p-Cymene
-
p-Cymene
structure -
-
CAS No:
99-87-6
-
Formula:
C10H14
-
Chemical Name:
p-Cymene
-
Synonyms:
Benzene,1-methyl-4-(1-methylethyl)-;p-Cymene;1-Methyl-4-(1-methylethyl)benzene;Camphogen;p-Isopropyltoluene;p-Cymol;Dolcymene;1-Methyl-4-isopropylbenzene;1-Isopropyl-4-methylbenzene;p-Methylisopropylbenzene;2-p-Tolylpropane;4-Isopropyl-1-methylbenzene;p-Methylcumene;4-Isopropyltoluene;para-Cymene;4-Methylisopropylbenzene;4-Cymene;NSC 4162;1-Methyl-4-(propan-2-yl)benzene
- Categories:
-
CAS No:
Description
p-Cymene has a citrusy aroma reminiscent of lemon. It is colorless liquid with a strong, characteristic odor reminiscent of carrot. It tends to darken with aging. It occurs naturally in orange peel oil, mandarin peel oil, satsuma mandarin peel oil, coldpressed lime peel oil, distilled lime peel oil, cinnamon leaf, etc. 4-isopropyltoluene has antimicrobial properties. It is used as a flavor ingredient permitted for direct addition to food for human consumption. p-Cymene is a monoterpene that i
P-cymene is a colorless liquid with a mild pleasant odor. Floats on water. (USCG, 1999)|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|Colourless to pale yellow mobile liquid; citrusy aroma reminiscent of lemon
P-cymene is a colorless liquid with a mild pleasant odor. Floats on water. (USCG, 1999)|P-cymene is a monoterpene that is toluene substituted by an isopropyl group at position 4. It has a role as a plant metabolite, a volatile oil component and a human urinary metabolite. It is a member of toluenes and a monoterpene.
p-Cymene Basic Attributes
134.22
134.22
1903377
202-796-7
1G1C8T1N7Q
0617
4162
2046
DTXSID3026645
Colorless transparent liquid
2902909090
Characteristics
0
4.1
Clear Liquid
0.8610 g/cm3 @ Temp: 20 °C
-68.9 °C
177.10 °C
117 °F
1.493
Practically insoluble in water
Flammables area
1.5 mm Hg ( 20 °C)
4.62 (vs air)
Oral-Rat LD50: 4750 mg/kg
Combustible in case of open flame, high temperature, strong oxidant; burning emits irritating smoke
vol% in air: 0.7.6
Sweetish aromatic odor
1.51e-11 cm3/molecule*sec
Liquid-water interfacial tension: 36.41 dynes/cm at 20 °C|Henry's Law constant = 0.011 atm-cu m/mol at 25 °C /Estimated from vapor pressure and water solubility/|Hydroxyl radical rate constant= 1.51X10-11 cu cm/molecule-sec at 22 °C
Insoluble in water.
Hydrocarbons, Aromatic
Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as CYMENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.
817 °F (USCG, 1999)|436 °C /From table/|435 °C
-10,400 cal/g = -437X10+5 J/kg
Lower flammable limit: 0.7% at 212 °F (100 °C) by volume; Upper flammable limit: 5.6% by volume
The vapour is heavier than air.
67.8 cal/g = 2.84X10+5 J/kg
Critical temperature: 652 deg K; critical pressure: 2.80X10+6 Pa
Safety Information
III
3
UN 2046 3/PG 3
2
10-36/37/38
26-36
GZ5950000
Xi
Completely packed, lightly placed; storeroom ventilated, away from open flames, high temperature, and stored separately from oxidants
Explosive when mixed with air
Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, strong bases.
P210-P301 + P310-P331-P370 + P378
H226-H304-H411
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.
Reacts with oxidants. Attacks rubber.
p-Cymene 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.
Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: 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. (ERG, 2016)|Flammable. Above 47 °C explosive vapour/air mixtures may be formed.
|Danger|H226 (99.67%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P273, P280, P301+P310, P303+P361+P353, P331, P370+P378, P391, P403+P235, P405, and P501|Aggregated GHS information provided by 2099 companies from 37 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P340, P312, P370+P378, P403+P233, P403+P235, P405, and P501|P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P312, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: 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 130 [Flammable Liquids (Water-Immiscible / Noxious)]: 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)
Self-contained or air-line breathing apparatus; solvent- resistant rubber gloves; chemical splash goggles. (USCG, 1999)|Protective gloves.|Wear safety spectacles.|Use ventilation.
Flammable liquid.
UEL: 5.6% /Technical/|Explosion hazard: slight in the form of vapor.|Above 47 °C explosive vapor/air mixtures may be formed.|Explosive limits , vol% in air: 0.7-5.6
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. /Cymenes/
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Cymenes/|Environmental considerations: Water spill: use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Cymenes/|Environmental considerations: Land spill: dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Cymenes/|Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: filter respirator for organic gases and vapors adapted to the airborne concentration of the substance.
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. Use water spray to knock-down vapors. /Cymenes/|Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Cymenes/|Do not eat, drink, or smoke during work.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ 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. /Cymenes/|/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Cymenes/|/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ 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. /Cymenes/|/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Cymenes/|For more DOT Emergency Guidelines (Complete) data for P-CYMENE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Vapor (gas) irritant characteristics: vapors are nonirritating to eyes and throat. Liquid or solid irritant characteristics: minimum hazard. If spilled on clothing and allowed to remain, may cause smarting and reddening of the skin.|p-Cymene is reported to be a primary skin irritant ... .
Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance.
Fireproof.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
The substance is irritating to the eyes and skin. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis.
The substance defats the skin, which may cause dryness or cracking.
NO open flames, NO sparks and NO smoking. Above 47 °C use a closed system, ventilation and explosion-proof electrical equipment. Prevent build-up of electrostatic charges (e.g., by grounding).
PREVENT GENERATION OF MISTS!
Use ventilation.
Protective gloves.
Wear safety spectacles.
| 1 - Materials that, under emergency conditions, can cause significant irritation.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.
p-Cymene concentration of 15.4 ug/L was detected in the effluent from a large, 5-yr-old community septic tank located near Tacoma, WA(1). p-Cymene levels as high as 80 ug/L were detected in wastewaters from two pulp mills in WA and OR(2). p-Cymene has been qualitatively detected in various wastewaters from the following industries: iron and steel manufacturing, petroleum refining, nonferrous metals, coal mining, pulp and paper, rubber processing, auto amd other laundries, electronics, and mechanical products(3). p-Cymene was identified, not quantified, in water samples collected from an advanced waste treatment facility in Pomona, CA on Sep 25, 1974(4). p-Cymene was identified, not quantified, in landfill gas at 7 waste disposal sites in the UK(5) and in common household waste(6). The average concentration of p-cymene detected in landfill gas emissions from the Fresh Kills Landfill in New York City was 13.14 ppm(7).
SEDIMENT: p-Cymene was detected at concentrations of less than 0.1 ng/g to 1.9 ng/g in sediment from rivers near Niigata, Japan(1).
URBAN/SUBURBAN: Ambient air samples collected in Long Beach, CA and Inglewood, CA contained p-cymene levels of 0.001 and 0.005-0.008 ppm, respectively(1). The ambient air concentration of p-cymene was 0.8 ug/cu m during a 1993 smog episode in Los Angeles CA(2).|INDOOR: Ambient air samples collected in Long Beach, CA and Inglewood, CA contained p-cymene levels of 0.001 and 0.005-0.008 ppm, respectively(1). p-Cymene was identified, not quantified, in indoor air samples of various office surveyed worldwide(2). Air samples collected from 15 micro environments in Birmingham UK (homes, offices, restaurants, cinemas, libraries, buses, cars, etc) contain mean p-cymene concentrations ranging from 0.3 to 4.9 ug/cu m(5).|RURAL/REMOTE: p-Cymene was identified, not quantified, at Whiteker's Forest in the Sierra Nevada Mountains, CA(1). p-Cymene concentrations of about 0.01 to 0.05 ppb were detected in the ambient air at a remote tropical forest in central Amazonia in 1998(2).|SOURCE DOMINATED: Monitoring in an auto-truck tunnel in Rio de Janerio Brazil detected a mean p-cymene level of 0.8 ug/cu m(1).
p-Cymene has been identified as a component of jet fuel(1).
Toxicity
moderately toxic
Previously, /the researchers/ have demonstrated the analgesic-like property of p-cymene in rodents. Short half-life is a limitation for p-cymene application and several approaches have been used to improve pharmaceutical properties of monoterpenes, including the employment of drug-delivery systems. Here, we used p-cymene/beta-cyclodextrin (beta-CD) complex and p-cymene (PC) isolated to evaluated whether the complex formulation is able to improve the antinociceptive activity of this monoterpene. Male mice (26-30 g) were pretreated with PC/beta-CD (20 or 40 mg/kg, p.o.), PC (20 or 40 mg/kg, p.o.) or vehicle (distilled water), 0.5 hr before painful tests and antinociceptive effect was evaluated at times: 0.5, 1, 2, 4, 8, and 16 hr after treatment. We evaluated the analgesic-like effect of PC/beta-CD and PC in acetic acid-induced abdominal writhes, hot-plate, carrageenan-induced paw edema and in rota-rod apparatus. ... Results demonstrated that acute treatment with complex PC/beta-CD produced an antinocicepitve effect (p < 0.01 or p < 0.001) for 8 hr followed whereas isolated PC produced the same effect for 2 hr. Similar results were obtained in hot-plate test, PC/beta-CD, in all doses, significantly reduces (p < 0.01 or p < 0.001) nociceptive behavior for 8 hr while isolated PC for 1 hr, did so only in higher dose. Such results were unlikely to be caused by motor abnormality. Systemic pretreatment with PC/beta-CD and PC inhibited the development paw edema by carrageenan 1%, but PC/beta-CD did so during a longer period when compared with isolated monoterpene alone. ... Results provide evidence to propose that the complex with beta-CD improved analgesic and anti-inflammatory effects of p-cymene.
LD50 Rat oral 4750 mg/kg
p-Cymene is emitted to the biosphere from natural sources such as California black sage and "disturbed" eucalyptus foliage(1); it is found in the gum terpentines of scotch pine and loblolly pine(1). p-Cymene is emitted from oak species, Quercus ilex L(2) and Japanese hinoki cypress and firs(3). p-Cymene has been found in a variety of arboreous plants including, European larch, Scots pine, European fir, Siberian pine, silver fir, common juniper, Zeravshan juniper, pencil cedar, evergreen cypress, northern white cedar and Chinese arbor vitae(4). p-Cymene has been identified in >1800 essential oils and plant extracts(5). p-Cymene emission rates have been measured from several Australian species of Eucalypts(6).
p-Cymene's production and use as a solvent, chemical intermediate for p-cresol, carvacrol and other organic compounds(1) and its use as a fragrance agent in commercial and consumer products(2) may result in its release to the environment through various waste streams(SRC).|p-Cymene is produced as a by-product in the manufacture of sulphite paper pulp(1), and it has been detected in wastewaters released from pulp manufacturing plants(2,3,4). p-Cymene's use as a solvent and thinner for lacquers and varnishes(3) will release the compound directly to air through evaporation(SRC). p-Cymene has been identified as a gaseous exhaust product from motor vehicles(5).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1120(SRC), determined from a structure estimation method(2), indicates that p-cymene is expected to have low mobility in soil(SRC). Volatilization of p-cymene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.011 atm-cu m/mole(SRC), derived from its vapor pressure, 1.50 mm Hg(3), and water solubility, 23.4 mg/L(4). However, adsorption may attenuate this process. p-Cymene is expected to volatilize from dry soil based on its vapor pressure(4). p-Cymene, present at 100 mg/L, reached 83-95% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L with the Japanese MITI test(5,6) which classifies p-cymene as readily biodegradable(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1120(SRC), determined from a structure estimation method(2), indicates that p-cymene 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 0.011 atm-cu m/mole(SRC), derived from its vapor pressure, 1.50 mm Hg(4), and water solubility, 23.4 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 3.5 hours and 4.6 days, respectively if adsorption is ignored(SRC). The volatilization half-life from a model pond is estimated as 30 days if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 236(SRC), from its log Kow of 4.10(8) suggests the potential for bioconcentration in aquatic organisms is high. p-Cymene, present at 100 mg/L, reached 83-95% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L with the Japanese MITI test(9,10) which classifies p-cymene as readily biodegradable(10). p-Cymene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-cymene, which has a vapor pressure of 1.50 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase p-cymene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and nitrate radicals(SRC); the half-life for the reaction with hydroxyl radicals is estimated to be about 1 day(SRC), calculated from its measured rate constant of 1.51X10-11 cu cm/molecule-sec at 22 °C(3). The half-life for the reaction with nitrate radicals is estimated to be 34 days(SRC), calculated from its rate constant of 9.9X10-16 cu cm/molecule-sec at 25 °C(3). p-Cymene's detection in snow(4) suggests that removal from air by wet deposition occurs(SRC).
The rate constant for the vapor-phase reaction of p-cymene with photochemically-produced hydroxyl radicals has been measured as 1.5X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of p-cymene with nitrate radicals has been measured as 9.9X10-16 cu cm/molecule-sec at 25 deg C(1). This corresponds to an atmospheric half-life of about 34 days at an atmospheric concentration of 2.4X10+8 nitrate radicals per cu cm(2). p-Cymene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). p-Cymene has a UV absorption maxima at 274 nm (log epsilon = 2.74) and a rapidly decreasing log epilson of about 1.1 at 280 nm(4); although p-cymene may have minor absorption >290 nm, direct photolysis is not expected to be an important environmental fate process(SRC).
An estimated BCF of 236 was calculated for p-cymene(SRC), using a log Kow of 4.10(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, provided the compound is not metabolized by the organism(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of p-cymene can be estimated to be 1120(SRC). According to a classification scheme(2), this estimated Koc value suggests that p-cymene is expected to have low mobility in soil.
The Henry's Law constant for p-cymene is estimated as 0.011 atm-cu m/mole(SRC), derived from its vapor pressure, 1.5 mm Hg(1), and water solubility, 23.4 mg/L(2). This Henry's Law constant indicates that p-cymene 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 3.5 hours if adsorption is neglected(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 4.6 days if adsorption is neglected(SRC). The volatilization half-life from a model pond is about 30 days if adsorption is considered(4). p-Cymene's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). p-Cymene is expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC).
GROUNDWATER: p-Cymene was detected in the leachate plume from a municipal landfill in Norman OK(1). As part of the National Water Quality Assessment Program of the US Geological Survey, groundwater samples were collected from 2948 wells between 1985 and 1995 throughout the US(2); positive p-cymene levels ranging from approximately 0.2 to 50 ug/L were detected in 0.3% of all samples(2).|DRINKING WATER: p-Cymene was identified, not quantified, in drinking water samples collected from Philadelphia, PA on Feb 10, 1976 and Cincinnati, OH on Nov 17, 1978(1). p-Cymene was detected at a max concentration of 3.4 ug/L in groundwater wells in the Denver, CO metropolitan area(2).|SURFACE WATER: Surface water samples collected from the lower 25 km of the Brazos River and at the river/ocean mixing in Texas (at the Gulf of Mexico) between Jun 25, 1981 and Aug 5, 1982 contained p-cymene levels of 0.001-0.01 ug/L(1). p-Cymene was detected in rivers in Osaka, Japan at concentrations of 0-0.33 ug/L(2).|RAIN/SNOW: p-Cymene was detected in snow in Austria at a concentration of 7 ug/L(1).
A p-cymene concentration of 0.1 ug/g was detected in fresh, ripe mangos(1). p-Cymene has been identified, not quantified, as a volatile constituent of nectarines(2), orange essence(3), chickpea flour(4), and roasted filbert nuts(5). p-Cymene was identified, not quantified, in peanut oil(6). p-Cymene was detected in the volatile odors of frankfurter sausages(7).
ENVIRONMENTAL: An analysis of 35 samples of cow's milk collected from 8 grocery stores in Las Vegas, NV in Jan and Feb 2002 found an average p-cymene concentration of 72.4 ng/mL in whole milk, 2.77 ng/mL in 2% milk and 1.24 ng/L in 1% milk(1).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of p-cymene is 1000 or greater; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 74,141 workers (12,723 of these are female) are potentially exposed to p-cymene in the US(1). Occupational exposure to p-cymene may occur through inhalation and dermal contact with this compound at workplaces where p-cymene is produced or used(SRC). Air samples collected inside a tire re-treading factory in Italy contained p-cymene levels of 1-450 ug/cu m(2). Monitoring data indicate that the general population may be exposed to p-cymene through inhalation of ambient air, ingestion of food products which contain p-cymene as a natural constituent and through dermal contact with plants and vegetation that contain p-cymene and through the use of fragrance products that contain this compound(SRC).
Drug Information
p-Cymene is well absorbed through the skin. In studies with (14)C-labelled p-cymene the penetration observed was 254 ug/sq cm in 60 minutes
Yields cumyl alcohol in pseudomonas ... . /From table/|Only small part is excreted unchanged, remainder being oxidized to water-soluble metabolites. Suggested that readily oxidized propyl side chain formed carboxyl-group ... ultimate product, in case of dogs and sheep, is cumic acid which is probably excreted as conjugate with glycine.|The metabolism of p-cymene was studied in rats and guinea-pigs. Following intragastric or inhalation dosage (100 mg/kg) urinary metabolite excretion was nearly complete within 48 hr, amounting to 60-80% dose. The inhalation experiments gave the lowest values. 18 urinary metabolites were detected and identified. Of these, rats did not excrete two and guinea-pigs did not excrete a third. No ring-hydroxylation of p-cymene was detected in rats, but guinea-pigs formed small amounts of carvacrol and hydroxycarvacrol. Oxidation of both the methyl and isopropyl groups of p-cymene occurred extensively in both species. The following types of metabolites were formed: monohydric alcohols, diols, mono- and di-carboxylic acids and hydroxyacids. Conjugation with glycine of the cumic acid formed was extensive in guinea-pigs.|Metabolites of the food additive eucalyptus maculata oil were investigated in the urine and feces of brushtail possum. p-Cymene was metabolized to p-cresol and cumic acid.|p-Cymene was metabolized in rabbits and the following four optically active metabolites, 2-(p-tolyl)-1-propanol (3': R/S = 65:35), 2-(p-tolyl)propanoic acid (5': R/S = 0:100), p-(2-hydroxy-1-methylethyl)benzoic acid (6': R/S = 91:9) and p-(1-carboxyethyl)benzoic acid (8': R/S = 30:70), were isolated in addition to three optically inactive metabolites, 2-(p-tolyl)-2-propanol, p-isopropylbenzoic acid (4'), and p-(1-hydroxy-1-methylethyl)benzoic acid (7'). The presumed metabolic pathways of p-cymene in rabbits were confirmed by the administration of the intermediate metabolites (2, 3', 4', and 5'). The enantiomeric ratios of the metabolites, 3' and 6', suggested that omega-hydroxylations of the isopropyl group in 1 and 4' occurred preferentially at the pro-S methyl group. In the metabolism of 1, the S-isomers are predominant in the propanoic acid derivatives, but the R-isomers are rich in the propanol derivatives. It is of interest that the metabolism of 4', however, produced predominantly the corresponding propanol derivative (6'; R/S = 91:9) and propanoic acid derivative (8'; R/S = 80:20) possessing the same R-configuration. Some optically active p-cymene derivatives were also synthesized as standard compounds.
The objective of this study was to test the hypothesis that p-cymene can attenuate acute lung injury induced by lipopolysaccharide (LPS) in vivo. In the mouse model of LPS-induced acute lung injury, intraperitoneal preconditioning with p-cymene resulted in a significant reduction of pro-inflammatory cytokines (TNF-alpha, IL-1beta and IL-6), lung water gain, inflammatory cell infiltration, lung tissue myeloperoxidase activity. In addition, p-cymene blocked the phosphorylation of IkBalpha protein and mitogen-activated protein kinases (MAPK) signaling pathway activation. Histopathologic examination of lung tissue indicated that p-cymene treatment markedly decreased focal thickening, congestion, pulmonary edema, and inflammatory cells infiltration. The results showed that p-cymene had a protective effect on LPS-induced ALI in mice.|The present study was designed to investigate the effects of p-cymene on lipopolysaccharide (LPS)-induced inflammatory cytokine production both in vitro and in vivo. The production of tumor necrosis factor-a (TNF-a), interleukin-1beta (IL-1beta), interleukin-6 (IL-6), and interleukin-10 (IL-10) in LPS-stimulated RAW 264.7 cells and C57BL/6 mice was evaluated by sandwich ELISA. Meanwhile, the mRNA levels of cytokine genes were examined in vitro by semiquantitative RT-PCR. In a further study, we analyzed the activation of nuclear factor-kB (NF-kB) and mitogen-activated protein kinase (MAPK) signaling pathways by western blotting. We found that p-cymene significantly regulated TNF-alpha, IL-1beta, and IL-6 production in LPS-stimulated RAW 264.7 cells. Furthermore, the levels of relative mRNAs were also found to be downregulated. In in vivo trail, p-cymene markedly suppressed the production of TNF-a and IL-1beta and increased IL-10 secretion. We also found that p-cymene inhibited LPS-induced activation of extracellular signal receptor-activated kinase 1/2, p38, c-Jun N-terminal kinase, and IkBalpha. These results suggest that p-cymene may have a potential anti-inflammatory action on cytokine production by blocking NF-kB and MAPK signaling pathways.
Inhalation causes impairment of coordination, headache. Contact with liquid causes mild irritation of eyes and skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)
INHALATION: remove victim from contaminated area; administer artificial respiration if necessary; call physician. EYES: flush with water for 15 min.; call a physician. SKIN: wipe off liquid; wash well with soap and water. INGESTION: induce vomiting; get medical attention. (USCG, 1999)
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Wear protective gloves when administering first aid.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
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. /Aromatic hydrocarbons 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 ... . Monitor for shock 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. Administer activated charcoal ... . /Aromatic hydrocarbons 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. Consider drug therapy for pulmonary edema ... . Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if 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 ... . /Aromatic hydrocarbons and related compounds/
/HUMAN EXPOSURE STUDIES/ A maximization test was carried out on 25 volunteers. The material /p-cymene/ was tested at 4% concentration in petrolatum and produced no sensitization reactions.|/HUMAN EXPOSURE STUDIES/ Tested at 4% in petrolatum, /p-cymene/ produced no irritation after a 48-hr closed-patch test in 25 human subjects|/SIGNS AND SYMPTOMS/ p-Cymene is reported to be a primary skin irritant; contact with the undiluted liquid can produce erythema, dryness and defatting, the intensity depending on the dose and duration of contact.|/SIGNS AND SYMPTOMS/ p-Cymene ... when given by mouth causes headache, nausea and vomiting.
4-cymene
The substance can be absorbed into the body by inhalation of its vapour and by ingestion.
Dizziness. Drowsiness. Vomiting.
Dry skin. Redness.
Redness.
p-Cymene Use and Manufacturing
Dehydrogenation and conversion of d-limonene or dipentene.
Used for organic synthesis and preparation of paint thinner. Used as an intermediate for dyes, medicines and spices.
Intermediates
Air care products
100,000 - 500,000 lb|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS|p-Cymene 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#5183]|For more U.S. Production (Complete) data for P-CYMENE (6 total), please visit the HSDB record page.
Grade: Technical /Cymene/|Grades of purity: 95+%
All other basic organic chemical manufacturing|Benzene, 1-methyl-4-(1-methylethyl)-: ACTIVE
Method: ASTM D5790; Procedure: gas chromatography/mass spectrometry; Analyte: p-cymene; Matrix: validated for treated drinking water, wastewater, and ground water; Detection Limit: 0.19 ug/L.|Method: EPA-EAD 1625; Procedure: gas chromatography/mass spectrometry; Analyte: p-cymene; Matrix: water; Detection Limit: 10 ug/L.|Method: EPA-NERL 502.2; Procedure: gas chromatography with photoionization detector; Analyte: p-cymene; Matrix: finished drinking water, raw source water, or drinking water in any treatment stage; Detection Limit: 0.1 ug/L.|Method: EPA-NERL 524.2; Procedure: gas chromatography/mass spectrometry; Analyte: p-cymene; Matrix: surface water, ground water, and drinking water in any stage of treatment; Detection Limit: 0.26 ug/L.|For more Analytic Laboratory Methods (Complete) data for P-CYMENE (11 total), please visit the HSDB record page.
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]|Cosmetics -> Masking
Flavoring Agents
Computed Properties
Molecular Weight:134.22
XLogP3:4.1
Rotatable Bond Count:1
Exact Mass:134.109550447
Monoisotopic Mass:134.109550447
Heavy Atom Count:10
Complexity:86.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It has expectorant and anti-inflammatory effects. Its expectorant effect may be due to the stimulation of gastric mucosal receptors, which reflexively increases the secretion of respiratory glands. It also accelerates the movement of cilia in the tracheal mucosal epithelium, thereby increasing the expectorant function.
Recommended Suppliers of p-Cymene
-
CN
5 YRS
Business licensedDistributor Supplier of DIMETHYL SULFOXIDE,NMP,MMT -
CN
5 YRS
Business licensed Certified factoryManufactory Supplier of Dichloromethane,Linocaine hydrochloride -
CN
8 YRS
Business licensedDistributor Supplier of Modified Resins,Rosin Derivatives,Turpentine Derivatives,Natural Extracts,Synthetic Ingredients,Polyterpene Resins,Agricultural Spray Adjuvant -
CN
4 YRS
Business licensed Certified factoryManufactory Supplier of Flavors & Fragrances,Catalyst & Auxiliary,Intermediates,Dyes & Pigments,Inorganic Chemistry,petro chemicals,Surfactant,Food Additives,Water Treatment Chemicals -
CN
3 YRS
Business licensedTrader Supplier of api,Intermediates,Organic Chemistry,Inorganic Chemistry,Daily Chemicals,Cosmetic Raw Materals,CATALYST AND AUXILIARY,FLAVORS AND FRAGRANCES,Chemical Pesticides,ADDITIVEInquiryUnit Price: $1 /KG EXWCAS No.: 99-87-6Grade: pharmaceutical gradeContent: 99%
Learn More Other Chemicals
-
Styrax balsam
8046-19-3
-
Frankincense resin
8050-07-5
-
Caffeic acid
331-39-5
-
Lilial Formula
80-54-6
-
(±)-α-Pinene Formula
80-56-8
-
Valeriana Formula
8057-49-6
-
9-Decen-1-ol Structure
13019-22-2
-
Decanoic acid Structure
334-48-5
-
What is 3-(4-Methyl-3-cyclohexenyl)butanol
15760-18-6
-
What is Saccharin
81-07-2