methylparaben (CHEBI:31835)

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ChEBI Name	methylparaben

ChEBI ID	CHEBI:31835

Definition	A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB2402938, eMolecules:502818, Selleckchem:Levodopa(Sinemet), ZINC000000895199

Download	Molfile XML SDF

Wikipedia	License
l-DOPA, also known as l-3,4-dihydroxyphenylalanine and used medically as levodopa, is made and used as part of the normal biology of some plants and animals, including humans. Humans, as well as a portion of the other animals that utilize l-DOPA, make it via biosynthesis from the amino acid l-tyrosine. l-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. Furthermore, l-DOPA itself mediates neurotrophic factor release by the brain and CNS. In some plant families (of the order Caryophyllales), l-DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called betalains. l-DOPA can be manufactured and in its pure form is sold as a drug with the INNTooltip International Nonproprietary Name levodopa. Trade names include Sinemet, Pharmacopa, Atamet, and Stalevo. As a drug, it is used in the treatment of Parkinson's disease and dopamine-responsive dystonia, as well as restless leg syndrome. l-DOPA has a counterpart with opposite chirality, d-DOPA. As is true for many molecules, the human body produces only one of these isomers (the l-DOPA form). The enantiomeric purity of l-DOPA may be analyzed by determination of the optical rotation or by chiral thin-layer chromatography.
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Formula

C8H8O3

Net Charge

Average Mass

152.14730

Monoisotopic Mass

152.04734

InChI

InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3

InChIKey

LXCFILQKKLGQFO-UHFFFAOYSA-N

SMILES

COC(=O)c1ccc(O)cc1

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. antimicrobial food preservative A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299). antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.

Application(s):	antimicrobial food preservative A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299). neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders.

ChEBI Ontology
Outgoing	methylparaben (CHEBI:31835) has role antifungal agent (CHEBI:35718) methylparaben (CHEBI:31835) has role antimicrobial food preservative (CHEBI:65256) methylparaben (CHEBI:31835) has role neuroprotective agent (CHEBI:63726) methylparaben (CHEBI:31835) has role plant metabolite (CHEBI:76924) methylparaben (CHEBI:31835) is a paraben (CHEBI:85122)

IUPAC Name

methyl 4-hydroxybenzoate

Synonyms	Sources
4-hydroxybenzoic acid methyl ester	ChemIDplus
E 218	ChEBI
E218	ChEBI
FEMA No. 2710	ChemIDplus
INS No. 218	ChEBI
INS number 218	ChEBI
methyl p-hydroxybenzoate	ChemIDplus
methyl paraben	ChemIDplus
Methyl parahydroxybenzoate	KEGG DRUG
p-carbomethoxyphenol	ChemIDplus
p-hydroxybenzoic acid methyl ester	ChemIDplus
p-methoxycarbonylphenol	ChemIDplus
p-Oxybenzoesauremethylester	ChemIDplus

Last Modified

22 February 2017