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Dihydrosafrole

Dihydrosafrole structure

Dihydrosafrole 

structure
  • CAS No:

    94-58-6

  • Formula:

    C10H12O2

  • Chemical Name:

    Dihydrosafrole

  • Synonyms:

    1,3-Benzodioxole,5-propyl-;Benzene,1,2-(methylenedioxy)-4-propyl-;5-Propyl-1,3-benzodioxole;Safrole,dihydro-;Dihydrosafrole;1,2-(Methylenedioxy)-4-propylbenzene;2′,3′-Dihydrosafrole;5-Propylbenz[1,3]dioxole;NSC 27867;NSC 33707

Description

Light Yellow Oil


Dihydrosafrole is an oily liquid.


Dihydrosafrole is an oily liquid.|Dihydrosafrole is a member of benzodioxoles.

Dihydrosafrole Basic Attributes

164.20100

164.20

202-344-9

2ML63PLH7G

33707|27867

3082

DTXSID7020475

Oily liquid|Colorless liquid|Colorless to yellowish liquid

2932999080

Characteristics

18.46000

2.36780

Dihydrosafrole is an oily liquid.

1.0695 g/cm3 @ Temp: 20 °C

228 °C

99.3ºC

1.533

In water, 56.9 mg/L at 25 deg C (est)

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 b

5.6X10-2 mm Hg at 25 deg C (est)

Odor reminiscent of sassafras

Henry's Law constant = 0.165 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 5.09X10-11 cu cm/molec-sec at 25 °C (est)

No rapid reaction with air. No rapid reaction with water.

Ethers

Safety Information

3082

P201, P202, P260, P264, P270, P281, P308+P313, P309+P311, P312, P405, P501

H303

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.

(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).

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Warning|H351 (97.44%): Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 130 companies from 3 notifications to the ECHA C&L Inventory.|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P281, P308+P313, P309+P311, P312, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal. FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|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/

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/

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.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

U090; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

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).

U090; As 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).

Toxicity

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.

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 NADPH; no 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.

LD50 Mouse oral 3700 mg/kg bw|LD50 Mouse oral 4300 mg/kg bw|LD50 Rat oral 2260 mg/kg bw

Dihydrosafrole has not been reported as found in nature(1).

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).

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 conditions; therefore, 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).

The rate constant for the vapor-phase reaction of dihydrosafrole with photochemically-produced hydroxyl radicals has been estimated as 5.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Dihydrosafrole is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Dihydrosafrole absorbs UV light at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

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).

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).

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 conditions; therefore, dihydrosafrole may volatilize from dry soil(SRC).

Occupational exposure to dihydrosafrole may occur through dermal contact with this compound at workplaces where dihydrosafrole is used. The general population is not likely to be exposed to dihydrosafrole. (SRC)

Drug Information

In mice given ... (14)C-labeled safrole or dihydrosafrole orally, 96% and 101% of radioactivity ... recovered; 64 and 61% were found in CO2, 18 & 23% in urine, 6 and 5% in feces and intestine, 2 & 2.5% in liver & 6 and 9% in carcasses ...

In mice, major metabolic pathway for ... dihydrosafrole ... incl cleavage of methylenedioxyphenol residue & exhalation of methylene carbon atom as CO2.|Dihydrosafrole yields 4-propylcatechol probably in mouse & fly. /From table/|Treatment of rats with safrole, isosafrole, dihydrosafrole, or methylenedioxystyrylamyl ketone (150 mg/kg, ip daily for 3 days) resulted in the formation of 455-nm cytochrome P450-methylenedioxyphenyl metabolite complex.|... Clearance of dihydrosafrole and its metabolites from both the ethmoid (olfactory) and maxillary (respiratory) turbinate regions of Beagle dogs and Cynomolgus monkeys was examined. Nasopharyngeal mucus was collected at frequent intervals during periodic instillation of dihydrosafrole (and, for the dogs, 24 hr after instillation). Blood, urine and feces were collected to examine dihydrosafrole clearance from the nose during instillations and up to 48 hr after completion of the nasal instillations of (3)H-dihydrosasfrole. ... Most of the recovered radioactivity was in urine and blood samples over the first 24 hr. Radioactivity was recovered from the nasopharyngeal mucus in both organic extractable and water soluble forms. ... (3)H-dihydrosafrole instilled in either turbinate region was metabolized to 2-methoxy-4-propylphenol, 2-methoxy-4-propenylphenol and 1-(3,4-methylenedioxyphenyl)propan-1-ol. A number of minor metabolites were produced in both species. One mucus sample from an ethmoid-instilled dog contained 1-(3,4-methylenedioxyphenyl)propene (isosafrole) as a metabolite. ... interspecies, inter-individual and inter-regional differences occur in the metabolism of nasally deposited dihydrosafrole in monkeys and dogs.|For more Metabolism/Metabolites (Complete) data for Dihydrosafrole (6 total), please visit the HSDB record page.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)|Carcinogens

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/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.

1,3-benzodioxole, 5-propyl-

Dihydrosafrole Use and Manufacturing

Methods of Manufacturing

CATALYTIC HYDROGENATION OF SAFROLE OR ISOSAFROLE.|From safrole or isosafrole by hydrogenation over nickel at 200 °C; by hyrdogenation of either safrole in alcoholic solution in the presence of palladium or activated carbon or of 3,4-methylenedioxy cinnamic aldehyde.

Uses

Safrole derivative. Carcinogenic.

Production

(1977) AT LEAST 1.82X10+8 G|(1982) NOT PRODUCED COMMERCIALLY IN USA.|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4304]|Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,2-(Methylenedioxy)-4-propylbenzene:

1,3-Benzodioxole, 5-propyl-: ACTIVE|Although there is no evidence that ... /it/ is produced commercially in USA, it is known to be produced as intermediate in the prodn of piperonyl butoxide ...

Method: EPA-RCA 8270D; Procedure: gas chromatography/mass spectrometry; Analyte: dihydrosafrole; Matrix: solid waste matrices, soils, air sampling media and water samples; Detection Limit: not provided.|Gas chromatographic method for determining dihydrosafrole in nonalcoholic beverages and concentrates.|Method: AOAC 969.13; Procedure: gas chromatography; Analyte: dihydrosafrole; Matrix: nonalcoholic beverages; Detection Limit: not provided.|An HPLC method for the simultaneous determination of safrole (S), dihydrosafrole (DHS), and chloromethyldihydrosafrole (CM-DHS) in piperonyl butoxide, with fluorimetric detection and elution gradient, is described. Samples with internal standard (piperonyl isobutyrate) are adsorbed on silica cartridges, then eluted with an appropriate solvent. Internal standard, S, DHS, and CMDHS are eluted together and injected into a reversed-phase chromatography column. The concentrations of the three products are calculated from calibration graphs, and linearity and reproducibility are verified. The limit of detection is 2 mg/kg. This analytical method allows for control of the synthesis process of piperonyl butoxide and determination of some carcinogenic substances, such as S and DHS.

Health Hazards -> Carcinogens

Computed Properties

Molecular Weight:164.20
XLogP3:3.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:164.083729621
Monoisotopic Mass:164.083729621
Topological Polar Surface Area:18.5
Heavy Atom Count:12
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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