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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:44:38 UTC

Update Date

2023-02-21 17:21:07 UTC

HMDB ID

HMDB0031648

Secondary Accession Numbers

HMDB31648

Metabolite Identification

Common Name

2,4-Pentanedione

Description

2,4-Pentanedione, also known as 2,4-dioxopentane or ACAC, belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom. Thus, 2,4-pentanedione is considered to be an oxygenated hydrocarbon. 2,4-Pentanedione has been detected, but not quantified in, a few different foods, such as blackberries (Rubus), evergreen blackberries (Rubus laciniatus), and papayas (Carica papaya). This could make 2,4-pentanedione a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,4-Pentanedione.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4-Dioxopentane	ChEBI
2,4-Pentadione	ChEBI
ACAC	ChEBI
Acetoacetone	ChEBI
Acetyl 2-propanone	ChEBI
CH3-CO-CH2-CO-CH3	ChEBI
Hacac	ChEBI
Pentan-2,4-dione	ChEBI
Acetylacetone	Kegg
2,4-Pentandione	HMDB
4-Hydroxy-3-penten-2-one	HMDB
Acetyl acetone	HMDB
Acetyl-2-propanone	HMDB
Acetyl-acetone	HMDB
Benzil-related compound, 44	HMDB
CH3COCH2COCH3	HMDB
Diacetylmethane	HMDB
Pentane-2,4-dione	HMDB
Pentanedione	HMDB
Pentanedione-2,4	HMDB
Indium-111-acetylacetone	MeSH, HMDB
2,4-Pentanedione	ChEBI

Chemical Formula

C₅H₈O₂

Average Molecular Weight

100.1158

Monoisotopic Molecular Weight

100.0524295

IUPAC Name

pentane-2,4-dione

Traditional Name

acetylacetone

CAS Registry Number

123-54-6

SMILES

CC(=O)CC(C)=O

InChI Identifier

InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3

InChI Key

YRKCREAYFQTBPV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Beta-diketones

Alternative Parents

Substituents

1,3-diketone
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

beta-diketone (CHEBI:14750 )
Oxygenated hydrocarbons (LMFA12000075 )
a small molecule (CPD-8879 )

Ontology

Not Available

Feces (PMID: 26416813)

Cellular substructure

Extracellular (HMDB: HMDB0031648)
Cytoplasm (HMDB: HMDB0031648)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031648)

Source

Endogenous

Endogenous (HMDB: HMDB0031648)

Plant

Plant (HMDB: HMDB0031648)

Exogenous

Food

Food (HMDB: HMDB0031648)

Fruit

Tropical fruit

Papaya (FooDB: FOOD00041)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Exogenous (HMDB: HMDB0031648)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-23 °C	Not Available
Boiling Point	136.00 to 138.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	166 mg/mL at 20 °C	Not Available
LogP	0.40	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	140 g/L	ALOGPS
logP	-0.2	ALOGPS
logP	0.33	ChemAxon
logS	0.15	ALOGPS
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	26.09 m³·mol⁻¹	ChemAxon
Polarizability	10.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	124.899	30932474
DeepCCS	[M-H]-	122.995	30932474
DeepCCS	[M-2H]-	158.717	30932474
DeepCCS	[M+Na]+	133.268	30932474
AllCCS	[M+H]+	123.7	32859911
AllCCS	[M+H-H2O]+	119.3	32859911
AllCCS	[M+NH4]+	127.8	32859911
AllCCS	[M+Na]+	129.0	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	128.7	32859911
AllCCS	[M+HCOO]-	132.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,4-Pentanedione	CC(=O)CC(C)=O	1179.2	Standard polar	33892256
2,4-Pentanedione	CC(=O)CC(C)=O	776.8	Standard non polar	33892256
2,4-Pentanedione	CC(=O)CC(C)=O	792.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,4-Pentanedione,1TMS,isomer #1	CC(=O)C=C(C)O[Si](C)(C)C	1050.1	Semi standard non polar	33892256
2,4-Pentanedione,1TMS,isomer #1	CC(=O)C=C(C)O[Si](C)(C)C	1003.6	Standard non polar	33892256
2,4-Pentanedione,1TMS,isomer #2	C=C(CC(C)=O)O[Si](C)(C)C	1026.4	Semi standard non polar	33892256
2,4-Pentanedione,1TMS,isomer #2	C=C(CC(C)=O)O[Si](C)(C)C	1008.1	Standard non polar	33892256
2,4-Pentanedione,2TMS,isomer #1	C=C(C=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1198.5	Semi standard non polar	33892256
2,4-Pentanedione,2TMS,isomer #1	C=C(C=C(C)O[Si](C)(C)C)O[Si](C)(C)C	1162.2	Standard non polar	33892256
2,4-Pentanedione,2TMS,isomer #2	C=C(CC(=C)O[Si](C)(C)C)O[Si](C)(C)C	1165.0	Semi standard non polar	33892256
2,4-Pentanedione,2TMS,isomer #2	C=C(CC(=C)O[Si](C)(C)C)O[Si](C)(C)C	1206.0	Standard non polar	33892256
2,4-Pentanedione,1TBDMS,isomer #1	CC(=O)C=C(C)O[Si](C)(C)C(C)(C)C	1268.7	Semi standard non polar	33892256
2,4-Pentanedione,1TBDMS,isomer #1	CC(=O)C=C(C)O[Si](C)(C)C(C)(C)C	1208.3	Standard non polar	33892256
2,4-Pentanedione,1TBDMS,isomer #2	C=C(CC(C)=O)O[Si](C)(C)C(C)(C)C	1225.4	Semi standard non polar	33892256
2,4-Pentanedione,1TBDMS,isomer #2	C=C(CC(C)=O)O[Si](C)(C)C(C)(C)C	1203.5	Standard non polar	33892256
2,4-Pentanedione,2TBDMS,isomer #1	C=C(C=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1632.0	Semi standard non polar	33892256
2,4-Pentanedione,2TBDMS,isomer #1	C=C(C=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1610.3	Standard non polar	33892256
2,4-Pentanedione,2TBDMS,isomer #2	C=C(CC(=C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1588.5	Semi standard non polar	33892256
2,4-Pentanedione,2TBDMS,isomer #2	C=C(CC(=C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1610.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-00kf-9100000000-46d8c1174b4626f67753	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-0006-9000000000-43699b9ce7635de34706	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-000f-9100000000-339a18cfa2c9fef9fc0e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-0006-9100000000-f1c22c3e7618740489d1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-0006-9100000000-bbf09a0b601d6c1b37f4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-0006-9100000000-d3295daaa18cb9c248cf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-00kf-9100000000-46d8c1174b4626f67753	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-0006-9000000000-43699b9ce7635de34706	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-000f-9100000000-339a18cfa2c9fef9fc0e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-0006-9100000000-f1c22c3e7618740489d1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-0006-9100000000-bbf09a0b601d6c1b37f4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)	splash10-0006-9100000000-d3295daaa18cb9c248cf	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Pentanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-33ab101159a7d4a6d98e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Pentanedione 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 - 2,4-Pentanedione 10V, Positive-QTOF	splash10-0ue9-7900000000-4812cbafad0eb4f8a68b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 20V, Positive-QTOF	splash10-0ue9-9500000000-985f6620ed06341c0d7a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 40V, Positive-QTOF	splash10-014l-9000000000-926b40c3b86762eb1664	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 10V, Negative-QTOF	splash10-0002-9000000000-198e7633acd8394443b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 20V, Negative-QTOF	splash10-0002-9000000000-d23c67af0511dd32e26d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 40V, Negative-QTOF	splash10-053r-9000000000-ccefb92ad120c18ac6ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 10V, Positive-QTOF	splash10-0006-9000000000-c7b1249dbd405b205390	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 20V, Positive-QTOF	splash10-0006-9000000000-afb1c573d3e6ae262efb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 40V, Positive-QTOF	splash10-0006-9000000000-96a8981ecdf0987e7d2e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 10V, Negative-QTOF	splash10-0a4i-9000000000-31737175df5f20440412	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 20V, Negative-QTOF	splash10-0a4i-9000000000-01cdf05ad77c40eb559b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Pentanedione 40V, Negative-QTOF	splash10-0a4i-9000000000-70ba0c83531aa46f69c5	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected and Quantified	23.306 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Feces	Detected and Quantified	6.659 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Feces	Detected and Quantified	16.647 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Acetylacetone

