Cannabis Compound Database: Showing Compound Card for Ethyl acetate (CDB000693)

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Record Information

Version

1.0

Created at

2020-03-19 00:51:32 UTC

Updated at

2020-12-07 19:07:41 UTC

CannabisDB ID

CDB000693

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Ethyl acetate

Description

Acetic acid-ethyl ester or ethyl 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 is a clear, colorless liquid. It is an ester of acetic acid and ethanol. It is found in essentially all organisms, from bacteria to yeast, to plants to humans. Ethyl acetate has an ethereal, sweet or fruity odor with a sweet, grape or cherry taste. Ethyl acetate is present in confectionery (it is used in artificial fruit essences), perfumes, and fruits. In perfumes, it evaporates quickly, leaving only the scent of the perfume on the skin. Ethyl acetate is found in many fruits such as pineapples, and sweet oranges and in a lower concentration in safflowers. Ethyl acetate has also been found in Cannabis sativa (PMID: 6991645 , 26657499 ). It has also been detected, but not quantified in, several different foods, such as oxheart cabbages, agaves, chervils, peaches (var.), cereal crops, radishes, fruit juices, beer, wine, spirits etc. Ethyl acetate is the most common ester in wine, being the product of acetic acid and ethanol generated during fermentation. The aroma of ethyl acetate is most intense in younger wines and contributes towards the general perception of 'fruitiness' in wine. Industrially, it is used as a solvent in glues, nail polish removers, and in the decaffeination process of tea and coffee. It is widely used as an organic solvent because of its low cost, low toxicity, and agreeable odor. It is also used in paints as an activator or hardener and for colour and inks used to mark fruit or vegetables. 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. Ethyl acetate has very low toxicity, however overexposure to ethyl acetate may cause irritation of the eyes, nose, and throat.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Acetoxyethane	ChEBI
Acetic acid ethyl ester	ChEBI
Acetic acid, ethyl ester	ChEBI
Acetic ester	ChEBI
Acetoxyethane	ChEBI
Acetyl ester	ChEBI
AcOEt	ChEBI
CH3-CO-O-CH3	ChEBI
Essigester	ChEBI
Essigsaeureethylester	ChEBI
Ethyl acetic ester	ChEBI
Ethyl ethanoate	ChEBI
Ethylacetat	ChEBI
Ethylazetat	ChEBI
EtOAc	ChEBI
Vinegar naphtha	ChEBI
Acetate ethyl ester	Generator
Acetate, ethyl ester	Generator
Ethyl ethanoic acid	Generator
Ethyl acetic acid	Generator
Acetic ether	HMDB
Acetic-acid-ethylester	HMDB
Acetidin	HMDB
Dibutylamine	HMDB
Ethyl ester OF acetic acid	HMDB

Chemical Formula

C₄H₈O₂

Average Molecular Weight

88.11

Monoisotopic Molecular Weight

88.0524

IUPAC Name

ethyl acetate

Traditional Name

ethyl acetate

CAS Registry Number

141-78-6

SMILES

CCOC(C)=O

InChI Identifier

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

InChI Key

XEKOWRVHYACXOJ-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

acetate ester (CHEBI:27750 )
a small molecule (ETHYLACETATE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Environmental:

Tobacco smoke

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Environmental role:

Air pollutant

Industrial application:

Laboratory chemical

Food and nutrition:

Flavoring agent

Personal care products:

Perfuming agent

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-83.6 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	80 mg/mL at 25 °C	Not Available
logP	0.73	Not Available

Predicted Properties

Property	Value	Source
logP	0.74	ALOGPS
logP	0.28	ChemAxon
logS	0.14	ALOGPS
pKa (Strongest Basic)	-7	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	2	ChemAxon
Refractivity	22.16 m³·mol⁻¹	ChemAxon
Polarizability	9.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-000dcb6fa74327b50a3b	2014-09-20	View Spectrum
GC-MS	Ethylacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f48a6e770df57144ce33	Spectrum
GC-MS	Ethylacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4fbfd506d2d6d053e57f	Spectrum
GC-MS	Ethylacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4950ee9233400dc5bfe6	Spectrum
GC-MS	Ethylacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-6209b0c76b2469152461	Spectrum
GC-MS	Ethylacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-f48a6e770df57144ce33	Spectrum
GC-MS	Ethylacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4fbfd506d2d6d053e57f	Spectrum
GC-MS	Ethylacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4950ee9233400dc5bfe6	Spectrum
GC-MS	Ethylacetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-6209b0c76b2469152461	Spectrum
Predicted GC-MS	Ethylacetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-9000000000-02a908aacbb859e863a6	Spectrum
Predicted GC-MS	Ethylacetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-f63aacf19cf8128e45b7	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-2f521fd52e7d4d4ca892	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0204-9000000000-ac5b9c25d1bbbc164b29	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-0e2695334ff196319a22	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-e76a0fdf754f6a64b87d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-3ac243b7106e4fd2963c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-d24572f8800bb077f98a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-87bbaed151efac084591	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-87bbaed151efac084591	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-e67f2acdbf749024e916	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0031217

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethyl_acetate

METLIN ID

Not Available

PubChem Compound

8857

PDB ID

EEE

ChEBI ID

27750

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Showing Compound Card for Ethyl acetate (CDB000693)

Structure for CDB000693 (Ethyl acetate)