Showing Compound Acetoxyacetone (FDB012876)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:24 UTC

Update date

2019-11-26 03:07:47 UTC

Primary ID

FDB012876

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Acetoxyacetone

Description

Acetoxyacetone 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). Acetoxyacetone is a buttery and fruity tasting compound. Acetoxyacetone has been detected, but not quantified in, pineapples (Ananas comosus). This could make acetoxyacetone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Acetoxyacetone.

CAS Number

592-20-1

Structure

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

Synonyms

Synonym	Source
1-(Acetyloxy)-2-propanone	HMDB
1-Acetoxy-2-propanone	HMDB
1-Acetoxy-propan-2-one	HMDB
1-Acetoxyacetone	HMDB
1-Acetyloxy-propan-2-one	HMDB
1-Hydroxy-2-propanone acetate	HMDB
2-Oxopropyl acetate	HMDB
2-Propanone, 1-hydroxy-, acetate	HMDB
2-Propanone, 1-hydroxy-, acetate (8ci)	HMDB
ACETIC ACID,(2-oxopropyl) ester acetonylacetATE	HMDB
Acetol acetate	HMDB
Acetonyl acetate	HMDB
Acetoxy-2-propanone	HMDB
Acetoxypropanone	HMDB
Acetylmethyl acetate	HMDB
O-Acetylacetol	HMDB
2-Oxopropyl acetic acid	Generator
2-Propanone, 1-(acetyloxy)-	biospider
2-Propanone, 1-hydroxy-, acetate (8CI)	biospider
ACETIC ACID,(2-OXOPROPYL) ESTER ACETONYLACETATE	biospider
acetoxy-2-propanone	biospider
Acetoxyacetone	db_source
O-acetylacetol	biospider

Predicted Properties

Property	Value	Source
Water Solubility	149 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.27	ChemAxon
logS	0.11	ALOGPS
pKa (Strongest Acidic)	17.51	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	27.05 m³·mol⁻¹	ChemAxon
Polarizability	11.36 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

C5H8O3

IUPAC name

2-oxopropyl acetate

InChI Identifier

InChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3

InChI Key

DBERHVIZRVGDFO-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)COC(C)=O

Average Molecular Weight

116.1152

Monoisotopic Molecular Weight

116.047344122

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

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 51.72%; H 6.94%; O 41.34%	DFC
Melting Point	Not Available
Boiling Point	Bp 172°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d1515 1.08	DFC
Refractive Index	n11D 1.4197	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Acetoxyacetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-081dd10fc4cec8f7a8d2	Spectrum
GC-MS	Acetoxyacetone, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-081dd10fc4cec8f7a8d2	Spectrum
Predicted GC-MS	Acetoxyacetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-be74d7212b518aff1241	Spectrum
Predicted GC-MS	Acetoxyacetone, 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	splash10-014i-2900000000-5c4d2eea3d4901362999	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016s-9500000000-f9bd2bd95ded46d57513	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-7dca30a1ecbbc3524dd8	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-df223813d335b54b3c19	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-7900000000-84c27d4b558cd2e8a35f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9000000000-aa982e016b815042bd5e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-9b28085e966959baa29b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-cee02bbbce1163482e92	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-0077b79d645b83018202	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-9600000000-9ce48973ba0bd39c76bd	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9000000000-31a616f5ae0f5db9de35	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9000000000-bc267c34e8d1ebde5036	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

11105

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

11593

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34466

CRC / DFC (Dictionary of Food Compounds) ID

HCS63-R:HMP84-B

EAFUS ID

Not Available

Dr. Duke ID

ACETOXYACETONE

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

rw1053041

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).