2-Dodecanone (BioCAD00000028441)
Metabolite Card
Formula: C12H24O (184.1827)
SMILES: CCCCCCCCCCC(C)=O
Synonyms [en]
Dodecan-2-one; 2-Dodecanone; METHYL DECYL KETONE; Decyl methyl ketone; Dodecanone-(2); n-DECYL METHYL KETONE
Last reviewed on 2024-06-28.
Cite this Page
2-Dodecanone. 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: BioCAD00000028441). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
2-Dodecanone, also known as dodecan-2-one or dodecanone-(2) is a 12-carbon long-chain aliphatic molecule that belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 2-Dodecanone is also considered to be a long-chain methyl ketone. 2-Dodecanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It has a low melting point of just 19 oC. 2-Dodecanone has a citrus, floral, or fruity aroma which is contrasted with a fatty taste. 2-Dodecanone has been found in the volatile components of human feces (PMID: 21970810) and saliva (PMID: 24421258). It has also been linked celiac disease in children (PMID: 21970810). Outside of the human body, 2-dodecanone has been found at levels of up to 1.8 mg/kg in blue cheese, milk and cocoa and up to 2700 mg/kg in hop oil (Humulus lupulus). It has also been detected, but not quantified in, several other oils, such as laurel leaf oil, rue oil (Ruta graveolens) and tomato leaves and trichomes (PMID: 11757742). This could make 2-dodecanone a potential biomarker for the consumption of these foods. 2-Dodecanone is a natural insecticide and exhibits strong insecticidal properties to several insect species including Tribolium castaneum (LD50 = 5.21 ug/adult), Lasioderma serricorne (LD50 = 2.54 ug/adult) and Liposcelis bostrychophila (LD50 = 23.41 ug/cm2) in contact assays (PMID: 31240663).
DBLinks
- CAS Registry Number: 6175-49-1
- PubChem CID: 22556
- ChEBI: 89284
- HMDB: HMDB0031019
- LipidMaps: LMFA12000163
- KEGG: C14996
- BioCyc:
- NCBI MeSH:
- Wikipedia:
Other DBLinks
- CAS Registry Number: 6175-49-1
- PubChem: 22556
- ChEBI: ChEBI:89284
- HMDB: HMDB0031019
- LipidMaps: LMFA12000163
- KEGG: C14996
- RefMet: RM0153420
- MoNA: FiehnLibVolatile0157
- MoNA: HMDB0031019_c_ms_100585
- MoNA: JP007052
- Metlin: METLIN_98163
- Coconut NaturalProduct: CNP0168691.0
Class / Ontology
- WishartLab ClassyFire: [Carbonyl compounds] Carbonyl compounds
- RefMet: [Oxygenated hydrocarbons] Oxygenated hydrocarbons
- LipidMaps: [Oxygenated hydrocarbons [FA12]] Oxygenated hydrocarbons [FA12]
- ChEBI: [CHEBI:89284] 2-Dodecanone
- Coconut NaturalProduct: [Oxygenated hydrocarbons] Oxygenated hydrocarbons
Taxonomy Source
- Akebia quinata [ncbi taxid: 13331]
- Akebia trifoliata [ncbi taxid: 155132]
- Flavobacterium aRK10267 [ncbi taxid: ]
- Hansenia forbesii [ncbi taxid: 165499]
- Hansenia weberbaueriana [ncbi taxid: 54724]
- Homo sapiens [ncbi taxid: 9606]
- Houttuynia cordata [ncbi taxid: 16752]
- Houttuynia emeiensis [ncbi taxid: ]
- Humulus lupulus [ncbi taxid: 3486]
- Kobus ellipsiprymnus [ncbi taxid: 9962]
- Ostericum grosseserratum [ncbi taxid: 182415]
- Pinellia ternata [ncbi taxid: 199225]
- Ruta graveolens [ncbi taxid: 37565]
- Zanthoxylum brachyacanthum [ncbi taxid: 1056464]
Pathway Synthetic
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