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ANISOLE

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Classification   |    Detailed evidence-based information

Substances Included Synonyms

Therapeutic Toxic Class

    A) Anisole is used as a food additive and meat flavoring. It is also used in fragrances and pharmaceuticals.

Specific Substances

    1) Anisole
    2) Anizol
    3) Benzene, methoxy-
    4) Ether, methyl phenyl
    5) Methoxybenzene
    6) Methyl phenyl ether
    7) Metil fenil eter (Spanish)
    8) Phenyl methyl ether
    9) ANISOLE (AROMATIC ETHER)
    10) METHOXYBENZENE (AROMATIC ETHER)
    11) PHENYL METHYL ETHER (AROMATIC ETHER)
    1.2.1) MOLECULAR FORMULA
    1) C7H8O
    2) C6H5OCH3

Available Forms Sources

    A) FORMS
    1) Anisole exists as a clear, colorless or straw-colored liquid. It possesses an aromatic odor, redolent of anise (AAR, 2002; Lewis, 2000).
    B) SOURCES
    1) Anisole is found in Artemisia dracunculus var turkestanica (tarragon), and has also been isolated from essential oil of Ocimum selloi (basil) (HSDB, 2003; Furia & Bellanca, 1975).
    2) Anisole is formed naturally and anthropogenically through hydrocarbon combustion. It may be emitted in automobile exhaust and in fumes from kerosene space heaters. Anisole may also occur naturally in meat or be formed during cooking (HSDB, 2003) .
    3) Anisole is derived through the following chemical reactions :
    1) phenol plus dimethyl sulfate (methylation) (Ashford, 2001)
    2) phenol plus methanol (catalytic gas-phase methylation) (Ashford, 2001)
    3) sodium phenate plus methyl chloride (Lewis, 2001a)
    4) phenol plus methyl chloride in presence of sodium hydroxide (Budavari, 2001)
    5) from bromobenzene by passing methyl chloride into a suspension of sodium phenolate in liquid ammonia (Budavari, 2001)
    4) Anisole may occur as an impurity in the production of o-cresol and 2,6-xylenol through alkylation of phenol with methanol (HSDB, 2003) .
    C) USES
    1) Anisole is an important intermediate in the manufacture of organic compounds, including pharmaceuticals, fragrances, and food flavoring, particularly for meats (HSDB, 2003).
    a) Anisole is permitted by the U.S. Food and Drug Administration (FDA) for use as a food additive and synthetic flavoring substance (HSDB, 2003).
    2) Anisole has been used in the manufacture of soaps, detergents, creams, lotions, and perfumes since the 1930s. It is also used as a solvent, vermicide, chemical intermediate, and heat transfer medium (HSDB, 2003; Budavari, 2001; Lewis, 1997; Opdyke, 1979).

Overview

Life Support

    A) This overview assumes that basic life support measures have been instituted.

Clinical Effects

    0.2.1) SUMMARY OF EXPOSURE
    A) Human volunteers exposed to anisole have experienced eye irritation, burning in the throat, and a foreign taste in the mouth. Other signs and symptoms of exposure may include cough; wheezing; sore throat; skin irritation; dry red skin; pain and redness of the eyes; dizziness; and lightheadedness. Prolonged exposure may cause drying and cracking of the skin.
    B) In experimental animals, anisole was an irritant and CNS depressant. Seizures or an effect on the seizure threshold, tremor, excitement, hematuria, and changes in the function or structure of salivary glands have also been observed.
    0.2.14) DERMATOLOGIC
    A) In a 48 hours closed patch test, a 4% mixture in petrolatum showed no irritation.
    0.2.20) REPRODUCTIVE
    A) At the time of this review, no data were available to assess the teratogenic potential of this agent.
    B) At the time of this review, no data were available to assess the potential effects of exposure to this agent during pregnancy or lactation.

Laboratory Monitoring

    A) No specific laboratory tests are necessary unless otherwise clinically indicated.

Treatment Overview

    0.4.2) ORAL/PARENTERAL EXPOSURE
    A) ACTIVATED CHARCOAL: Administer charcoal as a slurry (240 mL water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents, 25 to 50 g in children (1 to 12 years), and 1 g/kg in infants less than 1 year old.
    B) Observe patients with ingestion carefully for the possible development of esophageal or gastrointestinal tract irritation or burns. If signs or symptoms of esophageal irritation or burns are present, consider endoscopy to determine the extent of injury.
    C) Carefully observe patients with ingestion exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary.
    D) Patients symptomatic following exposure should be observed in a controlled setting until all signs and symptoms have fully resolved.
    0.4.3) INHALATION EXPOSURE
    A) INHALATION: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with an inhaled beta2-adrenergic agonist. Consider systemic corticosteroids in patients with significant bronchospasm.
    B) If respiratory tract irritation or respiratory depression is evident, monitor arterial blood gases, chest x-ray, and pulmonary function tests.
    0.4.4) EYE EXPOSURE
    A) DECONTAMINATION: Remove contact lenses and irrigate exposed eyes with copious amounts of room temperature 0.9% saline or water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist after 15 minutes of irrigation, the patient should be seen in a healthcare facility.
    0.4.5) DERMAL EXPOSURE
    A) OVERVIEW
    1) DECONTAMINATION: Remove contaminated clothing and jewelry and place them in plastic bags. Wash exposed areas with soap and water for 10 to 15 minutes with gentle sponging to avoid skin breakdown. A physician may need to examine the area if irritation or pain persists (Burgess et al, 1999).
    2) Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines.

Range Of Toxicity

    A) Anisole can be moderately toxic if ingested or inhaled. Anisole is an ether-type compound that can cause irritation in the nose, throat, skin, and eyes, along with dizziness and unconsciousness. A potential risk for chemical pneumonitis exists should liquid anisole be ingested and aspirated into the lungs .
    B) The minimum lethal human dose to this agent has not been delineated.
    C) The maximum tolerated human exposure to this agent has not been delineated.

Clinical Effects

Summary Of Exposure

    A) Human volunteers exposed to anisole have experienced eye irritation, burning in the throat, and a foreign taste in the mouth. Other signs and symptoms of exposure may include cough; wheezing; sore throat; skin irritation; dry red skin; pain and redness of the eyes; dizziness; and lightheadedness. Prolonged exposure may cause drying and cracking of the skin.
    B) In experimental animals, anisole was an irritant and CNS depressant. Seizures or an effect on the seizure threshold, tremor, excitement, hematuria, and changes in the function or structure of salivary glands have also been observed.

Dermatologic

    3.14.1) SUMMARY
    A) In a 48 hours closed patch test, a 4% mixture in petrolatum showed no irritation.
    3.14.2) CLINICAL EFFECTS
    A) SKIN FINDING
    1) LACK OF EFFECT
    a) In a 48 hour closed patch test, a 4% mixture in petrolatum showed no irritation (Epstein WL, 1976).
    3.14.3) ANIMAL EFFECTS
    A) ANIMAL STUDIES
    1) IRRITATION
    a) In test animals anisole was found moderately irritating when applied full strength, under occlusion, on intact or abraded skin for 24 hours (Moreno OM, 1976).

Reproductive

    3.20.1) SUMMARY
    A) At the time of this review, no data were available to assess the teratogenic potential of this agent.
    B) At the time of this review, no data were available to assess the potential effects of exposure to this agent during pregnancy or lactation.
    3.20.2) TERATOGENICITY
    A) LACK OF INFORMATION
    1) At the time of this review, no data were available to assess the teratogenic potential of this agent.
    3.20.3) EFFECTS IN PREGNANCY
    A) LACK OF INFORMATION
    1) At the time of this review, no data were available to assess the potential effects of exposure to this agent during pregnancy or lactation.

