2-Undecanone: Difference between revisions

2-Undecanone
Names
	Preferred IUPAC name Undecan-2-one
	Other names Methyl nonyl ketone (MNK); Nonyl methyl ketone; Methyldecananone; 2-Hendecanone; Undecanone; IBI-246
Identifiers
CAS Number	112-12-9 ;
3D model (JSmol)	Interactive image;
3DMet	B00364;
ChEBI	CHEBI:17700 ;
ChEMBL	ChEMBL1236582;
ChemSpider	7871 ;
DrugBank	DB08688 ;
ECHA InfoCard	100.003.579
EC Number	203-937-5;
KEGG	C01875 ;
PubChem CID	8163;
RTECS number	YQ2820000;
UNII	YV5DSO8CY9 ;
CompTox Dashboard (EPA)	DTXSID2021943 ;
	InChI InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3 Key: KYWIYKKSMDLRDC-UHFFFAOYSA-N ; InChI=1/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3 Key: KYWIYKKSMDLRDC-UHFFFAOYAV;
	SMILES O=C(CCCCCCCCC)C;
Properties
Chemical formula	C11H22O
Molar mass	170.296 g·mol−1
Appearance	Colorless liquid
Density	0.829 g/cm3, liquid
Melting point	15 °C (59 °F; 288 K)
Boiling point	231 °C (448 °F; 504 K)
Solubility in water	0.00179 g/100 mL (25 °C)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H400
Precautionary statements	P273, P391, P501
NFPA 704 (fire diamond)	1 2
Flash point	88 °C (190 °F; 361 K)
Safety data sheet (SDS)	External MSDS
Related compounds
Related Ketones	Acetone; Butan-2-one; 3-pentanone
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Latest revision as of 17:46, 19 June 2024

2-Undecanone, also known as methyl nonyl ketone and IBI-246, is the organic compound with the formula CH₃C(O)C₉H₁₉. It a colorless oil. It is usually produced synthetically, but it can also be extracted from various plant sources, including from essential oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, wild-grown tomatoes, and the perennial leaf vegetable Houttuynia cordata.^[1]

Uses

Because of its strong odor it is primarily used as an insect repellent or animal repellent. Typically, 1–2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray, or gel. 2-Undecanone is also used in the perfumery and flavoring industries.

It has been investigated as a mosquito repellant, like DEET.^[2]^[3]

Chemical properties

2-Undecanone is a ketone that is soluble in organic solvents but insoluble in water. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide.

CH₃CO(CH₂)₈CH₃ + 3 NaOCl → CH₃(CH₂)₈COONa + CHCl₃ + 2 NaOH

Notes

^ Liang, Minmin; Qi, M; Zhang, C; Zhou, S; Fu, R; Huang, J; et al. (2005). "Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation". Analytica Chimica Acta. 531 (1): 97–104. Bibcode:2005AcAC..531...97L. doi:10.1016/j.aca.2004.09.082. Archived from the original on 2020-09-14. Retrieved 2024-02-02.
^ Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET Archived 2023-09-28 at the Wayback Machine, Science Daily, June 2002
^ Stephen J. Toth, Jr. and Wayne G. Buhler (2002). "North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes". Pesticide Broadcast. 12 (5). Archived from the original on 2008-05-13. Retrieved 2009-01-24.

References

Lange's Handbook of Chemistry (14th Edition), McGraw-Hill, 1992; Section 1; Table 1.15
The Condensed Chemical Dictionary (10th Edition), Gesner G. Hawley
2-Undecanone from The Good Scents Company
MSDS for 2-Undecanone^{[permanent dead link‍]}

[gcmsav-1] Liang, Minmin; Qi, M; Zhang, C; Zhou, S; Fu, R; Huang, J; et al. (2005). "Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation". Analytica Chimica Acta. 531 (1): 97–104. Bibcode:2005AcAC..531...97L. doi:10.1016/j.aca.2004.09.082. Archived from the original on 2020-09-14. Retrieved 2024-02-02.

[2] Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET Archived 2023-09-28 at the Wayback Machine, Science Daily, June 2002

[3] Stephen J. Toth, Jr. and Wayne G. Buhler (2002). "North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes". Pesticide Broadcast. 12 (5). Archived from the original on 2008-05-13. Retrieved 2009-01-24.

[1]

[2]

[3]

@@ Line 5: / Line 5: @@
 | ImageFile = 2-undecanone.svg
 | ImageName = 2-undecanone
-| IUPACName = Undecan-2-one
+| PIN = Undecan-2-one
 | OtherNames = Methyl nonyl ketone (MNK)<br>Nonyl methyl ketone<br>Methyldecananone<br>2-Hendecanone<br>Undecanone<br>IBI-246
 |Section1={{Chembox Identifiers
@@ Line 19: / Line 19: @@
 | KEGG_Ref = {{keggcite|correct|kegg}}
 | KEGG = C01875
+| PubChem = 8163
+| EC_number = 203-937-5
+| ChEMBL = 1236582
+| 3DMet = B00364
 | InChI = 1/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
 | InChIKey = KYWIYKKSMDLRDC-UHFFFAOYAV
@@ Line 31: / Line 35: @@
 |Section2={{Chembox Properties
 | C=11 | H=22 | O=1
-| Appearance = Colorless or pale yellow liquid
+| Appearance = Colorless liquid
 | Density = 0.829 g/cm<sup>3</sup>, liquid
 | Solubility = 0.00179 g/100 mL (25 °C)
@@ Line 39: / Line 43: @@
 |Section7={{Chembox Hazards
 | ExternalSDS = [http://msds.chem.ox.ac.uk/UN/2-undecanone.html External MSDS]
-| EUClass = Flammable ('''F''')<br />Irritant ('''Xi''')
 | NFPA-H = 1
 | NFPA-F = 2
 | NFPA-R =
-| RPhrases = {{R50}} {{R51}}
+| GHSPictograms = {{GHS09}}
+| GHSSignalWord = Warning
-| SPhrases = {{S23}} {{S24}} {{S25}}
+| HPhrases = {{H-phrases|400}}
+| PPhrases = {{P-phrases|273|391|501}}
 | FlashPtC = 88
   }}
@@ Line 53: / Line 58: @@
 }}
-'''2-Undecanone''', also known as '''methyl nonyl ketone''' and '''IBI-246''', is an oily [[organic chemistry|organic]] liquid manufactured synthetically, but which can also be extracted from oil of [[rue]]. It is found naturally in [[banana]]s, [[clove]]s, [[ginger]], [[guava]], [[strawberries]], wild-grown [[tomato]]es, and the perennial ''[[Houttuynia cordata]]''.<ref name=gcmsav>{{cite journal
+'''2-Undecanone''', also known as '''methyl nonyl ketone''' and '''IBI-246''', is the [[organic compound]] with the formula CH<sub>3</sub>C(O)C<sub>9</sub>H<sub>19</sub>.  It a colorless oil.  It is usually produced synthetically, but it can also be extracted from various plant sources, including from essential oil of [[rue]]. It is found naturally in [[banana]]s, [[clove]]s, [[ginger]], [[guava]], [[strawberries]], wild-grown [[tomato]]es, and the perennial leaf vegetable ''[[Houttuynia cordata]]''.<ref name=gcmsav>{{cite journal
-| last = Liang
+| last1 = Liang
-| first = Minmin
+| first1 = Minmin
 | last2 = Qi
 | first2 = M
@@ Line 65: / Line 70: @@
 | first5 = R
 | last6 = Huang
+| first6 = J
-| first6 = J| title = Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation
+| title = Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation
 | journal = [[Analytica Chimica Acta]]
 | volume = 531
 | issue = 1
 | pages = 97–104
-| publisher =
-| location =
 | year = 2005
+| url = http://ir.rcees.ac.cn/handle/311016/23180
-| url =
-| doi = 10.1016/j.aca.2004.09.082|display-authors=etal}}</ref>
+| doi = 10.1016/j.aca.2004.09.082
+| bibcode = 2005AcAC..531...97L
+| display-authors = etal
+| access-date = 2024-02-02
+| archive-date = 2020-09-14
+| archive-url = https://web.archive.org/web/20200914184859/http://ir.rcees.ac.cn/handle/311016/23180
+| url-status = dead
+}}</ref>
 ==Uses==
--Undecanone is used in the [[perfumery]] and [[flavoring]] industries, but because of its strong odor it is primarily used as an [[insect repellent]] or [[animal repellent]]. Typically, 1&ndash;2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, [[aerosol spray]], or gel.
+Because of its strong odor it is primarily used as an [[insect repellent]] or [[animal repellent]]. Typically, 1&ndash;2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, [[aerosol spray]], or gel.  2-Undecanone is also used in the [[perfumery]] and [[flavoring]] industries.
-Research from North Carolina State University has shown that it may be useful as a [[mosquito]] repellent, as effective as, or even more effective than, [[DEET]].<ref>[http://www.sciencedaily.com/releases/2002/06/020611070622.htm Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET], ''Science Daily'', June 2002</ref><ref>{{cite journal | journal = Pesticide Broadcast | author = Stephen J. Toth, Jr. and Wayne G. Buhler | volume = 12 | issue = 5 | year = 2002 | title = North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes | url = http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html}}</ref>
+It has been investigated as a mosquito repellant, like [[DEET]].<ref>[https://www.sciencedaily.com/releases/2002/06/020611070622.htm Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET] {{Webarchive|url=https://web.archive.org/web/20230928005519/https://www.sciencedaily.com/releases/2002/06/020611070622.htm |date=2023-09-28 }}, ''Science Daily'', June 2002</ref><ref>{{cite journal | journal = Pesticide Broadcast | author = Stephen J. Toth, Jr. and Wayne G. Buhler | volume = 12 | issue = 5 | year = 2002 | title = North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes | url = http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html | access-date = 2009-01-24 | archive-date = 2008-05-13 | archive-url = https://web.archive.org/web/20080513030943/http://ipm.ncsu.edu/current_ipm/Broadcasts/broadcast06-02b.html | url-status = live }}</ref>
 ==Chemical properties==
--Undecanone is a [[ketone]] that  is soluble in [[ethanol]], [[benzene]], [[chloroform]], and [[acetone]], but its large carbon chain renders it insoluble in water. Like most [[methyl]] [[ketone]]s, 2-undecanone undergoes a [[haloform reaction]] when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and [[sodium hypochlorite]] yields [[sodium decanoate]], [[chloroform]], and [[sodium hydroxide]].
+-Undecanone is a [[ketone]] that  is soluble in [[organic solvents]] but insoluble in water. Like most [[methyl]] [[ketone]]s, 2-undecanone undergoes a [[haloform reaction]] when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and [[sodium hypochlorite]] yields [[sodium decanoate]], [[chloroform]], and [[sodium hydroxide]].
 :CH<sub>3</sub>CO(CH<sub>2</sub>)<sub>8</sub>CH<sub>3</sub> + 3 NaOCl → CH<sub>3</sub>(CH<sub>2</sub>)<sub>8</sub>COONa + CHCl<sub>3</sub> + 2 NaOH
@@ Line 96: / Line 107: @@
 * ''The Condensed Chemical Dictionary (10th Edition)'', Gesner G. Hawley
 * [http://www.thegoodscentscompany.com/data/rw1021151.html 2-Undecanone] from The Good Scents Company
-* [http://www.albochem.com/wps/wp-content/2009/01/mnkmsds.pdf MSDS for 2-Undecanone]
+* [http://www.albochem.com/wps/wp-content/2009/01/mnkmsds.pdf MSDS for 2-Undecanone]{{Dead link|date=March 2019 |bot=InternetArchiveBot |fix-attempted=yes }}
 {{DEFAULTSORT:Undecanone, 2-}}
-[[Category:Dialkylketones]]
+[[Category:Alkanones]]
 [[Category:Insect repellents]]

Latest revision as of 17:46, 19 June 2024

Uses

Chemical properties

See also

Notes

References