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Sigma-Aldrich

Benzyl 4-hydroxybenzoate

99%

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Synonym(s):
4-Hydroxybenzoic acid benzyl ester, Benzyl paraben
Linear Formula:
HOC6H4CO2CH2C6H5
CAS Number:
94-18-8
Molecular Weight:
228.24
Beilstein:
2115995
EC Number:
202-311-9
MDL number:
MFCD00016471
PubChem Substance ID:
24863764
NACRES:
NA.22

Quality Level

200

Assay

99%

form

powder

mp

109-112 °C (lit.)

solubility

ethanol: soluble 25 mg/mL, clear, colorless

SMILES string

Oc1ccc(cc1)C(=O)OCc2ccccc2

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

InChI key

MOZDKDIOPSPTBH-UHFFFAOYSA-N

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General description

Benzyl 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.

Application

Benzyl 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.

Disclaimer

The product is not intended for use as a biocide under global biocide regulations, including but not limited to US EPA′s Federal Insecticide Fungicide and Rodenticide Act, European Biocidal Products Regulation, Canada’s Pest Management Regulatory Agency, Turkey’s Biocidal Products Regulation, Korea’s Consumer Chemical Products and Biocide Safety Management Act (K-BPR) and others.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Contact allergy to benzyl alcohol and benzyl paraben.
G Würbach et al.
Contact dermatitis, 28(3), 187-188 (1993-03-01)
T Menné et al.
Contact dermatitis, 19(3), 189-191 (1988-09-01)
Paraben esters are the most widely used preservatives in cosmetics and topical medicaments. Their sensitization potential is low, based on both experimental and human experience. A paraben mixture is included in the ICDRG standard series, and in patch test studies
Jing G, et al.
Petrochemical Technology, 33(1), 54-56 (2004)
P D Darbre et al.
Journal of applied toxicology : JAT, 23(1), 43-51 (2003-01-09)
Previous work has demonstrated that the alkyl esters of p-hydroxybenzoic acid (parabens) possess oestrogenic activity, which increases with length of alkyl chain from methylparaben to n-butylparaben and with branching in the alkyl chain from n-butylparaben to isobutylparaben. This study reports
S C Rastogi et al.
Contact dermatitis, 32(1), 28-30 (1995-01-01)
The contents of methyl-, ethyl-, propyl-, butyl- and benzylparaben in 215 cosmetic products have been determined to elucidate the concentration and frequency of use of these parabens in cosmetic products, and to monitor whether the products complied with the Danish
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