Isobutyl 4-hydroxybenzoate

Structural formula
General
Surname	Isobutyl 4-hydroxybenzoate
other names	Isobutyl 4-hydroxybenzoate; Isobutyl paraben;
Molecular formula	C 11 H 14 O 3
Brief description	white solid
External identifiers / databases
EC number	224-208-8
ECHA InfoCard	100.022.008
PubChem	20240
ChemSpider	19066
Wikidata	Q27237117
properties
Molar mass	194.23 g mol −1
Physical state	firmly
Melting point	74-78 ° C
solubility	practically insoluble in water
safety instructions
H and P phrases	H: 315-319-411
	P: 305 + 351 + 338
Toxicological data	2600 mg kg −1 ( LD 50 , mouse , sc )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-Hydroxybenzoic acid isobutyl ester is a chemical compound from the group of parabens . It is the ester of isobutyl alcohol and 4-hydroxybenzoic acid .

Extraction and presentation

The compound can be obtained by reacting 4-hydroxybenzoic acid and 2-methylpropan-1-ol .

properties

Isobutyl 4-hydroxybenzoate is a white solid that is practically insoluble in water.

use

4-Hydroxybenzoic acid isobutyl ester can be used for the synthesis of lipophilic alkyl parabens and as an additive for food and flavorings. It is also widely used as a preservative in cosmetic products. In the EU, use has not been permitted in food or cosmetics since 2014. The reason is the estrogenic effect.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet isobutyl 4-hydroxybenzoate, 98% from AlfaAesar, accessed on December 14, 2019 ( PDF )(JavaScript required) .
↑ ^a ^b ^c data sheet isobutyl 4-hydroxybenzoate, 97% from Sigma-Aldrich , accessed on December 14, 2019 ( PDF ).
↑ ^a ^b Michael Ash: Handbook of Preservatives . Synapse Info Resources, 2004, ISBN 978-1-890595-66-1 , pp. 424 ( limited preview in Google Book search).
↑ ChemSink: Synthesis of isobutyl 4-hydroxybenzoate via Ester Formation from Carboxylic Acid , accessed on December 14, 2019.
^ Federal Environmental Specimen Bank : isobutyl paraben , accessed on December 14, 2019.

↑ PD Darbre, JR Byford, LE Shaw, RA Horton, GS Pope, MJ Sauer: Oestrogenic activity of isobutylparaben in vitro and in vivo. In: J. Appl. Toxicol. 22, pp. 219-226, PMID 12210538 .

[Alfa-1] ↑ ^a ^b ^c ^d ^e data sheet isobutyl 4-hydroxybenzoate, 98% from AlfaAesar, accessed on December 14, 2019 ( PDF )(JavaScript required) .

[Sigma-2] ta sheet isobutyl 4-hydroxybenzoate, 97% from Sigma-Aldrich , accessed on December 14, 2019 ( PDF ).

[Michael_Ash-3] Michael Ash: Handbook of Preservatives . Synapse Info Resources, 2004, ISBN 978-1-890595-66-1 , pp. 424 ( limited preview in Google Book search).

[chemsink.com-4] ChemSink: Synthesis of isobutyl 4-hydroxybenzoate via Ester Formation from Carboxylic Acid , accessed on December 14, 2019.

[umweltprobenbank.de-5] Federal Environmental Specimen Bank : isobutyl paraben , accessed on December 14, 2019.

[PMID12210538-6] PD Darbre, JR Byford, LE Shaw, RA Horton, GS Pope, MJ Sauer: Oestrogenic activity of isobutylparaben in vitro and in vivo. In: J. Appl. Toxicol. 22, pp. 219-226, PMID 12210538 .