Terpinolene Chemical Properties

Melting point:

<25 °C

Boiling point:

184-185 °C (lit.)

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.)

FEMA 

3046 | TERPINOLENE

Flash point:

148 °F

storage temp. 

2-8°C

solubility 

Chloroform: Slightly Soluble; Methanol: Slightly Soluble

form 

clear liquid

color 

Colourless or pale straw-coloured liquid.

Specific Gravity

0.84

Odor

at 10.00 % in dipropylene glycol. fresh woody sweet pine citrus

Odor Type

herbal

Water Solubility 

6.812mg/L(25 ºC)

JECFA Number

1331

BRN 

1851203

Dielectric constant

2.3（Ambient）

Stability:

Light Sensitive

InChIKey

MOYAFQVGZZPNRA-UHFFFAOYSA-N

LogP

4.33-4.38 at 20-37℃

CAS DataBase Reference

586-62-9(CAS DataBase Reference)

NIST Chemistry Reference

Cyclohexene, 1-methyl-4-(1-methylethylidene)-(586-62-9)

EPA Substance Registry System

Terpinolene (586-62-9)

Safety Information

Hazard Codes 

N

Risk 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

HS Code 

29021990

Hazardous Substances Data

586-62-9(Hazardous Substances Data)

Toxicity

The acute oral LD₅₀ value in rats was reported as 4.39 ml/kg (Levenstein, 1975) and similarly that in mice and rats was reported to be 4.4 ml/kg (Hisamitsu Pharmaceutical Co., Inc., 1973). The acute dermal LD₅₀ value in rabbits exceeded 5 g/kg (Levenstein, 1975).

MSDS

• Language:English Provider:p-Menth-1,4(8)-diene
• Language:English Provider:SigmaAldrich

Terpinolene Usage And Synthesis

Chemical Properties

Colorless liquid

Chemical Properties

Terpinolene has a pleasant sweet-piney odor with a somewhat sweet, citrus flavor.

Occurrence

Reported found in citrus juices and oils, black currant, guava, papaya, raspberry, various spice and mint oils, tea, passion fruit, litchi, lovage oil, distilled lime peel oil, ginger, nutmeg, pepper, mace, coriander seed, lovage seed, lovage root, myrtle leaf, pimento berry, pimento leaf, winter savory, smaller galanga, Ethiopian or guinea pepper and ashanti pepper.

Uses

Solvent for resins, essential oils; manufacture of synthetic resins, synthetic flavors.

Definition

ChEBI: A p-menthadiene with double bonds at positions 1 and 4(8).

Preparation

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

Production Methods

Terpinolene used to be extracted by fractional distillation of wood turpentine. It is now produced bytreatinga-pinene with aqueous H3PO4 at 75 ℃. It is preferable to distill terpinolene under vacuum to minimize the formation of polymeric products at elevated temperatures.

Aroma threshold values

Aroma characteristics at 1%: sweet, fresh, piney citrus with a woody, old lemon peel nuance.

Taste threshold values

Taste characteristics at 2 to 25 ppm: woody, terpy, lemon and lime-like with a slight herbal and floral nuance.

General Description

A water-white to light amber colored liquid. Insoluble in water and less dense than water. Flash point 99°F. Used to make plastics and resins.

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

Not classified

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.

Terpinolene(586-62-9)Related Product Information

• Methyl acrylate
• TERPINEN-4-OL(SG)
• (-)-alpha-Terpineol
• Methylparaben
• 2,2-Dimethyl-1,3-dioxolane-4-methanol
• Bensulfuron methyl
• alpha-Terpinene
• Cyclohexene oxide
• METHYL THIOPHENE-2-CARBOXYLATE
• Kresoxim-methyl
• Thiophanate-methyl
• Methyl
• 2,5-DIMETHYL-1,5-HEXADIENE
• (+)-DELTA-CADINENE
• Parathion-methyl
• DL-Limonene
• Terpenes and Terpenoids, turpentine-oil, limonene fraction
• Dipentene