METLIN ID

Not Available

PubChem Compound

31261

PDB ID

Not Available

ChEBI ID

14750

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1164641

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yuan XH, Liu LM, Ying WB: [Preparation and spectral analysis of Bi(4-x) La(x)Ti3O12 ferroelectric thin films by metal-organic deposition method]. Guang Pu Xue Yu Guang Pu Fen Xi. 2007 Jul;27(7):1355-8. [PubMed:17944413 ]
Li C, Wang S, Huang Y, Zheng B, Tian Z, Wen Y, Li F: Synthesis, characterization and electrochemiluminescent properties of cyclometalated platinum(II) complexes with substituted 2-phenylpyridine ligands. Dalton Trans. 2013 Mar 21;42(11):4059-67. doi: 10.1039/c2dt32466k. Epub 2013 Jan 23. [PubMed:23340796 ]
Rao Ch S, Subash Y E: The effect of chronic tobacco smoking and chewing on the lipid profile. J Clin Diagn Res. 2013 Jan;7(1):31-4. doi: 10.7860/JCDR/2012/5086.2663. Epub 2013 Jan 1. [PubMed:23449989 ]
Yao C, Xu X, Wang J, Shi L, Li L: Low-temperature, solution-processed hole selective layers for polymer solar cells. ACS Appl Mater Interfaces. 2013 Feb;5(3):1100-7. doi: 10.1021/am302878m. Epub 2013 Jan 31. [PubMed:23331483 ]
Muyskens KJ, Alsum JR, Thielke TA, Boer JL, Heetderks TR, Muyskens MA: Photochemistry of UV-excited trifluoroacetylacetone and hexafluoroacetylacetone I: infrared spectra of fluorinated methylfuranones formed by HF photoelimination. J Phys Chem A. 2012 Dec 20;116(50):12305-13. doi: 10.1021/jp307725z. Epub 2012 Dec 6. [PubMed:23176295 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,4-Pentanedione (HMDB0031648)

MOL for HMDB0031648 (2,4-Pentanedione)

3D MOL for HMDB0031648 (2,4-Pentanedione)

3D SDF for HMDB0031648 (2,4-Pentanedione)

3D-SDF for HMDB0031648 (2,4-Pentanedione)

PDB for HMDB0031648 (2,4-Pentanedione)

3D PDB for HMDB0031648 (2,4-Pentanedione)

SMILES for HMDB0031648 (2,4-Pentanedione)

INCHI for HMDB0031648 (2,4-Pentanedione)

Structure for HMDB0031648 (2,4-Pentanedione)

3D Structure for HMDB0031648 (2,4-Pentanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra