P. aeruginosa Metabolome Database: diacetyl (PAMDB120562)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB120562

Identification

Name:

diacetyl

Description:

An α-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2,3-Butadione
2,3-butandione
2,3-Butanedione
2,3-Diketobutane
2,3-Dioxobutane
Biacetyl
Diacetyl
diacetyl
Dimethyl glyoxal
Dimethylglyoxal

Chemical Formula:

C₄H₆O₂

Average Molecular Weight:

86.09

Monoisotopic Molecular Weight:

86.03678

InChI Key:

QSJXEFYPDANLFS-UHFFFAOYSA-N

InChI:

InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3

CAS number:

431-03-8

IUPAC Name:

butane-2,3-dione

Traditional IUPAC Name:

diacetyl

SMILES:

CC(C(C)=O)=O

Chemical Taxonomy

Taxonomy Description

This compound 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:16583)
Oxygenated hydrocarbons (LMFA12000012)
a small molecule (DIACETYL)

Physical Properties

State:

Liquid

Charge:

Melting point:

-2.4 °C

Experimental Properties:

Property	Value	Reference
Melting Point	-2.4 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	200 mg/mL at 15 °C	Not Available
LogP	-1.34	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	129.0 mg/mL	ALOGPS
logP	0.07	ALOGPS
logP	0.4	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	15.98	ChemAxon
pKa (Strongest Basic)	-8.3	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	1	ChemAxon
Refractivity	21.54 m³·mol^-1	ChemAxon
Polarizability	8.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

(S)-2-acetolactate + Acceptor + Hydrogen ion → diacetyl + Carbon dioxide + Donor-H2

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-4e7132ef8eb6971544b1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00r5-9000000000-0cc5c90a4394d550268f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-06dj-9000000000-a74bfecfcdb93a5c3e07	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-eeaaf8aa838a1d6a7dde	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-171c3774c90fd50b6d6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-e8c63126caa0f371f336	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9000000000-82affa84acc0579c193b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-f63598734c0af05eb392	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-e8c63126caa0f371f336	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9000000000-82affa84acc0579c193b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-f63598734c0af05eb392	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2599bbcd002f75cefa1d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-1171c0cf98959e7315c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-7dcc0fc66bb1e551b332	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2599bbcd002f75cefa1d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-1171c0cf98959e7315c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-7dcc0fc66bb1e551b332	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-8d1a3988261033033e03	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available

References

References:

Kovacic P, Cooksy AL (2005)Role of diacetyl metabolite in alcohol toxicity and addiction via electron transfer and oxidative stress. Archives of toxicology 79, Pubmed: 15654607
Gao X, Xu N, Li S, Liu L (2014)Metabolic engineering of Candida glabrata for diacetyl production. PloS one 9, Pubmed: 24614328

Synthesis Reference:

Xu, Ping; Chen, Hong; Du, Yi; Chen, Wanqiu; Xiao, Zijun. Method of preparation diacetyl by oxidization. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
HMDB	HMDB03407
CHEMSPIDER	630
PUBCHEM	650
CHEBI	16583
LIGAND-CPD	C00741
CAS	431-03-8

diacetyl (PAMDB120562)

Structure for diacetyl (PAMDB120562)