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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:03 UTC

Update Date

2023-02-21 17:20:49 UTC

HMDB ID

HMDB0031559

Secondary Accession Numbers

HMDB31559

Metabolite Identification

Common Name

4-Methyl-2,3-pentanedione

Description

4-Methyl-2,3-pentanedione belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. 4-Methyl-2,3-pentanedione is a sweet, buttery, and creamy tasting compound. 4-Methyl-2,3-pentanedione has been detected, but not quantified in, several different foods, such as robusta coffees (Coffea canephora), coffee and coffee products, alcoholic beverages, crustaceans, and arabica coffees (Coffea arabica). This could make 4-methyl-2,3-pentanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Methyl-2,3-pentanedione.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methylpentane-2,3-dione	HMDB
Acetyl isobutyryl	HMDB
Acetylisobutyryl	HMDB
FEMA 2730	HMDB
Isopropyl methyl diketone	HMDB
Isopropylmethylglyoxal	HMDB
Methyl isopropyl diketone	HMDB

Chemical Formula

C₆H₁₀O₂

Average Molecular Weight

114.1424

Monoisotopic Molecular Weight

114.068079564

IUPAC Name

4-methylpentane-2,3-dione

Traditional Name

4-methylpentane-2,3-dione

CAS Registry Number

7493-58-5

SMILES

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

InChI Identifier

InChI=1S/C6H10O2/c1-4(2)6(8)5(3)7/h4H,1-3H3

InChI Key

JENYBWHRLYZSSZ-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

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031559)
Cytoplasm (HMDB: HMDB0031559)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031559)

Source

Endogenous

Endogenous (HMDB: HMDB0031559)

Plant

Coffea (HMDB: HMDB0031559)
Poaceae (HMDB: HMDB0031559)

Animal

Animal (HMDB: HMDB0031559)

Exogenous

Food

Food (HMDB: HMDB0031559)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Aquatic origin

Crustacean

Crustaceans (FooDB: FOOD00862)

Exogenous (HMDB: HMDB0031559)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031559)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-2.40 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	116.00 to 118.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	244200 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.477 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	24.2 g/L	ALOGPS
logP	0.7	ALOGPS
logP	1.64	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	16.21	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	2	ChemAxon
Refractivity	30.74 m³·mol⁻¹	ChemAxon
Polarizability	12.15 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]+	124.333	31661259
DarkChem	[M-H]-	120.267	31661259
DeepCCS	[M+H]+	129.612	30932474
DeepCCS	[M-H]-	127.604	30932474
DeepCCS	[M-2H]-	163.67	30932474
DeepCCS	[M+Na]+	138.262	30932474
AllCCS	[M+H]+	127.1	32859911
AllCCS	[M+H-H2O]+	122.9	32859911
AllCCS	[M+NH4]+	131.0	32859911
AllCCS	[M+Na]+	132.1	32859911
AllCCS	[M-H]-	126.6	32859911
AllCCS	[M+Na-2H]-	129.9	32859911
AllCCS	[M+HCOO]-	133.6	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.	3.32 minutes	32390414
Predicted by Siyang on May 30, 2022	13.0333 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.23 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1583.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	479.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	298.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	471.8 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	532.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	940.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	353.5 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	1169.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	329.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	312.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	440.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	413.9 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	58.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-2,3-pentanedione	CC(C)C(=O)C(C)=O	1069.1	Standard polar	33892256
4-Methyl-2,3-pentanedione	CC(C)C(=O)C(C)=O	692.1	Standard non polar	33892256
4-Methyl-2,3-pentanedione	CC(C)C(=O)C(C)=O	769.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-2,3-pentanedione,1TMS,isomer #1	CC(=O)C(O[Si](C)(C)C)=C(C)C	1042.0	Semi standard non polar	33892256
4-Methyl-2,3-pentanedione,1TMS,isomer #1	CC(=O)C(O[Si](C)(C)C)=C(C)C	1028.3	Standard non polar	33892256
4-Methyl-2,3-pentanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)C(C)C	1025.3	Semi standard non polar	33892256
4-Methyl-2,3-pentanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)C(C)C	1033.3	Standard non polar	33892256
4-Methyl-2,3-pentanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C)C	1227.7	Semi standard non polar	33892256
4-Methyl-2,3-pentanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C)C	1210.0	Standard non polar	33892256
4-Methyl-2,3-pentanedione,1TBDMS,isomer #1	CC(=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C	1258.9	Semi standard non polar	33892256
4-Methyl-2,3-pentanedione,1TBDMS,isomer #1	CC(=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C	1238.8	Standard non polar	33892256
4-Methyl-2,3-pentanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)C	1253.6	Semi standard non polar	33892256
4-Methyl-2,3-pentanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)C	1218.7	Standard non polar	33892256
4-Methyl-2,3-pentanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C)C	1647.3	Semi standard non polar	33892256
4-Methyl-2,3-pentanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C)C	1641.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-2,3-pentanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-b21a4e12c58b6f8ac5a7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-2,3-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 - 4-Methyl-2,3-pentanedione 10V, Positive-QTOF	splash10-014j-7900000000-4d811288639a4663c68c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 20V, Positive-QTOF	splash10-00kb-9300000000-6cf30ee1a60b9db8138f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 40V, Positive-QTOF	splash10-0006-9000000000-ccd5020cf0ced601e047	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 10V, Negative-QTOF	splash10-03di-1900000000-f264a18a51fea16e2340	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 20V, Negative-QTOF	splash10-03k9-9600000000-9589249a8dbc7f024bdd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 40V, Negative-QTOF	splash10-0592-9000000000-038352b502a4b747cd94	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 10V, Negative-QTOF	splash10-03k9-5900000000-2b1aabc8363d31921a6b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 20V, Negative-QTOF	splash10-03di-9500000000-e58445c28e31b3794b6a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 40V, Negative-QTOF	splash10-052f-9000000000-642e748e087dd9cbc737	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 10V, Positive-QTOF	splash10-0007-9000000000-2646799b30311fc48506	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 20V, Positive-QTOF	splash10-006x-9000000000-8839be08eaab3d9c71ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-2,3-pentanedione 40V, Positive-QTOF	splash10-0006-9000000000-868a9e3d55bae3edaf55	2021-09-22	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

FDB008172

KNApSAcK ID

Not Available

Chemspider ID

22540

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24115

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1032821

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 4-Methyl-2,3-pentanedione (HMDB0031559)

MOL for HMDB0031559 (4-Methyl-2,3-pentanedione)

3D MOL for HMDB0031559 (4-Methyl-2,3-pentanedione)

3D SDF for HMDB0031559 (4-Methyl-2,3-pentanedione)

3D-SDF for HMDB0031559 (4-Methyl-2,3-pentanedione)

PDB for HMDB0031559 (4-Methyl-2,3-pentanedione)

3D PDB for HMDB0031559 (4-Methyl-2,3-pentanedione)

SMILES for HMDB0031559 (4-Methyl-2,3-pentanedione)

INCHI for HMDB0031559 (4-Methyl-2,3-pentanedione)

Structure for HMDB0031559 (4-Methyl-2,3-pentanedione)

3D Structure for HMDB0031559 (4-Methyl-2,3-pentanedione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra