Grundinformationen
- Standard-SMILES
C=C1C2CCC(C2)C1(C)C- InChIKey
CRPUJAZIXJMDBK-UHFFFAOYSA-N- Summenformel
- C10H16
- Durchschnittliche Molmasse
- 136,23 g/mol
- Monoisotopische Masse
- 136,12520051
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Camphene
- IUPAC
- 2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane
- Lokaler Name
- Camphen
- Englischer Name
- Camphene
- Summenformel
- C10H16
- Molmasse
- 136.23
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
79-92-5- PubChem CID
- 6616
- DTXSID
DTXSID8026488- ChEMBL
CHEMBL2268550- ChEBI
CHEBI:3830- UNII
- G3VG94Z26E
- EC Number
- 201-234-8
- Nikkaji
- J39.020H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,3
- Polarare Oberfläche (TPSA)
- 0 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 0
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 176
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = 4.22
4.1 (calculated)
4.56
Odor
Camphoraceous, cooling, piney wood with trephy nuances...citrus and green minty and green spicy notes
Insipid odor
Camphor-like
Taste
Camphoraceous taste
Terpene, camphoraceous taste...cooling, minty, with citrus and green spicy nuances
Density
0.87 at 59 °F (USCG, 1999) - Less dense than water; will float
0.839 g/mL at 20 °C
0.87 g/cm³
Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.01
Solubility
In water, 4.6 mg/L at 25 °C
In water, 4.2 mg/L
Soluble in ether; slightly soluble in alcohol
Solubility in water, g/100ml at 20 °C: 0.0004 (very poor)
Insoluble in water; soluble in oils
Soluble (in ethanol)
Flash Point
92 °F (USCG, 1999)
The Guide in the Emergency Response Guidebook is for "Flammable solid, organic, n.o.s." 26 °C
42 °C (open cup); 33 °C (closed cup)
108 °F Open cup; 92 °F closed cup
26 °C c.c.
Physikochemische Eigenschaften
- Schmelzpunkt
- 48 · 48-52 °C (lit.)
- Siedepunkt
- 159 · 159-160 °C (lit.)
- Dichte
- 0.85 g/mL · 0.85 g/mL at 25 °C (lit.)
- Dampfdruck
- 3.99 hPa · 3.99 hPa (20 °C)
- Brechungsindex
- 1.4551 · 1.4551
- FEMA
- 2229 · 2229 | CAMPHENE
- Flammpunkt
- 94 °F · 94 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 0.0042 g/l · 0.0042g/l
- Aggregatzustand
- Crystalline Low Melting Solid
- Wichte
- 0.85 · 0.85
- Farbe
- White
- PH
- 5.5 · 5.5 (H2O, 22℃)(saturated aqueous solution)
- Geruch (Odor)
- 10 % · at 10.00 % in dipropylene glycol. woody herbal fir needle camphor terpenic
- Geruchsart
- woody
- Biologische Quelle
- synthetic
- Odor Threshold
- 0.88 ppm · 0.88ppm
- Wasserlöslichkeit
- practically insoluble
- Merck
- 14 · 14,1730
- JECFA Number
- 1323 · 1323
- Henry's Law Constant
- 2.3 · 2.3×10-4 mol/(m3Pa) at 25℃, Plyasunov and Shock (2000)
- Dielectric constant
- 2.7 · 2.7(20℃)
- Kosmetik-Inhaltsstoffe Funktionen
- FRAGRANCEPERFUMING
- InChI
- 1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9+/m0/s1
- InChIKey
- CRPUJAZIXJMDBK-DTWKUNHWSA-N
- SMILES
- [H][C@]12CC[C@]([H])(C1)C(C)(C)C2=C
- LogP
- 4.22 at · 4.22 at 20℃
- CAS Datenbank
- 79 · 79-92-5(CAS DataBase Reference)
- NIST chemische Informationen
- Camphene(79-92-5)
- EPA chemische Informationen
- Camphene (79-92-5)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 2.3% (48 of 2128) of reports.
Danger
H228 (94.8%): Flammable solid [Danger Flammable solids]
P210, P240, P241, P264+P265, P273, P280, P301+P316, P305+P351+P338, P331, P337+P317, P370+P378, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2128 reports by companies from 36 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Gefahrenhinweise
Regulatory Information
Chemical: Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-
Regulation (EC) No 1831/2003 (amended)
Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene- 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: 18-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14290
Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
Excerpt from ERG Guide 133 [Flammable Solids]:
Flammable. Above 26 °C explosive vapour/air mixtures may be formed.
Hazards Summary
Emergency treatment: Camphor; Camphor is a CNS stimulant; After ingestion, it may cause nausea, vomiting, liver injury, and seizures; Severe toxicity occurs with doses >30 mg/kg; [HSDB] An eye irritant; [ICSC] A skin, eye, nose, and throat irritant; [CAMEO] An irritant; Effects in high-dose animal studies include fatty liver degeneration; [MSDSonline] See Camphor.
FDA Requirements
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.
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 133 [Flammable Solids]:
Use water spray, powder, carbon dioxide.
First Aid Measures
Fresh air, rest.
Rinse skin with plenty of water or shower.
Rinse with plenty of water (remove contact lenses if easily possible).
Rinse mouth. Give one or two glasses of water to drink.
Fire Fighting Procedures
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.
Storage Conditions
Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place.
Storage temperature: ambient; venting: open.
Cleanup Methods
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.
Disposal Methods
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.
Spillage Disposal
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.
Preventive Measures
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.
Toxikologische Informationen
Body Burden
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).
Interactions
... 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.
Ecotoxicity Values
LC50; Species: Cyprinodon variegatus (Sheepshead minnow); Concentration: 1.9 ppm for 96 hr (95% confidence limit 1.6-2.2 ppm) /Conditions of bioassay not specified/
LC50; Species: Cyprinodon variegatus (Sheepshead minnow); Conditions: static; Concentration: 1.8 mg/L for 24 hr, 2 mg/L for 48-72 hr
LC50; Species: Brachydanio rerio (Zebrafish); Conditions: flow through; Concentration: 1.4 mg/L for 24 hr, 1.21 mg/L for 48 hr, 0.94 mg/L for 72 hr, 0.72 mg/L for 96 hr /Camphen 87.6%/
LC50; Species: Brachydanio rerio (Zebrafish); Conditions: static; Concentration: 150 mg/L for 48-96 hr /Technical product/
For more Ecotoxicity Values (Complete) data for CAMPHENE (9 total), please visit the HSDB record page.
Environmental Fate
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).
Food Survey Values
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).
Toxicity Summary
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).
Ecotoxicity Excerpts
/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. ...
Plant Concentrations
The normalized emission rate of camphene from mature spruce branches at 30 °C was 0.07 (Picea glauca), 0.07 (Picea abies), and 0.02 (Picea pungens) ugC/g h(1). The emission rates of camphene in forested areas of Baton Rouge, Louisiana from loblolly pine, shortleaf pine, sweet gum, sweet gum (from separate environment), elm, cypress, water hickory, and hackberry were 170, 200, 60, 1300, 20, 140, and 390 ug/kg-foliage/hr, respectively(2). Camphene was identified as a volatile emission from balsam poplar, European larch, Scots Pine, Siberian pine, common juniper, European fir, and silver fir(3,4). Camphene was detected in Scots pine emissions from boreal forests in Finland and Sweden(1). Concentrations were not reported. Balkan pine (Pinus peuce) twig oil and needle oil contain 0.24 percent and 5.52 percent camphene, respectively; samples were collected from 25 to 100 year old tress in the forests of northern Greece during November 1997(6). Camphene was detected in the emissions of 35 out of 63 vegetation species in forests near Atlanta, GA, Rhinelander, WI, and Hayden CO(7). Measured camphene emission rates from these species ranged from 0.1 to 39 ug/hr-gdw with an average rate of 3.1 ug/hr-gdw during the summer of 1993. The mass percentage of camphene in Douglas Fir trees from Socorro, NM and from the nearby Magdalena Mountains during the summer of 1996 was 20 percent(8). In June 1996 camphene was detected in emissions from the remote forest region of Achenkirch/Tyrol, Austria with concentrations of 10 ppbC at the valley station and 6 ppbC at the middle and peak stations(9).
Camphene was detected as an emission from pistachio trees and chamise shrubs (Adenostoma fasciculatum) in Riverside, California(1). Camphene was identified in 10 of 82 wild mushroom species (Gomphidius glutinosus, Amanita ovoidea, Cystoderma carcharias, Mycena rosea, Bovista aestivalis, Suillus luteus, Hydnum repandum, Mycena pura and Tricholoma sulfureum); levels ranged from trace amounts to a relative percentage of 6%(2). Camphene was identified but not quantified as an emission from agricultural crops such as pistachio, tomato, carrot, cotton, lemon, orange and walnut, in California's Central Valley during the spring and summer of 1988 and 1989(3). Camphene was detected in the emissions of red maple (Acer rubrum), paper birch (Betula papyrifera), narrowleaf cottonwood (Populus angusstifolia), big-tooth aspen (Populus grandidentata), trembling aspen (Populus tremuloides), and Red oak (Quercus rubra)(4). Camphene was identified in the volatile emissions of Eucalyptus viminalis, Eucalyptus grandis, Eucalyptus camaldulensis, and Eucalyptus globulus from southern Australia at rates less than 1.5 nmol/m sq-min(5). In samples taken in May and June 2000, trace amounts of camphene were detected from Eucalyptus salinga grown in a nursery farm in Barba Negra in Brazil cultivated at the University of Waterloo, Ontario, Canada; camphene was not detected in Eucalyptus citriodora and inconsistently detected from samples of Eucalyptus dunni(6).
Essential oils extracted from leaves and fruits of Schinus areira (Anacardiaceae) were tested for their repellent .... properties. ... The essential oil of the leaves contained mainly monoterpenoids, with alpha-phellandrene, 3-carene and camphene predominant, whereas that from the fruits contained mainly alpha-phellandrene, 3-carene and beta-myrcene. ... /Schinus areira oil/
Camphene detections in various plants(1).[Table#2374]
Signs and Symptoms
Cough.
Redness. Pain.
Ongoing Test Status
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/]
Regulatorische Informationen
FDA Requirements
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.
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- ridadr
- UN 1325 4.1/PG 2
- hs_code
- 2902 19 00
- RTECS-Nr.
- EX1055000
- risk_code
- 11-10-50/53-36
- hazard_code
- F,N
- safety_code
- 16-33-61-60-26
- hazard_class
- 4.1
- packing_group
- III
- Speicherklasse
- 4.1B - Flammable solid hazardous materials
- Giftige Stoffe Daten
- 79-92-5(Hazardous Substances Data)
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Flam. Sol. 1
- Selbstentzündungstemperatur
- 265 °C
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
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.
Absorption, Distribution and Excretion
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.
Verwendung und Herstellung
Uses
Occurs in many essential oils; [Merck Index] Used as a food additive, flavoring agent, chemical intermediate, camphor substitute, mothproofing tablet, feedstock for polymerized terpene resins, fragrance, and plasticizer for resins and lacquers; [HSDB]
Chemical intermediate for the perfume component, isobornyl acetate, misc specialty aromatics, and the insecticides isobornyl thiocyanoacetate and toxaphene
Essential oils extracted from leaves and fruits of Schinus areira (Anacardiaceae) were tested for their repellent, toxic and feeding deterrent properties against Tribolium castaneum (Coleoptera: Tenebrionidae) larvae and adults. A topical application assay was employed for the contact toxicity study and filter paper impregnation for the fumigant assay. A treated diet was also used to evaluate the repellent activity and a flour disk bioassay for the feeding deterrent action and nutritional index alteration. The essential oil of the leaves contained mainly monoterpenoids, with alpha-phellandrene, 3-carene and camphene predominant, whereas that from the fruits contained mainly alpha-phellandrene, 3-carene and beta-myrcene. The leaf essential oil showed repellent effects, whereas that from the fruit was an attractant. Both oils produced mortality against larvae in topical and fumigant bioassays, but fumigant toxicity was not found against adults. Moreover, both essential oils produced some alterations in nutritional index. These results show that the essential oils from S. areira could be applicable to the management of populations of Tribolium castaneum. /Schinus areira oil/
Manufacture of synthetic camphor; camphor substitute.
Used in tablet form for mothproofing
For more Uses (Complete) data for CAMPHENE (8 total), please visit the HSDB record page.
U.S. Production
2023: 100,000 - <250,000 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
Methods of Manufacturing
(+)-alpha-Pinene is converted into (+)-bornyl chloride by the action of dry hydrogen chloride in a Wagner-Meerwein rearrangement. Base-catalyzed dehydrohalogenation of the (+)-bornyl chloride gives racemic camphene.
Isomerization of alpha-pinene in the presence of solid acidic mineral catalysts
From pinene by catalytic isomerization or from bornyl chloride by heating with alkali in the presence of abietenesulfonic acid.
By heating pinene hydrochloride with alkalis, aniline, or alkali salts such as sodium acetate.
Formulations/Preparations
GRADES OF PURITY: Commercial, 75% or greater
Technical
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
Paint and Coating Manufacturing
Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-: 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.
Anwendungen
OccurrenceReported found in carrot, dill, fennel, marjoram, nutmeg, parsley, pepper, tarragon and thyme.
VerwendenCamphene is used in the preparation of fragrances and as a food additive for flavoring.
Darstellung
synthetischeFrom pinene by catalytic isomerization or from bornyl chloride by heating with alkali in the presence of abietenesulfonic acid.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: 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.
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