13215-88-8

Basic information

• Product Name: Tabanone
• Synonyms: 3,5,5-trimethyl-4-butenylidene-2-cyclohexen-1-one;4-(2-Butenylidene)-3,5,5-trimethylcyclohex-2-en-1-one;megastigmatrienone;tabanone;2-Cyclohexen-1-one, 4-(2-butenylidene)-3,5,5-trimethyl-;4-(2-Butenyliden)-3,5,5-trimethylcyclohex-2-en-1-on;TABANON;4,6,8-Megastigmatrien-3-one
• CAS NO: 13215-88-8
• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.28142
• EINECS: 236-187-2
• Mol File: 13215-88-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 289°C
• Flash Point: 124.8°C
• Appearance: /
• Density: 0.968
• Vapor Pressure: 0.00223mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: 2-8°C
• Water Solubility: 361mg/L at 20℃
• CAS DataBase Reference: Tabanone(CAS DataBase Reference)
• NIST Chemistry Reference: Tabanone(13215-88-8)
• EPA Substance Registry System: Tabanone(13215-88-8)

Safety Data

• Hazardous Substances Data: 13215-88-8(Hazardous Substances Data)

Usage

Description

Tabanone is a slightly yellow to yellow liquid with a warm, dry, sweet, and tobacco-like odor. It is predominantly used in tobacco flavors and is also utilized to create powdery tobacco nuances in fragrances. Tabanone is found in the oils of Trifolium pratense L. and is recognized as a potential natural antioxidant.

Uses

Used in Tobacco Industry:
Tabanone is used as a flavoring agent for its warm, dry, sweet, and tobacco-like odor, enhancing the taste and aroma of tobacco products.
Used in Fragrance Industry:
Tabanone is used as a fragrance ingredient to create powdery tobacco nuances, adding depth and complexity to various scent compositions.
Used as a Natural Antioxidant:
Tabanone, being a potential natural antioxidant, can be utilized in various industries where antioxidants are required to prevent oxidation and extend the shelf life of products.

Flammability and Explosibility

Notclassified

Trade name

Tabanon (Symrise)

InChI:InChI=1/C13H18O/c1-5-6-7-12-10(2)8-11(14)9-13(12,3)4/h5-8H,9H2,1-4H3/b6-5+,12-7+

Synthetic route

3-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)-but-3-en-2-one (127-51-5) → 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8)

Conditions	Yield
Stage #1: 3-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)-but-3-en-2-one With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In acetone at 30 - 35℃; for 4h; Stage #2: With potassium borohydride In ethanol at 25℃;	52.7%

9-hydroxymegastigma-4,7-dien-3-one (896107-70-3) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 2,6,6-trimethyl-1,4-cyclohexanedione (20547-99-3) + 2,6,6-trimethyl-2-cyclohexene-1,4-dione (1125-21-9) + 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8) + megastigmatrienone

Conditions	Yield
In water Heating; pH=1;

3,4-Dehydro-3-phenylthio-β-ionol → 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8)

Conditions	Yield
With hydrogenchloride for 0.5h; Ambient temperature; Yield given;

6-Bromo-8-but-3-enyl-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-7-ene (149457-34-1) → 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8) + 4-<(E)-Buta-1,3-dienyl>-3,5,5-trimethylcyclohex-2-enone (38818-55-2) + 4-(But-3-enylidene)-3,5,5-trimethylcyclohex-2-enone

Conditions	Yield
With hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) toluene, reflux, 5 h, 2.) THF, 25 deg C, 5 h; Yield given. Multistep reaction. Yields of byproduct given;

7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one (14203-64-6) → 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / Li / tetrahydrofuran / 1.) 10-15 deg C, 2.) r.t., 1 h 2: 80 percent / PBr3, pyridine / toluene / 1 h / -10 °C 3: 1.) DBU, 2.) 1 M aq. HCl / 1.) toluene, reflux, 5 h, 2.) THF, 25 deg C, 5 h View Scheme

8-(But-3-enyl)-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-ol (149457-31-8) → 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / PBr3, pyridine / toluene / 1 h / -10 °C 2: 1.) DBU, 2.) 1 M aq. HCl / 1.) toluene, reflux, 5 h, 2.) THF, 25 deg C, 5 h View Scheme

(3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one (14398-35-7) → 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: CH3COOH / ethanol / 2 h / 40 °C 2: 2.) DBU / 1.) CH2Cl2, -30 deg C, 15 min, 2.) 0 deg C to r.t., 1 h 3: CH2O / tetrahydrofuran; H2O / 1 h / Ambient temperature 4: NaBH4 / methanol / 0.5 h / 0 °C 5: 2 N HCl / 0.5 h / Ambient temperature View Scheme

(E)-4-(2,6,6-Trimethyl-4-phenylsulfanyl-cyclohexa-1,3-dienyl)-but-3-en-2-one → 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / methanol / 0.5 h / 0 °C 2: 2 N HCl / 0.5 h / Ambient temperature View Scheme

N'-[(E)-1-Methyl-3-(2,6,6-trimethyl-cyclohexa-1,3-dienyl)-prop-2-en-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester → 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 2.) DBU / 1.) CH2Cl2, -30 deg C, 15 min, 2.) 0 deg C to r.t., 1 h 2: CH2O / tetrahydrofuran; H2O / 1 h / Ambient temperature 3: NaBH4 / methanol / 0.5 h / 0 °C 4: 2 N HCl / 0.5 h / Ambient temperature View Scheme

N'-[(E)-1-Methyl-3-(2,6,6-trimethyl-4-phenylsulfanyl-cyclohexa-1,3-dienyl)-prop-2-en-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester → 4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: CH2O / tetrahydrofuran; H2O / 1 h / Ambient temperature 2: NaBH4 / methanol / 0.5 h / 0 °C 3: 2 N HCl / 0.5 h / Ambient temperature View Scheme

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8) → 2,6,6-trimethyl-4-oxo-1-cyclohexenylidenacetaldehyde (16825-04-0)

Conditions	Yield
With pyridine; ozone; triphenylphosphine 1.) CH2Cl2, -78 deg C, 0.5 h; 2.) CH2Cl2, r.t., 1 h; Yield given. Multistep reaction;

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8) → 3,5,5-Trimethyl-4-[1-(3-methyl-oxiranyl)-meth-(Z)-ylidene]-cyclohex-2-enone (80945-22-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 4h;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 2h;

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8) + methyl iodide (74-88-4) → (E,Z)-2-methylmegastigma-4,6,8-trien-3-one + (E,E/Z)-2,2-dimethylmegastigma-4,6,8-trien-3-one + (Z,Z)-2,2-dimethylmegastigma-4,6,8-trien-3-one + (Z,E)-2,2-dimethylmegastigma-4,6,8-trien-3-one

Conditions	Yield
With potassium tert-butylate 1.) THF, -78 deg C, 5 h, 2.) THF, -78 deg C, 1 h; r.t., 1 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8) + methyl iodide (74-88-4) → (E,E)-2-methylmegastigma-4,6,8-trien-3-one + (E,E/Z)-2,2-dimethylmegastigma-4,6,8-trien-3-one + (Z,Z)-2,2-dimethylmegastigma-4,6,8-trien-3-one + (Z,E)-2,2-dimethylmegastigma-4,6,8-trien-3-one

Conditions	Yield
With potassium tert-butylate 1.) THF, -78 deg C, 5 h, 2.) THF, -78 deg C, 1 h; r.t., 1 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8) + methyl iodide (74-88-4) → (Z,Z)-2-methylmegastigma-4,6,8-trien-3-one + (E,E/Z)-2,2-dimethylmegastigma-4,6,8-trien-3-one + (Z,Z)-2,2-dimethylmegastigma-4,6,8-trien-3-one + (Z,E)-2,2-dimethylmegastigma-4,6,8-trien-3-one

Conditions	Yield
With potassium tert-butylate 1.) THF, -78 deg C, 5 h, 2.) THF, -78 deg C, 1 h; r.t., 1 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone (13215-88-8) + methyl iodide (74-88-4) → (Z,E)-2-methylmegastigma-4,6,8-trien-3-one + (E,E/Z)-2,2-dimethylmegastigma-4,6,8-trien-3-one + (Z,Z)-2,2-dimethylmegastigma-4,6,8-trien-3-one + (Z,E)-2,2-dimethylmegastigma-4,6,8-trien-3-one

Conditions	Yield
With potassium tert-butylate 1.) THF, -78 deg C, 5 h, 2.) THF, -78 deg C, 1 h; r.t., 1 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

Upstream product

• 127-51-5 3-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)-but-3-en-2-one 
• 14398-35-7 (3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one 
• 149457-31-8 8-(But-3-enyl)-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-ol 
• 14203-64-6 7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one 
• 149457-34-1 6-Bromo-8-but-3-enyl-7,9,9-trimethyl-1,4-dioxaspiro[4.5]dec-7-ene 
• 896107-70-3 9-hydroxymegastigma-4,7-dien-3-one 

Downstream Products

• 80945-22-8 3,5,5-Trimethyl-4-[1-(3-methyl-oxiranyl)-meth-(Z)-ylidene]-cyclohex-2-enone 
• 16825-04-0 2,6,6-trimethyl-4-oxo-1-cyclohexenylidenacetaldehyde 

Relevant articles and documents

Synthesis method of Megastigmatrienone

The invention discloses a synthesis method of Megastigmatrienone. The method is characterized by comprising the steps: performing oxidation on alpha-ionone by using tert-butyl hydroperoxide under thecatalysis action of Vanadiumoxy Acetylacetonate so as to generate 3-oxo-alpha-ionone, performing hydroboration on 3-oxo-alpha-ionone in an ethanol solution so as to obtain 3-oxo-alpha-ionol, adding solid p-toluenesulfonic acid directly, and performing reflux dehydration so as to obtain Megastigmatrienone. The method has a simple process and simple conditions, and is more beneficial to industrialized production.

Bromination and sulfenylation of polyenone hydrazones

Ethoxycarbonylhydrazones of dienones are brominated and sulfenylated at the δ-position. Reduction with borohydride and subsequent hydrolysis lead to a 1,5-transposition of the carbonyl group.