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Home > Encyclopedia > (±)-Camphene

(±)-Camphene

(±)-Camphene structure

(±)-Camphene 

structure
  • CAS No:

    79-92-5

  • Formula:

    C10H16

  • Chemical Name:

    (±)-Camphene

  • Synonyms:

    Bicyclo[2.2.1]heptane,2,2-dimethyl-3-methylene-;Camphene;2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane;2,2-Dimethyl-3-methylenenorbornane;3,3-Dimethyl-2-methylenenorcamphane;3,3-Dimethyl-2-methylenenorbornane;dl-Camphene;(±)-Camphene;DL-Camphene;NSC 4165;2-Methylene-3,3-dimethylbicyclo[2.2.1]heptane;YS Camphene;2,2-Dimethyl-3-methylidenebicyclo[2.2.1]heptane;565-00-4

  • Categories:

    Cosmetic Ingredient  >  Fragrance Ingredient

Description

WHITE CRYSTALLINE LOW MELTING SOLID Camphene is a colorless to white crystalline solid, Camphor, or turpentine odor. It may be shipped as a liquid. Freezing/Melting point 5 50C. Camphene has a terpene, camphoraceous taste.


Camphene is a bicyclic monoterpene. It is nearly insoluble in water, but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and as a food additive for flavoring. Its mid-19th century use as a fuel for lamps was limited by its explosiveness.


Camphene appears as a colorless to white crystalline solid with an insipid camphor-like odor. Dust and crystals are irritants to the eyes, nose and throat. Emits flammable vapors when heated. Emits acrid smoke and irritating fumes at high temperature. Used for the manufacture of synthetic camphor.|Liquid|COLOURLESS SOLID IN VARIOUS FORMS WITH CHARACTERISTIC ODOUR.|Colourless crystalline solid; mild, oil-camphoraceous aroma


Camphene appears as a colorless to white crystalline solid with an insipid camphor-like odor. Dust and crystals are irritants to the eyes, nose and throat. Emits flammable vapors when heated. Emits acrid smoke and irritating fumes at high temperature. Used for the manufacture of synthetic camphor.|Camphene is a monoterpene with a bicyclic skeleton that is bicyclo[2.2.1]heptane substituted by geminal methyl groups at position 2 and a methylidene group at position 3. It is a widespread natural product found in many essential oils. It has a role as a plant metabolite and a fragrance. It is a monoterpene and a carbobicyclic compound.

(±)-Camphene Basic Attributes

136.23

136.23

201-234-8

G3VG94Z26E

1704

4165

2319|1325

DTXSID8026488

Colorless crystals

29021900

Characteristics

0

4.1 (calculated)

White Crystalline Low Melting Solid

0.839 g/cm3 @ Temp: 20 °C

51.5 °C

158.5 °C

94 °F

1.484

Practically insoluble in water

Flammables area

Vapour pressure, kPa at 20°C: 0.4

Relative vapour density (air = 1): 4.7

Oral-rat LD50:> 5000 mg/kg; inhalation-rat LC50: 17100 mg/m3/4 hours

Inflammable in case of open flame, high temperature, oxidant; burning produces irritating smoke

Camphoraceous, cooling, piney wood with trephy nuances...citrus and green minty and green spicy notes

Camphoraceous taste

5.33e-11 cm3/molecule*sec

Henry's Law constant = 0.098 atm-cu m/mole at 25 °C (est)

130.63 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|133.01 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|129.8 Ų [M+H]+

Sublimes when heated|MP = 52 °C; BP = 160-162 °C; density = 0.8450 at 50 °C/4 °C; Index of refraction = 1.4570 at 25 °C/D; Max absorption (alcohol): 206 Nm (log e = 3.74); insoluble in water; soluble in ether; slightly soluble in alcohol /d-Camphene/|Cubic crystals from alcohol. Large dodecahedra by slow sublimation. Volatilizes on exposure to air. Insipid odor. mp 51-52 °C. BP at 760 mm Hg: 158.5-159.5 °C. BP at 100 mm Hg: 92.4 °C. BP at 16 mm Hg: 55-56 °C. density at 54 °C/4 °C: 0.8422. Index of refraction at 54 °C/D: 1.45514. Practically insoluble in water. Moderately soluble in alcohol; soluble in ether, cyclohexane, cyclohexene, dioxane, chloroform /dl-Camphene/|MP: 52 °C. Specific optical rotation: -119.11 deg at 21 °C/D (c = 2.33 in benzene). Density at 54 °C/4 °C: 0.8422. Index of refraction at 40 °C/D: 1.4620 /l-Camphene/|BP = 158 °C; density = 0.8446 at 50 °C/4 °C; Index of refraction = 1.4564 at 54 °C; Sadtler Reference Number: 1474 (IR, Prism; 248 (IR, Grating); soluble in ether; Specific optical rotation: -106.1 deg (4% in ether) /l-Camphene/|UV: 3-268 (Phillip et al., Organic Electronic Sprctral Data, John Wiley and Sons, New York) /dl-Camphene/|Hydroxyl radical reaction rate constant = 5.33X10-11 cu cm/molecule-sec at 23 °C|Ozone rate constant = 9.0X10-19 cu cm/molecule-sec|Nitrate radical reaction rate constant = 6.54X10-13 cu cm/molecule-sec

No rapid reaction with air No rapid reaction with water

Hydrocarbons, Aliphatic Unsaturated

CAMPHENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas.

265 °C

-19,400 BTU/LB= -10,800 CAL/G= -452X10+5 JOULES/KG

Safety Information

III

4.1

UN 1325 4.1/PG 2

2

11-10-50/53-36

16-33-61-60-26

EX1055000

F,N

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

Volatilizes on exposure to air. /dl-Form/

P210-P273-P305 + P351 + P338-P501

H228-H319-H410

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.|Product Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents.|Contact with strong oxidizers may cause fire and explosions. Emulsions in xylene may violently decompose on contact with iron and or aluminum above 70 °C. Contact with reducing agents may cause exothermic reaction, releasing flammable hydrogen gas.

2,2-Dimethyl-3-methylenenorbornane 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.

UN 9011

P210; P273; P305 + P351 + P338; P501

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: 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. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016)|Flammable. Above 26 °C explosive vapour/air mixtures may be formed.

|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P273, P280, P303+P361+P353, P305+P351+P338, P337+P313, P370+P378, P391, P403+P235, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|Danger|H228 (95.26%): Flammable solid [Danger Flammable solids]|P210, P240, P241, P264, P273, P280, P301+P310, P305+P351+P338, P331, P337+P313, P370+P378, P391, P405, and P501|Aggregated GHS information provided by 2122 companies from 32 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H228: Flammable solid [Danger Flammable solids]|P210, P240, P241, P264, P273, P280, P305+P351+P338, P337+P313, P370+P378, P391, and P501|H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Gloves and face shield (USCG, 1999)|Gloves and face shield.|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).|Skin protection: Handle with gloves.|Body Protection: Impervious clothing. Flame retardant antistatic protective clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) 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).

Combustible; yields flammable vapors when heated ...

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|Extinguish with dry chemicals, foam or carbon dioxide. Water may be ineffective on fire.

Accidental release measures: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Avoid breathing dust.; 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: Sweep up and shovel. Contain spillage, and then collect with an electrically protected vacuum cleaner or by wetbrushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal. Contain spillage, pick up with an electrically protected vacuum cleaner or by wet-brushing and transfer to a container for disposal according to local regulations.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|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.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

Contact can irritate the eyes and skin. Exposure can irritate the eyes, nose, and throat.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. Fireproof.

A nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

The substance is irritating to the eyes.

NO open flames, NO sparks and NO smoking. Above 26 °C use a closed system, ventilation and explosion-proof electrical equipment.

PREVENT DISPERSION OF DUST!

Avoid inhalation of dust.

Protective gloves.

Wear safety goggles.

The concentration of camphene in kraft pulp mill wastewater ranged from trace to 30 ppb in 2 Canadian mills monitored in 1973(1). Camphene was detected in 1 of 10 secondary effluent samples from Illinois POTWs, 1980(2). It was qualitatively detected in landfill gas at waste disposal sites in the UK, 1994-95(3). It was qualitatively identified in leachate from the Kin-Buc Landfill, Edison, NJ, 1981-3(4). Camphene was qualitatively identified in industrial landfill leachate(5). It was qualitatively detected in the volatile effluent from decaying refuse(6). Camphene was qualitatively detected as an emission from cologne and soap and a component of air fresheners(7).

SOIL: Camphene was detected, not quantified in soil samples at the site of a former pine-tar manufacturer in Gainesville, FL, operated from the 1930's to 1967(1).

URBAN/SUBURBAN: The concentration of camphene in air samples collected in Riverside, CA at the University of California during June 1990 was 0.014-0.019 ug/cu m(1). Camphene was detected in ambient air collected outside of 27 established dwellings in the suburbs of Melbourne, Australia at a concentration of <2 ug/cu m(geometric mean of 37 samples) (2).|INDOOR: In a study of volatile organic compound concentrations in the air of 4 newly manufactured and 7 new site-built houses, camphene was detected in air samples from the homes with a geometric mean between 0.5 and 1.5 ppb(1). Air samples from 44 established mobile dwellings collected in several countries between 1978 and 1990 contained camphene with a weighted average geometric mean of 14 ug/cu m and a 90th percentile concentration of 55 ug/cu m(2). In Melbourne Australia, camphene was detected in the ambient air collected inside 22 non-compliant buildings at a concentration of 1.4 ug/cu m(geometric mean of 61 samples); camphene was detected in the ambient air collected inside 5 compliant buildings at a concentration of 3.5 ug/cu m(geometric mean of 11 samples)(3). Camphene was identified but not quantified as a volatile organic compound emitted by electrical plug-in air fresheners(4).|RURAL/REMOTE: The concentration of camphene found in Whitaker's Forest, a coniferous forest located in Sierra Mountains, CA during June 1990 was 0.057-0.21 ug/cu m at ground level and 0.11-0.37 ug/cu m at the forest canopy(1). The average day and night-time concentration of camphene in the Rocky Mts, CO, between July and October, 1982 was 0.038 and 0.10 ppbv, respectively(2). The concentration of camphene at 1.7 and 13 m above a maple forest in Quebec ranged from approximately 10-250 parts per trillion over a two day period in June, 1989(3). In a compilation of published and non-published data on the atmospheric concentration of volatile organic compounds determined between 1970 to 1987, the daily mean concentration of camphene in rural areas was 0.045 ppb(4).|SOURCE DOMINATED: Camphene was identified in ambient air surrounding Eucalyptus globulus and Cedrus atlantica growing in El-Hamma Botanical Garden in Algiers City, Algieria(1).

Camphene was qualitatively detected in 4/81 categories of common household products(1). Camphene was found in the emissions of 3 day and 4 week old waxed parquets flooring samples at rates of 25 and 27 ug/m sq-hour (2). Camphene was detected in 9 top 5 selling fragranced consumer products of 2005 and 2007, 25 fragranced consumer products were examined in total, 4 laundry products (detergents, dryer sheets, and fabric softener), 9 personal care products (soaps, hand sanitizer, lotions, deodorant, shampoo, and baby shampoo), 4 cleaning supplies (household and industrial cleaning supplies, disinfectants, and dish detergent), and 8 air fresheners (sprays, gels, solids, and deodorant disks)(3).|Camphene is a component of tobacco, tobacco smoke, and tobacco substitute smoke(1).

Toxicity

practically nontoxic

IDENTIFICATION AND USE: Camphene is a colorless crystal with camphor-like odor. It is used in the manufacture of synthetic camphor and as a camphor substitute. Also used as a fragrance, plasticizer for resins and lacquers. Chlorination of camphene produces toxaphene (a persistent organochlorine pesticide of complex composition). HUMAN EXPOSURE AND TOXICITY: Camphene is not a sensitizer for human skin. Camphene dissolved in dimethylformamide and water at 1, 10, and 100 ug/mL showed no cytotoxic effects on HeLa cells in monolayer culture. ANIMAL STUDIES: Camphene has low toxicity; the oral LD50 for rats is greater than 5 g/kg. Camphene applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was slightly irritating. It was considered as irritating for the rabbits' eyes, but all symptoms were fully reversible within 7 days. Male rats were used in a 14-day feeding study with daily administration of 0.5% and 1% concentration of camphene in food. 0.5% was the concentration at which no toxic effects were observed after 14 days of exposure. Camphene at 1% concentration in the diet slightly reduced body weight gain. Pregnant rats were administered doses of 250-1000 mg/kg bw camphene from the 6th to 15th day of gestation by oral gavage. No toxic effect observed in treated dams nor in the fetuses at the dose of 250 mg/kg bw for 10 days. Camphene at 1000 mg/kg bw/day caused slight but not significant increase of the resorption rate, and consequently of the implantation loss. No further influence on the prenatal development was detected. Camphene was negative in the Ames test of Salmonella typhimurium TA 98, TA 100 with and without activation. ECOTOXICITY STUDIES: Camphene adversely affected larval growth rate and pupal weight of western spruce budworm (Choristoneura occidentalis).

... A combination of camphene and geraniol (CG; 1:1), when pre-administered in rats (10 mg/kg BW), accorded protection against nimesulide hepatotoxicity in vivo, as evident from normalized serum biomarkers and histopathology. mRNA expression and activity of key antioxidant and redox enzymes along with oxidative stress were also normalized due to CG pre-treatment. Downstream effects like decreased mitochondrial swelling, inhibition in release of apoptotic proteins, prevention of mitochondrial depolarization along with reduction in oxidized NAD(P)H and increased mitochondrial electron flow further supported protective action of selected terpenes against nimesulide toxicity. Therefore CG, a combination of natural terpenes prevented nimesulide induced cellular damage and ensuing hepatotoxicity.|Exploration of antioxidants of plant origin and scientific validation of their efficacies has unraveled bioactives from natural sources. In this study, two terpenoids camphene and geraniol were assessed for their cytoprotective and antioxidant potential using t-BHP stressed rat alveolar macrophages. Effect of these test substances along with a known plant derived antioxidant quercetin was seen on cell viability, some oxidative stress markers as well as on mitochondrial membrane potential. Both the test substances geraniol and camphene increased the cell viability significantly as indicated by MTT assay and LDH release assay, during pre-treatment of test compound. Camphene and geraniol showed 29% (P<0.05) and 45% (P<0.05) increase in SOD activity, 28% and 120% (P<0.001) increase in GSH content and restored the mitochondrial membrane potential during pre-treatment as compared to stressed cells. Camphene and geraniol were found to significantly decrease lipid peroxidation, inhibit NO release (83.84% and 64.61%) and ROS generation in the pre-treated cells as compared to stressed cells. The test compounds also showed significant protection against ROS during post-treatment of the test compounds. ...|An ointment containing camphene, menthol, and essential oils was found to have broncholytic effects in animals.|Development of atheromatosis of the aorta in rabbits fed 1 g cholesterol/day for 3 months was considerably inhibited by simultaneous administration of a mixture of terpenes including camphene, injected sc in a dose of 1 mL every other day for 6 weeks and then given orally in doses of 2 mL/day.

LD50 Rat oral >5 g/kg|LD50 Rabbit dermal >2.5 g/kg

/OTHER TERRESTRIAL SPECIES/ Monoterpenes, sesquiterpenes, and phenolic and flavonoid glycosides typical of the current year's foliage of Douglas fir (Pseudotsuga menziesii) were bioassayed using agar diets to determine the effect of these compounds on natural and colony populations of western spruce budworm (Choristoneura occidentalis). Several terpenes adversely affected budworm larval growth... . ...The Montana population, agar diet studies showed that camphene, myrcene, terpinolene, bornyl acetate, and tricyclene adversely affected larval growth rate and pupal weight. ...

Camphene has been identified as an emission from numerous tree species and plants(1-4). Camphene has been identified as a volatile component from a number of foods(5-7). Camphene occurs in a large number of essential oils in optically active form, both as the R and S enantiomers(8). Camphene has been found in various tissues and essential oils of numerous plant species including carrot, dill, fennel, marjoram, nutmeg, parsley, pepper, tarragon and thyme(9,10). Camphene occurs in essential oils of turpentine (levo and dextro forms), in cypress oil (dextro form), in camphor oil from species of Lauraceae (dextro), in bergamot oil, and in oil of citronella, neroli, ginger and valerian(11).|The l-form was isolated ... in the oil Abies sibirica ... it also occurs in the oils of: Tsuga canadensis, Thuja occidentalis, Artemisia herba alba and others. The d-form is present in ... orange flowers, camphor, lavender, calamus, curcuma aromatica and others. /l-Camphene/

Camphene's production and use as a food additive, synthetic feedstock, and starting material for fragrance compounds, in the manufacture of camphor and in the cosmetic, perfume, and food flavoring industries (1-3) 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 1000(SRC), determined from a structure estimation method(2), indicates that camphene is expected to have very low mobility in soil(SRC). Volatilization of camphene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.098 atm-cu m/mole(3) based upon its vapor pressure, 2.5 mm Hg(4), and water solubility, 4.6 mg/L(5). Camphene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.5 mm Hg at 25 °C(4). Utilizing the Japanese MITI test,2% of the Theoretical BOD was reached in 4 weeks indicating that biodegradation is not a fast environmental fate process. However, based on screening studies under aerobic conditions in which aqueous landfill leachate containing camphene was incubated with soil and sludge inocula and demonstrated approximately 80% degradation after 14 to 70 hours, camphene may biodegrade in aerobic soils under certain environmental conditions(6,7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1000(SRC), determined from a structure estimation method(2), indicates that camphene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant estimated as 0.098 atm-cu m/mole(SRC) derived from its vapor pressure, 2.5 mm Hg(4), and water solubility, 4.6 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 hour and 5 days, respectively(SRC). According to a classification scheme(6), a BCF range of 432 to 1,290(7) suggests that bioconcentration in aquatic organisms is high to very high(SRC). Based on screening studies under aerobic conditions in which aqueous landfill leachate containing camphene was incubated with soil and sludge inocula and demonstrated approximately 80% degradation after 14 to 70 hours, camphene may biodegrade under certain environmental conditions(8,9).|AQUATIC FATE: When incubated with seawater macrophytes from Resurrection Bay, AK, camphene, present at 0.24 ng/L in surface seawater samples without algae, was not detected when incubated with surface water and macroalgae, and was present at 0.13 ng/L at a depth of 2 meters(1).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), camphene, which has a vapor pressure of 2.5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase camphene 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 0.6 days(SRC), calculated from its rate constant of 5.3X10-11 cu cm/molecule-sec at 25 °C(6). Vapor-phase camphene is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is calculated to be 1 day(SRC) from its rate constant of 1.1X10-11 cu cm/molecule-sec(3). The atmospheric lifetime of camphene, from experimental calculations, for reaction with hydroxyl, ozone and nitrate radicals is estimated to be 2.6 hours, 18 days and 1.7 hours respectively(4). Camphene 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 camphene with photochemically-produced hydroxyl radicals is 5.3X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 0.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Camphene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Camphene does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). The rate constant for the vapor-phase reaction of camphene with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). The atmospheric lifetimes of camphene, from experimental calculations, for reaction with hydroxyl, ozone and nitrate radicals is estimated to be 2.6 hours, 18 days and 1.7 hours, respectively(5).

954.99|BCF values ranging from 432 to 1290 were measured in fish for camphene using carp (Cyprinus carpio) which were exposed over an 8-week period(1). According to a classification scheme(2), this BCF range suggests that bioconcentration in aquatic organisms is high to very high(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of camphene can be estimated to be 1000(SRC). According to a classification scheme(2), this estimated Koc value suggests that camphene is expected to have low mobility in soil.

The Henry's Law constant for camphene is estimated as 0.098 atm-cu m/mole(SRC) derived from its vapor pressure, 2.5 mm Hg(1), and water solubility, 4.6 mg/L(2). This Henry's Law constant indicates that camphene is expected to volatilize rapidly from water surfaces(3). 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)(3) is estimated as 1 hour(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 5 days(SRC). Camphene's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of camphene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2.5 mm Hg(1).

GROUNDWATER: Camphene was detected, not quantified in the leachate plume of a municipal landfill in Norman, Oklahoma(1). Samples were collected in 1995 and 1996.|SURFACE WATER: Water samples collected from Spirit Lake shortly after the eruption of Mount Saint Helens, 1980, contained camphene, concentration and detection limit not provided(1).|SEAWATER: The concentration of camphene in surface seawater samples from Resurrection Bay, AK, was 837 ng/L in June 1985 and 0.38 ng/L in June, 1986(1).

Camphene was identified as a volatile component of ginger (Zingiber officinale) and lovage (Levisticum officinale)(1). Camphene was detected as a volatile component from chickpea (Cicer arietinum L.) seed(2). Camphene was identified as a volatile constituent of stored and fresh mango at 1.6 and 0.3 ug/g, respectively(3). Camphene was detected (concentration not reported) as a volatile compound in the headspace of frankfurter sausages(4).

ENVIRONMENTAL: One of eight samples of mother's milk collected from 4 urban/industrial areas in the United States tested positive for the presence of camphene(1,2).

According to the 2012 TSCA Inventory Update Reporting data, 3 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of camphene in the United States may be as low as <10 workers and as high as 99 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 114,605 workers (29,452 of these are female) were potentially exposed to camphene in the US(1). Occupational exposure to camphene may occur through inhalation and dermal contact with this compound at workplaces where camphene is produced or used. Monitoring data indicate that the general population may be exposed to camphene via inhalation of ambient air and dermal contact with consumer products containing camphene(SRC).

One of eight samples of mother's milk collected from 4 urban/industrial areas in the United States was positive for the presence of camphene(1,2). In a heterogenous, nonsmoking population of 62 subjects, camphene was a common constituent in the expired air of control, diabetic, and prediabetic subjects(3).

Drug Information

In one study, 3.6% was eliminated unchanged in expired air within 3 hr following dermal application or iv injection of 0.6 ug/kg body weight (0.05 mL camphene in 2.5 mL 1,2-propanediol) into a young pig. The major portion appeared within 5 minutes and 90% within 30 minutes.|/Camphene/ absorbed through the skin was also partially excreted in expired air, appearing within 20 minutes of the start of a 30-minute full bath containing 150 mL pine bath oil ...in 450 L water, and was still detectable 1 day after the bath, although inhalation of volatiles from the bath was prevented. A maximal level was reached after 75 min, with 60% exhaled within first 2 hr and a total of 0.67 uL exhaled during the first 5 hr. This study suggested a major route of elimination of unchanged compound in bile with excretion through intestinal tract, followed by glucuronide formation and excretion via kidney.|Camphene is readily absorbed following inhalation, ingestion, or topical application.

Unlike most terpenes, camphene forms a glycol in rabbit. The compound excreted is camphene glycol monoglucuronide, which was isolated as a levorotatory potassium salt. On hydrolysis with acid, the compound breaks up to glucuronic acid and camphene glycol, which itself undergoes further change to camphenilaldehyde.|Camphene is converted by Aspergillus niger into 2-nonene-2,3-dicarboxylic acid anhydride, with formation of diacetone alcohol as an artifact.

9.12 Days

Inhalation causes irritation of nose and throat. Contact with eyes or skin causes irritation. (USCG, 1999)

INHALATION: move victim to fresh air; call physician immediately. EYES: flush immediately with clean, cool water; call physician immediately. SKIN: wash with alcohol, follow with soap and water wash. (USCG, 1999)


Fresh air, rest.


Rinse skin with plenty of water or shower.


Rinse with plenty of water (remove contact lenses if easily possible).

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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Camphor 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. Anticipate seizures and minimize all external stimuli. Treat seizures as necessary ... Monitor for shock and treat as necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% (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. Administer activated charcoal ... /Camphor and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or is in respiratory distress. Monitor and treat cardiac arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/ or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... /Camphor and related compounds/

/HUMAN EXPOSURE STUDIES/ Tested at 4% in petrolatum camphene produced no irritation after a 48-hour closed-patch test on human subjects. Camphene was also found not to be a sensitizer for human skin.|/ALTERNATIVE and IN VITRO TESTS/ Camphene dissolved in dimethylformamide and water at 1, 10, and 100 ug/mL showed no cytotoxic effects on HeLa cells in monolayer culture.

camphene

Cough.


Redness. Pain.

(±)-Camphene Use and Manufacturing

Methods of Manufacturing

Take high-quality turpentine oil (the main component is pinene) as raw material, after vacuum distillation, collect 70-80℃ (66.5-69.2kPa) distillate to obtain α-pinene, and then use hydrated titanium oxide as a catalyst, at 135-140℃ Isomerization, and then vacuum fractional distillation to obtain camphene products. Industrial product camphene content is ≥95%, melting point is above 45℃. Each ton of product consumes 1500kg of high-grade turpentine.

Uses

Used to synthesize camphor, fragrance (isoborneol acetate), insecticides (such as toxaphene, isocamphor thiocyanate), borneol, isocamphor acetate, etc.


Adhesives and sealant chemicals


Adhesives and sealants

Production

1,000,000 - 10,000,000 lb|(1972) PROBABLY GREATER THAN 1.36X10+6 GRAMS|(1976) PROBABLY GREATER THAN 6.81X10+6 GRAMS|Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene- 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).[EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. Bicyclo|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-. Aggregated National Production Volume: 1 to < 10 million pounds.[US EPA; Non-Confidential 2006 Inventory Update Reporting. National Chemical Information. Bicyclo|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-. National Production Volume: 500,000 - 1,000,000 lb/yr.[USEPA/Pollution Prevention and Toxics; 2012 Chemical Data Reporting Database. Bicyclo

GRADES OF PURITY: Commercial, 75% or greater|Technical

Adhesive manufacturing|Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-: ACTIVE|Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-, (1R,4S)-: ACTIVE|Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-, (1S,4R)-: ACTIVE|FEMA NUMBER 2229|In public use since the 1930's. Use in fragrances in the USA amounts to about 6000 lb/yr. Concentration in final product (%): soap: usual 0.01, max 0.1; detergent: usual 0.001, max 0.01; creams, lotions: usual 0.005, max 0.05; perfume: usual 0.08, max 0.4.|The council of Europe (1974) included camphene at a level of 0.5 ppm in the list of artificial flavoring substances that may be added temporarily to foodstuffs without hazard to the public health.

Camphene was determined in ambient air by gas chromatographic method.|Camphene was analyzed by gas chromatography-mass spectrometry.

EPA Safer Chemical Functional Use Classes -> Fragrances|Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues|Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index

Flavoring Agents

Computed Properties

Molecular Weight:136.23
XLogP3:3.3
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

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