Diacetyl (YMDB00367)

Identification

YMDB ID

YMDB00367

Name

Diacetyl

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Diacetyl, also known as dimethylglyoxal or 2,3-butadione, 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, diacetyl is considered to be an oxygenated hydrocarbon. Diacetyl exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Diacetyl.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

2,3-Butadione
2,3-Butandione
2,3-Butanedione
2,3-Diketobutane
2,3-Dioxobutane
Acetoacetaldehyde
Biacetyl
Butadione
Butan-2,3-dione
Butane-2,3-dione
Butanedione
Butanedione [UN2346]
Diacetyl
Dimethyl diketone
Dimethyl glyoxal
Dimethylglyoxal
2,3 Butanedione
Diketobutane
Dimethyldiketone

CAS number

431-03-8

Weight

Average: 86.0892
Monoisotopic: 86.036779436

InChI Key

QSJXEFYPDANLFS-UHFFFAOYSA-N

InChI

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

IUPAC Name

butane-2,3-dione

Traditional IUPAC Name

diacetyl

Chemical Formula

C₄H₆O₂

SMILES

[H]C([H])([H])C(=O)C(=O)C([H])([H])[H]

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

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
Water Solubility	200 mg/mL at 15 oC [YALKOWSKY,SH & HE,Y (2003)]	PhysProp
LogP	-1.34 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	129 g/L	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

Organoleptic Properties

Flavour/Odour	Source
Butter	FDB011930
Caramel	FDB011930
Creamy	FDB011930
Oily	FDB011930
Pungent	FDB011930
Strong	FDB011930
Sweet	FDB011930

SMPDB Pathways

Not Available

KEGG Pathways

Butanoate metabolism

ec00650

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-eeaaf8aa838a1d6a7dde	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-622030119adee3079d84	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-eeaaf8aa838a1d6a7dde	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-622030119adee3079d84	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-58f4b3973bdf0094a5e3	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-4e7132ef8eb6971544b1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00r5-9000000000-0cc5c90a4394d550268f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-06dj-9000000000-a74bfecfcdb93a5c3e07	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-eeaaf8aa838a1d6a7dde	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-171c3774c90fd50b6d6b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-6e218d8c4f1cb3a01254	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0ufr-9000000000-c27bd416a10df3c9c1d3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-49c29114e2316ba16f02	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-9000000000-0c5000d8f4b14cdc5b05	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-e8c63126caa0f371f336	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9000000000-82affa84acc0579c193b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-f63598734c0af05eb392	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-e8c63126caa0f371f336	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9000000000-82affa84acc0579c193b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-f63598734c0af05eb392	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2599bbcd002f75cefa1d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-1171c0cf98959e7315c6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-7dcc0fc66bb1e551b332	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2599bbcd002f75cefa1d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-1171c0cf98959e7315c6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-7dcc0fc66bb1e551b332	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-87bbaed151efac084591	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-87bbaed151efac084591	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-87bbaed151efac084591	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-ec20127c74818b1f634d	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-8d1a3988261033033e03	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828

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.

External Links:

Resource	Link
CHEBI ID	16583
HMDB ID	HMDB03407
Pubchem Compound ID	650
Kegg ID	C00741
ChemSpider ID	630
FOODB ID	FDB011930
Wikipedia	Diacetyl
BioCyc ID	NN-DIACETYLCHITOBIOSYLDIPHOSPHODOLICHO

Enzymes

Protein Details

1. Probable diacetyl reductase [(R)-acetoin forming] 2

General function:: Involved in zinc ion binding
Specific function:: Catalyzes the irreversible reduction of 2,3-butanediol to (S)-acetoin in the presence of NADH (Potential)
Gene Name:: BDH2
Uniprot ID:: P39713
Molecular weight:: 46098.19922

Reactions

(R)-acetoin + NAD(+) → diacetyl + NADH.

Protein Details

2. Diacetyl reductase [(R)-acetoin forming]

General function:: Involved in zinc ion binding
Specific function:: Catalyzes the irreversible reduction of 2,3-butanediol to (S)-acetoin in the presence of NADH
Gene Name:: BDH1
Uniprot ID:: P39714
Molecular weight:: 41537.69922

Reactions

(R)-acetoin + NAD(+) → diacetyl + NADH.

Structure for #<Compound:0xa4a3f38c>

Enzymes

Reactions

Reactions