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Home > Encyclopedia > β-Pinene

β-Pinene

β-Pinene structure

β-Pinene 

structure
  • CAS No:

    127-91-3

  • Formula:

    C10H16

  • Chemical Name:

    β-Pinene

  • Synonyms:

    Bicyclo[3.1.1]heptane,6,6-dimethyl-2-methylene-;2(10)-Pinene;6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane;Nopinene;Terebenthene;β-Pinene;Pseudopinen;Pseudopinene;Nopinen;PC 600;(±)-2(10)-Pinene;(±)-β-Pinene;(±)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane;PC 600 (pesticide);NSC 21447;NSC 406265;NSC 59190;beta-Pinene;23089-32-9

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

Liquid


Liquid|Colourless mobile liquid; dry woody, resinous piney aroma|Colorless, transparent liquid.


Beta-pinene is an isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants. It has a role as a plant metabolite.

β-Pinene Basic Attributes

136.23

136.23

204-872-5

406265|59190|21447

DTXSID7027049

Colorless transparent liquid

2902199090

Characteristics

0

4.16

Liquid

0.860 g/cm3 @ Temp: 25 °C

-61.5 °C

166 °C

43°C

1.484

In water, 4.89 mg/L at 25 deg C (est)

Keep container closed. Keep away from heat, sparks, and open flame. /(-)-Beta pinene/

2.93 mm Hg at 25 deg C

4.7 (Air = 1)

Oral-Rat  LD50: 4700 mg/kg

Inflammable in case of open flame, high temperature, oxidant; thermal decomposition spicy and stimulates smoke

CHARACTERISTIC TURPENTINE ODOR; DRY, WOODY OR RESINOUS AROMA

PINEY, TURPENTINE-LIKE TASTE

7.89e-11 cm3/molecule*sec

Henry's Law constant = 0.16 atm-cu m/mole at 25 °C (est)

Optically active and racemic beta-pinenes are present in turpentine oils|BP: 164-166 °C at 760 mm Hg; Density: 0.8654 at 20 °C/20 °C; Index of refraction: 1.4739 at 20 °C /d-form/|SPECIFIC OPTICAL ROTATION: +28.6 DEG/D; BP: 164-166 °C at 760 MM HG; DENSITY: 0.8654 at 20 °C/4 °C; MAX ABSORPTION (ALC): 208 NM (LOG E= 3.72); INDEX OF REFRACTION: 1.4789 at 20 °C; SADTLER REF NUMBER: 2188 (IR, PRISM); 274 (NMR, VARIAN) /D-FORM/|UV: HBCP /d-form/|SPECIFIC OPTICAL ROTATION: -21.5 DEG at 25 °C/D; MAX ABSORPTION (ALC): 208 NM (LOG E= 3.72); BP: 164 °C at 760 MM HG; DENSITY: 0.8694 at 20 °C/4 °C; INDEX OF REFRACTION: 1.4762 at 20 °C /L-FORM/|UV: 3-268 (Phillip et al., Organic Electronic Spectral Data. John Wiley & Sons, New York)|BP: 162-163 °C at 760 mm Hg; Density: 0.874 at 15 °C; Index of refraction: 1.4872 at 15 °C /l-form/|Hydroxyl radical reaction rate constant = 7.89X10-11 cu cm/molecule-sec at 25 °C

43,013.3 KJ/kg = 18,495.7 BTU/lb at 25 °C

5.0X10+7 J/kmol at 211.61 K

Critical temperature: 643 K; Critical pressure: 2.76X10+6 Pa

Safety Information

I; II; III

2368

10

16

DT5077000

F

Treasury is ventilated, low temperature and dry; stored separately from oxidant

Stable. Flammable. Incompatible with strong oxidizing agents.

P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P311, P312, P321, P331, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501

H226

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|Contact a licensed professional waste disposal service to dispose of this material. Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Observe all federal, state, and local environmental regulations. /(-)-Beta pinene/

Beta-Pinene 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 2) 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.

