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Showing NP-Card for Ethyl acetate (NP0000932)

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Record Information
Version2.0
Created at2012-09-11 17:41:40 UTC
Updated at2022-01-12 20:56:18 UTC
NP-MRD IDNP0000932
Secondary Accession NumbersNone
Natural Product 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
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0000932 (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 NP0000932 (Ethyl acetate)

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3D SDF for NP0000932 (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>
NP0000932

> <DATABASE_NAME>
NP-MRD

> <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 NP0000932 (Ethyl acetate)
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PDB for NP0000932 (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 NP0000932 (Ethyl acetate)
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SMILES for NP0000932 (Ethyl acetate)
CCOC(C)=O
Download
INCHI for NP0000932 (Ethyl acetate)
InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3
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View in JSmol
Synonyms
ValueSource
1-AcetoxyethaneChEBI
Acetic acid ethyl esterChEBI
Acetic acid, ethyl esterChEBI
Acetic esterChEBI
AcetoxyethaneChEBI
Acetyl esterChEBI
AcOEtChEBI
CH3-CO-O-CH3ChEBI
EssigesterChEBI
EssigsaeureethylesterChEBI
Ethyl acetic esterChEBI
Ethyl ethanoateChEBI
EthylacetatChEBI
EthylazetatChEBI
EtOAcChEBI
Vinegar naphthaChEBI
Acetate ethyl esterGenerator
Acetate, ethyl esterGenerator
Ethyl ethanoic acidGenerator
Ethyl acetic acidGenerator
Acetic etherHMDB
Acetic-acid-ethylesterHMDB
AcetidinHMDB
DibutylamineHMDB
Ethyl ester OF acetic acidHMDB
Chemical FormulaC4H8O2
Average Mass88.1051 Da
Monoisotopic Mass88.05243 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-12View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acca sellowianaLOTUS Database
Actinidia chinensisLOTUS Database
Agaricus bisporusLOTUS Database
Amorphophallus haematospadixLOTUS Database
Ananas comosusFooDB
Angelica gigasLOTUS Database
Aster scaberLOTUS Database
Averrhoa carambolaLOTUS Database
Basella albaLOTUS Database
Brassica oleracea var. italicaFooDB
    • Charles F. Forney, James P. Mattheis, and Rodney K. Austin. Volatile Compounds Produced by Brocco...
Cannabis sativaCannabisDB
      Not Available
Capsicum annuumFooDB
Carica papaya L.FooDB
Carthamus tinctoriusFooDB
Chamaemelum nobilePlant
Cinnamomum burmanniLOTUS Database
Citrus limoniaLOTUS Database
Citrus sinensisLOTUS Database
Citrus sinensis L.Plant
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Coffea arabicaLOTUS Database
Coffea arabica L.Plant
Croton lechleri Mull.Arg.Plant
Cucumis meloFooDB
Cucumis sativus L.FooDB
    • Ancheng Zhou and Roger F. McFeeters. Volatile Compounds in Cucumbers Fermented in Low-Salt Condit...
Dendrobium superbumPlant
Escherichia coliBacteria
Exospermum stipitatumPlant
Ficus caricaFooDB
Fusarium poaeFungi
Gossypium hirsutumLOTUS Database
Helianthus annuusLOTUS Database
Helianthus annuus L.FooDB
Helicobacter pylori-
Litsea cubebaPlant
Malus pumilaFooDB
Mangifera indicaLOTUS Database
Musa paradisiacaLOTUS Database
Olea europaeaFooDB
Opuntia ficus-indicaLOTUS Database
Peristeria elataLOTUS Database
Plectranthus glabratusLOTUS Database
Plumeria rubraLOTUS Database
Polygala senegaLOTUS Database
Prunus aviumFooDB
    • J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
Prunus persicaFooDB
Psidium guajavaFooDB
Pyrus communisFooDB
    • D. E. Heinz and W. C. Jennings. Volatile components of Bartlett Pear. V. Journal of Food Sci., 19...
Pyrus pyrifoliaFooDB
    • Gary R. Takeoka, Ron G. Buttery, and Robert A. Flath. Volatile Constituents of Asian Pear (Pyrus ...
Rhizophora mangleLOTUS Database
Ribes nigrumFooDB
Rubus idaeusFooDB
Rubus spp.Plant
Rumex thyrsiflorusPlant
Sergia lucensLOTUS Database
Sida galheirensisPlant
Spondias mombinLOTUS Database
Swertia japonicaLOTUS Database
Theobroma cacaoLOTUS Database
Tricholoma matsutakeLOTUS Database
Vaccinium angustifoliumFooDB
    • Lugemwa, F. N., Lwande, W., Bentley, M. D., Mendel, M. J., and Alford, A. R. (1989). Volatiles of...
Vaccinium corymbosumLOTUS Database
Vaccinium macrocarponLOTUS Database
Vasconcellea x heilborniiLOTUS Database
Vitis rotundifoliaLOTUS Database
Vitis viniferaLOTUS Database
Wickerhamomyces anomalusLOTUS Database
Zea maysLOTUS Database
Zea mays L.FooDB
    • Carlos Macku, and Takayuki Shibamoto. Headspace volatile compounds formed from heated corn oil an...
Zingiber miogaLOTUS Database
Zingiber officinaleFooDB
Zygogynum spp.Plant
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-83.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility80 mg/mL at 25 °CNot Available
LogP0.73Not Available
Predicted Properties
PropertyValueSource
Water Solubility123 g/LALOGPS
logP0.74ALOGPS
logP0.28ChemAxon
logS0.14ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.16 m³·mol⁻¹ChemAxon
Polarizability9.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031217  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
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. Zhang S, Guo F, Yan W, Dong W, Zhou J, Zhang W, Xin F, Jiang M: Perspectives for the microbial production of ethyl acetate. Appl Microbiol Biotechnol. 2020 Sep;104(17):7239-7245. doi: 10.1007/s00253-020-10756-z. Epub 2020 Jul 12. [PubMed:32656615  ] 
  7.  (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .