테르피놀렌

Biological Agents -> Terpenes

Flammable agents - 3rd degree

log Kow = 4.47

4.47

4.24

SWEET, PINE ODOR

PINE-LIKE AROMA

SOMEWHAT SWEET, CITRUS FLAVOR

TERPENE TASTE

0.8632 g/cu cm at 15 °C

Bulk density: wt/gal 7.2 lb at 15.5 °C

0.872-0.882

Water-white to pale amber liquid

Colorless liquid or oil

Danger

H226 (77.8%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P321, P331, P332+P317, P333+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2251 reports by companies from 44 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

Chemical: Cyclohexene, 1-methyl-4-(1-methylethylidene)-

Hazard Traits - Fragrance Allergen

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Cyclohexene, 1-methyl-4-(1-methylethylidene)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexene, 1-methyl-4-(1-methylethylidene)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 26-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/10412

Cyclohexene, 1-methyl-4-(1-methylethylidene)-: HSNO Approval: HSR001222 Approved with controls

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

A very dangerous fire hazard when exposed to heat or flame.

Flammable, moderate fire risk.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.

Safe when used as a flavoring agent; [JECFA] Not a sensitizer in the maximization test; A positive patch test was reported in a woman using a machine cleaner containing terpinolene. [NTP] Included in list of established contact allergens in humans; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] See 3-Carene and Limonene.

Terpinolene is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans for Monoterpene Hydrocarbons (May 2002). Information on usage patterns, toxicity, and ecological effects submitted by industry to the US EPA HPV Challenge Program.[Available from, as of September 06, 2006: http://cfpub.epa.gov/hpv-s/]

Opdyke DL; J Food Cosmet Toxicol 14 (Suppl): 877 (1976). A review with 23 references on terpinolene including toxicity, irritation, sensitization, pharmacology, effect on insects & microorganisms.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

General First Aid:

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. Use water spray to cool unopened containers.

Suitable extinguishing media: For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water.

To fight fire, use foam, CO2, dry chemical.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.

Control of environmental exposure: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

ACCIDENTAL RELEASE MEASURES. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.; Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Precautions for safe handling: Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Immediate precautionary measure

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Body Protection: impervious clothing, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Skin protection: Handle with gloves.

Eye/face protection: Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

LC50; Species: Daphnia magna (water flea); Conditions: flow-through; Concentration: 0.612 mg/L for 48 hr

LC50; Species: Daphnia magna (water flea); Conditions: flow-through; Concentration: 2.55 mg/L for 96 hr

LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through; Concentration: 0.720 mg/L for 96 hr

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7,600(SRC), determined from a log Kow of 4.47(2) and a regression-derived equation(3), indicates that terpinolene is expected to be immobile in soil(SRC). Volatilization of terpinolene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.62X10-2 atm-cu m/mole(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Terpinolene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.43X10-1 mm Hg at 25 °C(2). A 72% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7,600(SRC), determined from a log Kow of 4.47(2) and a regression-derived equation(3), indicates that terpinolene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 2.62X10-2 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 3 hours and 5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 48 days if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 400(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is high(SRC). A 72% of theoretical BOD using activated sludge in the Japanese MITI test(8) suggests that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), terpinolene, which has a vapor pressure of 7.43X10-1 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase terpinolene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 2.25X10-10 cu cm/molecule-sec at 25 deg(3). The rate constant for the vapor-phase reaction of terpinolene with ozone has been estimated as 7.3X10-16 cu cm/molecule-sec at 25 °C(4) and 1.0X10-14 cu cm/molecule-sec at 22 °C(4). This corresponds to atmospheric half-lives of about 23 and 1.7 minutes, respectively(SRC). The overall daylight half-life for these two photooxidation reactions can be calculated to range between 1.7 and 19 min(4,5). The rate constant for the vapor phase reaction of terpinolene with nitrate radicals present in nighttime air has been estimated to be 7.1X10-11 cu cm/molecule-sec at 25 °C(5) which corresponds to a nighttime atmospheric half-life of 41 sec(SRC). Terpinolene does not contain chromophores that absorb at wavelengths >290 nm(6) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Terpinolene was detected in the mixture of volatile components of mangoes grown in Florida at a concentration of 2.0 ug/g in fruit stored in a deep freeze at -15 °C for 14 months and at a concentration of 1.1 ug/g in fresh fruit(1). Terpinolene was detected in the mixture of volatile components of 3 of 4 varieties of California nectarines (detection limit not reported)(2). The concentration detected in Sunfre nectarines was 10 ppb and the concentration detected in 2 experimental varieties of nectarines were below the quantification limit of 10 ppb(2). The compound was not detected in Flavortop nectarines(2). In another study, the compound was detected in the mixture of volatile components of unspecified nectarines (detection limit not reported)(3). Terpinolene was detected but not quantified in Korean edible Chamchwi(4), detected below quantitative limits (<0.1 mg/kg) in paprika(5) and in 0.8% of the relative volatile compounds from chickpea seed(6).

IDENTIFICATION AND USE: Terpinolene is a colorless liquid or oil used as a solvent for resins and essential oils, and in the manufacture of synthetic resins and synthetic flavors. HUMAN EXPOSURE AND TOXICITY: Tested at 20% in petrolatum it produced no irritation after a 48 hr closed-patch test on human subjects in a maximization test carried out on 24 volunteers. The material was tested at a concentration of 20% in petrolatum and produced no sensitization reactions. Terpinolene was found not to be a sensitizer for human skin. ANIMAL STUDIES: Terpinolene applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was not irritating. A single 24 hour application of terpinolene (5 g/kg) was applied to the clipped abraded abdominal skin of 10 rabbits weighing from 1.9 to 2.4 kg. Observations for mortality and toxic effects were made for seven days following exposure. Gross necropsies were performed on all animals at study termination. No deaths during the course of the study. No evidence of toxicity from percutaneous absorption of the test substance. Erythema and edema were reported during the first few days of observation, but cleared by the study termination. Terpinolene promoted only slightly or did not affect deer rumen microbial activity, however it inhibited rumen microbial activity in sheep.

Terpinolene was detected in emissions from 9 to 17 species of arboreous plants studied and 1 of 5 plants species that grow under the canopy of coniferous forests (detection limit not specified)(1). It was qualitatively detected in emissions from the following arboreous plants (detection limit not specified): Scots pine, Siberian pine, Silver fir, Common juniper, Zeravshan vitae; it was also found in emissions from Marsh tea which grows under the canopy of coniferous forests(1). It was not detected (detection limit not specified) in emissions from the following arboreous plants: Bay-leave willow, Aspen, Balsam poplar, European oak, European birch, Sorb, European larch and European fir; nor was it found in emissions from the following plants which grow under the canopy of coniferous forests: Red billberry shrub, Billberry shrub, Fern and Deciduous moss(1). Terpinolene was released from 3 out of 15 Eucalyptus trees at rates ranging from 0.13-0.3 ug/g (leaf mass) per hour(2). Terpinolene was detected in the leaves of Eucalyptus saligna, but not in the leaves of E. citiodora or E. dunni(3). Terpinolene was emitted from sweet gum, cypress and hickory tress at 170, 80, 470 ug/kg foliage, respectively, growing north of Baton Rouge, LA(4).

Terpinolene detections in various plants(1).[Table#5516]

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of April 22, 2015: http://actor.epa.gov/dashboard/]

Terpinolene was detected in 1 out of >4000 samples of effluent from 1 of 46 categorized industrial waste water sources, monitored between November 1, 1979 through November 1, 1981; terpinolene was present in pulp and paper mill wastewater at a concentration of 28 ng/uL(1). The compound was detected in 1973 in kraft mill wastewater from both a bleached and an unbleached kraft mill at concentration ranging from trace levels to 40 ppb before secondary treatment in aerated lagoons and ranging from not detected to 10 ppb after treatment in the aerated lagoons (volumetric retention time of 7 days); detection limit and trace level concentration not specified(2).

The Koc of terpinolene is estimated as 7,600(SRC), using a log Kow of 4.47(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that terpinolene is expected to be immobile in soil.

Terpinolene is naturally emitted from various tissues and essential oils of a variety of plant species(1), especially trees(2). Terpinolene is a component of citrus fruit oils from orange species such as navel, bergamot, mandarin, sweet orange and tangerine(3). Terpinolene is a component of pine silvestris oil (Pinus silvestris) and tea tree oils (Melaleuca alternifolia, Melaleuca linariifolia, Melaleuca dissitiflora, other species)(4). It has been found in pine gum terpentines(5).

/HUMAN EXPOSURE STUDIES/ /Tested at 20% in petrolatum it produced no irritation after a 48 hr closed-patch test on human subjects. ... a maximization test was carried out on 24 volunteers. The material was tested at a concn of 20% in petrolatum and produced no sensitization reactions. Terpinolene was found not to be a sensitizer for human skin.

Terpinolene is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Used as a fragrance and food flavoring agent; Used as a solvent for resins and oils and a chemical intermediate; [HSDB]

Reported uses (ppm):

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

... Used to improve the odor of industrial and household products.

FRAGRANCE-EG, FOR PERFUMES & SOAPS

For more Uses (Complete) data for TERPINOLENE (6 total), please visit the HSDB record page.

2023: 550,000 - <700,000 lb

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Greater than ... 50,000 lbs of terpinolene ... /is/ consumed annually as natural components of food in the United States. The estimated poundage of ... terpinolene ... used as flavoring substances in 1995 were ... 1,170 lbs ...

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5517]

For more U.S. Production (Complete) data for TERPINOLENE (7 total), please visit the HSDB record page.

Consumption: Annual: 2633.33 lb. Individual: 0.002231 mg/kg/day

Use in fragrances in the USA exceeds 50,000 lb/yr. Concn in final product (%): usual- soap 0.02; detergent 0.002; creams, lotions 0.01; perfume 0.12; maximum- soap 0.4; detergent 0.04; creams, lotions 0.1; perfume 0.5.

Fractionation of wood turpentine.

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

Limonene can be isomerized to terpinolene using liquid SO2 and a hydroperoxide catalyst (tert-butyl hydroperoxide (TBHP)). Another method uses a specially prepared ortho-titanic acid catalyst with a buffer, such as sodium acetate. A selectivity of ~70% is claimed at ~50% conversion when run at 150 °C for 4 hr.

Cosmetics product ingredient: p-Mentha-1,4(8)-diene (Terpinolene)

Information on 76 consumer products that contain Terpinolene in the following categories is provided:

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

All Other Chemical Product and Preparation Manufacturing

Cyclohexene, 1-methyl-4-(1-methylethylidene)-: ACTIVE

The Council of Europe (1974) included it in the list of artificial flavoring substances that may be added temporarily to foodstuffs without hazard to public health.

The pure product was isolated and structurally identified by Baeyer.