The Flavor and Fragrance High Production Volume Consortia; Revised Robust Summaries for Bicyclic Terpene Hydrocarbons Submitted to the EPA under the HPV Challenge Program. 202 pp. (November 9, 2006). Available from a search of http://www.epa.gov/chemrtk/pubs/summaries/bictrphy/c13610tc.htm as of October 8, 2008

|Danger|H226 (97.44%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P321, P331, P332+P313, P333+P313, P362, P363, P370+P378, P391, P403+P235, P405, and P501|Aggregated GHS information provided by 2269 companies from 38 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P235, P405, and P501|Aggregated GHS information provided by 493 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|Aggregated GHS information provided by 9 companies from 2 notifications to the ECHA C&L Inventory.|H304: May be fatal if swallowed and enters airways [Danger Aspiration hazard]|P261, P264, P272, P280, P301+P310, P302+P352, P321, P331, P332+P313, P333+P313, P362, P363, P405, and P501|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P311, P312, P321, P331, P332+P313, P333+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

PERSONAL PROTECTIVE EQUIPMENT Respiratory: Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose 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. Hand: Compatible chemical-resistant gloves. Eye: Chemical safety goggles. /(-)-Beta pinene/|ENGINEERING CONTROLS. Safety shower and eye bath. Use nonsparking tools. Mechanical exhaust required.

EXTINGUISHING MEDIA. Suitable: 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. /(-)-Beta-pinene/|FIREFIGHTING. Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes. Specific Hazard(s): Flammable liquid. Emits toxic fumes under fire conditions. Specific Method(s) of Fire Fighting: Use water spray to cool fire-exposed containers. /(-)-Beta-pinene/|If material on fire or involved in fire: If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. 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. /Pinene/

Accidetntal Release. METHODS FOR CLEANING UP. Cover with dry-lime, sand, or soda ash. Place in covered containers using non-sparking tools and transport outdoors. /(-)-Beta pinene/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Do not breathe vapor. Avoid contact with eyes, skin, and clothing. Avoid prolonged or repeated exposure. /(-)-Beta pinene/|Wash thoroughly after handling. Wash contaminated clothing before reuse. /(-)-Beta pinene/|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. /Pinene/|For more Preventive Measures (Complete) data for BETA-PINENE (7 total), please visit the HSDB record page.

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substances may be transported hot. /alpha-Pinene/|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Health: 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. /alpha-Pinene/|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /alpha-Pinene/|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /alpha-Pinene/|For more DOT Emergency Guidelines (Complete) data for BETA-PINENE (8 total), please visit the HSDB record page.

Irritating to eyes, respiratory system and skin... /(-)-Beta-pinene/|...Irritant to skin and mucous membranes

An emission source profile was constructed based on data obtained from the Cassiar tunnel of Cairo, Egypt which revealed a 0.49% by weight concentration of beta-pinene in roadway emissions and 0.30% by weight in motorcycle emissions(1). Emissions of 0.36 and 0.77% by weight beta-pinene were obtained from regular and high grade whole gasoline emissions, respectively(1). The compound was detected, not quantified in emissions from a composting facility in Joyceville, Ontario, Canada(2). beta-Pinene emissions from the Fresh Kills Landfill in Staten Island, NY ranged from 0.2-0.7%(3).|beta-Pinene has been identified as a volatile organic ingredient of wood-based furniture with its possible source being an ecological coating system based on natural resins, nitrocellulose, and/or softwood construction(1). Building materials when humidified can support microbial growth of mold fungi, bacteria, actinomycetes and basdiomycetes which can produce metabolites such as beta-pinene(2).|beta-Pinene was identified in emissions from food preparation sites in Mexico City(1). There are more than 30,000 registered places where food is cooked and more than 2,500 sidewalk meal vendors; there are no control mechanisms to reduce emissions from these sources. Sampling was conducted from March 20-31, 1998. beta-Pinene concentrations were 0.37, 0.04, 0.58, 0.28 and 0 ppb C% ot total emissions from restaurants using charcoal grills, tortillerias, rotisseries, food frying places and restaurants using LP gas stoves, respectively(1). Mean concentrations of beta-pinene in residential wood combustion emissions using softwood and hardwood from Denver, CO were determined; emissions from a fireplace were 48.77 and 2.81 mg/kg, respectively; emission from a wood stove using hard wood was 15.37 mg/kg(2).

PLANT SPECIES RELEASE APPRECIABLE QUANTITIES OF VOLATILE ORGANIC SUBSTANCES TO THE ATMOSPHERE. THE MAJOR COMPD EMITTED ARE MONOTERPENES LIKE ALPHA-PINENE, BETA-PINENE, & LIMONENE & THE HEMITERPENE ISOPRENE.|INDOOR: beta-Pinene in indoor air was detected in buildings 1 (first floor), 2 (fourth floor) and 3 (exhaust) at concentrations of 7.9, 5.5, and 3.3 ug/m cu, respectively(1). Geometric mean concentrations of beta-pinene in four manufactured and seven site-built homes located in Florida ranged from 1.5 to 10.6 ppb and 5.9 to 26.3 ppb, respectively(2).|RURAL/REMOTE: The ambient air over the Borden Forest in Ontario, Canada during the leafless period was found to contain 0.01 ppbv beta-pinene(1). beta-Pinene concentrations from the forest ground and canopy in Whitaker's Forest, in the Sierra Nevada Mountains, California ranged from 0.47-2.0 and 1.1-6.8 ug/m-cu, respectively(2). GC-MS analysis of forest air from Eggegebirge, North Rhine-Westfalia, West Germany verified beta-pinene presence in the ambient air(3). Air samples from a Scots Pine forest located in Jadraas, Central Sweden contained measured beta-pinene concentrations in the range of 0.1-<0.5 ppbv(4). Average beta-pinene concentrations in ambient air from four sites in southern Taiwan sampled in December 1998 and May 1999 were: not reported, Shua-Hua; not reported, May-Nung; 4 ug/cu m, Ping-Ting; and not reported, Chao-Chou(5).

Household products containing beta-pinene include newspaper and floor wax pastes(1). The compound is one of the major monoterpenes found in pepper oil at 17% but is absent in pepper leaf oil(2). beta-Pinene has been detected, not quantified in some colognes and soaps(3).

Toxicity

moderately toxic

Beta-pinene vaporized from turpentine had no effect on hexobarbital sleeping time or parathion mortality in male rats, but increased heptachlor mortality and benzpyrene hydroxylation.

LD50 Rat (Wistar) oral >5000 mg/kg|LD50 Rat oral 4700 mg/kg|LD50 Rabbit (New Zealand white) dermal (24 hr application) >5000 mg/kg

THE ESSENTIAL OIL OF A SARDINIAN SAMPLE OF MYRTUS COMMUNIS WAS EXAMINED BY GAS-LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY (GLC-MS); 22 PEAKS WERE SEPARATED, FOR WHICH THE MASS SPECTRA ARE SHOWN, TOGETHER WITH THE RETENTION TIMES, THE AREAS OF THE PEAKS, & PERCENTAGE COMPOSITION. THE TERPENE CONTENT WAS VERY HIGH; ALPHA-PINENE & BETA-PINENE CONSTITUTED 52.43% & 0.68%, RESPECTIVELY, OF THE OIL.|USUALLY OCCURRING TOGETHER WITH ALPHA-PINENE BUT IN SMALLER AMT. THE D- & L-FORMS ARE REPORTED FOUND IN THE ESSENTIAL OILS OF VARIOUS ARTEMISIAE & SEVERAL CUPRESSACEAE, IN CORIANDER & CUMIN. THE L-FORM IS A CONSTITUENT OF SEVERAL CITRUS OILS.|THE MONOTERPENE HYDROCARBON FRACTION REPRESENTING 70.4% OF PINUS PUMILIO OIL WAS REPORTED...TO CONTAIN D-LIMONENE (42.1%), ALPHA-PINENE (18.4%), DELTA-CARENE (11.5%), BETA-PINENE (8.1%), BETA-PHELLANDRENE (8.0%), CAMPHENE (4.3%), MYRCENE (3.6%) & SMALLER AMT OF ALPHA-, & GAMMA-TERPINENE, P-CYMENE, TERPINOLENE & ALPHA-PHELLANDRENE.|THE MONOTERPENE HYDROCARBON FRACTION REPRESENTING 68.9% OF PINUS SYLVESTRIS OIL WAS REPORTED...TO CONTAIN ALPHA-PINENE (65.8%), DELTA-CARENE (11.1%), BETA-PINENE (9.5%), D-LIMONENE (4.1%), MYRCENE (3.6%), CAMPHENE (2.9%), BETA-PHELLANDRENE (1.2%) & SMALLER AMT OF TERPINOLENE, OCIMENE, SABINENE & GAMMA-TERPINENE.|beta-Pinene is a natural hydrocarbon emission product from softwood and some hardwood trees(SRC), in particular spruce species, Pinus glauca, P. abies and P. pungens(1), and eucalyptus species Eucalyptus dunnii, E. salgina and E. citriodora(2). The Mediterranean oak species Quercus ilex L. emits monoterpenes of which 22.92% is beta-pinene(3).

beta-Pinene's production and use as an intermediate for perfumes and flavorings, in polyterpene resins(1), and as a fragrance ingredient(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,400(SRC), determined from a log Kow of 4.16(2) and a regression-derived equation(3), indicates that beta-pinene is expected to have slight mobility in soil(SRC). Volatilization of beta-pinene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.16 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). beta-Pinene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.93 mm Hg(5). Biodegradation data were not available(SRC, 2008). However, by analogy to alpha-pinene which reached 95% of its theoretical BOD using activated sludge in the Japanese MITI test(6), biodegradation may be an important environmental fate process for beta-pinene in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,400(SRC), determined from a log Kow of 4.16(2) and a regression-derived equation(3), indicates that beta-pinene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), 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 340 days if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 320(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). beta-Pinene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2008). However, by analogy to alpha-pinene which reached 95% of its theoretical BOD using activated sludge in the Japanese MITI test(8), biodegradation may be an important environmental fate process for beta-pinene in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), beta-pinene, which has a vapor pressure of 2.93 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase beta-pinene 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 4.9 hours(SRC), calculated from its rate constant of 7.89X10-11 cu cm/molecule-sec at 25 °C(3). The rate constant for the vapor-phase reaction of beta-pinene with ozone has been estimated as 1.2X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). beta-Pinene does not contain chromophores that absorb at wavelengths >290 nm(5) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of beta-pinene with photochemically-produced hydroxyl radicals is 7.89X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 4.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The reaction of OH and beta-pinene results in the formation of formaldehyde and acetone(2). The rate constant for the vapor-phase reaction of beta-pinene with ozone has been estimated as 1.2X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). The main products from the reaction of ozone and gas-phase beta-pinene were identified as nopinone, HCHO; 3-hydroxynopinone, HCOOH and cis-pinic acid are also produced(5). beta-Pinene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(6). beta-Pinene 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).

An estimated BCF of 320 was calculated in fish for beta-pinene(SRC), using a log Kow of 4.16(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

The Koc of beta-pinene is estimated as 4,400(SRC), using a log Kow of 4.16(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that beta-pinene is expected to have slight mobility in soil.

The Henry's Law constant for beta-pinene is estimated as 0.16 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that beta-pinene is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5 days(SRC). beta-Pinene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 340 days when adsorption is considered(3). beta-Pinene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.93 mm Hg(4).

SURFACE WATER: beta-Pinene was detected in the Wolfegger, Ach and Schussen rivers in Southwest Germany, considered weakly polluted small rivers and brooks(1). GC-MS analysis of water from the Black Warrior River in Tuscaloosa, AL revealed the presence of beta-pinene(2).|RAIN/SNOW/FOG: beta-Pinene was not detected in snow samples collected in early March from Neulanieme (Kuopio, Central-Eastern Finalnd); Nellim (Lapland, Finland); Muonio (Lapland, Finland); Levi (Lapland, Finland); Moscow State University (clean area, Msocow, Russia); Moscow region - summer cottage area; Shuch'e (Volga River, Russia); Baikal'sk on Lake Baikal (near pulp/paper mill, Siveria(1). The compound was detected in samples from Butovo (clean area, southern Moscow, Russia) at 0.04 ug/kg(1).

beta-Pinene was detected in the aromas of 20 out of 26 and 19 out of 63 fresh wild mushrooms by dynamic headspace concentration and solvent extraction, respectively(1). A purge and trap gas chromatogram technique revealed a 0.0015 ppm beta-pinene concentration in fresh grapefruit juice(2). beta-Pinene was identified as one of the flavor compounds in tea derived from fresh pine sprouts or pine needles harvested from Korean red pine trees (Pinus densiflora Sieb. Et Zucc.) in May-June 1995(3). The compound was identified as a volatile odor compound from 30%, 12% and 5% of total emmsions from fat frankfurters at mean concentrations of 3,330, 3,570 and 5,060 relative peak areas (1 ng of bromobenzene = 100), respectively(4).

Occupationally, workers should be protected from inhaling pinene vapors and from direct skin contact. /Pinene/|NIOSH (NOES Survey 1981-1983) has statistically estimated that 77,244 workers (13,763 of these were female) were potentially exposed to beta-pinene in the US(1). Occupational exposure to beta-pinene may occur through inhalation and dermal contact with this compound at workplaces where beta-pinene is produced or used(SRC). Monitoring and use data indicate that the general population may be exposed to beta-pinene via inhalation of ambient air and dermal contact with this compound or other products containing beta-pinene(SRC).|beta-Pinene median concentration levels for children who attended two inner-city schools in Minneapolis, MN were reported as 0.1, 0.1 and 2.5 ug/cu m outdoors, indoors at school and indoors at home, respectively, during winter, 2000; levels for spring 2000 were 0.1, 0.1 and 1.5 ug/cu m, respectively(1). Pinene concentration, both alpha- and beta- combined, ranged from not detected (2 mg/cu m) to 193 mg/cu m in workplace air from a thermomechanical pulp production plant(2). beta-Pinene workroom air level in Swedish saw sheds of sawmills processing Norway spruce (Picea abies) and Scots pine (Pinus sylvestris) were reported at 6.3% relative to total terpene concentration during sawing of Scot's pine(3). Danish workers picking up household waste are susceptible because garden waste carried by garbage trucks emits beta-pinene into the surrounding air(4).

Drug Information

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OUNCE & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB). /PINENE/|About 150 mL may constitute a human oral fatal dose. /Pinene/

Pinene is easily absorbed through the pulmonary system, the skin, and the intestine. /Pinene/|Following immersion of young pigs & one human subject for 30 minutes in baths containing 150 mL of a pine-oil mixture (Fichtennadel-Latschenkieferol Kneipp) in 450 L of water, alpha- & beta-pinene & limonene (components of Latschenkieferol) were detected in exhaled air within 20 minutes reaching maximum levels 50-75 minutes after start of the bath & remaining detectable after 1 day.

The biotransformation of (+)-, (-)-, and (+-)-alpha-pinenes, (-)-beta-pinene (nopinene), (-)-cis-pinane, (+)-3-carene, (-)-cis-carane, myrcene, and p-cymene in rabbits was investigated. The major metabolites were as follows: (-)-trans-verbenol from (+)-, (-)-, and (+/-)-alpha-pinenes; (-)-10-pinanol and (-)-1-p-menthene-7,8-diol from (-)-beta-pinene; (-)-alpha-terpineol and (-)-trans-sobrerol from (-)-cis-pinane; (-)-m-mentha-4,6-dien-8-ol, 3-caren-9-ol, (-)-3-carene-9-carboxylic acid, and 3-carene-9,10-dicarboxylic acid from (+)-3-carene; carane-9,10-dicarboxylic acid from (-)-cis-carane; and myrcene-3(10)-glycol, myrcene-1,2-glycol, uroterpenol, and p-cymene-9-carboxylic acid from p-cymene. These metabolisms include allylic oxidation, epoxidation, stereoselective gem-dimethyl hydroxylation and its oxidation, cleavage of a conjugated double bond by epoxidation, and regioselective oxidation, some of which are not found usually in chemical reactions, and due to which various new compounds were determined. This biotransformation of the monoterpene hydrocarbons gave some insect pheromones in high yield.

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Turpentine, terpenes, and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. /Turpentine, terpenes, and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive- pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Turpentine, Terpenes, and related compounds/

/HUMAN EXPOSURE STUDIES/ ... Eight male volunteers were exposed to 450 mg/cu m turpentine by inhalation (2 hr, 50 W) in an exposure chamber. ...The mean relative uptakes of alpha-pinene, beta-pinene, and 3-carene were 62%, 66%, and 68% respectively, of the amount supplied. ... After experimental exposure to turpentine an increase in airway resistance was found that differed significantly from results of exposure to 3-carene at 10 mg/cu m (P = 0.021) or 450 mg/cu m (P = 0.047). ... ... Acute effects show small, if any, interactions between alpha-pinene, beta-pinene, and 3-carene. The subjects experienced discomfort in the throat and airways during exposure to turpentine and airway resistance was increased after the end of exposure.|/SIGNS AND SYMPTOMS/ Absorption of large doses may result in delirium, ataxia, & kidney damage. Inhalation may cause palpitation, dizziness, nervous disturbances, chest pain, bronchitis, and nephritis. /Pinene/|/SIGNS AND SYMPTOMS/ Harmful by inhalation, in contact with skin and if swallowed. Irritating to eyes, respiratory system and skin. May cause sensitization by skin contact. Harmful: may cause lung damage if swallowed. /(-)-Beta-pinene/|/CASE REPORTS/ A patient attempting suicide ingested 400-500 mL pine oil and was admitted to the clinic. Since more than the lethal dose had been ingested hemoperfusions with activated charcoal and amberlite and a hemodialysis were performed. The composition of the ingested pine oil was determined by gas chromatography/mass spectrometry. Four monoterpenes were identified: 57% alpha-pinene, 8% beta-pinene, 26% carene, 6% limonene and 3% other hydrocarbons. The blood and urine monoterpene concentrations were continuously monitored. The data suggest that monoterpenes are poorly resorbed in the gastrointestinal tract. The resorbed portion of the hydrocarbons cumulates in the lipophilic body compartments and is slowly metabolized and then excreted by the kidneys. The main metabolic pathways are hydration, hydroxylation, rearrangement, and acetylation. Five metabolites were identified.|/EPIDEMIOLOGY STUDIES/ ... To study work exposure and respiratory symptoms in New Zealand plywood mill workers ... personal inhalable dust (n = 57), bacterial endotoxin (n = 20), abietic acid (n = 20), terpene (n = 20) and formaldehyde (n = 22) measurements were taken and a respiratory health questionnaire was administered to 112 ... workers. ... Twenty-six percent of the dust exposures exceeded 1 mg/cu m, however, none of the samples exceeded the legal limit of 5 mg/cu m (geometric mean (GM) = 0.7 mg/m(3), geometric standard deviation (GSD) = 1.9). Workers in the composer area (where broken sheets are joined together) were significantly (P < 0.01) more highly exposed. Endotoxin levels were low to moderate (GM = 23.0 EU/cu m, GSD = 2.8). Abietic acid levels ranged from 0.3 to 2.4 ug/cu m (GM = 0.7 ug/cu m, GSD = 1.8) and were significantly (P < 0.05) higher for workers in the composer area of the process. Geometric mean levels of alpha-pinene, beta-pinene and Delta(3)-carene were 1.0 (GSD = 2.7), 1.5 (GSD = 2.8) and 0.1 (GSD = 1.4), respectively, and alpha-pinene and beta-pinene levels were significantly (P < 0.001) higher for workers in the 'green end' of the process, up to and including the veneer dryers. Formaldehyde levels ranged from 0.01 to 0.74 mg/cu m (GM = 0.08 mg/cu m (= 0.06 ppm), GSD = 3.0). Asthma symptoms were more common in plywood mill workers (20.5%, n = 112) than in the general population (12.8%, n = 415, adjusted OR (95% CI) = 1.5 (0.9-2.8)). Asthma symptoms were associated with duration of employment and were reported to lessen or disappear during holidays. No clear association with any of the measured exposures was found, with the exception of formaldehyde, where workers with high exposure reported more asthma symptoms (36.4%) than low exposed workers (7.9%, adjusted OR (95% CI) = 4.3 (0.7-27.7))...

beta-pinene

β-Pinene Use and Manufacturing

Methods of Manufacturing

It is generally obtained from turpentine fractionation, but the content of α-pinene is low.

Uses

It is an important raw material for artificial synthesis of various spices, camphor, borneol, vitamins A, E, K, terpene resin, etc.


Intermediates


Air care products

Production

10,000,000 - 50,000,000 lb|(1979) 2.15X10+10 GRAMS|(1981) 2.04X10+10 GRAMS|beta-Pinene is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5463]

Most commonly available as the l-isomer

All other basic organic chemical manufacturing|Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-: ACTIVE|Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-, (1S,5S)-: ACTIVE|Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|Alcoholic beverages 9.64 ppm; Gelatins, puddings 9.77 ppm; Non-alcoholic beverages 11.24 ppm; Chewing gum 17.24 ppm; Condiments, relishes 20.00 ppm; Frozen dairy 20.12 ppm; Hard Candy 14.90 ppm; Meat products 8.81 ppm; Soft candy 20.34 ppm; Baked goods 26.12 ppm.|Flavors useful in: Spice flavors (nutmeg), citrus imitations|Irreversible isomerization of beta-pinene to alpha-pinene occurs on shaking with platinum black saturated with hydrogen

PINENES ARE DETERMINED IN AIR BY A HIGH-RESOLUTION IR INTERFEROMETER IN THE PARTS PER TRILLION RANGE AT 100 KM PATHLENGTH. THIS METHOD IS USEFUL IN DETERMINING THE BUILDUP OF PINENES IN AIR AT NIGHT WHEN PLANT EMISSIONS CONTINUE AFTER PHOTOCHEMICAL PROCESSES HAVE STOPPED.|/Pinene/ can be quantified using gas chromatographic procedures. /Pinene/|Method: NIOSH 1552, Issue 1; Procedure: gas chromatography with flame ionization detector; Analyte: beta-pinene; Matrix: air; Detection Limit: 0.4 ug/sample.

Food additives -> Flavoring Agents

Flavoring Agents

Computed Properties

Molecular Weight:136.23
XLogP3:3.1
Exact Mass:136.125200510
Monoisotopic Mass:136.125200510
Heavy Atom Count:10
Complexity:177
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Drug Function and Efficacy

Synergistically produces antipyretic and analgesic effects

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Recommended Suppliers of β-Pinene

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