5-Nonanone

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5-Nonanone
5-Nonanone.svg
Names
Preferred IUPAC name
Nonan-5-one[1]
Other names
Dibutyl ketone; n-Butylketone
Identifiers
3D model (JSmol)
1743583
ChemSpider
ECHA InfoCard 100.007.224 Edit this at Wikidata
EC Number
  • 207-946-5
MeSH 5-nonanone
UNII
UN number 1224
  • InChI=1S/C9H18O/c1-3-5-7-9(10)8-6-4-2/h3-8H2,1-2H3
    Key: WSGCRAOTEDLMFQ-UHFFFAOYSA-N
  • CCCCC(=O)CCCC
Properties
C9H18O
Molar mass 142.242 g·mol−1
Appearance Colorless
Density 0.82 g/mL[1]
Melting point −4 °C; 25 °F; 269 K
Boiling point 188.5 °C; 371.2 °F; 461.6 K
log P 2.88[1]
Vapor pressure 0.073 kPa (at 25.0 °C)[1]
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H226, H319, H335, H336, H372
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P314, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5-Nonanone, or dibutyl ketone, is the organic compound with the formula (CH3CH2CH2CH2)2CO. This colorless liquid is a symmetrical ketone.[2]

Synthesis[edit]

5-Nonanone, which is potentially of interest as a diesel fuel, can be produced from levulinic acid, which can be produced from fructose. Levulinic acid is converted to valeric acid, which undergoes ketonization.[3]

Toxicology[edit]

Metabolic pathway[edit]

5-Nonanone was expected to be metabolized to a γ-diketone (a diketone with the second oxygen three carbons away from the first, e.g. 2,5- or 3,6-diketones).

Metabolic studies confirmed the in vivo ω-oxidation of 5-nonanone to 2,5-nonanedione and 2-hexanone. Subsequent oxidative and decarboxylative steps also produce 2,5-hexanedione. Besides these metabolites, 38% of the 5-nonanone dose is converted to carbon dioxide. No unchanged 5-nonanone is detected in the urine after administration.[4]

Of these metabolites, 2,5-hexanedione is believed to be the most neurotoxic compound. Of all the aforementioned metabolites, the toxicity is believed to be due to the metabolic transformation to this γ-diketone.[5]

Toxicological effects[edit]

In rats, the neurotoxicity of 5-nonanone is enhanced by methyl ethyl ketone. This suggests induction of microsomal oxidizing enzymes, which results in greater production of toxic metabolites. Chronic exposure to the compound has been shown to produce a clinical neuropathy, characterized by giant axonal swellings filled with neurofilaments. It also resulted in an orange/brown discoloration of the hair of the rats.[2]

Another study was done on rats to explore the enhancement of the toxicity of 5-nonanone by 5-methyl-2-octanone. The combination of these two compounds increases the neurotoxic effect of 5-nonanone approximately sixfold. When only exposed to 5-methyl-2-octanone liver swelling was observed, indicating that metabolic activation of hepatic oxidative enzymes may be the cause of the increase in toxicity in co-administration.[5]

See also[edit]

References[edit]

  1. ^ a b c d e f "5-nonanone - Compound Summary". PubChem Compound Database. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved December 18, 2018.
  2. ^ a b Mark A. Shifman; Doyle G. Graham; Jeff W. Priest; Thomas W. Bouldin (1981). "The neurotoxicity of 5-nonanone: Preliminary report". Toxicology Letters. 8 (4–5): 283–288. doi:10.1016/0378-4274(81)90114-4. PMID 7268811.
  3. ^ Pileidis, Filoklis D.; Titirici, Maria-Magdalena (2016). "Levulinic Acid Biorefineries: New Challenges for Efficient Utilization of Biomass". ChemSusChem. 9 (6): 562–582. doi:10.1002/cssc.201501405. PMID 26847212.
  4. ^ Bingham, E.; Cohrssen, B.; Powell, C.H. (2012). Patty's Toxicology. John Wiley & Sons. p. 6–316. ISBN 978-0-470-41081-3.
  5. ^ a b John L. O'Donoghue; Walter J. Krasavage; George D. DiVincenzo; Donald A. Ziegler (1982). "Commercial-grade methyl heptyl ketone (5-methyl-2-octanone) neurotoxicity: Contribution of 5-nonanone". Toxicology and Applied Pharmacology. 62 (2): 307–316. doi:10.1016/0041-008X(82)90129-6. PMID 7058532.