5-Nonanone

Names
IUPAC name

Nonan-5-one[1]

Other names

Dibutyl ketone; n-Butylketone

Identifiers

CAS Number

* 502-56-7 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1743583
ChemSpider |

* 9976 Y

EC Number |

* 207-946-5

MeSH | 5-nonanone

PubChem CID

* 10405

UNII |

* V8B2Y1BZ3S

UN number | 1224

InChI

* InChI=1S/C9H18O/c1-3-5-7-9(10)8-6-4-2/h3-8H2,1-2H3

Key: WSGCRAOTEDLMFQ-UHFFFAOYSA-N

SMILES

* CCCCC(=O)CCCC

Properties

Chemical formula

| 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 pictograms |
GHS Signal word | Danger

GHS hazard statements

| H226, H319, H335, H336, H372

GHS precautionary statements

| P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P303+361+353, P304+340, P305+351+338, P312, P314, P337+313, P370+378, P403+233, P403+235, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

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

## Contents

* 1 Synthesis
* 2 Toxicology
* 2.1 Metabolic pathway
* 2.2 Toxicological effects
* 3 See also
* 4 References

## Synthesis

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

### Metabolic pathway

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

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

* Higher alkanes
* Ketones

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 "5-nonanone - Compound Summary". PubChem Compound Database. National Center for Biotechnology Information, U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/10405. Retrieved December 18, 2018.
2. ↑ 2.0 2.1 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. http://qmro.qmul.ac.uk/xmlui/handle/123456789/16048.
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. ↑ 5.0 5.1 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.

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:5-Nonanone&oldid=366168"
*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[H336]: May cause drowsiness or dizziness
*[H372]: Causes damage to organs through prolonged or repeated exposure
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P314]: Get Medical advice/attention if you feel unwell
*[P337+313]: Get medical advice/attention
*[P370+378]: In case of fire: Use … for extinction
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P403+235]: Store in a well ventilated place. Keep cool
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …