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Showing metabocard for Ethyl acetate (HMDB0031217)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:41:40 UTC
Update Date2023-02-21 17:20:05 UTC
HMDB IDHMDB0031217
Secondary Accession Numbers
  • HMDB31217
Metabolite Identification
Common NameEthyl acetate
DescriptionEthyl acetate, also known as 1-acetoxyethane or acetic ester, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Ethyl acetate exists in all eukaryotes, ranging from yeast to humans. Ethyl acetate is a sweet, anise, and balsam tasting compound. Ethyl acetate is found, on average, in the highest concentration within a few different foods, such as milk (cow), pineapples, and sweet oranges and in a lower concentration in safflowers. Ethyl acetate has also been detected, but not quantified, in several different foods, such as alcoholic beverages, oxheart cabbages, agaves, chervils, ryes, and peach. It is used in artificial fruit essences. In the field of entomology, ethyl acetate is an effective asphyxiant for use in insect collecting and study. Because it is not hygroscopic, ethyl acetate also keeps the insect soft enough to allow proper mounting suitable for a collection. In a killing jar charged with ethyl acetate, the vapors will kill the collected (usually adult) insect quickly without destroying it. In organic and in natural products chemistry ethyl acetate is often used as a solvent for reactions or extractions. Ethyl acetate is a potentially toxic compound. Ethyl acetate, with regard to humans, has been found to be associated with several diseases such as perillyl alcohol administration for cancer treatment, crohn's disease, nonalcoholic fatty liver disease, and pervasive developmental disorder not otherwise specified; ethyl acetate has also been linked to the inborn metabolic disorder celiac disease.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031217 (Ethyl acetate)

  Mrv1652303202019022D          

  6  5  0  0  0  0            999 V2000
  -10.0179    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3034    4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5889    4.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8744    4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1600    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3034    5.3036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  2  0  0  0  0
M  END
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3D MOL for HMDB0031217 (Ethyl acetate)

HMDB0031217
     RDKit          3D
Ethyl acetate
 14 13  0  0  0  0  0  0  0  0999 V2000
   -1.8559    0.6021    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2588   -0.7619    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1228   -0.6037    0.5704 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -0.0635   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049    0.0714   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4924    0.2873   -1.4566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616    0.5363   -0.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745    1.3826   -0.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4962    0.8962    0.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625   -1.4682   -0.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871   -1.1771    1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9893   -0.8262   -0.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703    0.9312   -0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428    0.1936    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  5 12  1  0
  5 13  1  0
  5 14  1  0
M  END
Download

3D SDF for HMDB0031217 (Ethyl acetate)

  Mrv1652303202019022D          

  6  5  0  0  0  0            999 V2000
  -10.0179    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3034    4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5889    4.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8744    4.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1600    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3034    5.3036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031217

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3

> <INCHI_KEY>
XEKOWRVHYACXOJ-UHFFFAOYSA-N

> <FORMULA>
C4H8O2

> <MOLECULAR_WEIGHT>
88.1051

> <EXACT_MASS>
88.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.282047002265692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl acetate

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
0.2793562963333335

> <ALOGPS_LOGS>
0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.993208384115184

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
22.1614

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031217 (Ethyl acetate)

HMDB0031217
     RDKit          3D
Ethyl acetate
 14 13  0  0  0  0  0  0  0  0999 V2000
   -1.8559    0.6021    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2588   -0.7619    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1228   -0.6037    0.5704 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -0.0635   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049    0.0714   -0.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4924    0.2873   -1.4566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616    0.5363   -0.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745    1.3826   -0.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4962    0.8962    0.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625   -1.4682   -0.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871   -1.1771    1.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9893   -0.8262   -0.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703    0.9312   -0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428    0.1936    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  5 12  1  0
  5 13  1  0
  5 14  1  0
M  END
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PDB for HMDB0031217 (Ethyl acetate)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0     -18.700   7.590   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.366   8.360   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -16.033   7.590   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0     -14.699   8.360   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.365   7.590   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0     -17.366   9.900   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for HMDB0031217 (Ethyl acetate)

