586-62-9

Basic information

• Product Name: Terpinolene
• Synonyms: 1,4(8)-terpadiene;1-Methyl-4-(1-methylethylidene)-1-cyclohexene;1-methyl-4-(1-methylethylidene)-cyclohexen;1-methyl-4-(1-methylethylidene)-cyclohexene (alpha-terpinolene);1-methyl-4-isopropylidene-1-cyclohexene;3-methyl-6-(1-methylethylidene)-cyclohexen;alpha- Terpinolen;femanumber3046
• CAS NO: 586-62-9
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23404
• EINECS: 205-341-0
• Product Categories: Biochemistry;Monocyclic Monoterpenes;Terpenes
• Mol File: 586-62-9.mol
• Article Data: 89

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 184-185 °C(lit.)
• Flash Point: 148 °F
• Appearance: /
• Density: 0.861 g/mL at 25 °C(lit.)
• Vapor Density: ~4.7 (vs air)
• Vapor Pressure: ~0.5 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.489(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: 6.812mg/L(25 oC)
• BRN: 1851203
• CAS DataBase Reference: Terpinolene(CAS DataBase Reference)
• NIST Chemistry Reference: Terpinolene(586-62-9)
• EPA Substance Registry System: Terpinolene(586-62-9)

Safety Data

• Hazard Codes: N
• Statements: 50/53-65-43
• Safety Statements: 60-61-24/25-22-23-62
• RIDADR: UN 2541 3/PG 3
• WGK Germany: 3
• RTECS: WZ6870000
• F: 10
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 586-62-9(Hazardous Substances Data)

Usage

Description

Terpinolene, a p-menthadiene with double bonds at positions 1 and 4(8), is a colorless liquid that is insoluble in water and less dense than water. It has a pleasant sweet-piney odor with a somewhat sweet, citrus flavor. Terpinolene is found in various natural sources such as citrus juices and oils, black currant, guava, papaya, raspberry, and various spice and mint oils, among others.

Uses

Used in Flavor and Fragrance Industry:
Terpinolene is used as a flavoring agent for its sweet, citrus taste and as a fragrance component for its sweet, fresh, piney citrus aroma with a woody, old lemon peel nuance. It is commonly found in essential oils and contributes to the characteristic scents of various plants and fruits.
Used in Solvent Applications:
Terpinolene serves as a solvent for resins and essential oils, facilitating the blending and processing of these substances in various industrial applications.
Used in Plastics and Resins Manufacturing:
Terpinolene is utilized in the production of synthetic resins and plastics, thanks to its compatibility with other chemicals and its ability to enhance the properties of the final products.
Used in the Manufacture of Synthetic Flavors:
Terpinolene is employed in the creation of synthetic flavors, leveraging its sweet, citrus taste to enhance the flavor profiles of various food and beverage products.

Preparation

By alcoholic sulphuric acid treatment of pinene (Arctander, 1969).

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Terpinolene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions.

Hazard

Flammable, moderate fire risk.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Flammability and Explosibility

Notclassified

Pharmacology

Combinations of terpenes, such as terpinolene, with nonionic surfactants and stabilizers have been patented for use as gallstone solvents. Human cholesterol calculi heated in mixtures containing terpinolene and human bile were dissolved within 1-2 hr (Hisamitsu Pharmaceutical Co., Inc., 1973).

Safety Profile

Mildly toxic by ingestion. A very dangerous fire hazard when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. Can react with oxidning materials. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,9H,5,7H2,1-3H3

Synthetic route

2,2,6-trimethyl-1-oxa-spira[2.5]oct-ene (4584-23-0) → Terpinolene (586-62-9)

Conditions	Yield
With lithium; biphenyl In 1,2-dimethoxyethane for 5.5h;	75%

terpinolene oxide (6784-10-7) → Terpinolene (586-62-9)

Conditions	Yield
With lithium In tetrahydrofuran for 98h; Heating;	75%

terpinolene sulphide → Terpinolene (586-62-9)

Conditions	Yield
With biphenyl; lithium In 1,2-dimethoxyethane for 12h; Heating;	70.1%

carbon monoxide (201230-82-2) + limonene. (138-86-3) → Terpinolene (586-62-9) + 3-(4-methyl-3-cyclohexen-1-yl)-butyraldehyde (6784-13-0)

Conditions	Yield
With hydrogen In toluene at 80℃; under 30402 Torr; for 24h; Catalytic behavior; Autoclave;	A 32% B 68%

(2E)-1-fluoro-3,7-dimethylocta-2,6-diene (117969-60-5) → Terpinolene (586-62-9) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5) + 4-(1-fluoro-1-methylethyl)-1-methylcyclohexene (1543-97-1) + 3-fluoro-3,7-dimethylocta-1,6-diene (125081-51-8)

Conditions	Yield
In C6D6 at 60℃; for 24h; Inert atmosphere; NMR tube (teflon insert);	A 6% B 10% C 59% D 10%

D-limonene (5989-27-5) → 1-methyl-4-isopropenylbenzene (1195-32-0) + Terpinolene (586-62-9) + 1-methyl-4-isopropyl-1,3-cyclohexadiene (99-86-5)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; palladium(II) trifluoroacetate; copper dichloride In N,N-dimethyl-formamide at 80℃; for 40h; Inert atmosphere; Molecular sieve;	A 57% B 8% C 5%

2,2,6-trimethyl-1-oxa-spira[2.5]oct-ene (4584-23-0) → Terpinolene (586-62-9) + p-cymene-8-ol (1197-01-9) + TERPINEN-4-OL (562-74-3) + terpineol (98-55-5)

Conditions	Yield
With sodium In tetrahydrofuran at 65℃; for 12h;	A 4% B 16% C 48% D 26%

Upstream product

• 64-18-6 formic acid 
• 98-55-5 terpineol 
• 586-81-2 γ-terpineol 
• 80-56-8 rac-α-pinene 
• 138-86-3 limonene. 
• 2451-01-6 cis-4-hydroxy-α,α,4-trimethyl-cyclohexanemethanol, monohydrate 
• 177698-19-0 Beta-pinene 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 4584-23-0 2,2,6-trimethyl-1-oxa-spira[2.5]oct-ene 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 586-63-0 isoterpinolene 
• 39864-10-3 α-terpinyl chloride 
• 557-34-6 zinc diacetate 
• 6784-10-7 terpinolene oxide 

Downstream Products

• 99-87-6 4-methylisopropylbenzene 
• 98-55-5 terpineol 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 1197-01-9 p-cymene-8-ol 
• 99-85-4 crithmene 
• 80699-58-7 1-methyl4-<1-(3,7-dimethyloctyloxy)-1-methylethyl>-1-cyclohexene 
• 80699-57-6 1-methyl-4-<1-(3,7-dimethyloctyloxy)-1-methylethyl>benzene 
• 4584-23-0 2,2,6-trimethyl-1-oxa-spira[2.5]oct-ene 
• 6784-10-7 terpinolene oxide 
• 30576-84-2 C₁₀H₁₆O₂ 
• 64-19-7 acetic acid 
• 123-76-2 levulinic acid 
• 500-00-5 3-p-menthene 
• 138-86-3 limonene. 

Relevant articles and documents

Sustainable p-cymene and hydrogen from limonene

A fine chemical intermediate in a wide range of chemical processes, p-cymene, has been obtained from Limonene, solids based on a natural clay (sepiolite) modified with sodium, nickel, iron or manganese oxides and programmable focalised microwaves. The process has the added bonus of one mol of hydrogen being produced per mol of limonene converted to p-cymene.

Aromatization of Hydrocarbons y Oxidative Dehydrogenation Catalyzed by the Mixed Addenda Heteropoly Acid H5PMo10V2O40

The mixed addenda heteropoly acid H5PMo10V2O40 dissolved in 1,2-dichloroethane with tetraglyme, forming the (tetraglyme)3-H5PMo10V2O40 complex, catalyzes the aromatization of cyclic dienes at moderate temperatures in the presence of molecular oxygen.Dehydrogenations of exocyclic dienes such as limonene show that dehydrogenation is preceded by isomerization to their endocyclic isomers.Aromatization takes place by succesive one-electron transfers and proton abstractions from the organic substrate to the heteropoly acid, the latter being reoxidized by dioxygen coupled with the formation of water.

Preparation method of isopentylene

The method comprises the following steps: taking dipentene as a raw material, and using acetic acid in a high-pressure carbon dioxide environment. Isoterpinene is prepared by reacting acetate and an axial chiral nitrogen-containing compound as a catalyst. The axial chiral nitrogen-containing compound is one or more of an axial chiral nitrogen-containing binaphthyl or biphenyl compound. The selectivity and yield of terpinene are high.

Monoterpenes etherification reactions with alkyl alcohols over cesium partially exchanged Keggin heteropoly salts: effects of catalyst composition

In this work, cesium partially exchanged Keggin heteropolyacid (HPA) salts were prepared, characterized, and evaluated as solid catalysts in monoterpenes etherification reactions with alkyl alcohols. A comparison of the activity of soluble HPAs and their insoluble cesium salts showed that among three different Keggin anions the phosphotungstate was the most efficient catalyst. Assessments on the effects of the level of the protons exchange by cesium cations demonstrated that Cs2.5H0.5PW12O40 solid salt was the most active and selective phosphotungstate catalyst, converting β-pinene to α-terpinyl methyl ether. The influences of the main reaction parameters such as reaction temperature, time, catalyst load, substrate nature (i.e., alcohols and monoterpenes) were investigated. We have demonstrated that the simultaneous presence of the cesium ions and protons in the catalyst plays an essential role, being the 2.5–0.5 the optimum molar ratio. The Cs2.5H0.5PW12O40 salt was efficiently recovered and reused without loss of catalytic activity. Graphic abstract: [Figure not available: see fulltext.]