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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:27:16 UTC

Update Date

2023-02-21 17:23:31 UTC

HMDB ID

HMDB0033698

Secondary Accession Numbers

HMDB33698

Metabolite Identification

Common 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acetoin acetic acid	Generator
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
FEMA 3526	HMDB
3-Oxobutan-2-yl acetic acid	Generator

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

IUPAC Name

3-oxobutan-2-yl acetate

Traditional Name

3-oxobutan-2-yl acetate

CAS Registry Number

4906-24-5

SMILES

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

InChI Identifier

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

InChI Key

ZKPTYCJWRHHBOW-UHFFFAOYSA-N

Chemical Taxonomy

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

Cellular substructure

Extracellular (HMDB: HMDB0033698)
Cytoplasm (HMDB: HMDB0033698)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033698)

Source

Exogenous

Food

Food (HMDB: HMDB0033698)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0033698)
Theobroma cacao (HMDB: HMDB0033698)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033698)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033698)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	74.00 to 75.00 °C. @ 20.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	0.680 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.472	31661259
DarkChem	[M-H]-	123.062	31661259
DeepCCS	[M+H]+	128.276	30932474
DeepCCS	[M-H]-	126.029	30932474
DeepCCS	[M-2H]-	162.36	30932474
DeepCCS	[M+Na]+	136.956	30932474
AllCCS	[M+H]+	131.0	32859911
AllCCS	[M+H-H2O]+	126.9	32859911
AllCCS	[M+NH4]+	134.8	32859911
AllCCS	[M+Na]+	135.9	32859911
AllCCS	[M-H]-	128.1	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	134.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetoin acetate	CC(OC(C)=O)C(C)=O	1271.5	Standard polar	33892256
Acetoin acetate	CC(OC(C)=O)C(C)=O	809.9	Standard non polar	33892256
Acetoin acetate	CC(OC(C)=O)C(C)=O	890.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetoin acetate,1TMS,isomer #1	CC(=O)OC(C)=C(C)O[Si](C)(C)C	1124.3	Semi standard non polar	33892256
Acetoin acetate,1TMS,isomer #1	CC(=O)OC(C)=C(C)O[Si](C)(C)C	1129.5	Standard non polar	33892256
Acetoin acetate,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(C)OC(C)=O	1038.8	Semi standard non polar	33892256
Acetoin acetate,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(C)OC(C)=O	1073.5	Standard non polar	33892256
Acetoin acetate,1TBDMS,isomer #1	CC(=O)OC(C)=C(C)O[Si](C)(C)C(C)(C)C	1324.0	Semi standard non polar	33892256
Acetoin acetate,1TBDMS,isomer #1	CC(=O)OC(C)=C(C)O[Si](C)(C)C(C)(C)C	1341.9	Standard non polar	33892256
Acetoin acetate,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(C)OC(C)=O	1250.0	Semi standard non polar	33892256
Acetoin acetate,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(C)OC(C)=O	1283.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Acetoin acetate EI-B (Non-derivatized)	splash10-0006-9000000000-e7ac49abd7363a6c2ff9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Acetoin acetate EI-B (Non-derivatized)	splash10-0006-9000000000-e7ac49abd7363a6c2ff9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetoin acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-0cb5acd665431e37d1e4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetoin acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

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

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011808

KNApSAcK ID

Not Available

Chemspider ID

454676

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

521246

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036691

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Acetoin acetate (HMDB0033698)

MOL for HMDB0033698 (Acetoin acetate)

3D MOL for HMDB0033698 (Acetoin acetate)

3D SDF for HMDB0033698 (Acetoin acetate)

3D-SDF for HMDB0033698 (Acetoin acetate)

PDB for HMDB0033698 (Acetoin acetate)

3D PDB for HMDB0033698 (Acetoin acetate)

SMILES for HMDB0033698 (Acetoin acetate)

INCHI for HMDB0033698 (Acetoin acetate)

Structure for HMDB0033698 (Acetoin acetate)

3D Structure for HMDB0033698 (Acetoin acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra