Benzyl 4-hydroxybenzoate

Structural formula
General
Surname	Benzyl 4-hydroxybenzoate
other names	Benzyl 4-hydroxybenzoate; Benzyl paraben;
Molecular formula	C 14 H 12 O 3
Brief description	white odorless solid
External identifiers / databases
EC number	202-311-9
ECHA InfoCard	100.002.102
PubChem	7180
ChemSpider	6912
DrugBank	DB14176
Wikidata	Q27116155
properties
Molar mass	228.25 g mol −1
Physical state	firmly
Melting point	110-114 ° C
solubility	soluble in ethanol and propylene glycol ; practically insoluble in water;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-302 + 352-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-Hydroxybenzoic acid benzyl ester is a chemical compound from the group of parabens .

Extraction and presentation

The compound can be prepared by esterification of p- hydroxybenzoic acid with benzyl alcohol or by reaction of benzyl chloride with the sodium salt of p- hydroxybenzoic acid.

properties

Benzyl 4-hydroxybenzoate is a white, odorless solid that is soluble in ethanol. The compound can form salts with strong alkalis and is subject to hydrolysis by both acids and alkalis.

use

Benzyl 4-hydroxybenzoate has been used as a preservative for cosmetics since 1943 . It is more effective against fungi and gram-positive bacteria than against gram-negative bacteria. In the EU, the compound may no longer be used in cosmetics.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Data sheet Benzyl 4-hydroxybenzoate, 99% from AlfaAesar, accessed on December 14, 2019 ( PDF )(JavaScript required) .
↑ ^a ^b ^c F.v. Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hager's handbook of pharmaceutical practice substances AD . Springer-Verlag, 2013, ISBN 978-3-642-57995-0 , pp. 441 ( limited preview in Google Book search).
↑ ^a ^b ^c Data sheet Benzyl 4-hydroxybenzoate, 99% from Sigma-Aldrich , accessed on December 14, 2019 ( PDF ).
↑ ^a ^b ^c ^d Final Report on the Safety Assessment of Benzylparaben , In: Journal of the American College of Toxicology , Volume 5, Number 5, 1986. doi : 10.3109 / 10915818609141913 (currently unavailable) .
↑ Parabens in cosmetics: EU tightened the rules for parabens in 2015: Parabens in cosmetics: EU tightened the rules for parabens in 2015 , accessed on December 14, 2019.

[Alfa-1] ↑ ^a ^b ^c ^d ^e ^f Data sheet Benzyl 4-hydroxybenzoate, 99% from AlfaAesar, accessed on December 14, 2019 ( PDF )(JavaScript required) .

[F.v._Bruchhausen,_S._Ebel,_A.W._Frahm,_E._Hackenthal-2] F.v. Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hager's handbook of pharmaceutical practice substances AD . Springer-Verlag, 2013, ISBN 978-3-642-57995-0 , pp. 441 ( limited preview in Google Book search).

[Sigma-3] Data sheet Benzyl 4-hydroxybenzoate, 99% from Sigma-Aldrich , accessed on December 14, 2019 ( PDF ).

[Journal-4] Final Report on the Safety Assessment of Benzylparaben , In: Journal of the American College of Toxicology , Volume 5, Number 5, 1986. doi : 10.3109 / 10915818609141913 (currently unavailable) .

[wiwo.de-5] Parabens in cosmetics: EU tightened the rules for parabens in 2015: Parabens in cosmetics: EU tightened the rules for parabens in 2015 , accessed on December 14, 2019.