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5-Propyl-1,3-benzodioxol
DIHYDROSAFROLE · NSC 33707 · NSC 27867 · AKOS 208-12 · DIHYDROSAFROL · Dihydroisosafrole · Safrole, dihydro- · rcrawastenumberu090
Identifikatoren & physikalische Daten
| CAS No. | 94-58-6 |
|---|---|
| Summenformel | C10H12O2 |
| Durchschnittliche Molmasse | 164,2 g/mol |
| Monoisotopische Masse | 164,08372962 g/mol |
| SMILES | CCCc1ccc2c(c1)OCO2 |
| InChIKey | MYEIDJPOUKASEC-UHFFFAOYSA-N |
| PubChem CID | 7197 |
| ChEBI | CHEBI:82319 |
| EC No. | 202-344-9 |
| DTXSID | DTXSID7020475 |
| Lokaler Name | 5-Propyl-1,3-benzodioxol |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 18,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 147 |
| Stoffklassen | Biological Agents -> Plant ToxinsCarcinogens |
| Kosmetika | Cosmetics ingredient -> Fragrance |
| Geruch | Odor reminiscent of sassafras |
| Dichte | 1.065 at 25 °C/25 °C1.0326 (rough estimate) |
| Color/Form | Oily liquidColorless liquidColorless to yellowish liquid |
| Löslichkeit | Miscible with ethanol, ether, acetic acid, benzeneSomewhat soluble in alcoholSoluble in carbon tetrachlorideChloroform (Slightly), Ethyl Acetate (Slightly) |
| Siedepunkt | 228 °C251.67°C (rough estimate) |
| Dampfdruck | 0.05 [mmHg] |
| Brechungsindex | Inedx of refraction: 1.5187 at 25 °C/D1.5320 (estimate) |
| Physical Description | Dihydrosafrole is an oily liquid.Colorless oily liquid[HSDB] Colorless to yellow liquid[MSDSonline] |
| Aggregatzustand | Oil |
| Farbe | Colourless to Brown |
| Geruch | at 10.00 % in dipropylene glycol. spicy sassafrass |
| Geruchsart | spicy |
| Henry-Konstante | 8.2×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| LogP (Verteilungskoeffizient) | 3.587 (est) |
| CAS Datenbank | 94-58-6 |
| EPA chemische Informationen | Dihydrosafrole (94-58-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 63.4% (92 of 145) of all reports.WarningH351 (26.9%): Suspected of causing cancer [Warning Carcinogenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 145 reports by companies from 5 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 1,3-Benzodioxole, 5-propyl-Hazard Traits - Carcinogenicity1,3-Benzodioxole, 5-propyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Benzodioxole, 5-propyl- 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: 08-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/127711,3-Benzodioxole, 5-propyl-: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - 1,3-Benzodioxole, 5-propyl-: Environment tier I assessment |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Gesundheitsgefahren | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Gefahrenübersicht | Emergency treatment: Sassafras oilSafrole is the toxic agent in sassafras oilSafrole is classified as 2B (possible human carcinogen) by IARCSafrole is metabolized in the body to 1'-hydroxysafroleIngestion of 5 ml of sassafras oil can cause severe symptoms (tachycardia, hypotension, and respiratory paralysis) or deathLarge doses may damage the liverDrinking 10 cups of sassafras tea caused sweating in one adult subject[HSDB] Sassafras is an abortifacient and narcotic[Olson, p. 389] Used as a stimulant, antispasmodic, and purifier, sassafras has potential hepatotoxic and carcinogenic effects[Goldfrank, p. 643] The lethal dose of sassafras oil is about 5 mLThe oil contains about 80% saffrole[Leikin, p. 955] A skin irritant[MSDSonline] See Safrole. |
| FDA-Anforderungen | (a) Safrole is the chemical 4-allyl-1,2-methylenedioxy-benzene, C10H10O2. It is a natural constituent of the sassafras plant. Oil of sassafras is about 80 percent safrole. Isosafrole and dihydrosafrole are derivatives of safrole, and have been used as flavoring compounds. (b) Food containing any added safrole, oil of sassafras, isosafrole, or dihydrosafrole, as such, or food containing any safrole, oil of sassafras, isosafrole, or dihydrosafrole, e.g., sassafras bark, which is intended solely or primarily as a vehicle for imparting such substances to another food, e.g., sassafras tea, is deemed to be adulterated in violation of the act based upon an order published in the Federal Register of December 3, 1960 (25 FR 12412). |
| Reaktive Gruppe | Ethers |
| RCRA-Anforderungen | U090As stipulated in 40 CFR 261.33, when dihydrosafrole, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| EPA Hazardous Waste Number | U090A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate. |
| CERCLA-Meldepflichtmengen | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| Brandbekämpfung | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Erste Hilfe | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Lagerbedingungen | PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/ |
| Reinigungsverfahren | PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/ |
| Freisetung ohne Brand | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U090, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/For more Disposal Methods (Complete) data for Dihydrosafrole (6 total), please visit the HSDB record page. |
| Preventive Measures | PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/For more Preventive Measures (Complete) data for Dihydrosafrole (9 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/ |
| Wechselwirkungen | Safrole, isosafrole and dihydrosafrole have been shown experimentally to be active synergists for pyrethrum and 1-naphthyl methyl carbamate (Sevin) in common with other methylene-dioxyphenyl cmpd. As class, these substances act as competitive inhibitors of microsomal mixed-function oxidases in houseflies.Pyrethrin synergists such as ... /certain/ methylenedioxyphenyl compounds serve to synergize many of modern insecticides against houseflies that have become resistant to them. They are thus effective for DDT, ... carbamates, ... diazinon, trichlorfon, & other phosphates ... they inhibit ... microsomal hydroxylation. /Methylenedioxyphenyl cmpd/Methylenedioxybenzenes (MDBs) and structurally related alkenylbenzenes were compared for their effectiveness in preventing carbon tetrachloride (CCl4)-induced liver necrosis in mice. Pretreatment with isosafrole, safrole, dihydrosafrole, and benzodioxole at dosages as low as 10 mg/kg significantly prevented the increase in plasma transaminase levels and histochemical changes associated with CCl4-induced liver necrosis, whereas piperonyl butoxide (PBO), eugenol, isoeugenol, sesamol, and curcumin did not prevent CCl4 hepatotoxicity even at 200 mg/kg. However, isosafrole was only partly hepatoprotective if administered 10 min after the toxicant. Liver microsomes isolated 1 hr after isosafrole but not after PBO administration had a markedly decreased CYP2E1 activity. Isosafrole, safrole, dihydrosafrole, and benzodioxole in vitro also inhibited CYP2E1-dependent metabolism more effectively than eugenol and isoeugenol, whereas PBO did not inhibit CYP2E1 activity. The protective effects of isosafrole, safrole, and benzodioxole were therefore predominantly attributed to their ability to inactivate CYP2E1, the major isozyme involved in CCl4 bioactivation. The marked potentiation of CCl4 hepatotoxicity in CYP2E1-induced mice was also completely prevented by isosafrole but not PBO pretreatment, supporting the hypothesis that CYP2E1 inhibition by isosafrole contributes to its hepatoprotective effect against CCl4. Isosafrole and safrole also prevented bromotrichloromethane (BrCCl3)-induced hepatocyte cytotoxicity, whereas PBO was ineffective.1. Inhibitory activity of dihydrosafrole towards benzo[a]pyrene (BP) hydroxylase activity in hepatic microsomes from beta-naphthoflavone (BNF)-induced rats, and in reconstituted systems containing cytochrome P-450c, increased dramatically on preincubation of the inhibitor with NADPHno inhibition occurred without preincubation. The level of BP hydroxylase inhibition was associated with the progressive formation of the 456 nm dihydrosafrole metabolite-cytochrome P-450c spectral complex during preincubation. 2. Inhibition of BP hydroxylase by dihydrosafrole in control microsomes, and inhibition of ethoxyresorufin O-deethylase (EROD) in microsomes (control or BNF-induced) and in reconstituted systems with cytochrome P-450c, did not require preincubation and apparently was not dependent on prior formation of the dihydrosafrole metabolite-cytochrome P-450 complex. 3. Kinetic studies established that, following preincubation with NADPH, dihydrosafrole was a noncompetitive inhibitor of both BP hydroxylase and EROD activities. In the absence of preincubation, dihydrosafrole was an effective competitive inhibitor of EROD in BNF-induced microsomes and in reconstituted systems with cytochrome P-450c. 4. Both ethoxyresorufin and benzo[a]pyrene inhibited the development of the type I optical difference spectrum of dihydrosafrole in reconstituted systems containing cytochrome P-450c. Inhibition by ethoxyresorufin was competitive while that caused by benzo[a]pyrene was noncompetitive in nature. 5. The type II ligand phenylimidazole was an effective noncompetitive inhibitor of EROD activity but failed to exert any inhibitory effect on cytochrome P-450c-mediated BP hydroxylase activity. Phenylimidazole inhibited formation of the dihydrosafrole type I optical difference spectrum non-competitively. 6. The results indicate that ethoxyresorufin and benzo[a]pyrene may occupy different binding sites on cytochrome P-450c and that dihydrosafrole binds primarily to the site utilized by ethoxyresorufin. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 210(SRC), determined from a structure estimation method(2), indicates that dihydrosafrole is expected to have moderate mobility in soil(SRC). Volatilization of dihydrosafrole from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.17 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Dihydrosafrole has an estimated vapor pressure of 0.055 mm Hg(SRC), determined from a fragment constant method(2) and exists as a liquid under environmental conditionstherefore, dihydrosafrole may volatilize from dry soil(SRC). Biodegradation data in soil were not available(SRC, 2018).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 210(SRC), determined from a structure estimation method(2), indicates that dihydrosafrole 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 0.17 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 hrs and 5 days, respectively(SRC). According to a classification scheme(4), an estimated BCF of 110(SRC), from an estimated log Kow of 3.58(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data in water were not available(SRC, 2018).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dihydrosafrole, which has an estimated vapor pressure of 0.055 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dihydrosafrole 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 8 hrs(SRC), calculated from its rate constant of 5.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Dihydrosafrole absorbs UV light at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Dihydrosafrole is a colorless oily liquid. It is used in fragrances. The FDA does not permit dihydrosafrole to be used in foods. HUMAN STUDIES: Tested at 12% in petrolatum, it produced no irritation after a 48 hr closed-patch test in 25 human subjects. It was not sensitizing in the maximization test in volunteers. ANIMAL STUDIES: Applied full strength on intact or abraded rabbit skin it was mildly irritating. Dihydrosafrole 1000 ppm fed to rats in the diet for 2 yr retarded growth in females and caused macroscopic and microscopic liver changes. Tumors of esophagus (papillomas and epidermoid carcinomas) developed in 75% of rats fed 5000 or 10,000 mg/kg of diet levels and in 20% of rats fed 2500 mg/kg of diet. Hepatomas, pulmonary tumors and lymphomas were observed in dihydrosafrole-treated mice. Hepatoma incidence tended to be higher in males than females with dihydrosafrole. No significant mutagenic activity was noted in Salmonella typhimurium strains TA1535 and TA100 with or without metabolic activation. |
| Medical Surveillance | PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/ |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of dihydrosafrole can be estimated to be 210(SRC). According to a classification scheme(2), this estimated Koc value suggests that dihydrosafrole is expected to have moderate mobility in soil(SRC). |
| Natural Pollution Sources | Dihydrosafrole has not been reported as found in nature(1). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ A maximization test was carried out on 25 volunteers. The material was tested at a concentration of 12% in petrolatum and produced no sensitization reactions./HUMAN EXPOSURE STUDIES/ Tested at 12% in petrolatum, it produced no irritation after a 48 hr closed-patch test in 25 human subjects. |
| Artificial Pollution Sources | Dihydrosafrole's production as a byproduct in the production of piperonyl butoxide which is a synergist for pyrethroid pesticides(1) may result in its release to the environment through various waste streams(SRC). The use of dihydrosafrole as an additive in foods is not permitted in the US(2). Until 1960, dihydrosafrole was used as a flavoring agent in root beer in the US(1). |
| Carcinogen Classification | DihydrosafroleGroup 2B: Possibly carcinogenic to humansVolume 10: (1976) Some Naturally Occurring Substances1987 |
| Environmental Bioconcentration | An estimated BCF of 110 was calculated in fish for dihydrosafrole(SRC), using an estimated log Kow of 3.58(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for dihydrosafrole is estimated as 0.17 atm-cu m/mole(SRC) developed using a fragment constant estimation method(1). This Henry's Law constant indicates that dihydrosafrole is expected to volatilize rapidly from water surfaces(2). 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)(2) is estimated as 4 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5 days(SRC). Dihydrosafrole's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Dihydrosafrole has an estimated vapor pressure of 0.055 mm Hg(SRC), determined from a fragment constant method(1) and exists as a liquid under environmental conditionstherefore, dihydrosafrole may volatilize from dry soil(SRC). |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29329990 |
| Gefahrstoffdaten | 94-58-6(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
Has apparently not been reported to occur in nature.
Verwenden
Safrole derivative. Carcinogenic.
Herstellung & Synthese
synthetische
By catalytic hydrogenation of safrole (Arctander, 1969).