1117-41-5

Basic information

• Product Name: 3,6,10-trimethylundeca-3,5,9-trien-2-one
• Synonyms: 3,6,10-trimethylundeca-3,5,9-trien-2-one;3,5,9-Undecatrien-2-one, 3,6,10-trimethyl-;3,6,10-TRIMETHYL-3,5,9-UNDECATRIEN-2-ONE;METHYLISOPSEUDOIONONE;2,6,9-Trimethyl-2,6,8-undecatriene-10-one;3-Methylpseudoionone
• CAS NO: 1117-41-5
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.32388
• EINECS: 214-245-8
• Product Categories: Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1117-41-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 285.19°C (rough estimate)
• Flash Point: 137.6°C
• Appearance: /
• Density: 0.9438 (rough estimate)
• Vapor Pressure: 0.000493mmHg at 25°C
• Refractive Index: 1.5162 (estimate)
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: 3,6,10-trimethylundeca-3,5,9-trien-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6,10-trimethylundeca-3,5,9-trien-2-one(1117-41-5)
• EPA Substance Registry System: 3,6,10-trimethylundeca-3,5,9-trien-2-one(1117-41-5)

Safety Data

• Hazardous Substances Data: 1117-41-5(Hazardous Substances Data)

Usage

Uses

Methylisopseudoionone, is the derivative of Ionone (I731275), which is a aroma compound found in essential oils such as rose oil, and thus can be used in the perfumery industry.

InChI:InChI=1/C14H22O/c1-11(2)7-6-8-12(3)9-10-13(4)14(5)15/h7,9-10H,6,8H2,1-5H3

Synthetic route

butanone (78-93-3) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → pseudoionone (1117-41-5) + 7,10-dimethyl-dodeca-4,6,10-trien-3-one

Conditions	Yield
With alkali

Geraniol (106-24-1) + butanone (78-93-3) → pseudoionone (1117-41-5) + 7,10-dimethyl-dodeca-4,6,10-trien-3-one

Conditions	Yield
With aluminium(III) phenoxide; benzene
With aluminum tri-tert-butoxide; benzene

1-Bromo-2-butanone (816-40-0) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → pseudoionone (1117-41-5) + 7,10-dimethyl-dodeca-4,6,10-trien-3-one

Conditions	Yield
With magnesium; toluene; mercury dichloride beim Behandeln des nicht naeher beschriebenen Reaktionsprodukts mit Natriumaethylat-Loesung und folgenden Destillieren;

3-(triphenylphosphoranylidene)butan-2-one (26487-92-3) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → pseudoionone (1117-41-5)

Conditions	Yield
In dibutyl ether

3,6,10-trimethyl-undeca-3,5,9-trien-2-ol (60437-18-5) → pseudoionone (1117-41-5)

Conditions	Yield
With manganese(IV) oxide In Petroleum ether

2,5,9-trimethyl-deca-2,4,8-trienal (60437-19-6) → pseudoionone (1117-41-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: MnO2 / petroleum ether View Scheme

butanone (78-93-3) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → pseudoionone (1117-41-5) + 7,11-dimethyl-dodeca-4,6,10-trien-3-one (26651-96-7)

Conditions	Yield
With sodium hydroxide In water at 120 - 138℃; for 0.0666667h; Product distribution / selectivity;
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 60℃; for 6h; Inert atmosphere;
With AMBERLYSTA26OH In ethanol at 40℃; for 8h; Temperature; Aldol Condensation; Inert atmosphere;

pseudoionone (1117-41-5) → alpha-isomethylionone (15789-90-9)

Conditions	Yield
With sulfuric acid

pseudoionone (1117-41-5) → 3,6,10-trimethyl-undecan-2-one (60437-20-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol

pseudoionone (1117-41-5) + bromoacetic acid methyl ester (96-32-2) → (2E,4E,6E)-3,4,7,11-Tetramethyl-dodeca-2,4,6,10-tetraenoic acid methyl ester (60437-09-4)

Conditions	Yield
(i) Zn, benzene, (ii) POCl3, Py; Multistep reaction;

pseudoionone (1117-41-5) + methyl (triphenylphosphoranylidene)acetate (21204-67-1) → (2E,4E,6E)-3,4,7,11-Tetramethyl-dodeca-2,4,6,10-tetraenoic acid methyl ester (60437-09-4)

Conditions	Yield
With benzoic acid In benzene

pseudoionone (1117-41-5) + 7,10-dimethyl-dodeca-4,6,10-trien-3-one → (E)-8-methyl-β-ionone (51703-99-2) + 1t(?)-<2.2.6-trimethyl-cyclohexen-(6)-yl>-penten-(1)-one-(3)

Conditions	Yield
With sulfuric acid

pseudoionone (1117-41-5) + 7,10-dimethyl-dodeca-4,6,10-trien-3-one → alpha-isomethylionone (15789-90-9) + (+-)-1t(?)-<2.2.6-trimethyl-cyclohexen-(5)-yl>-penten-(1)-one-(3)

Conditions	Yield
With formic acid bei Siedetemperatur;
With phosphoric acid at 30 - 35℃;
With sulfuric acid
With formic acid bei Siedetemperatur;

pseudoionone (1117-41-5) + 7,10-dimethyl-dodeca-4,6,10-trien-3-one → (4E)-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-penten-3-one (63429-28-7) + 2-methyl-1t(?)-<2.2.6-trimethyl-cyclohexen-(6)-yl>-buten-(1)-one-(3)

Conditions	Yield
With sulfuric acid

pseudoionone (1117-41-5) + 7,10-dimethyl-dodeca-4,6,10-trien-3-one → alpha-Methyl-ionone (93302-56-8) + 2-methyl-1t(?)-<2.2.6-trimethyl-cyclohexen-(5)-yl>-buten-(1)-one-(3)

Conditions	Yield
With formic acid bei Siedetemperatur;
With sulfuric acid
With phosphoric acid at 30 - 35℃;
With formic acid bei Siedetemperatur;

pseudoionone (1117-41-5) → 3-methyl-4t-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-one semicarbazone (17737-40-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid View Scheme

pseudoionone (1117-41-5) → (+/-)-3-methyl-4t-(2,6,6-trimethyl-cyclohex-2-enyl)-but-3-en-2-one semicarbazone (1028-07-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous phosphoric acid / 30 - 35 °C View Scheme

pseudoionone (1117-41-5) → C17H32O2 (60437-14-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd-C / ethanol 2: (i) Zn, benzene, (ii) POCl3, Py View Scheme
Multi-step reaction with 2 steps 1: H2 / Pd-C / ethanol 2: PhCO2H / benzene View Scheme

pseudoionone (1117-41-5) → C13H20O2

Conditions	Yield
With ferredoxin reductase; [2Fe-2S] ferredoxin; Novosphingobium aromaticivorans DSM12444 monooxygenase CYP101B1; NADH; bovine liver catalase In aq. buffer Enzymatic reaction; regioselective reaction;

Upstream product

• 78-93-3 butanone 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 106-24-1 Geraniol 
• 816-40-0 1-Bromo-2-butanone 
• 26487-92-3 3-(triphenylphosphoranylidene)butan-2-one 
• 60437-18-5 3,6,10-trimethyl-undeca-3,5,9-trien-2-ol 
• 60437-19-6 2,5,9-trimethyl-deca-2,4,8-trienal 

Downstream Products

• 15789-90-9 alpha-isomethylionone 
• 1028-07-5 (+/-)-3-methyl-4t-(2,6,6-trimethyl-cyclohex-2-enyl)-but-3-en-2-one semicarbazone 
• 17737-40-5 3-methyl-4t-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-one semicarbazone 
• 93302-56-8 alpha-Methyl-ionone 
• 63429-28-7 (4E)-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-4-penten-3-one 
• 51703-99-2 (E)-8-methyl-β-ionone 

Relevant articles and documents

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Aldol Condensations Catalyzed by Basic Anion-Exchange Resins

The aldol condensations of various aldehydes with ketones in the presence of anionic (basic) ion-exchange resins have been investigated. Both batch and continuous modes were studied and compared for the reaction of citral (a mixture of geranial and neral) with acetone to give ψ-ionone. Different reaction conditions were investigated, and the performances of five different ion-exchange resins were compared. The most stable resins could be used for 10 cycles in batch mode or 1000 min in continuous mode without a significant loss in activity or selectivity.

Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions

Choline hydroxide was used as a basic catalyst for aldol condensation reactions to produce new C-C bonds between several ketones and aldehydes. Choline supported on MgO exhibits higher TOF values than other well known basic catalysts in these reactions.