Showing Compound Acetoin acetate (FDB011808)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:50 UTC

Update date

2019-11-26 03:05:28 UTC

Primary ID

FDB011808

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Acetoin acetate

Description

Acetoin acetate belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). Acetoin acetate is a sweet, buttery, and creamy tasting compound. Acetoin acetate has been detected, but not quantified in, several different foods, such as alcoholic beverages, cocoa and cocoa products, cocoa beans (Theobroma cacao), and fruits. This could make acetoin acetate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Acetoin acetate.

CAS Number

4906-24-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-Acetoxy-3-butanone	HMDB
2-Butanon-3-ol, acetate	HMDB
2-Ketobutan-3-yl acetate	HMDB
3-(Acetyloxy)-2-butanone	HMDB
3-Acetoxy-2-butanone	HMDB
3-oxo-2-Butyl acetate	HMDB
3-Oxobutan-2-yl acetic acid	Generator
Acetoin acetic acid	Generator
FEMA 3526	HMDB

Showing 1 to 9 of 9 entries

Predicted Properties

Property	Value	Source
Water Solubility	58.7 g/L	ALOGPS
logP	0.19	ALOGPS
logP	0.3	ChemAxon
logS	-0.35	ALOGPS
pKa (Strongest Acidic)	17.63	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	31.54 m³·mol⁻¹	ChemAxon
Polarizability	13.02 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H10O3

IUPAC name

3-oxobutan-2-yl acetate

InChI Identifier

InChI=1S/C6H10O3/c1-4(7)5(2)9-6(3)8/h5H,1-3H3

InChI Key

ZKPTYCJWRHHBOW-UHFFFAOYSA-N

Isomeric SMILES

CC(OC(C)=O)C(C)=O

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

Classification

Description

Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-acyloxy ketones

Alternative Parents

Substituents

Alpha-acyloxy ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Theobroma cacao

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp 169-173°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 55.37%; H 7.74%; O 36.88%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Acetoin acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-e7ac49abd7363a6c2ff9	Spectrum
GC-MS	Acetoin acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-e7ac49abd7363a6c2ff9	Spectrum
Predicted GC-MS	Acetoin acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-0cb5acd665431e37d1e4	Spectrum
Predicted GC-MS	Acetoin acetate, 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	splash10-01x9-9700000000-44a3d578b4cfb8344142	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h99-9100000000-af1bacb02f3c148ba22d	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-9000000000-f01d31d37b643621ca6f	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0570-9600000000-ffb0d80cd438e8a3088b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9100000000-76ac94891263941d8d61	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-915d80e05a156301a8f6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-9000000000-2d05de6fc16fb0aaba59	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-b62977f32ee5dcfb3a16	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9e2bab7e30574fd7ec65	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-5af9adb4c1ef6f1d7a60	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-cf7748127e0cc9a22d28	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-492cd06c14ee7be1db8f	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

454676

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

521246

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33698

CRC / DFC (Dictionary of Food Compounds) ID

GZG79-M:GZJ85-A

EAFUS ID

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1036691

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
buttery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
creamy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pungent	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.