HuagongsheHuagongshe Chemistry Print Report · For research reference only
Linalool
1,6-Octadien-3-ol, 3,7-dimethyl- · Linalol · 3,7-Dimethyl-1,6-octadien-3-ol · 3,7-Dimethylocta-1,6-dien-3-ol · LINALOOL COEUR · Linanool · beta-Linalool · Phantol
Identifiers & Physical Properties
| CAS No. | 22564-99-4 |
|---|---|
| Molecular formula | C10H18O |
| Average molar mass | 154.25 g/mol |
| Monoisotopic mass | 154.1357652 g/mol |
| SMILES | C=CC(C)(O)CCC=C(C)C |
| InChIKey | CDOSHBSSFJOMGT-UHFFFAOYSA-N |
| PubChem CID | 6549 |
| ChEMBL | CHEMBL25306 |
| ChEBI | CHEBI:17580 |
| EC No. | 201-134-4 |
| DTXSID | DTXSID7025502 |
Chemical & Physical Properties
| XLogP | 2.7 |
|---|---|
| Topological polar surface area | 20.2 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 4 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 154 |
| Chemical classes | Biological Agents -> Plant Oils and Extracts |
| Cosmetics | Cosmetics ingredient -> Anticaking/AbsorbentsConditioning/EmollientFlavorFragranceMoisturizing/HumectantOther (Specify)Preservative/StabilizerSurfactantDeodorant |
| Fragrances | Fragrance Ingredient (Linalool) -> IFRA transparency List |
| LogP (partition coefficient) | log Kow = 2.97 |
| Odor | Odor similar to that of bergamot oil and French lavenderTypical floral odor free from camphoraceous and terpenic notesFloral, spicy, wood odorFlowery-fresh odor and reminiscent of Lily of the Valleyat 100.00 %. citrus floral sweet bois de rose woody green blueberry |
| Taste | Taste characteristics at 30 ppm: Floral, woody, sweet with a green, spicy tropical nuanceFlavor characteristics: light, floralSpicy, citrus taste |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Density | 0.865 at 15 °CDensity: 0.870 g/cu cm at 15 °C/4 °CRelative density (water = 1): 0.90.858-0.8670.87 g/mL at 25 °C (lit.) |
| Flavoring agents | EU Flavoring substances |
| Viscosity | 4.465 mPa s at 25 °C (dynamic) |
| Color/Form | Colorless liquidColorless to pale yellow liquid |
| Solubility | In water, 1590 mg/L at 25 °CSoluble in alcohol, ether, fixed oils, propylene glycolinsoluble in glycerin1.59 mg/mL at 25 °CSolubility in water, g/100ml at 25 °C: 0.16soluble in fixed oils, propylene glycolinsoluble in glycerol and water1 ml in 4 ml 60% alcohol1 ml in 2 ml 70% alcohol (in ethanol)ethanol: soluble1ml/4ml, clear, colorless (60% ethanol)1.45 g/L (25 ºC) |
| Melting point | 25°C |
| Boiling point | 194-197 °C/720 mmHg (lit.) |
| Vapor pressure | 0.17 mm Hg ( 25 °C) |
| Refractive index | n20/D 1.462(lit.) |
| FEMA | 2635 | LINALOOL |
| FLAVIS Number | 02.013 | Linalool |
| Flash point | 174 °F |
| Storage conditions | 2-8°C |
| Physical state | Liquid |
| pKa (acidity coefficient) | 14.51±0.29(Predicted) |
| Specific gravity | 0.860 (20/4℃) |
| Color | Clear colorless to pale yellow |
| pH | 4.5 (1.45g/l, H2O, 25℃) |
| Odor type | floral |
| Biological source | synthetic |
| Explosive limits | 0.9-5.2%(V) |
| Merck | 14,5495 |
| JECFA Number | 356 |
| BRN | 1721488 |
| Henry's law constant | 2.0×10-1 mol/(m3Pa) at 25℃, Leng et al. (2013) |
| Stability | Stable. Incompatible with strong oxidizing agents. Combustible. |
| Cosmetics Ingredients Functions | DEODORANTPERFUMING |
| InChI | 1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3 |
| InChIKey | CDOSHBSSFJOMGT-UHFFFAOYSA-N |
| SMILES | C\C(C)=C\CCC(C)(O)C=C |
| LogP (partition coefficient) | 2.9 at 20℃ |
| Substances Added to Food (formerly EAFUS) | LINALOOL |
| FDA 21 CFR | 182.60 |
| CAS DataBase Reference | 78-70-6(CAS DataBase Reference) |
| EWG's Food Scores | 2-5 |
| FDA UNII | D81QY6I88E |
| NIST Chemistry Reference | 2,6-Dimethylocta-2,7-dien-6-ol(78-70-6) |
| Pesticides Freedom of Information Act (FOIA) | Linalool |
| EPA Substance Registry System | 3,7-Dimethyl-1,6-octadien-3-ol (78-70-6) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H317-H319 |
| GHS precautionary statements | P261-P264-P272-P280-P302+P352-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xi,Xn |
| Risk statements (R) | 36/37/38-20/21/22 |
| Safety statements (S) | 26-36 |
| UN transport number | NA 1993 / PGIII |
| Water hazard class (WGK) | 1 |
| RTECS number | RG5775000 |
| Autoignition temperature | 235 °C |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Eye Irrit. 2Skin Irrit. 2Skin Sens. 1 |
| Customs code | 29052210 |
| Storage class | 10 - Combustible liquids |
| Hazardous substances data | 78-70-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 2790 mg/kg LD50 dermal Rabbit 5610 mg/kg |
| REACH registrations | Active |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | WarningH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatory information | Chemical: 1,6-Octadien-3-ol, 3,7-dimethyl-Hazard Traits - Fragrance AllergenRegulation (EC) No 1831/2003 (amended)1,6-Octadien-3-ol, 3,7-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,6-Octadien-3-ol, 3,7-dimethyl- 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: 22-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14501Linalool: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - 1,6-Octadien-3-ol, 3,7-dimethyl-: Environment tier I assessment |
| Fire hazards | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 75 °C explosive vapour/air mixtures may be formed. |
| Fire potential | Combustible liquid |
| Hazards summary | A skin and eye irritantMay cause liver injury[ICSC] Emergency treatment: Linalool[HSDB] Safe to use as a flavoring agent in food[JECFA] Slight sedative effects after inhalationNot a sensitizerNot mutagenicCauses effects on liver and kidneys in 28-day rat feeding study (72.9% linalool) with a NOAEL of 160 mg/kg/day[OECD SIDS: Linalool - 2002] Included in list of established contact allergens in humans[EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] |
| FDA requirements | Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Linalool is included on this list.Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Linalool is included on this list. |
| Special Reports | Organization for Economic Cooperation and DevelopmentScreening Information Data Set for Linalool (78-70-6) 157 pp. (March 2002).This OECD Initial Assessment of HPV Chemicals is part of a series of OECD SIDS documents published by UNEP Chemicals to facilitate the access to information needed for health and environmental risk assessments of chemicals.[Available from, as of November 9, 2015: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html]Letizia CS, Cocchiara J, Lalko J, Api AMFragrance material review on linalool. Food Chem Toxicol 41 (7): 943-64 (2003). A toxicologic and dermatologic review of linalool when used as a fragrance ingredient, is presented.Bickers D, Calow P, Greim H, Hanifin JM, Rogers AE, Saurat JH, Sipes IG, Smith RL, Tagami H. A toxicologic and dermatologic assessment of linalool and related esters when used as fragrance ingredients. Food Chem Toxicol 41 (7): 919-42 (2003)Api AM et alRIFM fragrance ingredient safety assessment, Linalool, CAS registry number 78-70-6. Food Chem Toxicol 82: S29-S38 (2015) |
| FIFRA requirements | New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Linalool is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128838Type of Pesticide: biological - insecticide/repellentUse Site: food use, domestic, petsYear: 1985. |
| Chemical Dangers | Decomposes on heating. This produces acrid smoke and irritating fumes. Reacts with strong oxidants. |
| Flammable Limits | Lower flammable limit: 0.9% by volumeUpper flammable limit: 5.2% by volume |
| NFPA Hazard Classification | 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. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides.CO, CO2 |
| Fire fighting | Use foam, alcohol-resistant foam, powder, carbon dioxide. |
| First aid measures | Fresh air, rest. Refer for medical attention.Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give one or two glasses of water to drink. Refer for medical attention . |
| Safe storage | Separated from strong oxidants. Well closed. |
| 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.Use water spray to cool unopened containers.Protective equipment: full fire-fighting equipment including pressure breather. Extinguishing Medium: foam, powder, carbon dioxide, water mist. Unsuitable Medium: water jet (splash hazard).Extinguishing methods: Alcohol foam. |
| Storage conditions | Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature 2-8 °C. Store under inert gas. Storage class (TRGS 510): Combustible liquids.Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. /Residential uses/Container: tightly closing, stainless steel, glass, enamel, polyethylene. Unsuitable Container: aluminum. ... Test plastics before use. |
| Cleanup methods | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.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: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential uses/If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential uses/ |
| 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 qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand 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: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. 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.SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal. |
| Spillage disposal | 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. |
| Preventive Measures | Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. 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.Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face. /Residential uses/For more Preventive Measures (Complete) data for LINALOOL (10 total), please visit the HSDB record page. |
| Eye Prevention | Wear safety goggles or face shield. |
| Fire Prevention | NO open flames. Above 75 °C use a closed system and ventilation. |
| Inhalation Risk | 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. |
| Interactions | Acrylamide (ACR) is a water-soluble monomer which has broad application in different industries and also can form in food during heating process. This monomer is a potent neurotoxicant and damages the central and the peripheral nervous system in human and animals. Oxidative stress has been mentioned as an important pathway in ACR neurotoxicity, therefore the purpose of the current study was evaluation of possible effects of linalool which is a natural enantiomer monoterpene compound. Linalool has shown antioxidant properties in several studies. Male Wistar rats were treated with ACR (50 mg/kg ip) alone or with linalool (12.5, 25, 50 and 100 mg/kg ip) for 11 days. In another 2 groups rats were treated with linalool (12.5 mg/kg ip) 3 days after and before ACR administration. Then behavior index (gait score) was examined for rats. After that, rats were sacrified and malondialdehyde (MDA) as a marker of lipid peroxidation and glutathione (GSH) content were determined in brain tissue. Exposure to ACR led to severe gait abnormalities and treatment with linalool significantly reduced abnormalities. ACR reduced GSH content and increased level of MDA in cerebral cortex. Linalool increased GSH content while decreased ACR-induced lipid peroxidation in rat brain tissue and the best protocols were initiation of supplementation before or simultaneous with ACR administration.We studied 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 present work ... reports data evaluating the chemopreventive effects of limonene and five other monoterpenes with various chemical structures using a 7,12-dimethylbenz(a)anthracene (DMBA)-induced rat mammary carcinogenesis model. The terpenes tested include: oxygenated ((-)-menthol) and non-oxygenated (d-limonene) monocyclic forms, oxygenated (1,8-cineole) and non-oxygenated ((+/-)-alpha-pinene) bicyclic forms and oxygenated ((+/-)-linalool) and non-oxygenated (beta-myrcene) acyclic forms. Dietary additions of each of the monocyclic terpenes, d-limonene or (-)-menthol resulted in a significant inhibition of mammary carcinogenesis. Furthermore, menthol was found to be a more potent chemopreventive agent than limonene during the DMBA initiation of rat mammary tumors. The acyclic and bicyclic terpenes had no significant chemopreventive activities at the dose levels used in these studies.The sedative properties of the essential oil of Lavender (Lavandula angustifolia Miller) and of its main constituents--linalool and linalyl acetate--were investigated in mice followed up in a series of experimental procedures. The significant decrease in the mobility of female and male laboratory animals under standardized experimental conditions is found to be closely dependent on the exposure time to the drugs. Nevertheless after an injection of caffeine into mice a hyperactivity was observed which was reduced to nearly a normal motility only by inhalation of these fragrance drugs. ... |
| Ecotoxicity values | LC50Species: Oncorhynchus mykiss (Rainbow trout) juvenile, average length 63 mm (57-72 mm), weight 2.12 g (1.51-2.75 g)Conditions: static, 180 mg CaCO3/L hardness, 14 + or - 0.5 °CConcentration: 27.8 mg/L for 96 hr (95% confidence limit: 22.9-33.7 mg/L) /dl-Linalool purity 97.8%/Species: Oncorhynchus mykiss (Rainbow Trout)Conditions: freshwater, staticConcentration: 28800 ug/L for 96 hr (95% confidence interval: 25700-31900 ug/L) /100% purity/Species: Leuciscus idus (Golden orfe) average length 6.0 (5.5-7.1) cm, weight 1.8 (1.2-2.8) g)Conditions: static, 21 °CConcentration: 22-46 mg/L for 96 hr /97.7% purity/EC50Species: Daphnia magna (water flea)Conditions: static, 21 + or - 1 °CConcentration: 59 (95% confidence limit: 53-65) mg/L for 48 hrEffect: immobilization /dl-Linalool purity 97.8%/For more Ecotoxicity Values (Complete) data for LINALOOL (8 total), please visit the HSDB record page. |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 75(SRC), determined from a structure estimation method(2), indicates that linalool is expected to have high mobility in soil(SRC). Volatilization of linalool from moist soil surfaces may be an important fate process(SRC) given a Henry's Law constant of 2.15X10-5 atm-cu m/mole(3). Linalool exists as a liquid environmentally at standard temperature and pressure, therefore, it is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.159 mm Hg(4). A 90% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is an important environmental fate process in soil(SRC). A variety of screening tests have found linalool to be readily biodegradable(6). In the soil and sediment compartments, linalool is expected to be readily biodegraded under both aerobic and anaerobic conditions(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 75(SRC), determined from a structure estimation method(2), indicates that linalool is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 2.15X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 54 hours and 20 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 42(SRC), from its log Kow of 2.97(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). A 90% of theoretical BOD using activated sludge in the Japanese MITI test(7) suggests that biodegradation is an important environmental fate process in water(SRC). A variety of screening tests have found linalool to be readily biodegradable(8). In the aquatic compartment, linalool is expected to be readily biodegraded under both aerobic and anaerobic conditions(8). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), linalool, which has a vapor pressure of 0.159 mm Hg at 23.5 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase linalool 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 2.3 hours(SRC), calculated from its rate constant of 1.70X10-10 cu cm/molecule-sec at 23 deg(3). Linalool is also degraded in the atmosphere by reaction with ozone and nitrate radicals. The half-life for the reaction with ozone is estimated to be 0.7 hours(SRC), calculated from its rate constant of 4.1X10-16 cu cm/molecule-sec at 23 °C(3). The half-life for the reaction with nitrate radicals is estimated to be 4 minutes(SRC), calculated from its rate constant of 1.12X10-11 cu cm/molecule-sec at 25 °C(4). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(5)therefore, night-time degradation appears to be a major fate process for linalool(SRC). Linalool does not absorb at wavelengths >290 nm(6) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Food survey values | Linalool has been detected as a volatile components of pineapple guava (2.67 ug/g)(1), in three different varieties of nectarines (<10 ppb, 10 ug/kg, and 500 ug/kg)(2,9), in edible Korean chamchwi(3), in apricots (671, 365, and 150 ug/kg)(4), in plums (18 and 8 ug/kg)(4), Harvester peaches(5), orange essences(6), unpasteurized orange juices(7), chicken(8), Kogyoku apple juice(10). Linalool has been qualitatively identified as a volatile flavor compound in pine sprout tea and pine needle tea(11), frankfurters(12), and Australian yellow box honey(13). Both raw and roasted earth-almonds have been found to contain linalool(14). Linalool was identified as a flavor-aroma component of lemon-lime carbonated beverages such as Sprite, Sierra Mist and 7UP(15).Linalool occurs in apple, citrus juices, berries, grapes, guava, celery, peas, potato, tomato, cinnamon, cloves, cassia, cumin, ginger, mustard, nutmeg, pepper, thymus, cheeses, grape wines, butter, milk, rum, cider, tea, passion fruit, olive, mango, beans, coriander and rice(1). |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Exposure routes | The substance can be absorbed into the body by inhalation of its aerosol and by ingestion. |
| Milk Concentrations | Linalool occurs in dairy milk(1). |
| Toxicity summary | IDENTIFICATION AND USE: Linalool is a colorless liquid with a spicy herbal odor. It is used as fragrance component in perfumes, cosmetics, soaps, and detergentsflavoring agent in foods. It is also used as a synthetic intermediate. It is registered for pesticide use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. HUMAN EXPOSURE AND TOXICITY: Linalool at concentrations up to 20% was consistently found not to be a sensitizer in human maximization tests. It was not phototoxic or photoallergenic in human tests. Linalool can cause allergic contact dermatitis. Linalool was not genotoxic when tested in vitro by the micronucleus test on peripheral human lymphocytes. ANIMAL STUDIES: Linalool was irritating to rabbit skin. Series of Draize tests with fragrance materials indicated that linalool was not a sensitizer in guinea pigs. Repeated application on sheep skin caused signs comparable to acanthosis. Rats were admin linalool 1500 mg/kg/day by gavage for 5 days. Absolute and relative liver weights were increased in treated animalsmicrosomal protein content was decreased. Psychopharmacological evaluation of linalool in vivo in rats showed that it has marked dose-dependent sedative effects on the central nervous system, including hypnotic, anticonvulsant and hypothermic properties. The study reports an inhibitory effect of linalool on glutamate binding in the rat cortex. In cats signs of toxicosis include hypersalivation, muscle tremors, ataxia, depression, and hypothermia. The sedative properties of linalool were investigated in mice. The significant decrease in the motility of female and male laboratory animals under standardized experimental conditions is found to be closely dependent on the exposure time. 10/sex/treatment rats received daily oral doses of 160, 400 or 1000 mg/kg bw linalool during 28 days. One male and one female of the high dose group were found dead. From a 28-day subchronic toxicity study with the essential oil of coriander with 72.9% linalool and 22.3% other identified terpenoids no remarkable effects on the primary reproductive organs in both females (ovaries and uteri) and males (testes and epididymides) was noted in any animal from any dosage group up to 1000 mg/kg bw/day, both macroscopically at dissection and also microscopically during histopathology of every (10 male, 10 female) high-dose animal. The genotoxic potential of linalool has been evaluated for mutagenicity in bacteria and in cultured mouse L5718Y tk+/. cells, and by cytogenicity in Chinese hamster ovary (CHO) cells via SCE, a chromosome aberration study, and an in vivo micronucleus test. The mutagenicity and clastogenicity data are sufficient to indicate that linalool is not genotoxic. ECOTOXICITY STUDIES: For linalool, LC50 > 28.8 ppm for Rainbow Trout, a LC50 of 36.8 ppm for Bluegill, and a LC50 of 36.7ppm for aquatic invertebrates. |
| Average Daily Intake | A 1999 study was extrapolated the daily per capita intake of linalool to 72 ug/kg/day for Europeans and 21 ug/kg/day for US Americans(1). A 2001 estimate, based on data published by the FAO/WHO Joint Expert Committee on Food Additives (JECFA), calculated a daily intake of 0.0438 mg/kg/d for both US and EU populations(1).Annual consumption /of linalool/ is 21,500 lb. Individual consumption is 0.01822 mg/kg/day. |
| Ecotoxicity excerpts | /BIRDS and MAMMALS/ Avian acute toxicity testing is not required for biopesticide products with indoor uses only. However, the registrant did cite or submit acute dietary toxicity data (for the Bobwhite Quail). The /EPA/ determined that the data were acceptable to support a LC50 > 5620 ppm which is considered practically non-toxic. For outdoor uses, a waiver request from the requirement of a guideline study for avian testing was granted because there is no direct exposure of Linalool to birds.../AQUATIC SPECIES/ Aquatic organism testing is not required for indoor use only biopesticides. However, the registrant did cite or submit fresh water fish (Rainbow Trout and Bluegill) studies and aquatic organism testing studies. The /EPA/ determined that the data were acceptable to support an LC50 > 28.8 ppm for Rainbow Trout, a LC50 of 36.8 ppm for Bluegill, and a LC50 of 36.7ppm for aquatic invertebrates. The above LC 50s for fresh water fish and aquatic organisms are considered practically non-toxic and slightly toxic respectively. For outdoor uses of linalool, a waiver was requested and granted for aquatic organism testing based on rationale stated above for the waiver sought and granted for avian testing./FIELD STUDIES/ As part of its environmental risk assessment of linalool, EPA considered any effects from the use of linalool on non-target species. Since linalool products registered for outdoor use (candles and fragrance generators) only affect (repel) biting insects and indoor uses preclude any exposure to other non-targets, EPA has determined that there is no exposure to non-target organisms ... . Linalool uses preclude any exposure to aquatic sites and/or drinking water. |
| Plant Concentrations | Linalool has been qualitatively detected in the headspace and essential oil of honeysuckle(1). A linalool concentration of 6854 ug/kg was measured in freshly opened Japanese honeysuckle flowersblossoms open for 12 and 24 hours contained 186 ug/kg and 3858 ug/kg linalool, respectively(2). The rhizome of the ginger plant has been found to contain linalool(3). Linalool has been qualitatively detected in emissions collected from the leaves of Eucalyptus citriodora(4), Quercus ilex(5) and Callicarpa japonica Thunb(6). Linalool was identified as a major scent component (38.06%) of Glochidion plants(7). The Plumeria alba L. (Apocynaceae) plant grown in Nigeria was found contain linalool in the leaf oil (13.2%) and flower oil(7.9%)(8). Analysis of the essential oil composition of flowering aerial parts of Iranian Silene morganae Freyn (Caryophyllaceae) found linalool (7.4%)(9).Linalool has been qualitatively detected in fruiting bodies of the wild mushrooms Lepista nuda, Mycena rosea, Tricholoma sulfureum, Clitocybe odora, Hydrum repandum, Lactarius salmonicolor, Gomphidius glutinosus, Agrocybe aegerita, Boletus erythropos, Clitocybe nebularis, and Tricholoma saponaceum(1). The optically active forms (d- and l-) and optically inactive form occur in more than 200 oils from herbs, leaves, flowers and wood(2).Linalool was detected in Gueyoto shoots (Origanum sipyleum L.Lamiaceae) at a concentration range of 0-35 ppm. The compound was detected in Funk's thyme shoots (Thymus funkii COUSS.Lamiaceae) at a range of 0-35 ppm(1). |
| Signs and Symptoms | Redness. Pain. |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | RG5775000 |
| UN transport number | NA 1993 / PGIII |
| Customs code | 29052210 |
| Toxicity | LD50 orally in Rabbit: 2790 mg/kg LD50 dermal Rabbit 5610 mg/kg |
| Risk statements (R) | 36/37/38-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi,Xn |
| Safety statements (S) | 26-36 |
| Hazard class | 3Eye Irrit. 2Skin Irrit. 2Skin Sens. 1 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H315-H317-H319 |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| Autoignition temperature | 235 °C |
| GHS precautionary statements | P261-P264-P272-P280-P302+P352-P305+P351+P338 |
| Hazardous substances data | 78-70-6(Hazardous Substances Data) |
Applications & Uses
Uses
1. It is used for the preparation of cosmetics, soaps, detergents, food and other flavors. 2. GB 276011996 states it is classified into food flavor allowed for temporary use. It is mainly used for the preparation of flavors or aromatic seasoning of pineapple, peach, and chocolate. 3. It is widely presented in flowers, fruits, stems, leaves, roots and green Rosa Chinensis viridiflora. It has a wide range of application, not only for all the floral flavors, such as sweet bean curd, jasmine, Convallaria majalis, lilac, etc., it can also be applied in fruit flavor type, Fen-flavor type, wood flavor type, aldehyde flavor type, oriental flavor type, amber scent type, chypre type, fern-type and other non-flower type of flavor. It can also be used in formulating orange leaf, bergamot, lavender, and some kinds of artificial oils such as hybrid lavender oil. It is mostly used in soap or flavor. It can be used for food flavor. 4. Linalool is a kind of important spices and is the blending raw materials for producing various kinds of artificial oil, also used extensively for the manufacturing of various esters of linalool. Linalool has an important position in the ester-type perfumes and other cosmetic formulations. Linalool can generate citral through oxidation and can also be used for the synthesis of many other kinds of spices.
Description
Linalool has a typical floral odor free from camphoraceous and terpenic notes.1 Synthetic linalool exhibits a cleaner and fresher note than the natural product. It can be prepared synthetically starting from myrcene or from dehydrolinalool.The optically active forms (d- and ι-) and the optically inactive form occur naturally in more than 2 0 0 oils from herbs, leaves, flowers, and wood; the ι-form is present in the largest amounts (80 - 85%) in the distillates from leaves of Cinnamomum cam phora var. orientalis and Cinnamomum camphora var. occidentalis and in the distillate from Cajenne rosewood; it also has been reported in: champaca, ylang-ylang, neroli, Mexican linaloe, ber gamot, lavandin, and others; a mixture of d- and ι-linalool has been reported in Brazil rosewood (85%); the d-form has been found in palmarosa, mace, sweet orange-flower distillate, petit grain, coriander (60 - 70%), marjoram, Orthodon linalooliferum (80%), and others; the inactive form has been reported in clary sage, jasmine, and Nectandra elaiophora.
Occurrence
The optically active forms (d- and l-) and the optically inactive form occur naturally in more than 200 oils from herbs, leaves, flowers and wood; the l-form is present in the largest amounts (80 to 85%) in the distillates from leaves of Cinnamomum camphora var. orientalis and Cinnamomum camphora var. occidentalis and in the distillate from Cajenne rosewood; it also has been reported in champaca, ylang-ylang, neroli, Mexican linaloe, bergamot and lavandin; a mixture of d- and l-linalool has been reported in Brazil rosewood (85%); the d-form has been found in palmarosa, mace, sweet orange-flower distillate, petitgrain, coriander (60 to 70%), marjoram and Orthodon linalooliferum (80%); the inactive form has been reported in clary sage, jasmine and Nectandra elaiophora. Also reported found in over 280 products including apple, citrus peel oils and juices, berries, grapes, guava, celery, peas, potato, tomato, cinnamon, cloves, cassia, cumin, ginger, mentha oils, mustard, nutmeg, pepper, thymus, cheeses, grape wines, butter, milk, rum, cider, tea, passion fruit, olive, mango, beans, coriander, cardamom and rice.
Uses
linalool is a fragrant component of both lavender and coriander. It can be incorporated into cosmetics for perfuming, deodorant, or odor-masking activity.
Uses
Linalool is one of the allergens of Ylang-Ylang oil (extract from Cananga odorata).
Uses
perfume use
General Description
Linalool is a monoterepene compound. It is the major component of many essential oils. Anti-inflammatory properties of () linalool, a naturally occurring enantiomer, has been studied. It is also the major constituent of the basil and thyme essential oil and its anti-microbial effect was determined using the agar well diffusion assay. Linalool is reported to have dose-dependent marked sedative effects at the central nervous system (CNS), including hypnotic, anticonvulsant and hypothermic properties. Linalool is reported to have a lemon like odor.
Preparation & Synthesis
Preparation
In the 1950s, nearly all linalool used in perfumery was isolated from essential oils, particularly from rosewood oil. Currently, this method no longer plays a commercial role. Since linalool is an important intermediate in the manufacture of vitamin E, several large-scale processes have been developed for its production. Preferred starting materials and/or intermediates are the pinenes and 6-methyl-5-hepten- 2-one. Most perfumery-grade linalool is synthetic. 1) Isolation from essential oils: Linalool can be isolated by fractional distillation of essential oils, for example, rosewood oil and coriander oil, of which Brazilian rosewood oil was the most important. 2) Synthesis from α-pinene: α-Pinene from turpentine oil is selectively hydrogenated to cis-pinane, which is oxidized with oxygen in the presence of a radical initiator to give a mixture of about 75% cis-pinane and 25% transpinane hydroperoxide.The mixture is reduced to the corresponding pinanols either with sodium bisulfite (NaHSO3) or with a catalyst. The pinanols can be separated by fractional distillation and are pyrolyzed to linalool: ()-α- pinene yields cis-pinanol and (+)-linalool, whereas ()-linalool is obtained from trans-pinanol. 3) Synthesis from -pinene: For a description of this route, see under Geraniol. Addition of hydrogen chloride to myrcene (obtained from β-pinene) results in a mixture of geranyl, neryl, and linalyl chlorides. Reaction of this mixture with acetic acid–sodium acetate in the presence of copper(I) chloride gives linalyl acetate in 75–80% yield. Linalool is obtained after saponification. 4) Synthesis from 6-methyl-5-hepten-2-one:The total synthesis of linalool starts with 6-methyl-5-hepten-2-one; several large-scale processes have been developed for synthesizing this compound: a. Addition of acetylene to acetone results in the formation of 2-methyl-3- butyn-2-ol, which is hydrogenated to 2-methyl-3-buten-2-ol in the presence of a palladium catalyst.This product is converted into its acetoacetate derivative with diketene or with ethyl acetoacetate. The acetoacetate undergoes rearrangement when heated (Carroll reaction) to give 6-methyl-5-hepten-2-one: b. In another process, 6-methyl-5-hepten-2-one is obtained by reaction of 2-methyl-3-buten-2-ol with isopropenyl methyl ether followed by a Claisen rearrangement: c. A third synthesis starts fromisoprene, which is converted into 3-methyl-2- butenyl chloride by addition of hydrogen chloride. Reaction of the chloride with acetone in the presence of a catalytic amount of an organic base leads to 6-methyl-5-hepten-2-one: d. In another process, 6-methyl-5-hepten-2-one is obtained by isomerization of 6-methyl-6-hepten-2-one.The latter can be prepared in two steps from isobutylene and formaldehyde. 3-Methyl-3-buten-l-ol is formed in the first step and is converted into 6-methyl-6-hepten-2-one by reaction with a