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Terpinolene

Product NameTerpinolene
CAS586-62-9
MFC10H16
MW136.23
EINECS209-578-0
MOL File586-62-9.mol

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)
FEMA	3046 \| TERPINOLENE
refractive index	n20/D 1.489(lit.)
Flash point	148 °F
storage temp.	2-8°C
solubility	Chloroform: Slightly Soluble; Methanol: Slightly Soluble
form	clear liquid
Specific Gravity	0.84
color	Colourless or pale straw-coloured liquid.
Odor	at 10.00 % in dipropylene glycol. fresh woody sweet pine citrus
Odor Type	herbal
biological source	synthetic
Water Solubility	6.812mg/L(25 ºC)
JECFA Number	1331
BRN	1851203
Henry's Law Constant	7.9×10^-4 mol/(m³Pa) at 25℃, Plyasunov and Shock (2000)
Dielectric constant	2.3（Ambient）
Stability	Light Sensitive
Major Application	cleaning products cosmetics food and beverages personal care
Cosmetics Ingredients Functions	FRAGRANCE
InChI	1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3
InChIKey	MOYAFQVGZZPNRA-UHFFFAOYSA-N
SMILES	C\C(C)=C1/CCC(C)=CC1
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
WGK Germany	3
RTECS	WZ6870000
F	10
TSCA	TSCA listed
HazardClass	3
PackingGroup	III
HS Code	29021990
Storage Class	3 - Flammable liquids
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 3 Asp. Tox. 1 Skin Sens. 1
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

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

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).

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.

Preparation

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

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

Terpinolene Supplier

Terpinolene manufacturers

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