Myrcene

log Kow = 4.33

4.17

Pleasant

Terpene odor

SWEET, CITRUS

0.794 at 20 °C/4 °C

Density: 0.7959 at 25 °C/25 °C; max absorption (isooctane): 224.5 nm /alpha-Myrcene/

0.789-0.793

Yellow, oily liquid

Soluble in alcohol, chloroform, ether, glacial acetic acid

Soluble in ethanol and benzene

Soluble in oxygenated and chlorinated solvents.

In water, 5.60 mg/L at 25 °C

In water, 4.09 mg/L at 25 °C

0.0056 mg/mL at 25 °C

103 °F (USCG, 1999)

332.6 °F at 760 mmHg (USCG, 1999)

167 °C

166.00 to 167.00 °C. @ 760.00 mm Hg

166-167 °C

When heated to decomposition it emits acrid smoke and irritating fumes.

< -10 °C

< -10 °C

4.61 mmHg (USCG, 1999)

2.01 [mmHg]

2.09 mm Hg at 25 °C

Triply unsaturated aliphatic hydrocarbon; Index of refraction: 1.471 at 20 °C (81% Myrcene)

Index of refraction: 1.4709 at 20 °C; max absorption (ethanol): 226 nm (epsilon = 16,100)

1.466-1.471

Danger

H226 (99.8%): Flammable liquid and vapor [Warning Flammable liquids]；H304 (99%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]；H315 (85.6%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (85.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H400 (14.6%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H412 (18.7%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P210, P233, P240, P241, P242, P243, P264, P264+P265, P273, P280, P301+P316, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2180 reports by companies from 35 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Chemical: 1,6-Octadiene, 7-methyl-3-methylene-

Hazard Traits - Carcinogenicity；Authoritative List - IARC Carcinogens - 2B; Prop 65；Report - regardless of intended function of ingredient in the product

Regulation (EC) No 1831/2003 (amended)

1,6-Octadiene, 7-methyl-3-methylene- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,6-Octadiene, 7-methyl-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: 30-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14795；Status: Active Update: 11-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33150

1,6-Octadiene, 7-methyl-3-methylene-: Does not have an individual approval but may be used under an appropriate group standard

Evaluation - 1,6-Octadiene, 7-methyl-3-methylene-(Myrcene)

Flammable Liquid

Special Hazards of Combustion Products: Vapor may travel considerable distance to a source of ignition and flashback. (USCG, 1999)

A flammable liquid.

May be harmful by inhalation, ingestion or skin absorption. (USCG, 1999)

Moderately irritating to skin and eyes; [HSDB] Causes somnolence and ataxia in lethal dose studies; Causes kidney tubular injury at doses >65 gm/kg given intermittently over 13 weeks; Moderately irritating to the skin of rabbits; [RTECS] Embryotoxic in rats exposed to more than 500 mg/kg/day; [REPROTOX] Safe when used in food as a flavoring agent; [JECFA] See TERPENES. See Dihydromyrcene.

Myrcene 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.

Hydrocarbons, Aliphatic Unsaturated；Conjugated Dienes

The unsaturated aliphatic hydrocarbons, such as MYRCENE, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions. Many of these compounds undergo autoxidation upon exposure to the air to form explosive peroxides. Violent explosions have occurred at low temperatures in ammonia synthesis gas units. These explosions have been traced to the addition products of dienes and oxides of nitrogen, produced from the interaction of nitrogen oxide and oxygen [Bretherick, 1995].

Insoluble in water.

Flam. Liq. 3 (99.8%)；Asp. Tox. 1 (99%)；Skin Irrit. 2 (85.6%)；Eye Irrit. 2 (85.5%)；Aquatic Acute 1 (14.6%)；Aquatic Chronic 3 (18.7%)

Flammable liquids - Category 3；Skin corrosion/irritation - Category 2；Carcinogenicity - Category 2；Reproductive toxicity - Category 2；Hazardous to the aquatic environment (Acute) - Category 1；Hazardous to the aquatic environment (Long-term) - Category 1

Flammable liquids - Category 3；Skin corrosion/irritation - Category 2；Serious eye damage/eye irritation - Category 2A；Carcinogenicity - Category 2；Reproductive toxicity - Category 1B；Hazardous to the aquatic environment (Acute) - Category 1；Hazardous to the aquatic environment (Long-term) - Category 1

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:；CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: For mixtures containing alcohol or polar solvent, alcohol-resistant foam may be more effective.；SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.；LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.；FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. For petroleum crude oil, do not spray water directly into a breached tank car. This can lead to a dangerous boil over. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

INHALATION: Call for medical aid. Remove the victim to fresh air. If not breathing give artificial respiration. If breathing is difficult give oxygen.；SKIN: Wash with soap and copious amounts of water.；EYES: Immediately flush with copious amounts of water. Insure adequate flushing of the eyes by holding the eyelids open with the fingers. (USCG, 1999)

If material on fire or involved in a fire: Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical, or carbon dioxide.

Store in a cool place from which light and air are excluded.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:；ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from 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, 2024)

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.

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.

If material not on fire and not involved in a fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without hazard.

Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. ... Do not handle broken packages without protective equipment.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:；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 tank car or highway tank 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, 2024)

Wear self-contained breathing apparatus, rubber boots and heavy rubber gloves. (USCG, 1999)

Myrcene has been detected in pre-diabetic, diabetic and normal subjects in expired air samples, concns not specified(1).

Monitor for respiratory distress in case of inhalation exposure. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Administer symptomatic treatment as necessary. (T36)

.../the study tested/ the protective effect of monoterpenes myrcene, eucalyptol and linalool against t-butyl hydroperoxide (t-BOOH) induced genotoxicity in reverse mutation assay with Escherichia coli WP2 IC185 strain and its oxyR mutant IC202, and with the comet assay in human hepatoma HepG2 and human B lymphoid NC-NC cells. The monoterpenes were tested in concentration ranges 0.05-1.5 mg/plate and 0.01-1.0 ug/mL in bacteria and mammalian cells, respectively. Suppression of t-BOOH induced mutagenesis was detected only in IC202 strain, and correlated with the observed inhibition of lipid peroxidation by the three monoterpenes. Linalool and myrcene strongly suppressed t-BOOH induced mutagenesis. Eucalyptol, in addition to moderate suppression of t-BOOH induced mutagenesis, suppressed also spontaneous mutagenesis. In NC-NC cells linalool and myrcene reduced t-BOOH induced DNA damage by about 50% at 0.01 ug/mL, while eucalyptol was less efficient (about 50% reduction at 1.0 ug/mL). In HepG2 cells linalool and eucalyptol reduced DNA damage by 30% and 40%, respectively, while myrcene was ineffective. The repair of t-BOOH induced DNA damage, studied in HepG2 cells, was not affected by monoterpenes. The results indicate that linalool, eucalyptol and myrcene have substantial protective effect against oxidant induced genotoxicity, which is predominately mediated by their radical scavenging activity.

The leafy parts of thyme and its essential oil have been used in foods for the flavor, aroma and preservation and also in folk medicines. The aim of the current study was to determine the components of Thymus vulgaris L essential oil and to evaluate the protective effects of this oil against aflatoxin-induce oxidative stress in rats. Thirty six mature male Sprague-Dawley were divided into six treatment groups and treated for 2 weeks as follows: control group; the groups treated orally with low and high doses of T. vulgaris oil (5 and 7.5 mg/kg b.w.); the group fed AFs-contaminated diet (2.5 mg/kg diet) and the groups fed AFs-contaminated diet and treated orally with the oil at the two tested doses. Blood and tissue samples were collected at the end of treatment period for biochemical study and histological examination. The results indicated that the oil contains Carvarcrol (45 mg/g), Thymol (24.7 mg/g), beta-Phellandrene (9.7 mg/g), Linalool (4.1 mg/g), Humuline (3.1 mg/g), alpha-Phellandrene (2.3 mg/g) and Myrcene (2.1 mg/g). However, alpha and beta-pinene, Myrcene, alpha-thyjone, Tricyclene, 1, 8-cineole, and beta-sabinene were found in lower concentrations. Treatment with AFs alone disturbs lipid profile in serum, decreases Total antioxidant capacity, increase creatinine, uric acid and nitric oxide in serum and lipid peroxidation in liver and kidney accompanied with a sever histological changes in the liver tissues. The oil alone at the two tested doses did not induce any significant changes in the biochemical parameters or the histological picture. The combined treatment showed significant improvements in all tested parameters and histological pictures in the liver tissues. Moreover, this improvement was more pronounced in the group received the high dose of the oil. It could be concluded that the essential oil of T. vulgaris has a potential antioxidant activity and a protective effect against AFs toxicity and this protection was dose dependent.

Health effects may include dermatitis (A334).

THE INFLUENCE OF LIGHT & TEMP ON MONOTERPENE EMISSIONS FROM SLASH PINE WERE ASSESSED. QUANT PRESENT IN VAPOR PHASE WERE SUFFICIENT TO MEASURE RELIABLY.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1074(SRC), determined from a structure estimation method(2), indicates that myrcene is expected to have low mobility in soil(SRC). Volatilization of myrcene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.0916 atm-cu m/mole(SRC), derived from its vapor pressure, 2.09 mm Hg(3), and water solubility, 4.09 mg/L(4). However, adsorption to soil may attenuate volatilization(SRC). Myrcene is expected to volatilize from dry soil surfaces(SRC) based upon the vapor pressure of 2.09 mm Hg at 25 °C(3). Myrcene, present at 100 mg/L, reached 82-92% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(5) which classifies the compound as readily biodegradable. Monoterpene compounds similar in structure to myrcene (limonene, pinene, terpinene, terpinolene) were readily degraded in aerobic batch experiments using forest soil(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1074(SRC), determined from a structure estimation method(2), indicates that myrcene 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 0.0916 atm-cu m/mole(SRC), derived from its vapor pressure, 2.09 mm Hg(4), and water solubility, 4.09 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 3.4 hours and 4.6 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 334(SRC), from its log Kow of 4.33(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC). Myrcene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Myrcene, present at 100 mg/L, reached 82-92% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(8) which classifies the compound as readily biodegradable. Myrcene has been observed to undergo biodegradation in aerated lagoons(9). Monoterpene compounds similar in structure to myrcene (limonene, pinene, terpinene, terpinolene) were readily degraded in aerobic batch experiments using forest soil and enriched cultures(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), myrcene, which has a vapor pressure of 2.09 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase myrcene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, ozone and nitrate radicals(SRC); the half-life for the reaction with hydroxyl radicals is estimated to be 1.8 hrs(SRC), calculated from its rate constant of 2.15X10-10 cu cm/molecule-sec at 25 °C(3); the half-life for the reaction with ozone is estimated to be 34 minutes(SRC), calculated from its rate constant of 4.90X10-16 cu cm/molecule-sec(4); the half-life for the reaction with nitrate radicals in nighttime air is estimated to be 4 minutes(SRC), calculated from its rate constant of 1.10X10-11 cu cm/molecule-sec(4). Hydroxyl radical and ozone oxidation of myrcene in the ambient atmosphere yields acetone, formaldehyde and formic acid as degradation products(5). Myrcene does not contain chromophores that absorb at wavelengths >290 nm(6), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Myrcene has been detected as an emission from apricots, carrots, cotton, Valencia oranges, pistachios, walnuts and whitehorn at 0.1, 0.6, 0.4, 0.5, 0.5, 0.2, and 1.9 ug/g respectively(1). Volatiles from fresh guava fruit pulp obtained by vacuum distillation revealed that myrcene is 0.001 ug/g of pineapple guava. Myrcene has been reportedly found in common guava and in strawberry and yellow guava, concentrations not specified(2). Myrcene comprises 22.41% of volatile hydrocarbons identified in extract of Korean Chamchwi(3). The concentration of myrcene in relation to ethyl acetate, defined as 1, in Idaho Russet Burbank potatoes is 0.08(4). Myrcene has been detected in emissions from the roasting of filberts, thick shelled sweet flavored tree nuts, concentrations not specified(5). Volatile components of mango stored at -15 °C for 1 year contained 2.7 ug/g, while fresh mangos from Florida contained 1.0 ug/g(6). Concentrated natural orange essence used in orange juice concentrate, contains myrcene, concentration not specified(7). Myrcene has been detected in freshly squeezed unpasteurized orange juice at concentrations ranging from 0.34-4.1 ppm(8). Myrcene is found within clove essential oil ranging from 0.30-0.45% of total volatile compounds(9). Myrcene was detected at 0.51% of total volatile constituents in headspace samples of fresh, tree-ripened nectarines(10). Myrcene was qualitatively detected in the flavor components of pine sprout tea and pine needle tea(11). Myrcene was qualitatively detected in volatile odor compounds from frankfurter sausages(12).

Neurotoxin - Acute solvent syndrome；IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.

Dermal ; inhalation

Myrcene exhibits tyrosinase inhibitory activities, which plays an important role in neuromelanin formation (A2448).

/OTHER TERRESTRIAL SPECIES/ A comparative study was conducted to assess the contact and fumigant toxicities of eleven monoterpenes on two important stored products insects, Sitophilus oryzae, the rice weevil, and Tribolium castaneum, the rust red flour beetle. The monoterpenes included: camphene, (+)-camphor, (-)-carvone, 1-8-cineole, cuminaldehyde, (L: )-fenchone, geraniol, (-)-limonene, (-)-linalool, (-)-menthol, and myrcene. The inhibitory effect of these compounds on acetylcholinesterase (AChE) activity also was examined to explore their possible mode(s) of toxic action. Although most of the compounds were toxic to S. oryzae and T. castaneum, their toxicity varied with insect species and with the bioassay test. In contact toxicity assays, (-)-carvone, geraniol, and cuminaldehyde showed the highest toxicity against S. oryzae with LC50 values of 28.17, 28.76, and 42.08 ug/sq cm, respectively. (-)-Carvone (LC50 = 19.80 ug/sq cm) was the most effective compound against T. castaneum, followed by cuminaldehyde (LC50 = 32.59 ug/sq cm). In contrast, camphene, (+)-camphor, 1-8-cineole, and myrcene had weak activity against both insects (i.e., LC50 values above 500 ug/sq cm). In fumigant toxicity assays, 1-8-cineole was the most effective against S. oryzae and T. castaneum (LC50 = 14.19 and 17.16 mg/L, respectively). Structure-toxicity investigations revealed that (-)-carvone, a ketone, had the highest contact toxicity against both insects. 1-8-Cineole, an ether, was the most potent fumigant against both insects. In vitro inhibition studies of AChE from adults of S. oryzae showed that cuminaldehyde most effectively inhibited enzyme activity at the two tested concentrations (0.01 and 0.05 M) followed by 1-8-cineole, (-)-limonene, and (L)-fenchone. 1-8-Cineole was the most potent inhibitor of AChE activity from T. castaneum larvae followed by (-)-carvone and (-)-limonene. The results of the present study indicate that (-)-carvone, 1,8-cineole, cuminaldehyde, (L)-fenchone, a

/OTHER TERRESTRIAL SPECIES/ The repellency and fumigant toxicities of the peel essential oils of Citrus sinensis var. pera (LP), C. sinensis var. mimo (LM), and C. aurantium (LL) cultivated in northeast Brazil were evaluated against Tetranychus urticae. Analysis of the oils by GC and GC/MS led to the identification of twenty-eight components, which represented 99.9%, 99.7% and 99.3% of the total constituents of the LP, LM and LL oils, respectively. Limonene was the main component found in all three oils. Other main components were alpha-pinene (1.5% in LP; 1.4% in LM), myrcene (5.7% in LP; 5.9% in LM and 5.6% in LL) and linalool (2.4% in LP; 2.3% in LM and 3.9% in LL). The best repellency action was observed for LM at 2.0%, followed by LL oil and eugenol, both of them at 2.5%. The Citrus oils were less active than eugenol (LC50 = 0.004 microL/L air) and phosphine, which revealed 100% mortality at 2 x 10(-3) g/L (66.7% of the recommended dose). However, the most potent fumigant toxicity was found with LL oil, with an LC50 value of 1.63 uL/L air, followed by the oils from LM and LP with LC50 values of 2.22 uL/L air and 4.63 uL/L air, respectively. The associated fumigant and repellent properties of these Citrus peel oils, particularly those of C. aurantium and C. senensis var. mimo, could be used to advantage for the control of T. urticae.

/OTHER TERRESTRIAL SPECIES/ Leaves of Myrica gale Linnaeus (Myricaceae), Rhododendron tomentosum (Stokes) H. Harmaja (formerly Ledum palustre Linnaeus: Ericaceae) and Artemisia absinthium Linnaeus (Asteraceae) were extracted with organic solvents of different polarities and the essential oils of leaves were obtained by steam distillation. The extracts or oils were tested in the laboratory for repellency against host-seeking nymphs of Ixodes ricinus Linnaeus (Acari: Ixodidae). Rhododendron tomentosum oil, 10%, diluted in acetone, exhibited 95% repellency; R. tomentosum and A. absinthium extracts in ethyl acetate, > 70% repellency; A. absinthium extract in hexane, approximately 62% repellency; and M. gale oil, 10%, approximately 50% repellency on I. ricinus nymphs. Compounds in the leaf extracts or in the oils were collected by solid phase microextraction (SPME) and identified by gas chromatography-mass spectrometry (GC-MS) and/or MS. Characteristic volatiles detected from oil or extract of M. gale were the monoterpenes 1,8-cineole, alpha-terpineol, 4-terpineol and thujenol; and of R. tomentosum myrcene and palustrol. Characteristic volatiles from leaf extracts of A. absinthium were sabinene, oxygenated monoterpenes, e.g. thujenol and linalool, and geranyl acetate. Each plant species synthesized numerous volatiles known to exhibit acaricidal, insecticidal, 'pesticidal' and/or arthropod repellent properties. These plants may be useful sources of chemicals for the control of arthropods of medical, veterinary or agricultural importance.

/OTHER TERRESTRIAL SPECIES/ 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.

/PLANTS/ ...The chemical composition and phytotoxicity of the essential oil extracted from leaves of Artemisia scoparia Waldst. et Kit. (red stem wormwood, Asteraceae) /was investigated/. GC/GC-MS analyses revealed 33 chemical constituents representing 99.83% of the oil. The oil, in general, was rich in monoterpenes that constitute 71.6%, with beta-myrcene (29.27%) as the major constituent followed by (+)-limonene (13.3%), (Z)-beta-ocimene (13.37%), and gamma-terpinene (9.51%). The oil and beta-myrcene were evaluated in a dose-response bioassay under laboratory conditions for phytotoxicity against three weeds-Avena fatua, Cyperus rotundus, and Phalaris minor. A significant reduction in germination, seedling growth, and dry matter accumulation was observed in the test weeds. At the lowest treatment of 0.07 mg/mL Artemisia oil, germination was reduced by 39%, 19%, and 10.6% in C. rotundus, P. minor, and A. fatua, respectively. However, the inhibitory effect of beta-myrcene was less. In general, a dose-dependent effect was observed and the growth declined with increasing concentration. Among the three weeds, the inhibitory effect was greatest on C. rotundus, so it was selected for further studies. ...The explanation for observed growth inhibition in terms of reactive oxygen species (ROS: lipid peroxidation, membrane integrity, and amounts of conjugated dienes and hydrogen peroxide)-induced oxidative stress /was explored/. Exposure of C. rotundus to Artemisia oil or beta-myrcene enhanced solute leakage, indicating membrane disintegration. There were increased levels of malondialdehyde and hydrogen peroxide, indicating lipid peroxidation and induction of oxidative stress. ...Artemisia oil inhibits plant root growth through generation of ROS-induced oxidative damage.

Myrcene has been detected in emissions from Norway spruce, fir, Scots pine (Pinus sylvestris), and larch trees in the country of Switzerland, concentrations not specified. Highest emission rates take place during the summer month of July(1). Myrcene has been detected in emissions from Scots Pine at 2.3-6.3% of total terpenes(2). Myrcene has been detected in emissions from Siberian pine (P. Sibirica), silver fir (Picea silvestris), common juniper, zeravskar juniper, pencil cedar, evergreen cypress, northern white cedar, Chinese arbor vitae and deciduous moss, concentrations not specified. These plants are characteristic of northern Europe and Asia(2). Myrcene has been detected in emissions from the oak species Quercus ilex L. at Castel Porziano, Rome, Italy on June 1993 at 2.25% of total plant emissions between the hours of 11 a.m. to 1 p.m.(3). Myrcene has been detected in dynamic headspace samples of mushrooms Cystoderma carcharias, Aanita ovoidea, and Mycena rosea at 0.2, <0.1, and <0.1 percent relative to all identified volatile compounds(4). Through solvent extraction, myrcene was detected at 3 and 2 percent relative to all identified volatile compounds in Gomphidius glutinosus mushrooms(4). Average emission rate of myrcene for an 18 yr old Norway spruce (Picea abies) tree was 3 ug/sq m-hr with highest concentrations at noon and lowest concentrations at night(5). Myrcene has been detected ranging from 100-1,750 parts per trillion at 13 m height inside the canopy of maple forest (Duchesnay forest station) in Quebec, Canada from July 28-30, 1989(6). Myrcene was detected ranging from 3.1-58 ng/cu m at 1 m above ground Aug 30-Dec 16, 1985 in Kalbelescherer in the Southern Black Forest, Germany. The suspected sources of emission were Picea abies and Abies alba tree species(7). Myrcene was detected at 0.04% of total volatile constituents in headspace samples of kiwi fruit flowers (Actinidia chinensis Planch.)(8). Myrcene was detected at 1-34% of monoterpene emissions

Sneezing, itching, and increased nasal congestion (A334).

Chemical: 1,6-Octadiene, 7-methyl-3-methylene-

Hazard Traits - Carcinogenicity；Authoritative List - IARC Carcinogens - 2B; Prop 65；Report - regardless of intended function of ingredient in the product

Regulation (EC) No 1831/2003 (amended)

1,6-Octadiene, 7-methyl-3-methylene- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,6-Octadiene, 7-methyl-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: 30-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14795；Status: Active Update: 11-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33150

1,6-Octadiene, 7-methyl-3-methylene-: Does not have an individual approval but may be used under an appropriate group standard

Myrcene 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.

... After oral administration of 1.0 g/kg bw (7300 umol/kg bw) beta-myrcene to female rats, the elimination half-life of beta-myrcene at this concentration was 285 min. ...

Metabolites isolated from the urine of rats after oral administration of beta-myrcene were: 10-hydroxylinalool, 7-methyl-3-methylene-oct-6-ene-1,2-diol, 1-hydroxymethyl-4-isopropenyl cyclohexanol, 10-carboxylinalool and 2-hydroxy-7-methyl-3-methylene-oct-6-enoic acid. Liver microsomes prepared from phenobarbital-treated rats convert beta-myrcene to 10-hydroxylinalool in the presence of NADPH and oxygen. NADH neither supported this reaction nor did it show any synergistic effect. The rate of conversion was significantly greater in microsomes prepared from phenobarbital-treated rats than from 3-methylcholanthrene-treated or control microsomal preparations. The formation of 10-hydroxylinalool was inhibited by metyrapone, carbon monoxide, SKF-525A, p-chloromercuric benzoate (p-CMB) and cytochrome c. ...

In a pharmacokinetic study, blood levels as high as 14.1+/- 3.0 ug/mL beta-myrcene (peak value) were detected sixty minutes after oral administration of 1.0 g/kg bw (7300 umol/kg bw) beta-myrcene to female rats. ... The compound was concentrated in adipose tissue and in many organs, including the brain, liver, kidneys, and testes.

Membrane

Beta-myrcene: Found in oil of bay, verbena, hops, and other natural sources; Alpha-myrcene: Not found in nature; [Merck Index] Used as a fragrance, flavoring agent, insect repellent, and detergent additive; [HSDB]

... Myrcene is the starting material for a range of industrially important products, e.g., geraniol, nerol, linalool, and isophytol. ... Besides its main use as an intermediate for the production of terpene alcohols, myrcene is used in the production of terpene polymers, terpene-phenol resins, and terpene-maleate resins. It can also be used as a solvent or diluting agent for dyes and varnishes.

Preparation of perfume chemicals and flavoring.

INSECT REPELLENT

Detergents

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

2023: 10,000,000 - <50,000,000 lb；2022: 10,000,000 - <50,000,000 lb；2021: 10,000,000 - <50,000,000 lb；2020: 10,000,000 - <50,000,000 lb

1,6-Octadiene, 7-methyl-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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3076]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,6-Octadiene, 7-methyl-3-methylene-. Aggregated National Production Volume: 10 to < 50 million pounds.

Fragrance；Not Known or Reasonably Ascertainable；Odor agents

Other；Intermediates；Not Known or Reasonably Ascertainable；Fragrance

Obtained by pyrolysis of beta-pinene

Cosmetics product ingredient: beta-Myrcene (Myrcene)；Source of Chemical；Beta-myrcene is naturally occuring in some plants and essential oils of plants such as hops, bay leaf, lemongrass, and may be present in ingredients that are used as frgrance or flavors in cosmetics.；How People Are Exposed and Potential Health Impacts；People are exposed to beta-myrcene mostly through skin contact and breathing it in. There is sufficient evidence that it causes cancer in experimental animal studies. Beta-myrcene is listed under Proposition 65 as known to the state to cause cancer. The International Agency for Research on Cancer concluded that beta-myrcene is possibly carcinogenic to humans (Group 2B carcinogen).；Links to Authoritative Source Lists；- OEHHA/Proprosition 65 - Beta-Myrcene Listing；- National Toxicology Program Technical Report on the Toxicology and Carcinogenesis Studies of Beta-Myrcene (PDF)；- International Agency for Research on Cancer Monographs on the Evaluation of Carcinogenic Risks to Humans, Volume 119；Product count: 2942

Information on 52 consumer products that contain Myrcene in the following categories is provided:；• Auto Products；• Commercial / Institutional；• Inside the Home；• Personal Care

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

All Other Basic Organic Chemical Manufacturing；Not Known or Reasonably Ascertainable；Soap, Cleaning Compound, and Toilet Preparation Manufacturing

1,6-Octadiene, 7-methyl-3-methylene-: ACTIVE

A triply unsaturated aliphatic hydrocarbon found in oil of bay, verbena, hops, and others

FLAVORS USEFUL IN CITRUS IMITATIONS, FRUIT BLENDS.

REPELLENCY OF MONOTERPENE & RESIN VAPORS FOR THE FIR ENGRAVER BEETLE, SCOLYTUS VENTRALIS, DECREASED IN THE FOLLOWING ORDER: LIMONENE, DELTA3-CARENE, ALPHA-PINENE, MYRCENE, BETA-PINENE, PREFORMED RESIN, CAMPHENE, & TRICYCLENE.

ADDITION OF MYRCENE TO MIXTURE OF FRASS COMPONENTS ISOLATED FROM THE FEMALE BOLL WEEVIL IMPROVED THE ATTRACTION RESPONSE BY MALES.