T3DB: Ethyl benzoate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2014-09-11 05:23:09 UTC

Update Date

2014-12-24 20:27:00 UTC

Accession Number

T3D4935

Identification

Common Name

Ethyl benzoate

Class

Small Molecule

Description

Ethyl benzoate is found in alcoholic beverages. Ethyl benzoate is found in various fruits, e.g. apple, banana, sweet cherry. Also present in milk, butter, wines, black tea, bourbon vanilla and fruit brandies. Ethyl benzoate is a flavouring agent As with many volatile esters, ethyl benzoate has a pleasant odor. It is a component of some artificial fruit flavors. Ethyl benzoate is the ester formed by the condensation of benzoic acid and ethanol. It is a colorless liquid that is almost insoluble in water, but miscible with most organic solvents.

Compound Type

Ester
Ether
Flavouring Agent
Food Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin
Solvent

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
2,4-Dihydroxy-6-methylbenzoate
2,4-Dihydroxy-6-methylbenzoic acid
2-Methoxy-1-phenyl-ethanone
4,6-Dihydroxy-O-toluic acid
Benzoic acid, C12-13-alkyl esters
Benzoic acid, C14-15-alkyl esters
Benzoic acid, C9-11-alkyl esters
Benzoic acid, ethyl ester
Benzoic acid,ethyl ester
Benzoic ether
Benzoyl ethyl ether
Ethyl benzenecarboxylate
Ethyl benzoic acid
Ethylester kyseliny benzoove
FEMA 2422
O-Orsellinic acid
Orsellinate

Chemical Formula

C₉H₁₀O₂

Average Molecular Mass

150.175 g/mol

Monoisotopic Mass

150.068 g/mol

CAS Registry Number

93-89-0

IUPAC Name

ethyl benzoate

Traditional Name

ethyl benzoate

SMILES

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

InChI Identifier

InChI=1S/C9H10O2/c1-2-11-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3

InChI Key

InChIKey=MTZQAGJQAFMTAQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
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

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-34 °C
Boiling Point	213°C (415.4°F)
Solubility	0.72 mg/mL at 25 °C
LogP	2.64

Predicted Properties

Property	Value	Source
Water Solubility	0.83 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.33	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.83 m³·mol⁻¹	ChemAxon
Polarizability	16.22 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-2900000000-37faa5967536e1c37df1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-5900000000-c9d5dba851f474dd9456	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-5900000000-240d67885345369282f3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-5b05b2c2170f6252ca9a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-1900000000-4dfdb3091a0b0e276d97	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0ab9-2900000000-642cce491cf1fc2d7784	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pdi-7900000000-da9006b983d81f077196	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pdi-8900000000-44a1b5b320f6a221cb8a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-1900000000-f9719df41d062495f650	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-2900000000-37faa5967536e1c37df1	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-5900000000-c9d5dba851f474dd9456	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-5900000000-240d67885345369282f3	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-6900000000-5b05b2c2170f6252ca9a	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-1900000000-4dfdb3091a0b0e276d97	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0ab9-2900000000-642cce491cf1fc2d7784	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pdi-7900000000-da9006b983d81f077196	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pdi-8900000000-44a1b5b320f6a221cb8a	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-1900000000-f9719df41d062495f650	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3900000000-5e6280da53233e98e415	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-86368d5a557887feaf32	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-1900000000-b8ded68691c400a7c3ac	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8900000000-58fb24e660c8d2bff189	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-ddca82f0ff01b64c98d8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f92-3900000000-dab9271d0d827cbe329c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9400000000-36b3029eb6eec5567af5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-20bd5ddcafdc7ff644b8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9400000000-d120db94c385cdc93275	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fc58e0949de9ca4842ff	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-2900000000-345e7e905026a0d866d6	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-5900000000-e1fcea40403e16c81fc0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-8900000000-8279275c91418beaccbe	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-4900000000-b14d01178eaee5ec18d3	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB33967

PubChem Compound ID

7165

ChEMBL ID

Not Available

ChemSpider ID

6897

KEGG ID

C01839

UniProt ID

Not Available

OMIM ID

ChEBI ID

32807

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Ethyl_benzoate

References

Synthesis Reference

Not Available

MSDS

Link

General References

Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Steroid hormone receptor ERR1

General Function:: Zinc ion binding
Specific Function:: Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle.
Gene Name:: ESRRA
Uniprot ID:: P11474
Molecular Weight:: 45509.11 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.687 uM	ATG_ERRa_TRANS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

2. Retinoic acid receptor alpha

General Function:: Zinc ion binding
Specific Function:: Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
Gene Name:: RARA
Uniprot ID:: P10276
Molecular Weight:: 50770.805 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	9.49 uM	ATG_RARa_TRANS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Ethyl benzoate (T3D4935)

Structure for T3D4935: Ethyl benzoate

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References