Hexyl acetate (YMDB01384)

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Identification

YMDB ID

YMDB01384

Name

Hexyl acetate

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Hexyl acetate, also known as N-hexyl ethanoate or hexyl acetic acid, 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). Based on a literature review a significant number of articles have been published on Hexyl acetate.

Structure

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

Synonyms

1-Hexyl acetate
ACETATE ION
Acetic acid n-hexyl ester
Acetic acid, hexyl ester
acetic acid, ion(1-)
CH3-COO(-)
Cyclohexyl acetate
Ethanoat
ethanoate
Hexyl alcohol, acetate
Hexyl ester of acetic acid
Hexyl ethanoate
Hexylester kyseliny octove
l-Hexyl acetate
MeCO2 anion
Methylamyl acetate
n-Hexyl acetate
n-Hexyl ethanoate
N-Hexyl ethanoic acid
Hexyl acetic acid
1-Octanamine, hydrochloride
Acetate C6
FEMA 2565

CAS number

142-92-7

Weight

Average: 144.2114
Monoisotopic: 144.115029756

InChI Key

AOGQPLXWSUTHQB-UHFFFAOYSA-N

InChI

InChI=1S/C8H16O2/c1-3-4-5-6-7-10-8(2)9/h3-7H2,1-2H3

IUPAC Name

hexyl acetate

Traditional IUPAC Name

hexyl acetate

Chemical Formula

C₈H₁₆O₂

SMILES

CCCCCCOC(C)=O

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:87510 )
Wax monoesters (LMFA07010184 )

Physical Properties

State

Liquid

Charge

Melting point

-80.9 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.511 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.45 g/L	ALOGPS
logP	3.02	ALOGPS
logP	2.14	ChemAxon
logS	-2.5	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	6	ChemAxon
Refractivity	40.49 m³·mol⁻¹	ChemAxon
Polarizability	17.57 Å³	ChemAxon
Number of Rings	0	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

extracellular

Organoleptic Properties

Flavour/Odour	Source
Apple	FDB001267
Banana	FDB001267
Bitter	FDB001267
Fruit	FDB001267
Fruity	FDB001267
Green	FDB001267
Herb	FDB001267
Sweet	FDB001267

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)	splash10-052f-9000000000-a501dc38f24dd902d772	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-8bde2be982cc06c303c6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a5c-9000000000-6b68e54666d458c23e6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-9000000000-d6e7e57e88fb673af069	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-88601f99d038175f4279	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-a501dc38f24dd902d772	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-8bde2be982cc06c303c6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a5c-9000000000-6b68e54666d458c23e6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ab9-9000000000-d6e7e57e88fb673af069	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-88601f99d038175f4279	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-3491fb3e8a6ab76ee998	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-4900000000-28caa8bae540fff6cabf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9200000000-18516c816e1df27baa97	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-1a25a9f1204ec52e74df	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-5900000000-c31f6fce2a7579cc03eb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9300000000-50527105286023147cca	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-898dec7fbf687dff6f20	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-9000000000-14261d9db48ae9874c3a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-baac9328bd41e72b1fb6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-3db04ec4ac853aef0df9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1900000000-2ac8b7ac46df462cdaaa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-3e44aaba3cc3df109037	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9000000000-f72b4cda7606150aa804	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C 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

References

References:

Vianna, E., Ebeler, S. E. (2001). "Monitoring ester formation in grape juice fermentations using solid phase microextraction coupled with gas chromatography-mass spectrometry." J Agric Food Chem 49:589-595.11261997
Verstrepen, K. J., Van Laere, S. D., Vanderhaegen, B. M., Derdelinckx, G., Dufour, J. P., Pretorius, I. S., Winderickx, J., Thevelein, J. M., Delvaux, F. R. (2003). "Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters." Appl Environ Microbiol 69:5228-5237.12957907
Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	87510
HMDB ID	HMDB0029980
Pubchem Compound ID	8908
Kegg ID	Not Available
ChemSpider ID	8568
FOODB ID	FDB001267
Wikipedia	Hexyl_acetate
BioCyc ID	Not Available

Enzymes

Protein Details

1. Alcohol O-acetyltransferase 1

General function:: Involved in alcohol O-acetyltransferase activity
Specific function:: Catalyzes the esterification of isoamyl alcohol and various other alcohols by acetyl-CoA
Gene Name:: ATF1
Uniprot ID:: P40353
Molecular weight:: 61035.5

Reactions

Acetyl-CoA + an alcohol → CoA + an acetyl ester.

Structure for #<Compound:0x9ff5f40c>

Enzymes

Reactions