isobutyl acetate (YMDB00572)

Identification

YMDB ID

YMDB00572

Name

isobutyl acetate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

2-Methylpropyl acetate, also known as acetate d'isobutyle or essigsaeureisobutylester, 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 very few articles have been published on 2-Methylpropyl acetate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

β-Methylpropyl ethanoate
2-Methyl-1-propanol, acetate
2-Methyl-1-propyl acetate
2-Methylpropyl acetate
2-Methylpropyl ethanoate
Acetate d'isobutyle
Acetic acid, 2-methylpropyl ester
Acetic acid, isobutyl ester
beta-Methylpropyl ethanoate
Essigsaeureisobutylester
i-Butyl acetate
isobutyl acetate
Isobutyl acetate fcc
Isobutyl ethanoate
Isobutylacetat
Isobutylazetat
Isobutylester kyseliny octove
2-Methyl-1-propyl acetic acid
2-Methylpropyl ethanoic acid
Acetic acid d'isobutyle
Acetate, 2-methylpropyl ester
Acetate, isobutyl ester
b-Methylpropyl ethanoate
b-Methylpropyl ethanoic acid
beta-Methylpropyl ethanoic acid
Β-methylpropyl ethanoate
Β-methylpropyl ethanoic acid
I-butyl acetic acid
Isobutyl ethanoic acid
2-Methylpropyl acetic acid
2-Methylpropyl acetate, 9ci
beta -Methylpropyl ethanoate
FEMA 2175
Isobutyl acetate, 8ci
Isobutyl acetic acid
Isobutylacetate

CAS number

110-19-0

Weight

Average: 116.1583
Monoisotopic: 116.083729628

InChI Key

GJRQTCIYDGXPES-UHFFFAOYSA-N

InChI

InChI=1S/C6H12O2/c1-5(2)4-8-6(3)7/h5H,4H2,1-3H3

IUPAC Name

2-methylpropyl acetate

Traditional IUPAC Name

isobutyl acetate

Chemical Formula

C₆H₁₂O₂

SMILES

CC(C)COC(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:50569 )

Physical Properties

State

Liquid

Charge

Melting point

-98.8 °C

Experimental Properties

Property	Value	Reference
Water Solubility	6.3 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	1.78 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	7.71 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.17	ChemAxon
logS	-1.2	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	3	ChemAxon
Refractivity	31.16 m³·mol⁻¹	ChemAxon
Polarizability	13.11 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
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Apple	FDB003275
Banana	FDB003275
Bitter	FDB003275
Ethereal	FDB003275
Fruit	FDB003275
Fruity	FDB003275
Sweet	FDB003275
Tropical	FDB003275

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Acetyl-CoA + isobutanol → isobutyl acetate + Coenzyme A

isobutyl acetate + water → Acetic acid + isobutanol + hydron

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)	splash10-0006-9000000000-f217b5e6b92235a1dd71	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-25cc25b3ba0651c0ba45	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-47909851abe2172156c6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-32ed7cd25a7cd585255a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-497069f05d541433b66e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-49585f528507ace5b393	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014i-1900000000-bb28c34b11812942773d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-ef6ece5c35a5dd154ad5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-f217b5e6b92235a1dd71	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-25cc25b3ba0651c0ba45	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-47909851abe2172156c6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-32ed7cd25a7cd585255a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-497069f05d541433b66e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-49585f528507ace5b393	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014i-1900000000-bb28c34b11812942773d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-ef6ece5c35a5dd154ad5	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-df6cefc23abcd1e80417	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	splash10-066r-9700000000-a748f357862b1b998434	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-edefa0d353dff24eb16b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f40694d799cd17a2cec4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-7900000000-6534ebe4a3a380503d44	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-9200000000-fd7dc8a883948134a340	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-e0b525315cc093f0fd0c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-6eb8c377976b6fa47cd1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-75ca9d459a88c83adee2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4531d1e7d918cb3881e5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0600-9200000000-9d3e1ac44fb825b68474	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	splash10-0a4l-9000000000-e19c8390ed8f55d45a2d	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
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Fukuda, K., Kiyokawa, Y., Yanagiuchi, T., Wakai, Y., Kitamoto, K., Inoue, Y., Kimura, A. (2000). "Purification and characterization of isoamyl acetate-hydrolyzing esterase encoded by the IAH1 gene of Saccharomyces cerevisiae from a recombinant Escherichia coli." Appl Microbiol Biotechnol 53:596-600.10855721
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

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	50569
HMDB ID	HMDB0031246
Pubchem Compound ID	8038
Kegg ID	Not Available
ChemSpider ID	7747
FOODB ID	FDB003275
Wikipedia	Isobutyl_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.

Protein Details

2. Alcohol O-acetyltransferase 2

General function:: Involved in alcohol O-acetyltransferase activity
Specific function:: Acetyl-CoA + an alcohol = CoA + an acetyl ester
Gene Name:: ATF2
Uniprot ID:: P53296
Molecular weight:: 61897.5

Reactions

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

Protein Details

3. Isoamyl acetate-hydrolyzing esterase

General function:: Involved in hydrolase activity
Specific function:: Plays a crucial role in the hydrolysis of isoamyl acetate in sake mash
Gene Name:: IAH1
Uniprot ID:: P41734
Molecular weight:: 27346.0

Reactions

Structure for #<Compound:0xad1f7324>

Enzymes

Reactions

Reactions

Reactions