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

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

HMDB0031492

Secondary Accession Numbers

HMDB31492

Metabolite Identification

Common Name

3,4-Hexanedione

Description

3,4-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, 3,4-hexanedione is considered to be an oxygenated hydrocarbon. 3,4-Hexanedione is an almond, buttery, and caramel tasting compound. Based on a literature review a significant number of articles have been published on 3,4-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
Hexane 3	ChEMBL, HMDB
4-Dione	ChEMBL, HMDB
3,4-Hexandione	HMDB
Bipropionyl	HMDB
Diethyl diketone	HMDB
Dipropionyl	HMDB
FEMA 3168	HMDB

Chemical Formula

C₆H₁₀O₂

Average Molecular Weight

114.1424

Monoisotopic Molecular Weight

114.068079564

IUPAC Name

hexane-3,4-dione

Traditional Name

3,4-hexanedione

CAS Registry Number

4437-51-8

SMILES

CCC(=O)C(=O)CC

InChI Identifier

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

InChI Key

KVFQMAZOBTXCAZ-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

Oxygenated hydrocarbons (LMFA12000016 )
a small molecule (CPD-9078 )

Ontology

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0031492)
Cytoplasm (HMDB: HMDB0031492)

Source

Endogenous

Endogenous (HMDB: HMDB0031492)

Exogenous

Food

Food (HMDB: HMDB0031492)

Exogenous (HMDB: HMDB0031492)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031492)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-10 °C	Not Available
Boiling Point	123.00 to 125.00 °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	30.7 g/L	ALOGPS
logP	1.1	ALOGPS
logP	1.8	ChemAxon
logS	-0.57	ALOGPS
pKa (Strongest Acidic)	16.54	ChemAxon
pKa (Strongest Basic)	-8.5	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	30.79 m³·mol⁻¹	ChemAxon
Polarizability	12.24 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]+	125.785	31661259
DarkChem	[M-H]-	120.671	31661259
DeepCCS	[M+H]+	125.227	30932474
DeepCCS	[M-H]-	122.089	30932474
DeepCCS	[M-2H]-	159.088	30932474
DeepCCS	[M+Na]+	133.991	30932474
AllCCS	[M+H]+	128.3	32859911
AllCCS	[M+H-H2O]+	124.0	32859911
AllCCS	[M+NH4]+	132.4	32859911
AllCCS	[M+Na]+	133.5	32859911
AllCCS	[M-H]-	128.0	32859911
AllCCS	[M+Na-2H]-	131.2	32859911
AllCCS	[M+HCOO]-	134.8	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.	3.02 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0283 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1586.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	432.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	150.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	279.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	121.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	449.1 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	512.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	971.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	336.7 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	1068.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	303.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	421.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	385.3 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	54.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Hexanedione	CCC(=O)C(=O)CC	1132.5	Standard polar	33892256
3,4-Hexanedione	CCC(=O)C(=O)CC	714.3	Standard non polar	33892256
3,4-Hexanedione	CCC(=O)C(=O)CC	799.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Hexanedione,1TMS,isomer #1	CC=C(O[Si](C)(C)C)C(=O)CC	1091.8	Semi standard non polar	33892256
3,4-Hexanedione,1TMS,isomer #1	CC=C(O[Si](C)(C)C)C(=O)CC	1044.1	Standard non polar	33892256
3,4-Hexanedione,2TMS,isomer #1	CC=C(O[Si](C)(C)C)C(=CC)O[Si](C)(C)C	1287.5	Semi standard non polar	33892256
3,4-Hexanedione,2TMS,isomer #1	CC=C(O[Si](C)(C)C)C(=CC)O[Si](C)(C)C	1233.4	Standard non polar	33892256
3,4-Hexanedione,1TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C(=O)CC	1326.5	Semi standard non polar	33892256
3,4-Hexanedione,1TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C(=O)CC	1256.0	Standard non polar	33892256
3,4-Hexanedione,2TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C(=CC)O[Si](C)(C)C(C)(C)C	1730.7	Semi standard non polar	33892256
3,4-Hexanedione,2TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C(=CC)O[Si](C)(C)C(C)(C)C	1653.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,4-Hexanedione EI-B (Non-derivatized)	splash10-0a6r-9000000000-14fe8c5d96403ec9248f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Hexanedione EI-B (Non-derivatized)	splash10-0a6r-9000000000-caf9127e49f75f70f432	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Hexanedione EI-B (Non-derivatized)	splash10-0a6r-9000000000-14fe8c5d96403ec9248f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Hexanedione EI-B (Non-derivatized)	splash10-0a6r-9000000000-caf9127e49f75f70f432	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Hexanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-916aa28ef0a92a9e6256	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-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 - 3,4-Hexanedione 10V, Positive-QTOF	splash10-014i-1900000000-8152f30ff61353542a19	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 20V, Positive-QTOF	splash10-066r-9600000000-f9596a67d893c1e63ef7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 40V, Positive-QTOF	splash10-0a4i-9000000000-e6165b1ac41c889423d9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 10V, Negative-QTOF	splash10-03di-1900000000-860fac2428c5fb79bd4c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 20V, Negative-QTOF	splash10-08fr-9800000000-79da12dbd869dd5096be	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 40V, Negative-QTOF	splash10-0a4i-9000000000-d498227da81bae7322d1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 10V, Positive-QTOF	splash10-0a4i-9200000000-b6bbbcc9cecbc76a18e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 20V, Positive-QTOF	splash10-0a4i-9000000000-87b9ad496965ff3eaa77	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 40V, Positive-QTOF	splash10-0a4l-9000000000-eeb617333f9bbde8d487	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 10V, Negative-QTOF	splash10-03dr-9700000000-85aa840d4a1d1557241e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 20V, Negative-QTOF	splash10-0a4i-9000000000-813dfe710acfe518a772	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Hexanedione 40V, Negative-QTOF	splash10-0a4l-9000000000-8e1220339a0c901fb185	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

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 but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	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

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

FDB008071

KNApSAcK ID

Not Available

Chemspider ID

56310

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62539

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1026461

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 3,4-Hexanedione (HMDB0031492)

MOL for HMDB0031492 (3,4-Hexanedione)

3D MOL for HMDB0031492 (3,4-Hexanedione)

3D SDF for HMDB0031492 (3,4-Hexanedione)

3D-SDF for HMDB0031492 (3,4-Hexanedione)

PDB for HMDB0031492 (3,4-Hexanedione)

3D PDB for HMDB0031492 (3,4-Hexanedione)

SMILES for HMDB0031492 (3,4-Hexanedione)

INCHI for HMDB0031492 (3,4-Hexanedione)

Structure for HMDB0031492 (3,4-Hexanedione)

3D Structure for HMDB0031492 (3,4-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