CAS 94-18-8 Benzyl 4-Hydroxybenzoate (HCID 7180)

Overview

Benzyl parahydroxybenzoate is a benzoate ester and a benzyl ester.

Names & identifiers

Preferred name: Benzyl 4-Hydroxybenzoate
IUPAC: benzyl 4-hydroxybenzoate
English name: Benzylparaben
Molecular formula: C14H12O3
Molecular weight: 228.24

Names & synonyms

Benzyl 4-hydroxybenzoate94-18-8BenzylparabenBenzyl parabenBenzyl p-hydroxybenzoateNipabenzylBenzyl TegoseptBenzyl parahydroxybenzoatep-Hydroxybenzoic acid benzyl esterBenzoic acid, 4-hydroxy-, phenylmethyl esterPhenylmethyl 4-hydroxybenzoateDTXSID9022526

Show more names

POB-BZBASEPTOLNSC 8080Solbrol ZPARABEN,BUTYLBenzyl parabe

8Y41DYV4VGNSC-8080DTXCID2025264-Hydroxybenzoic acid, benzyl esterRefChem:118993202-311-9ParoseptBenzyl Parasept

Database identifiers

CAS: 94-18-8
PubChem CID: 7180
DTXSID: DTXSID9022526
ChEMBL: CHEMBL447861
ChEBI: CHEBI:34571
UNII: 8Y41DYV4VG
EC Number: 202-311-9
Nikkaji: J61.591I

Properties

Computed structural properties

XLogP: 3.6
Topological polar surface area: 46.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 17
Formal charge: 0
Complexity: 238

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Cosmetics · 2 items

Cosmetic ingredients (Benzylparaben) -> CIR (Cosmetic Ingredient Review)

Antimicrobial

Endocrine DisruptorsPotential endocrine disrupting compound

Collision Cross Section158.5 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID9022526]

Physicochemical properties

Melting point: 109 · 109-112 °C(lit.)
Boiling point: 170 ℃ · 170℃
Density: 1.1799 · 1.1799
vapor pressure: 0 Pa · 0Pa at 25℃
refractive index: 1.5805 · 1.5805
Flash point: 167 ℃ · 167℃
storage temp.: 2 · Inert atmosphere,2-8°C
solubility: 25 mg/mL, · ethanol: soluble25mg/mL, clear, colorless
form: Powder
pka: 8.18 · 8.18±0.15(Predicted)
color: White to Almost white
Water Solubility: 92 mg/L · 92mg/L(25 ºC)
BRN: 2115995 · 2115995
Major Application: environmental
Cosmetics Ingredients Functions: PRESERVATIVEANTIMICROBIAL
Cosmetic Ingredient Review (CIR): Benzylparaben (94-18-8)
InChI: 1S/C14H12O3/c15-13-8-6-12(7-9-13)14(16)17-10-11-4-2-1-3-5-11/h1-9,15H,10H2
InChIKey: MOZDKDIOPSPTBH-UHFFFAOYSA-N
SMILES: Oc1ccc(cc1)C(=O)OCc2ccccc2
LogP: 2.185 at · 2.185 at 25℃
CAS DataBase Reference: 94 · 94-18-8(CAS DataBase Reference)
EWG's Food Scores: 2 · 2-5
FDA UNII: 8 Y41DYV4VG · 8Y41DYV4VG
NIST Chemistry Reference: 4 · Benzyl 4-hydroxybenzoate(94-18-8)
EPA Substance Registry System: 4 · Benzoic acid, 4-hydroxy-, phenylmethyl ester (94-18-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36-37/39
RIDADR: 3077 · 3077
WGK Germany: 3 · 3
RTECS: 2691000 · DH2691000
TSCA: TSCA listed
HazardClass: IRRITANT
PackingGroup: III
HS Code: 29181990 · 29181990
Storage Class: 13 · 13 - Non Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations: Inactive

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.8% (6 of 339) of reports.

Warning

H315 (98.2%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 339 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Benzoic acid, 4-hydroxy-, phenylmethyl ester

Status: Cease Manufacture Update: 04-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17658

Benzoic acid, 4-hydroxy-, phenylmethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Parabens: Environment tier II assessment

Hazard Classes and CategoriesSkin Irrit. 2 (98.2%)

Toxicology

Toxicity Summary · 2 items

The CIR Expert Panel also concluded that the available data are insufficient to support a conclusion of safety for Benzylparaben in cosmetics.

The available data are insufficient to support safety

Safety data

wgk: 3
tsca: TSCA listed
rtecs: DH2691000
ridadr: 3077
hs_code: 29181990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-37/39
hazard_class: IRRITANT
Storage Class: 13 - Non Combustible Solids
packing_group: III
target organs: Respiratory system
Hazard statements: H315-H319-H335
REACH Registrations: Inactive
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

FDA Pharmacological Classification · 6 items

8Y41DYV4VG

BENZYLPARABEN

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

Uses & manufacturing

UsesCIR ingredient: Benzylparaben

Use ClassificationCosmetics -> Antimicrobial

General Manufacturing InformationBenzoic acid, 4-hydroxy-, phenylmethyl ester: ACTIVE

Applications · 4 items

Usespreservative in cosmetics and pharmaceutical preparations

UsesBenzyl 4-hydroxybenzoate may be used as internal standard for the simultaneous analysis of non-steroidal anti-inflammatory drugs in human plasma and urine using microextraction by packed sorbent and HPLC method. It may be employed as internal standard for the HPLC determination of rutin, kaempferol, genistein, formononetin and biochanin A in Ononis spinosu roots.

UsesAn antimicrobial

General DescriptionBenzyl 4-hydroxybenzoate (Paraben, Benzyl Paraben) is an ester of para-hydroxy benzoic acid. It has been added to various cosmetics and personal care products as a preservative. Its quantification in cosmetics has been reported by HPLC methods. Microwave assisted synthesis of benzyl 4-hydroxybenzoate by reaction between (4-hydroxybenzoic) acid and K2CO3 in presence of phase transfer catalyst has been reported. It is an endocrine disrupting chemical (EDC). It is a promising candidate for use in pharmaceutical and personal care products. Its visible-light assisted photosensitized degradation in homogeneous aqueous solution of 4,4′,4′′,4′′′-(porphine-5,10,15,20-tetrayl)tetrakis(benzenesulphonic acid) has been investigated.