Diacetyl (BioCAD00000009846)

feces saliva neuron ovary skeletal muscle testis plant natural products microbial natural products

Metabolite Card

Formula: C4H6O2 (86.0368)
SMILES: CC(=O)C(C)=O

Synonyms [en]

diacetyl; 2,3-butanedione; dimethylglyoxal; biacetyl; 2,3-diketobutane; dimethyl diketone

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Diacetyl. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000009846). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Diacetyl, also known as 2,3-butadione or dimethylglyoxal, 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 lipid molecule. Diacetyl is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Diacetyl exists in all living species, ranging from bacteria to humans. Diacetyl is a strong, sweet, and butter tasting compound. Outside of the human body, diacetyl is found, on average, in the highest concentration in kohlrabis. diacetyl has also been detected, but not quantified in several different foods, such as nances, tartary buckwheats, tamarinds, pineapples, and celeriacs. This could make diacetyl a potential biomarker for the consumption of these foods. Diacetyl is a potentially toxic compound. Diacetyl has been found to be associated with several diseases such as crohn's disease, ulcerative colitis, and nonalcoholic fatty liver disease; also diacetyl has been linked to the inborn metabolic disorders including celiac disease.

Cytoplasm
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 431-03-8
  • PubChem: 650
  • ChEBI: ChEBI:16583
  • HMDB: HMDB0003407
  • HMDB: HMDB03407
  • LipidMaps: LMFA12000012
  • KEGG: C00741
  • BioCyc: DIACETYL
  • NCBI MeSH: Diacetyl
  • Wikipedia: Diacetyl
  • RefMet: RM0150612
  • MoNA: BAF_UVA_POS000691
  • MoNA: EMBL-MCF_spec204777
  • MoNA: HMDB0003407_c_ms_99812
  • MoNA: HMDB0003407_c_ms_99813
  • MoNA: HMDB0003407_ms_ms_2286
  • MoNA: HMDB0003407_ms_ms_2287
  • MoNA: HMDB0003407_ms_ms_2288
  • MoNA: JP006940
  • MoNA: JP008878
  • MoNA: MoNA016590
  • MoNA: MoNA035768
  • MoNA: MoNA035769
  • MoNA: MoNA035770
  • Metlin: METLIN_6921
  • Coconut NaturalProduct: CNP0153215.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02343 acetoin:NAD+ oxidoreductase
KEGG:R02855 1.1.1.303 (R)-acetoin:NAD+ oxidoreductase
KEGG:R02856 C00810 + C00006<=>C00741 + C00005 + C00080
KEGG:R09078 1.1.1.304 (S)-acetoin:NAD+ oxidoreductase
KEGG:R10506 C06010 + C00028<=>C00741 + C00011 + C00030
BioCyc:RXN-6081 2-ACETO-LACTATE + Acceptor + PROTON --> DIACETYL + CARBON-DIOXIDE + Donor-H2
BioCyc:RXN-11032 1.1.1.304 DIACETYL + NADH + PROTON --> CPD-255 + NAD
Rhea:RHEA:22901 1.1.1.303 (R)-acetoin + NAD+ => diacetyl + NADH + H+
Rhea:RHEA:22902 1.1.1.303 diacetyl + NADH + H+ => (R)-acetoin + NAD+
Rhea:RHEA:22903 1.1.1.303 (R)-acetoin + NAD+ <=> diacetyl + NADH + H+
Rhea:RHEA:27287 1.1.1.304 (S)-acetoin + NAD+ => diacetyl + NADH + H+
Rhea:RHEA:27288 1.1.1.304 diacetyl + NADH + H+ => (S)-acetoin + NAD+
Rhea:RHEA:27289 1.1.1.304 (S)-acetoin + NAD+ <=> diacetyl + NADH + H+
Rhea:RHEA:35608 acetoin + NADP+ => diacetyl + NADPH + H+
Rhea:RHEA:35609 diacetyl + NADPH + H+ => acetoin + NADP+
Rhea:RHEA:35610 acetoin + NADP+ <=> diacetyl + NADPH + H+
BioCyc:RXN-11036 1.1.1.303 DIACETYL + NADH + PROTON --> CPD-10353 + NAD
BioCyc:ACETOINDEHYDROG-RXN 1.1.1.- DIACETYL + NADH + PROTON --> ACETOIN + NAD
BioCyc:ACETOINDEHYDROG-A-RXN 1.1.1.- acetoin:NADP+ oxidoreductase
Manual Audit:BIOCAD_RXN-85539 1.1.1.5 Stereospecific Reduction to (S)-Acetoin
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Organism Source

Taxonomy Source

  1. Alangium premnifolium [ncbi taxid: 2918396]
  2. Aloe africana [ncbi taxid: 1080010]
  3. Aloe ferox [ncbi taxid: 117798]
  4. Aloe spicata [ncbi taxid: 992642]
  5. Aloe vera [ncbi taxid: 34199]
  6. Angelica tarokoensis [ncbi taxid: 2831630]
  7. Artemisia argyi [ncbi taxid: 259893]
  8. Artemisia montana [ncbi taxid: 669134]
  9. Artemisia princeps [ncbi taxid: 223870]
  10. Bombax ceiba [ncbi taxid: 45325]
  11. Bragantia wallichii [ncbi taxid: ]
  12. Brassica oleracea [ncbi taxid: 3712]
  13. Citrullus lanatus [ncbi taxid: 3654]
  14. Colobocentrotus atratus [ncbi taxid: 39290]
  15. Delphinium andersoni [ncbi taxid: ]
  16. Diphasia angolensis [ncbi taxid: ]
  17. Epimedium davidii [ncbi taxid: 253605]
  18. Erysimum odoratum [ncbi taxid: 1137569]
  19. Eupolyphaga sinensis [ncbi taxid: 367774]
  20. Eutypella scoparia [ncbi taxid: ]
  21. Fagopyrum esculentum [ncbi taxid: 3617]
  22. Frullania tamarisci [ncbi taxid: 95764]
  23. Galenia africana [ncbi taxid: ]
  24. Globba malaccensis [ncbi taxid: ]
  25. Gnidia lamprantha [ncbi taxid: ]
  26. Gossypium herbaceum [ncbi taxid: 34274]
  27. Hericium erinaceus [ncbi taxid: 91752]
  28. Heterotheca inuloides [ncbi taxid: 3015714]
  29. Homo sapiens [ncbi taxid: 9606]
  30. Ilex amara [ncbi taxid: 185490]
  31. Isodon japonicus [ncbi taxid: 425908]
  32. Knightia excelsa [ncbi taxid: 35944]
  33. Laurencia distichophylla [ncbi taxid: ]
  34. Leonurus glaucescens [ncbi taxid: 445399]
  35. Lepidium draba [ncbi taxid: 153317]
  36. Maba buxifolia [ncbi taxid: ]
  37. Micromeria pineolens [ncbi taxid: 306397]
  38. Nemalion vermiculare [ncbi taxid: 935621]
  39. Nidula candida [ncbi taxid: 1348642]
  40. Ophiocoma scolopendrina [ncbi taxid: 1365868]
  41. Penicillium citreonigrum [ncbi taxid: 69768]
  42. Prunus mume [ncbi taxid: 102107]
  43. Quercus sessiliflora [ncbi taxid: ]
  44. Salacia madagascariensis [ncbi taxid: 670374]
  45. Saussurea carthamoides [ncbi taxid: ]
  46. Solanum acaule [ncbi taxid: 103871]
  47. Spodoptera eridania [ncbi taxid: 37547]
  48. Streptomyces griseovariabilis [ncbi taxid: 284636]
  49. Swertia delavayi [ncbi taxid: 166617]
  50. Vaccinium vitis-idaea [ncbi taxid: 180772]
  51. Vallota purpurea [ncbi taxid: ]
  52. Vinegar [ncbi taxid: ]
  53. Vismia jefensis [ncbi taxid: ]
  54. Vitex rotundifolia [ncbi taxid: 413484]
  55. Zanthoxylum bungeanum [ncbi taxid: 328401]
  56. Zanthoxylum piperitum [ncbi taxid: 354529]
  57. Zanthoxylum schinifolium [ncbi taxid: 354530]
  58. Zea mays [ncbi taxid: 4577]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5920 superpathway of b heme biosynthesis from glycine
BioCyc:META_PWY-5667 CDP-diacylglycerol biosynthesis I
BioCyc:META_PWY-7384 anaerobic energy metabolism (invertebrates, mitochondrial)
BioCyc:META_P125-PWY superpathway of (R,R)-butanediol biosynthesis
BioCyc:META_PWY-6396 superpathway of 2,3-butanediol biosynthesis
BioCyc:META_THRDLCTCAT-PWY L-threonine degradation III (to methylglyoxal)
BioCyc:LEISH_P125-PWY superpathway of (R,R)-butanediol biosynthesis
BioCyc:TRYPANO_P125-PWY superpathway of (R,R)-butanediol biosynthesis
BioCyc:ANTHRA_PWY-5938 (R)-acetoin biosynthesis I
BioCyc:BSUB_P125-PWY superpathway of (R,R)-butanediol biosynthesis
BioCyc:CORYNE_PWY-6389 (S)-acetoin biosynthesis
BioCyc:META_PWY-7140 myricetin gentiobioside biosynthesis
BioCyc:META_PWY-7544 pyruvate to cytochrome bo oxidase electron transfer
BioCyc:META_PWY-7389 superpathway of anaerobic energy metabolism (invertebrates)
BioCyc:META_PWY-5529 superpathway of bacteriochlorophyll a biosynthesis
BioCyc:META_THREOCAT-PWY superpathway of L-threonine metabolism
BioCyc:ECO_PWY-5667 CDP-diacylglycerol biosynthesis I
BioCyc:ECO_THREOCAT-PWY superpathway of L-threonine metabolism
BioCyc:ECO_THRDLCTCAT-PWY L-threonine degradation III (to methylglyoxal)
BioCyc:ECO_PWY-7545 pyruvate to cytochrome bd oxidase electron transfer
View All Pathways