international multicenter study using quasi-standardized methods and materials.
2005 Mar
Effect of homocysteine-lowering nutrients on blood lipids: results from four randomised, placebo-controlled studies in healthy humans.
2005 May
Simultaneous determination of preservatives (benzoic acid, sorbic acid, methylparaben and propylparaben) in foodstuffs using high-performance liquid chromatography.
2005 May 6
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 May 6
The effect of unsaturated fatty acids in benzyl alcohol on the percutaneous permeation of three model penetrants.
2005 Sep 14
Patents

Sample Use Guides

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
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 Fri Dec 15 15:22:50 UTC 2023
Edited
by admin
on Fri Dec 15 15:22:50 UTC 2023
Record UNII
A2I8C7HI9T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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 HYDROXYBENZOATE
MART.   WHO-IP  
Systematic 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 [INCI]
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 Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
CODEX ALIMENTARIUS (GSFA) INS-218
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
JECFA EVALUATION INS-218
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
DSLD 1906 (Number of products:2)
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
NCI_THESAURUS C92608
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
EPA PESTICIDE CODE 61201
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
CFR 21 CFR 184.1490
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
Code System Code Type Description
NSC
3827
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
NCI_THESAURUS
C76720
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY Allergens [Chemical/Ingredient]
CHEBI
31835
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY Cell-mediated Immunity [PE]
RXCUI
29903
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY RxNorm
CAS
99-76-3
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
WIKIPEDIA
METHYLPARABEN
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
DRUG CENTRAL
1766
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
SMS_ID
100000088519
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
MESH
C015358
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
RS_ITEM_NUM
1432005
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
MERCK INDEX
m7450
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY Merck Index
PUBCHEM
7456
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
USAN
Y-26
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
DRUG BANK
DB14212
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
EVMPD
SUB12154MIG
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY Increased Histamine Release [PE]
ChEMBL
CHEMBL325372
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METHYLPARABEN
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
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 Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
NSC
406127
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID4022529
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
HSDB
1184
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
DAILYMED
A2I8C7HI9T
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
202-785-7
Created by admin on Fri Dec 15 15:22:50 UTC 2023 , Edited by admin on Fri Dec 15 15:22:50 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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
ACTIVE MOIETY