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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:11:42 UTC

Update Date

2023-02-21 17:24:43 UTC

HMDB ID

HMDB0035243

Secondary Accession Numbers

HMDB35243

Metabolite Identification

Common Name

1-Phenyl-1,2-propanedione

Description

1-Phenyl-1,2-propanedione, also known as acetyl benzoyl or phenyl methyl diketone, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. 1-Phenyl-1,2-propanedione is a buttery, honey, and pepper tasting compound. 1-Phenyl-1,2-propanedione has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 1-phenyl-1,2-propanedione a potential biomarker for the consumption of these foods. 1-Phenyl-1,2-propanedione is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 1-Phenyl-1,2-propanedione.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Phenyl-1,2-dioxopropane	ChEBI
3-Phenyl-2,3-propanedione	ChEBI
Acetyl benzoyl	ChEBI
Acetylbenzoyl	ChEBI
Benzoyl methyl ketone	ChEBI
Benzoylacetyl	ChEBI
Methyl phenyl diketone	ChEBI
Methyl phenyl glyoxal	ChEBI
Methylphenylglyoxal	ChEBI
Phenyl methyl diketone	ChEBI
Phenylmethyldiketone	ChEBI
Pyruvophenone	ChEBI
1-Phenyl-1,2-propandione	HMDB
1-Phenylpropane-1,2-dione	HMDB
FEMA 3226	HMDB

Chemical Formula

C₉H₈O₂

Average Molecular Weight

148.1586

Monoisotopic Molecular Weight

148.0524295

IUPAC Name

1-phenylpropane-1,2-dione

Traditional Name

acetyl benzoyl

CAS Registry Number

579-07-7

SMILES

CC(=O)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C9H8O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6H,1H3

InChI Key

BVQVLAIMHVDZEL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Aryl ketone
Benzoyl
Alpha-diketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ketone (CHEBI:63552 )
alpha-diketone (CHEBI:63552 )
a small molecule (CPD-9949 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0035243)
Cytoplasm (HMDB: HMDB0035243)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035243)

Source

Exogenous

Exogenous (HMDB: HMDB0035243)

Food

Food (HMDB: HMDB0035243)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0035243)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0035243)

Biological role

Nutrient (HMDB: HMDB0035243)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 20 °C	Not Available
Boiling Point	103.00 to 105.00 °C. @ 14.00 mm Hg	The Good Scents Company Information System
Water Solubility	2.6 mg/mL at 20 °C	Not Available
LogP	1.169 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.92 g/L	ALOGPS
logP	0.94	ALOGPS
logP	1.82	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	16.92	ChemAxon
pKa (Strongest Basic)	-8.1	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	41.81 m³·mol⁻¹	ChemAxon
Polarizability	15.23 Å³	ChemAxon
Number of Rings	1	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]+	132.203	31661259
DarkChem	[M-H]-	129.79	31661259
DeepCCS	[M+H]+	132.778	30932474
DeepCCS	[M-H]-	129.96	30932474
DeepCCS	[M-2H]-	166.152	30932474
DeepCCS	[M+Na]+	141.555	30932474
AllCCS	[M+H]+	129.8	32859911
AllCCS	[M+H-H2O]+	125.2	32859911
AllCCS	[M+NH4]+	134.1	32859911
AllCCS	[M+Na]+	135.4	32859911
AllCCS	[M-H]-	129.1	32859911
AllCCS	[M+Na-2H]-	130.3	32859911
AllCCS	[M+HCOO]-	131.8	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.	5.55 minutes	32390414
Predicted by Siyang on May 30, 2022	12.6607 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.24 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1789.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	455.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	279.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	169.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	468.7 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	548.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	107.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1063.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	381.8 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	1162.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	406.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	320.1 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	59.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Phenyl-1,2-propanedione	CC(=O)C(=O)C1=CC=CC=C1	1817.4	Standard polar	33892256
1-Phenyl-1,2-propanedione	CC(=O)C(=O)C1=CC=CC=C1	1125.0	Standard non polar	33892256
1-Phenyl-1,2-propanedione	CC(=O)C(=O)C1=CC=CC=C1	1217.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Phenyl-1,2-propanedione,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(=O)C1=CC=CC=C1	1438.5	Semi standard non polar	33892256
1-Phenyl-1,2-propanedione,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(=O)C1=CC=CC=C1	1374.0	Standard non polar	33892256
1-Phenyl-1,2-propanedione,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC=C1	1664.0	Semi standard non polar	33892256
1-Phenyl-1,2-propanedione,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC=C1	1566.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1-Phenyl-1,2-propanedione EI-B (Non-derivatized)	splash10-0a6r-9500000000-0ad1ba839fdf36b66932	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1-Phenyl-1,2-propanedione EI-B (Non-derivatized)	splash10-0a6r-9500000000-0ad1ba839fdf36b66932	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Phenyl-1,2-propanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-0995a26dda9c3bc5dbec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Phenyl-1,2-propanedione 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 - 1-Phenyl-1,2-propanedione 10V, Positive-QTOF	splash10-000t-0900000000-23a8b7ff76e850b79b3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 20V, Positive-QTOF	splash10-001j-0900000000-fb650b96ad441c16bed7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 40V, Positive-QTOF	splash10-0pc0-6900000000-6693984118df075408bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 10V, Negative-QTOF	splash10-0002-0900000000-02e11fb73ce9229aee3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 20V, Negative-QTOF	splash10-052b-0900000000-11eb6ccaabf1484aba79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 40V, Negative-QTOF	splash10-0zi0-2900000000-2ba7d36b3c9387c11907	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 10V, Positive-QTOF	splash10-0002-1900000000-9c4104ddeb2be69ca7cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 20V, Positive-QTOF	splash10-0a4i-3900000000-978783f78075cb704283	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 40V, Positive-QTOF	splash10-004i-9100000000-d4f8904f7ef35220495f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 10V, Negative-QTOF	splash10-0002-0900000000-f55a05e2292ed812db8a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 20V, Negative-QTOF	splash10-056s-6900000000-d8f40443c310f8ed55fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Phenyl-1,2-propanedione 40V, Negative-QTOF	splash10-004i-9100000000-e37b1d1d767deab85b70	2021-09-24	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

FDB013903

KNApSAcK ID

Not Available

Chemspider ID

10885

KEGG Compound ID

C17268

BioCyc ID

CPD-9949

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11363

PDB ID

Not Available

ChEBI ID

63552

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035591

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 1-Phenyl-1,2-propanedione (HMDB0035243)

MOL for HMDB0035243 (1-Phenyl-1,2-propanedione)

3D MOL for HMDB0035243 (1-Phenyl-1,2-propanedione)

3D SDF for HMDB0035243 (1-Phenyl-1,2-propanedione)

3D-SDF for HMDB0035243 (1-Phenyl-1,2-propanedione)

PDB for HMDB0035243 (1-Phenyl-1,2-propanedione)

3D PDB for HMDB0035243 (1-Phenyl-1,2-propanedione)

SMILES for HMDB0035243 (1-Phenyl-1,2-propanedione)

INCHI for HMDB0035243 (1-Phenyl-1,2-propanedione)

Structure for HMDB0035243 (1-Phenyl-1,2-propanedione)

3D Structure for HMDB0035243 (1-Phenyl-1,2-propanedione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra