Ethyl-4-hydroxybenzoate (YMDB01688)

Identification

YMDB ID

YMDB01688

Name

Ethyl-4-hydroxybenzoate

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Ethylparaben, also known as e-214 or aseptin a, belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. Based on a literature review a significant number of articles have been published on Ethylparaben.

Structure

MOL SDF PDB SMILES InChI

Synonyms

4-(Ethoxycarbonyl)phenol
4-Carbethoxyphenol
4-Hydroxybenzoic acid, ethyl ester
Aseptin a
Aseptine a
Aseptoform E
Benzoic acid, 4-hydroxy-, ethyl ester
Benzoic acid, p-hydroxy-, ethyl ester
Bonomold OE
Easeptol
Ester etylowykwasu p-hydroksybenzoesowego
Ethyl 4-hydroxybenzoate
Ethyl Butex
Ethyl p-hydroxybenzoate
Ethyl p-oxybenzoate
Ethyl para-hydroxybenzoate
Ethyl paraben
Ethyl parasept
Ethylester kyseliny p-hydroxybenzoove
Ethylparaben
Keloform
Mycocten
Napagin A
Nipagin A
Nipagina A
Nipazin A
p-Carbethoxyphenol
p-Hydroxybenzoate ethyl ester
p-Hydroxybenzoic acid ethyl ester
p-Hydroxybenzoic acid, ethyl ester
p-Hydroxybenzoic ethyl ester
p-Oxybenzoesaeureaethylester
Para-hydroxybenzoic acid ethyl ester
Sobrol A
Solbrol A
Tegosept E
4-Hydroxybenzoic acid ethyl ester
e-214
e214
Ethyl parahydroxybenzoate
4-Hydroxybenzoate ethyl ester
Ethyl p-hydroxybenzoic acid
Ethyl parahydroxybenzoic acid
Ethyl chemosept
Ethyl-4-hydroxybenzoate
Ethyl-p-hydroxybenzoate
Ethylparaben, inn, usan
Mekkings e
Ethyl hydroxybenzoic acid

CAS number

120-47-8

Weight

Average: 166.1739
Monoisotopic: 166.062994186

InChI Key

NUVBSKCKDOMJSU-UHFFFAOYSA-N

InChI

InChI=1S/C9H10O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3

IUPAC Name

ethyl 4-hydroxybenzoate

Traditional IUPAC Name

ethylparaben

Chemical Formula

C₉H₁₀O₃

SMILES

CCOC(=O)C1=CC=C(O)C=C1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:86616 )

Physical Properties

State

Solid

Charge

Melting point

117 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.885 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]	PhysProp
LogP	2.47 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	2.49 g/L	ALOGPS
logP	2.76	ALOGPS
logP	2.03	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.81 m³·mol⁻¹	ChemAxon
Polarizability	17.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Mild	FDB020182
Phenolic	FDB020182

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-2900000000-489a671c1deb7c34c07b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00y0-3900000000-c1ca8c4a3e26621c8959	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-6900000000-6a0e4e400b0c9ced0ae9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-2900000000-489a671c1deb7c34c07b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00y0-3900000000-c1ca8c4a3e26621c8959	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-6900000000-6a0e4e400b0c9ced0ae9	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3900000000-7c9963244828bfd6dc09	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0006-2910000000-520330358fe2a32ba595	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0900000000-026024910ee96b0887cf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0900000000-9a9b6e693b1424978dce	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0900000000-2e5dbef1d0fad386068f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0900000000-59447059cdee325cfc8a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014r-0900000000-3eb9e5cfcd05f833bb11	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0900000000-026024910ee96b0887cf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0900000000-9a9b6e693b1424978dce	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0900000000-2e5dbef1d0fad386068f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0900000000-59447059cdee325cfc8a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0072-7900000000-2570ac4f0cac9ddf3e64	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00dj-9800000000-568849783aecc83f7c2e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-5e9f881d152f5b3fa0be	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-caa573c6bab6939082d2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0072-7900000000-2570ac4f0cac9ddf3e64	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00dj-9800000000-568849783aecc83f7c2e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-5e9f881d152f5b3fa0be	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-caa573c6bab6939082d2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014r-0900000000-f8e625a2de6fb1fb4c1c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-0072-7900000000-2570ac4f0cac9ddf3e64	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-5edabab1a6ee50991a47	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-1900000000-608dc4a8887a0295554f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9400000000-ba68420db383fea306c5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1900000000-3e62aae4552f1c87f2a9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3900000000-8afb30175a5535ef38ed	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9400000000-48796a631e1530fccfe2	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-00di-4900000000-890e881678f1ceddd23e	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	31575
HMDB ID	HMDB0032573
Pubchem Compound ID	8434
Kegg ID	Not Available
ChemSpider ID	13846749
FOODB ID	FDB020182
Wikipedia	Ethylparaben
BioCyc ID	Not Available

Structure for #<Compound:0xaa428efc>