Diacetyl
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Basic Info
| Common Name | Diacetyl(F04827) |
| 2D Structure | |
| Description | Diacetyl is a natural by-product of secondary or malolactic fermentation. It is a vicinal diketone (two C=O groups, side-by-side) with the molecular formula C4H6O2. Carrier of aroma of butter, vinegar, coffee, and other foods. Beer sometimes undergoes a diacetyl rest, which entails waiting two or three days after fermentation is complete, to allow the yeast to absorb the diacetyl it produced earlier in the fermentation cycle. The makers of some wines, such as chardonnay, deliberately promote the production of diacetyl because of the feel and flavors it imparts. |
| FRCD ID | F04827 |
| CAS Number | 431-03-8 |
| PubChem CID | 650 |
| Formula | C4H6O2 |
| IUPAC Name | butane-2,3-dione |
| InChI Key | QSJXEFYPDANLFS-UHFFFAOYSA-N |
| InChI | InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3 |
| Canonical SMILES | CC(=O)C(=O)C |
| Isomeric SMILES | CC(=O)C(=O)C |
| Wikipedia | Diacetyl |
| Synonyms |
biacetyl
2,3-butanedione
diacetyl
Butane-2,3-dione
431-03-8
dimethylglyoxal
2,3-diketobutane
Dimethyl glyoxal
Butanedione
dimethyl diketone
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbonyl compounds |
| Intermediate Tree Nodes | Ketones |
| Direct Parent | Alpha-diketones |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Alpha-diketone - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound |
| 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 86.09 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Complexity | 71.5 |
| Monoisotopic Mass | 86.037 |
| Exact Mass | 86.037 |
| XLogP | -1.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 6 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9813 |
| Human Intestinal Absorption | HIA+ | 0.9922 |
| Caco-2 Permeability | Caco2+ | 0.6125 |
| P-glycoprotein Substrate | Non-substrate | 0.8244 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8348 |
| Non-inhibitor | 0.8863 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9307 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7560 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8512 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Non-substrate | 0.7288 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9376 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9437 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9294 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9728 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9484 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9727 |
| Non-inhibitor | 0.9653 | |
| AMES Toxicity | AMES toxic | 0.5873 |
| Carcinogens | Carcinogens | 0.6451 |
| Fish Toxicity | Low FHMT | 0.8654 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6543 |
| Honey Bee Toxicity | High HBT | 0.7305 |
| Biodegradation | Ready biodegradable | 0.9040 |
| Acute Oral Toxicity | III | 0.8776 |
| Carcinogenicity (Three-class) | Non-required | 0.7465 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.6035 | LogS |
| Caco-2 Permeability | 1.2439 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7047 | LD50, mol/kg |
| Fish Toxicity | 2.9210 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.2977 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Burden of respiratory abnormalities in microwave popcorn and flavouring manufacturing workers. | Occup Environ Med | 2018 Oct | 30045951 |
| New Insight into the Role of Sucrose in the Generation of α-Diketones upon CoffeeRoasting. | J Agric Food Chem | 2018 Mar 14 | 28013547 |
| Key Odorants of Lazur, a Polish Mold-Ripened Cheese. | J Agric Food Chem | 2018 Mar 14 | 28145120 |
| Investigation of hypersensitivity potential of diacetyl by determining cytokineprofiles. | Hum Exp Toxicol | 2018 Mar | 29233007 |
| Safety assessment and functional properties of four enterococci strains isolated from regional Argentinean cheese. | Int J Food Microbiol | 2018 Jul 20 | 29669304 |
| The genetic basis underlying variation in production of the flavour compounddiacetyl by Lactobacillus rhamnosus strains in milk. | Int J Food Microbiol | 2018 Jan 16 | 29121515 |
| Necrotic enteritis challenge and high dietary sodium level affect odorantcomposition or emission from broilers. | Poult Sci | 2018 Jan 1 | 29077885 |
| Occupational exposures of flour dust and airborne chemicals at bakeries inTaiwan. | J Occup Environ Hyg | 2018 Apr 30:1-25 | 29708861 |
| Increased chemical acetylation of peptides and proteins in rats after dailyingestion of diacetyl analyzed by Nano-LC-MS/MS. | PeerJ | 2018 Apr 25 | 29713565 |
| Flavoring Chemicals and Aldehydes in E-Cigarette Emissions. | Environ Sci Technol | 2017 Sep 19 | 28817267 |
| Functional Properties of Lactobacillus mucosae Strains Isolated from Brazilian Goat Milk. | Probiotics Antimicrob Proteins | 2017 Sep | 27943049 |
| Electronic Cigarettes: Their Constituents and Potential Links to Asthma. | Curr Allergy Asthma Rep | 2017 Oct 5 | 28983782 |
| Characterization of the Key Aroma Compounds in White Alba Truffle (Tuber magnatumpico) and Burgundy Truffle (Tuber uncinatum) by Means of the Sensomics Approach. | J Agric Food Chem | 2017 Oct 25 | 28965409 |
| Airway injury in an in vitro human epithelium-fibroblast model of diacetyl vapor exposure: diacetyl-induced basal/suprabasal spongiosis. | Inhal Toxicol | 2017 Jun | 28984536 |
| The Diacetyl-Exposed Human Airway Epithelial Secretome: New Insights intoFlavoring-Induced Airways Disease. | Am J Respir Cell Mol Biol | 2017 Jun | 28248570 |
| Diacetyl/l-Xylulose Reductase Mediates Chemical Redox Cycling in Lung Epithelial Cells. | Chem Res Toxicol | 2017 Jul 17 | 28595002 |
| A protease-resistant α-galactosidase from Pleurotus djamor with broad pHstability and good hydrolytic activity toward raffinose family oligosaccharides. | Int J Biol Macromol | 2017 Jan | 27717787 |
| Proteomic Analysis of Primary Human Airway Epithelial Cells Exposed to theRespiratory Toxicant Diacetyl. | J Proteome Res | 2017 Feb 3 | 27966365 |
| Development and validation of a HS/GC-MS method for the simultaneous analysis of diacetyl and acetylpropionyl in electronic cigarette refills. | J Pharm Biomed Anal | 2017 Aug 5 | 28521275 |
| Diacetyl and related flavorant α-Diketones: Biotransformation, cellular interactions, and respiratory-tract toxicity. | Toxicology | 2017 Aug 1 | 28179188 |
Targets
- General Function:
- Methylumbelliferyl-acetate deacetylase activity
- Specific Function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
- Gene Name:
- CES2
- Uniprot ID:
- O00748
- Molecular Weight:
- 61806.41 Da
References
- Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
- General Function:
- Triglyceride lipase activity
- Specific Function:
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
- Gene Name:
- CES1
- Uniprot ID:
- P23141
- Molecular Weight:
- 62520.62 Da
References
- Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]