Terpinolene

Terpinolene Basic information
Product Name:Terpinolene
Synonyms:isoterpinene;nofmertp;p-Mentha-1,4(8)-diene;p-mentha-2,4(8)-diene;1,4(8)-p-Menthadiene;4-ISOPROPYLIDENE-1-METHYLCYCLOHEXENE;ALPHA-TERPINOLENE;1-methyl-4-(1-methylethylidene)cyclohexene
CAS:586-62-9
MF:C10H16
MW:136.23
EINECS:209-578-0
Product Categories:Biochemistry;Monocyclic Monoterpenes;Terpenes
Mol File:586-62-9.mol
Terpinolene Structure
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)
FEMA 3046 | TERPINOLENE
refractive index n20/D 1.489(lit.)
Fp 148 °F
storage temp. 2-8°C
solubility Chloroform: Slightly Soluble; Methanol: Slightly Soluble
form clear liquid
Specific Gravity0.84
color Colourless or pale straw-coloured liquid.
Odorat 10.00 % in dipropylene glycol. fresh woody sweet pine citrus
Odor Typeherbal
Water Solubility 6.812mg/L(25 ºC)
JECFA Number1331
BRN 1851203
Stability:Light Sensitive
InChIKeyMOYAFQVGZZPNRA-UHFFFAOYSA-N
LogP4.33-4.38 at 20-37℃
CAS DataBase Reference586-62-9(CAS DataBase Reference)
NIST Chemistry ReferenceCyclohexene, 1-methyl-4-(1-methylethylidene)-(586-62-9)
EPA Substance Registry SystemTerpinolene (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
10
HazardClass 3.2
PackingGroup III
HS Code 29021990
Hazardous Substances Data586-62-9(Hazardous Substances Data)
toxicityThe 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 Information
ProviderLanguage
p-Menth-1,4(8)-diene English
SigmaAldrich English
Terpinolene Usage And Synthesis
Chemical PropertiesColorless liquid
Chemical PropertiesTerpinolene has a pleasant sweet-piney odor with a somewhat sweet, citrus flavor.
OccurrenceReported 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.
UsesSolvent for resins, essential oils; manufacture of synthetic resins, synthetic flavors.
DefinitionChEBI: A p-menthadiene with double bonds at positions 1 and 4(8).
PreparationBy alcoholic sulphuric acid treatment of pinene (Arctander, 1969).
Aroma threshold valuesAroma characteristics at 1%: sweet, fresh, piney citrus with a woody, old lemon peel nuance.
Taste threshold valuesTaste characteristics at 2 to 25 ppm: woody, terpy, lemon and lime-like with a slight herbal and floral nuance.
General DescriptionA 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 ReactionsHighly flammable. Insoluble in water.
Reactivity ProfileTerpinolene 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.
HazardFlammable, moderate fire risk.
Health HazardInhalation 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 ExplosibilityNotclassified
PharmacologyCombinations 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 ProfileMildly 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.
Methylparaben 2,6-DIMETHYL-2-TRANS-6-OCTADIENE Methyl TERPINEN-4-OL(SG) Bensulfuron methyl 2,5-DIMETHYL-1,5-HEXADIENE Parathion-methyl (+)-DELTA-CADINENE 2,2-Dimethyl-1,3-dioxolane-4-methanol ALPHA-TERPINENE Kresoxim-methyl Terpinolene Thiophanate-methyl Methyl acrylate Methyl bromide (-)-alpha-Terpineol Cyclohexene oxide METHYL THIOPHENE-2-CARBOXYLATE

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