3-Hydroxy-4,5-dimethyl-2(5H)-furanone (BioCAD00000028690)

urine plant natural products microbial natural products

Metabolite Card

Formula: C6H8O3 (128.0473)
SMILES: CC1OC(=O)C(O)=C1C

Synonyms [en]

3-Hydroxy-4,5-dimethyl-2(5H)-furanone; sotolone; 3-Hydroxy-4,5-dimethyl-5H-furan-2-one; sotolon; 4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one; 3-hydroxy-4,5-dimethyl-2,5-dihydrofuran-2-one

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

3-Hydroxy-4,5-dimethyl-2(5H)-furanone. 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: BioCAD00000028690). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Description: 3-Hydroxy-4,5-dimethyl-2(5H)-furanone or sotolone is key flavoring compound found in raw cane sugar, aged sake, coffee, fenugreek, lovage and wines. Sotolon (also known as sotolone) is a lactone and an extremely powerful aroma compound, with the typical smell of fenugreek or curry at high concentrations and maple syrup, caramel, or burnt sugar at lower concentrations. In 1999 it was shown that sotolone is the cause of the odor found in patients with maple syrup urine disease (MSUD) - PMID 10234605. This compound was found in the urine of 7 MSUD patients but was undetectable in normal individuals. 3-Hydroxy-4,5-dimethyl-2(5H)-furanone belongs to the family of Butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Cytoplasm Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 131222-82-7
  • CAS Registry Number: 28664-35-9
  • CAS Registry Number: 87068-69-7
  • CAS Registry Number: 87068-70-0
  • PubChem: 62835
  • ChEBI: ChEBI:67890
  • HMDB: HMDB0031306
  • HMDB: HMDB31306
  • BioCyc: CPD-23998
  • NCBI MeSH: 4,5-dimethyl-3-hydroxy-2(5H)-furanone
  • Wikipedia: Sotolon
  • RefMet: RM0200247
  • Metlin: METLIN_87572
  • Coconut NaturalProduct: CNP0310181.1
  • Coconut NaturalProduct: CNP0310181.2
  • Coconut NaturalProduct: CNP0413738.1
  • Coconut NaturalProduct: CNP0413738.2
  • Coconut NaturalProduct: CNP0600080.0

Class / Ontology

Metabolic Network
ID EC Number Name
BioCyc:RXN-22021 ACETALD + 2-OXOBUTANOATE + PROTON --> CPD-23998 + WATER
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Organism Source

Taxonomy Source

  1. Acacia adunca [ncbi taxid: 204988]
  2. Adiantum lunulatum [ncbi taxid: ]
  3. Alstonia spathulata [ncbi taxid: ]
  4. Amathia pinnata [ncbi taxid: ]
  5. Anacystis montana [ncbi taxid: ]
  6. Annona cornifolia [ncbi taxid: 502529]
  7. Artemisia assoana [ncbi taxid: 1227617]
  8. Asterospicularia laurae [ncbi taxid: 1540332]
  9. Astragalus sempervirens [ncbi taxid: 1532287]
  10. Bishovia boliviensis [ncbi taxid: ]
  11. Blastochloris viridis [ncbi taxid: 1079]
  12. Calostephane divaricata [ncbi taxid: 1548555]
  13. Caragana aurantiaca [ncbi taxid: 626687]
  14. Chaenomeles sinensis [ncbi taxid: ]
  15. Cotyledon secunda [ncbi taxid: ]
  16. Drechslera avenae [ncbi taxid: 33199]
  17. Dumortiera hirsuta [ncbi taxid: 56917]
  18. Eucalyptus melliodora [ncbi taxid: 183838]
  19. Gnetum latifolium [ncbi taxid: 225592]
  20. Goniothalamus malayanus [ncbi taxid: 261094]
  21. Hedysarum connatum [ncbi taxid: ]
  22. Helipterum roseum [ncbi taxid: ]
  23. Hypericum laricifolium [ncbi taxid: 1136989]
  24. Ipomoea digitata [ncbi taxid: ]
  25. Laurencia spectabilis [ncbi taxid: ]
  26. Leathesia nana [ncbi taxid: ]
  27. Lepisorus ussuriensis [ncbi taxid: 699700]
  28. Lysimachia mauritiana [ncbi taxid: 306286]
  29. Marrubium anisodon [ncbi taxid: 2291693]
  30. Nasutitermes ephratae [ncbi taxid: 114633]
  31. Naucleopsis ternstroemiiflora [ncbi taxid: 241899]
  32. Pastinaca sativa [ncbi taxid: 4041]
  33. Peltostigma guatemalense [ncbi taxid: 1136780]
  34. Phoebe pittieri [ncbi taxid: ]
  35. Premna odorata [ncbi taxid: 1037421]
  36. Pseudoalteromonas luteoviolacea [ncbi taxid: 43657]
  37. Rauvolfia vomitoria [ncbi taxid: 403115]
  38. Rumex maritimus [ncbi taxid: 467604]
  39. Sabina sargentii [ncbi taxid: ]
  40. Salvia syriaca [ncbi taxid: 1685717]
  41. Scutellaria amoena [ncbi taxid: 1052904]
  42. Sinularia depressa [ncbi taxid: ]
  43. Solanum laxum [ncbi taxid: 205558]
  44. Streptomyces avermectinius [ncbi taxid: ]
  45. Swertia franchetiana [ncbi taxid: 50785]
  46. Vaccinium oxycoccos [ncbi taxid: 516948]
  47. Viguiera incana [ncbi taxid: 1048928]
  48. Vitis vinifera [ncbi taxid: 29760]
  49. Wikstroemia retusa [ncbi taxid: 1872696]
  50. Zanthoxylum tetraspermum [ncbi taxid: ]

Pathway Synthetic

pathway id name
Reactome:R-HSA-9709957 Sensory Perception
Reactome:R-HSA-381753 Olfactory Signaling Pathway
View All Pathways