COMPND    HMDB0031217
HETATM    1  C1  UNL     1      -1.856   0.602   0.041  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.259  -0.762   0.320  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.123  -0.604   0.570  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.974  -0.064  -0.368  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.405   0.071  -0.037  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.492   0.287  -1.457  1.00  0.00           O  
HETATM    7  H1  UNL     1      -2.562   0.536  -0.820  1.00  0.00           H  
HETATM    8  H2  UNL     1      -1.074   1.383  -0.112  1.00  0.00           H  
HETATM    9  H3  UNL     1      -2.496   0.896   0.912  1.00  0.00           H  
HETATM   10  H4  UNL     1      -1.463  -1.468  -0.520  1.00  0.00           H  
HETATM   11  H5  UNL     1      -1.687  -1.177   1.278  1.00  0.00           H  
HETATM   12  H6  UNL     1       2.989  -0.826  -0.338  1.00  0.00           H  
HETATM   13  H7  UNL     1       2.870   0.931  -0.531  1.00  0.00           H  
HETATM   14  H8  UNL     1       2.543   0.194   1.060  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3   10   11
CONECT    3    4
CONECT    4    5    6    6
CONECT    5   12   13   14
END
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SMILES for HMDB0031217 (Ethyl acetate)

CCOC(C)=O
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INCHI for HMDB0031217 (Ethyl acetate)

InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Nameethyl acetate
Traditional Nameethyl acetate
CAS Registry Number141-78-6
SMILES
CCOC(C)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
InChI KeyXEKOWRVHYACXOJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationEnvironmental roleBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-83.6 °CNot Available
Boiling Point76.50 to 77.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility80 mg/mL at 25 °CNot Available
LogP0.73Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
  2. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
  3. De Angelis M, Vannini L, Di Cagno R, Cavallo N, Minervini F, Francavilla R, Ercolini D, Gobbetti M: Salivary and fecal microbiota and metabolome of celiac children under gluten-free diet. Int J Food Microbiol. 2016 Dec 19;239:125-132. doi: 10.1016/j.ijfoodmicro.2016.07.025. Epub 2016 Jul 19. [PubMed:27452636 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003240
KNApSAcK IDC00001308
Chemspider ID8525
KEGG Compound IDC00849
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl_acetate
METLIN IDNot Available
PubChem Compound8857
PDB IDEEE
ChEBI ID27750
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004691
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Li DW, Hyun JE, Jeong CS, Kim YS, Lee EB: Antiinflammatory activity of alpha-hederin methyl ester from the alkaline hydrolysate of the butanol fraction of Kalopanax pictus bark extract. Biol Pharm Bull. 2003 Apr;26(4):429-33. [PubMed:12673020 ]
  2. Buzzini P, Pieroni A: Antimicrobial activity of extracts of Clematis vitalba towards pathogenic yeast and yeast-like microorganisms. Fitoterapia. 2003 Jun;74(4):397-400. [PubMed:12781815 ]
  3. Nascimento MV, Galdino PM, Florentino IF, Sampaio BL, Vanderlinde FA, de Paula JR, Costa EA: Antinociceptive effect of Lafoensia pacari A. St.-Hil. independent of anti-inflammatory activity of ellagic acid. J Nat Med. 2011 Jul;65(3-4):448-54. doi: 10.1007/s11418-011-0517-y. Epub 2011 Feb 22. [PubMed:21340514 ]
  4. Panovska TK, Kulevanova S, Gjorgoski I, Bogdanova M, Petrushevska G: Hepatoprotective effect of the ethyl acetate extract of Teucrium polium L. against carbontetrachloride-induced hepatic injury in rats. Acta Pharm. 2007 Jun;57(2):241-8. [PubMed:17507320 ]
  5. Kim TH, Bae JS: Ecklonia cava extracts inhibit lipopolysaccharide induced inflammatory responses in human endothelial cells. Food Chem Toxicol. 2010 Jun;48(6):1682-7. doi: 10.1016/j.fct.2010.03.045. Epub 2010 Apr 2. [PubMed:20363280 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .