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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:42:09 UTC

Update Date

2023-02-21 17:20:16 UTC

HMDB ID

HMDB0031293

Secondary Accession Numbers

HMDB31293

Metabolite Identification

Common Name

2,3-Octanedione

Description

2,3-Octanedione belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. 2,3-Octanedione is a broccoli, buttery, and cooked tasting compound. 2,3-Octanedione has been detected, but not quantified in, several different foods, such as evergreen blackberries (Rubus laciniatus), arabica coffees (Coffea arabica), blackberries (Rubus), rosemaries (Rosmarinus officinalis), and robusta coffees (Coffea canephora). This could make 2,3-octanedione a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,3-Octanedione.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Dioxooctane	HMDB
2,3-Octadione	HMDB
2,3-Octandione	HMDB
Methyl pentyl diketone	HMDB

Chemical Formula

C₈H₁₄O₂

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

IUPAC Name

octane-2,3-dione

Traditional Name

octane-2,3-dione

CAS Registry Number

585-25-1

SMILES

CCCCCC(=O)C(C)=O

InChI Identifier

InChI=1S/C8H14O2/c1-3-4-5-6-8(10)7(2)9/h3-6H2,1-2H3

InChI Key

XCBBNTFYSLADTO-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

Not Available

Ontology

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Cellular substructure

Extracellular (HMDB: HMDB0031293)
Cytoplasm (HMDB: HMDB0031293)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031293)

Source

Endogenous

Endogenous (HMDB: HMDB0031293)

Plant

Plant (HMDB: HMDB0031293)
Coffea (HMDB: HMDB0031293)

Exogenous

Food

Food (HMDB: HMDB0031293)

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Fruit

Berry

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

Exogenous (HMDB: HMDB0031293)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031293)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	169.00 to 170.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	23840 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.698 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.1 g/L	ALOGPS
logP	2.31	ALOGPS
logP	2.43	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	16.22	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	5	ChemAxon
Refractivity	39.97 m³·mol⁻¹	ChemAxon
Polarizability	16.28 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]+	133.132	31661259
DarkChem	[M-H]-	130.88	31661259
DeepCCS	[M+H]+	138.326	30932474
DeepCCS	[M-H]-	135.643	30932474
DeepCCS	[M-2H]-	172.548	30932474
DeepCCS	[M+Na]+	147.404	30932474
AllCCS	[M+H]+	134.5	32859911
AllCCS	[M+H-H2O]+	130.4	32859911
AllCCS	[M+NH4]+	138.4	32859911
AllCCS	[M+Na]+	139.5	32859911
AllCCS	[M-H]-	134.6	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	139.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Octanedione	CCCCCC(=O)C(C)=O	1337.6	Standard polar	33892256
2,3-Octanedione	CCCCCC(=O)C(C)=O	934.6	Standard non polar	33892256
2,3-Octanedione	CCCCCC(=O)C(C)=O	979.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Octanedione,1TMS,isomer #1	CCCCC=C(O[Si](C)(C)C)C(C)=O	1266.4	Semi standard non polar	33892256
2,3-Octanedione,1TMS,isomer #1	CCCCC=C(O[Si](C)(C)C)C(C)=O	1210.5	Standard non polar	33892256
2,3-Octanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)CCCCC	1264.4	Semi standard non polar	33892256
2,3-Octanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)CCCCC	1222.3	Standard non polar	33892256
2,3-Octanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(=CCCCC)O[Si](C)(C)C	1409.3	Semi standard non polar	33892256
2,3-Octanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(=CCCCC)O[Si](C)(C)C	1367.8	Standard non polar	33892256
2,3-Octanedione,1TBDMS,isomer #1	CCCCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O	1509.4	Semi standard non polar	33892256
2,3-Octanedione,1TBDMS,isomer #1	CCCCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O	1419.9	Standard non polar	33892256
2,3-Octanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCCCC	1463.8	Semi standard non polar	33892256
2,3-Octanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCCCC	1405.9	Standard non polar	33892256
2,3-Octanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=CCCCC)O[Si](C)(C)C(C)(C)C	1856.5	Semi standard non polar	33892256
2,3-Octanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=CCCCC)O[Si](C)(C)C(C)(C)C	1748.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Octanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-64da66dfa75c6c26bb11	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Octanedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Octanedione 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-Octanedione 10V, Positive-QTOF	splash10-002f-1900000000-80095b918c7f36c7c5e7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 20V, Positive-QTOF	splash10-05i3-9500000000-3f95e1391470d0d177bb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 40V, Positive-QTOF	splash10-052f-9000000000-2773cbabfa18d25aba06	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 10V, Negative-QTOF	splash10-0006-1900000000-8a5c60aef76fbd632ad4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 20V, Negative-QTOF	splash10-0005-9400000000-facdc257ab1efc088b07	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 40V, Negative-QTOF	splash10-00rf-9100000000-436f7735623dfb3b5330	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 10V, Positive-QTOF	splash10-009y-9200000000-7f119b97cd3a2ea5b0dc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 20V, Positive-QTOF	splash10-006x-9000000000-3939c078bd1e95fd0263	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 40V, Positive-QTOF	splash10-0006-9000000000-597374cc7b3cde032425	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 10V, Negative-QTOF	splash10-0006-6900000000-40ec4ecf97d76555cd6c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 20V, Negative-QTOF	splash10-0006-9000000000-0e08a0dd1a3578683efe	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Octanedione 40V, Negative-QTOF	splash10-0006-9000000000-7bcd74a858701b6b8ad7	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)	2021-09-16	Wishart Lab	View Spectrum
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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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, 1000 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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

FDB003341

KNApSAcK ID

Not Available

Chemspider ID

10965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11449

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1569281

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-Octanedione (HMDB0031293)

MOL for HMDB0031293 (2,3-Octanedione)

3D MOL for HMDB0031293 (2,3-Octanedione)

3D SDF for HMDB0031293 (2,3-Octanedione)

3D-SDF for HMDB0031293 (2,3-Octanedione)

PDB for HMDB0031293 (2,3-Octanedione)

3D PDB for HMDB0031293 (2,3-Octanedione)

SMILES for HMDB0031293 (2,3-Octanedione)

INCHI for HMDB0031293 (2,3-Octanedione)

Structure for HMDB0031293 (2,3-Octanedione)

3D Structure for HMDB0031293 (2,3-Octanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra