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2-Undecanone

April 18, 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]

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
  • 112-12-9 Y
3D model (JSmol)
  • Interactive image
3DMet
  • B00364
ChEBI
  • CHEBI:17700 Y
ChEMBL
  • ChEMBL1236582
ChemSpider
  • 7871 Y
DrugBank
  • DB08688 Y
ECHA InfoCard 100.003.579
EC Number
  • 203-937-5
KEGG
  • C01875 Y
  • 8163
RTECS number
  • YQ2820000
UNII
  • YV5DSO8CY9 Y
  • DTXSID2021943
  • InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3 Y
    Key: KYWIYKKSMDLRDC-UHFFFAOYSA-N Y
  • InChI=1/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3
    Key: KYWIYKKSMDLRDC-UHFFFAOYAV
  • O=C(CCCCCCCCC)C
Properties
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)
0.00179 g/100 mL (25 °C)
Hazards
GHS labelling:
Warning
H400
P273, P391, P501
NFPA 704 (fire diamond)
Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
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).
Y verify (what is YN ?)

Uses edit

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 edit

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

See also edit

Notes edit

  1. ^ Liang, Minmin; Qi, M; Zhang, C; Zhou, S; Fu, R; Huang, J; et al. (2005). . Analytica Chimica Acta. 531 (1): 97–104. 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 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). from the original on 2008-05-13. Retrieved 2009-01-24.

References edit

  • 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]

April 18, 2024
undecanone, also, known, methyl, nonyl, ketone, organic, compound, with, formula, ch3c, c9h19, colorless, usually, produced, synthetically, also, extracted, from, various, plant, sources, including, from, essential, found, naturally, bananas, cloves, ginger, g. 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 2 Undecanone NamesPreferred IUPAC name Undecan 2 oneOther names Methyl nonyl ketone MNK Nonyl methyl ketoneMethyldecananone2 HendecanoneUndecanoneIBI 246IdentifiersCAS Number 112 12 9 Y3D model JSmol Interactive image3DMet B00364ChEBI CHEBI 17700 YChEMBL ChEMBL1236582ChemSpider 7871 YDrugBank DB08688 YECHA InfoCard 100 003 579EC Number 203 937 5KEGG C01875 YPubChem CID 8163RTECS number YQ2820000UNII YV5DSO8CY9 YCompTox Dashboard EPA DTXSID2021943InChI InChI 1S C11H22O c1 3 4 5 6 7 8 9 10 11 2 12 h3 10H2 1 2H3 YKey KYWIYKKSMDLRDC UHFFFAOYSA N YInChI 1 C11H22O c1 3 4 5 6 7 8 9 10 11 2 12 h3 10H2 1 2H3Key KYWIYKKSMDLRDC UHFFFAOYAVSMILES O C CCCCCCCCC CPropertiesChemical formula C 11H 22OMolar mass 170 296 g mol 1Appearance Colorless liquidDensity 0 829 g cm3 liquidMelting 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 HazardsGHS labelling PictogramsSignal word WarningHazard statements H400Precautionary statements P273 P391 P501NFPA 704 fire diamond 12Flash point 88 C 190 F 361 K Safety data sheet SDS External MSDSRelated compoundsRelated Ketones AcetoneButan 2 one3 pentanoneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Uses 2 Chemical properties 3 See also 4 Notes 5 ReferencesUses editBecause 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 edit2 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 NaOHSee also editPerfume allergyNotes edit 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 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 editLange 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 Retrieved from https en wikipedia org w index php title 2 Undecanone amp oldid 1202469311, wikipedia, wiki, book, books, library,

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