Sodium 4- (methoxycarbonyl) phenate

Structural formula
General
Surname	Sodium 4- (methoxycarbonyl) phenate
other names	4-Hydroxybenzoic acid methyl ester, sodium salt; Sodium [4- (methoxycarbonyl) phenolate]; Sodium methyl p- hydroxybenzoate; Sodium methyl 4-hydroxybenzoate ( Ph.Eur. ); Methyl 4-hydroxybenzoate, sodium salt; Sodium methyl paraben; SODIUM METHYL PARABS ( INCI ) ; E 219;
Molecular formula	C 8 H 7 NaO 3
Brief description	white, almost odorless solid
External identifiers / databases
EC number	225-714-1
ECHA InfoCard	100.023.377
PubChem	23663626
ChemSpider	19863
Wikidata	Q3963920
properties
Molar mass	174.13 g mol −1
Physical state	firmly
density	1.42 g cm −3
solubility	Easily soluble in water (418 g l −1 at 20 ° C); soluble in ethanol; practically insoluble in non-volatile oils; practically insoluble in dichloromethane ;
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 315-318-412
	P: 264-273-280-302 + 352-305 + 351 + 338-310
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sodium 4- (methoxycarbonyl) phenolate ( sodium methyl paraben ) is a chemical compound from the group of substituted phenolates and carboxylic acid esters . It is a paraben derivative , more precisely the sodium salt of methyl paraben .

Extraction and presentation

For the synthesis of sodium 4- (methoxycarbonyl) phenolate, potassium salicylate is heated to 215 to 220 ° C in air or under a carbon dioxide atmosphere. The resulting p-hydroxybenzoic acid is esterified with methanol under sulfuric acid catalysis and converted into the sodium salt with a base such as an alkali hydroxide or phenolate.

properties

Sodium 4- (methoxycarbonyl) phenolate is a flammable, difficult to ignite, crystalline, white, almost odorless solid that is easily soluble in water. It is hygroscopic and decomposes when heated above 313 ° C.

use

Sodium 4- (methoxycarbonyl) phenolate is used to preserve cosmetics and food, and in industry to preserve technical products. In the additive approval regulation it is listed under E 219.

Individual evidence

↑ Entry on SODIUM METHYLPARABEN in the CosIng database of the EU Commission, accessed on December 28, 2019.
↑ ^a ^b ^c ^d ^e ^f ^g Entry on sodium 4- (methoxycarbonyl) phenolate in the GESTIS substance database of the IFA , accessed on December 10, 2019(JavaScript required) .
↑ ^a ^b ^c ^d Franz v. Bruchhausen, Siegfried Ebel, Eberhard Hackenthal, Ulrike Holzgrabe: Hager's Handbook of Pharmaceutical Practice, Volume 5: Substances LZ . Springer-Verlag, 2013, ISBN 978-3-642-58388-9 , pp. 162 ( limited preview in Google Book search).
↑ ^a ^b European Pharmacopoeia, 8th edition, Grundwerk 2014, p. 4256.
↑ Data sheet sodium 4- (methoxycarbonyl) phenolate (PDF) from Merck , accessed December 10, 2019.
↑ Additive Admission Ordinance, Annex 5

[CosIng-1] Entry on SODIUM METHYLPARABEN in the CosIng database of the EU Commission, accessed on December 28, 2019.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on sodium 4- (methoxycarbonyl) phenolate in the GESTIS substance database of the IFA , accessed on December 10, 2019(JavaScript required) .

[Franz_v._Bruchhausen,_Siegfried_Ebel,_Eberhard_Hackenthal,_Ulrike_Holzgrabe-3] Franz v. Bruchhausen, Siegfried Ebel, Eberhard Hackenthal, Ulrike Holzgrabe: Hager's Handbook of Pharmaceutical Practice, Volume 5: Substances LZ . Springer-Verlag, 2013, ISBN 978-3-642-58388-9 , pp. 162 ( limited preview in Google Book search).

[ep80-4] European Pharmacopoeia, 8th edition, Grundwerk 2014, p. 4256.

[Merck-5] Data sheet sodium 4- (methoxycarbonyl) phenolate (PDF) from Merck , accessed December 10, 2019.

[ZZulV-6] Additive Admission Ordinance, Annex 5