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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:43:38 UTC

Update Date

2023-02-21 17:20:39 UTC

HMDB ID

HMDB0031491

Secondary Accession Numbers

HMDB31491

Metabolite Identification

Common Name

2,3-Hexanedione

Description

2,3-Hexanedione belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. Thus, 2,3-hexanedione is considered to be an oxygenated hydrocarbon. 2,3-Hexanedione is a sweet, butter, and caramel tasting compound. 2,3-Hexanedione has been detected, but not quantified in, several different foods, such as pulses, fruits, mollusks, arabica coffees (Coffea arabica), and coffee and coffee products. This could make 2,3-hexanedione a potential biomarker for the consumption of these foods. 2,3-Hexanedione is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 2,3-Hexanedione.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl propyl diketone	ChEBI
2,3-Hexandione	HMDB
2,3-Hexanodione	HMDB
Acetyl butyryl	HMDB
Acetylbutyryl	HMDB
Butyryl acetyl	HMDB
FEMA 2558	HMDB
Methyl propyl glyoxal	HMDB
2,3-Hexanedione	MeSH

Chemical Formula

C₆H₁₀O₂

Average Molecular Weight

114.1424

Monoisotopic Molecular Weight

114.068079564

IUPAC Name

hexane-2,3-dione

Traditional Name

2,3-hexanedione

CAS Registry Number

3848-24-6

SMILES

CCCC(=O)C(C)=O

InChI Identifier

InChI=1S/C6H10O2/c1-3-4-6(8)5(2)7/h3-4H2,1-2H3

InChI Key

MWVFCEVNXHTDNF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-diketones

Alternative Parents

Substituents

Alpha-diketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-diketone (CHEBI:87583 )
Oxygenated hydrocarbons (LMFA12000247 )
a small molecule (CPD-9081 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-30.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	128.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	-0.321 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	19.7 g/L	ALOGPS
logP	0.8	ALOGPS
logP	1.54	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	16.23	ChemAxon
pKa (Strongest Basic)	-8.4	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	3	ChemAxon
Refractivity	30.77 m³·mol⁻¹	ChemAxon
Polarizability	12.21 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
DarkChem	[M+H]+	124.747	31661259
DarkChem	[M-H]-	120.37	31661259
DeepCCS	[M+H]+	127.724	30932474
DeepCCS	[M-H]-	125.676	30932474
DeepCCS	[M-2H]-	161.634	30932474
DeepCCS	[M+Na]+	136.106	30932474
AllCCS	[M+H]+	127.6	32859911
AllCCS	[M+H-H2O]+	123.3	32859911
AllCCS	[M+NH4]+	131.6	32859911
AllCCS	[M+Na]+	132.8	32859911
AllCCS	[M-H]-	127.4	32859911
AllCCS	[M+Na-2H]-	130.6	32859911
AllCCS	[M+HCOO]-	134.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.27 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2837 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.59 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1564.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	441.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	284.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	151.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	449.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	523.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	979.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	339.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1080.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	309.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	433.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	392.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	54.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Hexanedione	CCCC(=O)C(C)=O	1122.7	Standard polar	33892256
2,3-Hexanedione	CCCC(=O)C(C)=O	723.2	Standard non polar	33892256
2,3-Hexanedione	CCCC(=O)C(C)=O	780.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Hexanedione,1TMS,isomer #1	CCC=C(O[Si](C)(C)C)C(C)=O	1094.4	Semi standard non polar	33892256
2,3-Hexanedione,1TMS,isomer #1	CCC=C(O[Si](C)(C)C)C(C)=O	1026.5	Standard non polar	33892256
2,3-Hexanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)CCC	1091.6	Semi standard non polar	33892256
2,3-Hexanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)CCC	1041.6	Standard non polar	33892256
2,3-Hexanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(=CCC)O[Si](C)(C)C	1274.6	Semi standard non polar	33892256
2,3-Hexanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(=CCC)O[Si](C)(C)C	1213.5	Standard non polar	33892256
2,3-Hexanedione,1TBDMS,isomer #1	CCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O	1329.3	Semi standard non polar	33892256
2,3-Hexanedione,1TBDMS,isomer #1	CCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O	1240.9	Standard non polar	33892256
2,3-Hexanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCC	1297.1	Semi standard non polar	33892256
2,3-Hexanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCC	1220.7	Standard non polar	33892256
2,3-Hexanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=CCC)O[Si](C)(C)C(C)(C)C	1688.3	Semi standard non polar	33892256
2,3-Hexanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=CCC)O[Si](C)(C)C(C)(C)C	1609.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,3-Hexanedione EI-B (Non-derivatized)	splash10-0006-9000000000-834d76c0fa32b0bcd9c1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,3-Hexanedione EI-B (Non-derivatized)	splash10-0006-9000000000-834d76c0fa32b0bcd9c1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Hexanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9000000000-6cc1f9b72cb71211cc22	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Hexanedione 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 - 2,3-Hexanedione 10V, Positive-QTOF	splash10-014j-9800000000-612406ea640d09730a54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 20V, Positive-QTOF	splash10-00kg-9200000000-4f79cd9cdc18c3e22a97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 40V, Positive-QTOF	splash10-0006-9000000000-387cca6d53a765a6dfad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 10V, Negative-QTOF	splash10-03di-2900000000-cb49b3ee37c679bcc3c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 20V, Negative-QTOF	splash10-02mi-9300000000-1af4fffdf89c5f9cce79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 40V, Negative-QTOF	splash10-00r7-9000000000-8330ebeb82c0199b73ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 10V, Negative-QTOF	splash10-03di-2900000000-7bf242f20d30e9aba5ec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 20V, Negative-QTOF	splash10-00kf-9100000000-8f88b789399c1a26bc2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 40V, Negative-QTOF	splash10-0006-9000000000-37e44729943464324a91	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 10V, Positive-QTOF	splash10-006x-9000000000-3676db2ad0f79e04caa2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 20V, Positive-QTOF	splash10-0006-9000000000-cc51ec420718bb0a29b4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Hexanedione 40V, Positive-QTOF	splash10-0006-9000000000-5201674b6f5b3e8c01d8	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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
Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008070

KNApSAcK ID

Not Available

Chemspider ID

18563

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19707

PDB ID

Not Available

ChEBI ID

87583

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1014711

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 2,3-Hexanedione (HMDB0031491)

MOL for HMDB0031491 (2,3-Hexanedione)

3D MOL for HMDB0031491 (2,3-Hexanedione)

3D SDF for HMDB0031491 (2,3-Hexanedione)

3D-SDF for HMDB0031491 (2,3-Hexanedione)

PDB for HMDB0031491 (2,3-Hexanedione)

3D PDB for HMDB0031491 (2,3-Hexanedione)

SMILES for HMDB0031491 (2,3-Hexanedione)

INCHI for HMDB0031491 (2,3-Hexanedione)

Structure for HMDB0031491 (2,3-Hexanedione)

3D Structure for HMDB0031491 (2,3-Hexanedione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra