53623-10-2

Basic information

• Product Name: 3,11-dimethylnonacosan-2-one
• Synonyms: 3,11-dimethylnonacosan-2-one;3,11-dimethylnonacosanone
• CAS NO: 53623-10-2
• Molecular Formula: C₃₁H₆₂O
• Molecular Weight: 450.82
• Mol File: 53623-10-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 489.2°Cat760mmHg
• Flash Point: 119.6°C
• Appearance: /
• Density: 0.837g/cm³
• Vapor Pressure: 1.02E-09mmHg at 25°C
• Refractive Index: 1.453
• CAS DataBase Reference: 3,11-dimethylnonacosan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,11-dimethylnonacosan-2-one(53623-10-2)
• EPA Substance Registry System: 3,11-dimethylnonacosan-2-one(53623-10-2)

Safety Data

• Hazardous Substances Data: 53623-10-2(Hazardous Substances Data)

Usage

General Description

3,11-Dimethylnonacosan-2-one is an organic chemical compound categorized as a member of the methyalkanones class. It belongs to the group of Hydrocarbon Derivatives and specifically to Triterpenoids. Also known as izukaenone, this chemical is mainly present in certain plant species and may play a role in their chemical ecology. As a type of lipid molecule, it may contribute to cell membrane structure and function in these organisms. Its role in industrial applications or its implications for human health are not well documented and tend to be more specific to expert domains. 3,11-dimethylnonacosan-2-one is composed of carbon, hydrogen, and oxygen atoms.

InChI:InChI=1/C31H62O/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-23-26-29(2)27-24-21-19-22-25-28-30(3)31(4)32/h29-30H,5-28H2,1-4H3

Synthetic route

3,11-dimethyl-3-nonacosen-2-one (83165-94-0) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
With hydrogen; platinum(IV) oxide In ethanol	90%

3,11-dimethyl 3-ethylcarbonylcosan-2-one (944153-92-8) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrahydrofuran; water at 20℃; for 2h;	73%

1-methyl-2-(8-methylhexacosyl)-1-cyclopropanol (204848-20-4) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 12h; Ambient temperature;	57%

5-methyl-6-oxoheptanoic acid (57998-45-5) + 6-Methyltetracosansaeure (73087-74-8) → 3,11-dimethylnonacosan-2-one (53623-10-2) + 3,10-Dimethyl-2,11-dodecandion (73087-78-2) + 19,28-Dimethylhexatetracontan (73087-79-3)

Conditions	Yield
With potassium hydroxide In methanol coelectroylsis up to pH 9;	A 42.5% B 50% C n/a
With potassium hydroxide In methanol coelectroylsis up to pH 9; Yield given;	A 42.5% B 50% C n/a

1-bromo-8-methylhexacosane (55590-34-6) + triphenylphosphoranylidene-2-butanone (19753-66-3) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
(i) nBuLi, THF, hexane, (ii) /BRN= 1818630/, THF; Multistep reaction;

2,10-dimethyl-octacosanoic acid (56599-07-6) + methyllithium (917-54-4) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
In diethyl ether

2-acetyl-2,10-dimethyl-octacos-10-enoic acid benzyl ester (64245-77-8) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal

3,11-dimethyl-nonacosan-2-ol (59410-40-1) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In acetone

hexanedial (1072-21-5) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 7 steps 1: 65 percent / benzene / 10 h / Heating 2: 80 percent / ammonium nitrate / ethanol / 15 h / 20 - 23 °C 3: 1) Bu-Li / 1) ether, hexane, 0 deg C, 1 h; 2) 20-23 deg C, 2 h 4: 90 percent / H2 / PtO2 / ethanol 5: 50percent H2SO4 / dioxane / 2 h / 40 - 50 °C 6: 1) NaH / 1) THF , t<20 deg C; 2) ether, 35 deg C, 8 h 7: 90 percent / H2 / PtO2 / ethanol View Scheme

8-oxo-non-6-enal (85110-98-1) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: 80 percent / ammonium nitrate / ethanol / 15 h / 20 - 23 °C 2: 1) Bu-Li / 1) ether, hexane, 0 deg C, 1 h; 2) 20-23 deg C, 2 h 3: 90 percent / H2 / PtO2 / ethanol 4: 50percent H2SO4 / dioxane / 2 h / 40 - 50 °C 5: 1) NaH / 1) THF , t<20 deg C; 2) ether, 35 deg C, 8 h 6: 90 percent / H2 / PtO2 / ethanol View Scheme

1,1-diethoxy-6-nonen-8-one (83165-91-7) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) Bu-Li / 1) ether, hexane, 0 deg C, 1 h; 2) 20-23 deg C, 2 h 2: 90 percent / H2 / PtO2 / ethanol 3: 50percent H2SO4 / dioxane / 2 h / 40 - 50 °C 4: 1) NaH / 1) THF , t<20 deg C; 2) ether, 35 deg C, 8 h 5: 90 percent / H2 / PtO2 / ethanol View Scheme

1-bromomethylhexacosan-8-ol (944153-91-7) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / triethylsilane; BF3*OEt2 / CH2Cl2 / 2 h / 0 °C 2: 93 percent / K2CO3; KI / acetone / 20 h / Heating 3: 73 percent / NaOH; tetrabutylammonium hydroxide / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme

1-octadecanol (112-92-5) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 95 percent / phosphorus tribromide / diethyl ether / 2 h / Heating 2.1: Li / diethyl ether / -10 - 10 °C 2.2: 60 percent / diethyl ether / 3 h / 0 °C 3.1: 93 percent / triethylsilane; BF3*OEt2 / CH2Cl2 / 2 h / 0 °C 4.1: 93 percent / K2CO3; KI / acetone / 20 h / Heating 5.1: 73 percent / NaOH; tetrabutylammonium hydroxide / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme

1,8-Octanediol (629-41-4) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: 72 percent / HBr / benzene / 18 h / Heating 2.1: 80 percent / Jones reagent / acetone / 1 h / 0 - 20 °C 3.1: 64 percent / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 4.1: Li / diethyl ether / -10 - 10 °C 4.2: 60 percent / diethyl ether / 3 h / 0 °C 5.1: 93 percent / triethylsilane; BF3*OEt2 / CH2Cl2 / 2 h / 0 °C 6.1: 93 percent / K2CO3; KI / acetone / 20 h / Heating 7.1: 73 percent / NaOH; tetrabutylammonium hydroxide / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme

8-bromooctanoic acid (17696-11-6) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 64 percent / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 2.1: Li / diethyl ether / -10 - 10 °C 2.2: 60 percent / diethyl ether / 3 h / 0 °C 3.1: 93 percent / triethylsilane; BF3*OEt2 / CH2Cl2 / 2 h / 0 °C 4.1: 93 percent / K2CO3; KI / acetone / 20 h / Heating 5.1: 73 percent / NaOH; tetrabutylammonium hydroxide / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme

1-bromo-8-methylhexacosane (55590-34-6) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / K2CO3; KI / acetone / 20 h / Heating 2: 73 percent / NaOH; tetrabutylammonium hydroxide / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: KOH / ethanol / 0.75 h / 180 - 185 °C 2: diethyl ether View Scheme

8-bromooctanol (50816-19-8) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: 80 percent / Jones reagent / acetone / 1 h / 0 - 20 °C 2.1: 64 percent / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C 3.1: Li / diethyl ether / -10 - 10 °C 3.2: 60 percent / diethyl ether / 3 h / 0 °C 4.1: 93 percent / triethylsilane; BF3*OEt2 / CH2Cl2 / 2 h / 0 °C 5.1: 93 percent / K2CO3; KI / acetone / 20 h / Heating 6.1: 73 percent / NaOH; tetrabutylammonium hydroxide / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme

8-bromononan-2-one (52330-02-6) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Li / diethyl ether / -10 - 10 °C 1.2: 60 percent / diethyl ether / 3 h / 0 °C 2.1: 93 percent / triethylsilane; BF3*OEt2 / CH2Cl2 / 2 h / 0 °C 3.1: 93 percent / K2CO3; KI / acetone / 20 h / Heating 4.1: 73 percent / NaOH; tetrabutylammonium hydroxide / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme

1-Bromooctadecane (112-89-0) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Li / diethyl ether / -10 - 10 °C 1.2: 60 percent / diethyl ether / 3 h / 0 °C 2.1: 93 percent / triethylsilane; BF3*OEt2 / CH2Cl2 / 2 h / 0 °C 3.1: 93 percent / K2CO3; KI / acetone / 20 h / Heating 4.1: 73 percent / NaOH; tetrabutylammonium hydroxide / tetrahydrofuran; H2O / 2 h / 20 °C View Scheme

3-Methylheneicosansaeure (66344-19-2) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 66 percent / KOH (neutralisation to 2.8percent) / methanol / coelectrolysis up to pH 8 2: 80 percent / NaOH / methanol; H2O / 10 h / Heating 3: 42.5 percent / KOH (neutralisation to 6percent) / methanol / coelectroylsis up to pH 9 View Scheme

1-octadecylmagnesium bromide (92206-73-0) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: CuCl / diethyl ether / 3 h / 0 °C 2: KOH / methanol / 20 h 3: 66 percent / KOH (neutralisation to 2.8percent) / methanol / coelectrolysis up to pH 8 4: 80 percent / NaOH / methanol; H2O / 10 h / Heating 5: 42.5 percent / KOH (neutralisation to 6percent) / methanol / coelectroylsis up to pH 9 View Scheme

2-Acetyl-2-methyladipinsaeure-diethylester (73087-75-9) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / aq. HCl, 50percent HAc / 24 h / Heating 2: 42.5 percent / KOH (neutralisation to 6percent) / methanol / coelectroylsis up to pH 9 View Scheme

3-Methylheneicosansaeure-sek-butylester → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: KOH / methanol / 20 h 2: 66 percent / KOH (neutralisation to 2.8percent) / methanol / coelectrolysis up to pH 8 3: 80 percent / NaOH / methanol; H2O / 10 h / Heating 4: 42.5 percent / KOH (neutralisation to 6percent) / methanol / coelectroylsis up to pH 9 View Scheme

6-Methyltetracosansaeure-methylester (73087-76-0) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / NaOH / methanol; H2O / 10 h / Heating 2: 42.5 percent / KOH (neutralisation to 6percent) / methanol / coelectroylsis up to pH 9 View Scheme

8-oxononanoic acid (25542-64-7) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 7 steps 1: diethyl ether / 5 °C 2: dimethylformamide; tetrahydrofuran / 36 h / 25 °C 3: H2 / PtO2 4: LiAlH4 / diethyl ether / 6 h / 25 °C 5: aq. HBr, H2SO4 / 5 h / Heating 6: KOH / ethanol / 0.75 h / 180 - 185 °C 7: diethyl ether View Scheme

8-methyl-hexacosan-1-ol (56599-05-4) → 3,11-dimethylnonacosan-2-one (53623-10-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. HBr, H2SO4 / 5 h / Heating 2: KOH / ethanol / 0.75 h / 180 - 185 °C 3: diethyl ether View Scheme

Upstream product

• 57998-45-5 5-methyl-6-oxoheptanoic acid 
• 73087-74-8 6-Methyltetracosansaeure 
• 204848-20-4 1-methyl-2-(8-methylhexacosyl)-1-cyclopropanol 
• 917-54-4 methyllithium 
• 90290-49-6 (2S,10S)-1-((2S,5S)-2,5-Bis-methoxymethoxymethyl-pyrrolidin-1-yl)-2,10-dimethyl-octacosan-1-one 
• 112-89-0 1-Bromooctadecane 
• 52330-02-6 9-bromononan-2-one 
• 50816-19-8 8-bromooctanol 
• 944153-91-7 1-bromomethylhexacosan-8-ol 
• 83165-92-8 1,1-diethoxy-8-methyl-6,8-hexacosadiene 
• 83165-93-9 8-Methyl-hexacosanal 
• 85110-96-9 1,1-diethoxy-8-methylhexacosane 
• 83165-91-7 1,1-diethoxy-6-nonen-8-one 
• 85110-98-1 8-oxo-non-6-enal 

Relevant articles and documents

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A simple and cost effective synthesis of 3,11-dimethylnonacosan-2-one, a female sex pheromone of the German cockroach

A convenient synthesis of 3,11-dimethylnonacosan-2-one (1) is described. Our strategy involves the use of well known C-alkylation and ethyl acetoacetate synthesis reactions as key steps. We expect that this method will prove to be useful for large scale preparation of 1 and modification of dimethylnonacosanones.

A new synthesis of the four stereoisomers of 3,11-dimethyl-2-nonacosanone, the female-produced sex pheromone of the German cockroach

The pure four stereoisomers of 3,11-dimethyl-2-nonacosanone (1), the female-produced sex pheromone of the German cockroach, were synthesized starting from (R)-citronellol (2a) and ethyl (R)-3-hydroxybutanoate (3). The key step was the chromatographic separation of (5RS,6R)-6-hydroxy-5-methyl-2-heptanone (16a) to give pure (5R,6R- and) 5S,6R-isomers. All of the four stereoisomers of 1 were bioactive.

SYNTHETIC INVESTIGATIONS INTO THE ATTRACTING SUBSTANCES (SEX ATTRACTANTS) OF INSECTS. V. SYNTHESIS OF 3,11-DIMETHYL-2-NONACOSANONE, ONE OF THE COMPONENTS OF THE SEX PHEROMONE OF THE GERMAN COCKROACH Blattella germanica L. AND ITS ANALOG 11-METHYL-2-NONACOSANONE

8-Oxo-6-nonenal was obtained by the reaction of adipaldehyde with acetylmethylenetriphenylphosphorane and was converted by acetalization into the unsaturated ketoacetal 1,1-diethoxy-6-nonen-8-one.The latter was converted by reaction with heptadecylmethylenetriphenylphosphorane into 1,1-diethoxy-8-methyl-6,8-hexacosadiene, the hydrogenation of which over platinum oxide led to the saturated 1,1-diethoxy-8-methylhexacosane.This acetal was hydrolyzed under acidic conditions to the corresponding aldehyde 8-methylhexacosanal, which was condensed with 3-diethylphosphono-2-butanone by the Horner reaction without further purification to 3,11-dimethyl-2-nonacosen-2-one.Hydrogenation of the latter over platinum oxide gave the final 3,11-dimethyl-2-nonacosanone, which is one of the components of the sex pheromone of the female German cockroach Blattella germanica L.The reaction of heptadecylmethylenetriphenylphosphorane at one carbonyl group of 2,11-dodecanedione gave 11-methyl-11-nonacosen-2-one, which was converted by hydrogenation over platinum oxide into the analog 11-methyl-2-nonacosanone.