Carcinogenicity

    3.21.1) IARC CATEGORY
    A) IARC Carcinogenicity Ratings for CAS100-66-3 (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004):
    1) Not Listed
    3.21.4) ANIMAL STUDIES
    A) CARCINOMA
    1) MICE - Female mice had a 20% solution of anisole in acetone applied to their skin twice weekly after application of the carcinogen dimethylbenz(a)anthracene. Nine percent of the survivors (34 of 36 survived) had papillomas and 3% had carcinomas (Boutwell & Bosch, 1959).

Genotoxicity

    A) Anisole has caused DNA inhibition in human lymphocytes, but no other mutagenic or genotoxic effects have been found.

Laboratory Monitoring

Monitoring Parameters Levels

    4.1.1) SUMMARY
    A) No specific laboratory tests are necessary unless otherwise clinically indicated.

Methods

    A) CHROMATOGRAPHY
    1) Anisole concentrations may be determined by gas chromatogram (Opdyke, 1979).

Treatment

Life Support

    A) Support respiratory and cardiovascular function.

Patient Disposition

    6.3.1) DISPOSITION/ORAL EXPOSURE
    6.3.1.1) ADMISSION CRITERIA/ORAL
    A) Patients symptomatic following exposure should be observed in a controlled setting until all signs and symptoms have fully resolved.

Monitoring

    A) No specific laboratory tests are necessary unless otherwise clinically indicated.

Oral Exposure

    6.5.1) PREVENTION OF ABSORPTION/PREHOSPITAL
    A) Esophageal or gastrointestinal tract irritation or burns may occur following an ingestion. The role of gastric decontamination is unclear.
    B) ACTIVATED CHARCOAL
    1) PREHOSPITAL ACTIVATED CHARCOAL ADMINISTRATION
    a) Consider prehospital administration of activated charcoal as an aqueous slurry in patients with a potentially toxic ingestion who are awake and able to protect their airway. Activated charcoal is most effective when administered within one hour of ingestion. Administration in the prehospital setting has the potential to significantly decrease the time from toxin ingestion to activated charcoal administration, although it has not been shown to affect outcome (Alaspaa et al, 2005; Thakore & Murphy, 2002; Spiller & Rogers, 2002).
    1) In patients who are at risk for the abrupt onset of seizures or mental status depression, activated charcoal should not be administered in the prehospital setting, due to the risk of aspiration in the event of spontaneous emesis.
    2) The addition of flavoring agents (cola drinks, chocolate milk, cherry syrup) to activated charcoal improves the palatability for children and may facilitate successful administration (Guenther Skokan et al, 2001; Dagnone et al, 2002).
    2) CHARCOAL DOSE
    a) Use a minimum of 240 milliliters of water per 30 grams charcoal (FDA, 1985). Optimum dose not established; usual dose is 25 to 100 grams in adults and adolescents; 25 to 50 grams in children aged 1 to 12 years (or 0.5 to 1 gram/kilogram body weight) ; and 0.5 to 1 gram/kilogram in infants up to 1 year old (Chyka et al, 2005).
    1) Routine use of a cathartic with activated charcoal is NOT recommended as there is no evidence that cathartics reduce drug absorption and cathartics are known to cause adverse effects such as nausea, vomiting, abdominal cramps, electrolyte imbalances and occasionally hypotension (None Listed, 2004).
    b) ADVERSE EFFECTS/CONTRAINDICATIONS
    1) Complications: emesis, aspiration (Chyka et al, 2005). Aspiration may be complicated by acute respiratory failure, ARDS, bronchiolitis obliterans or chronic lung disease (Golej et al, 2001; Graff et al, 2002; Pollack et al, 1981; Harris & Filandrinos, 1993; Elliot et al, 1989; Rau et al, 1988; Golej et al, 2001; Graff et al, 2002). Refer to the ACTIVATED CHARCOAL/TREATMENT management for further information.
    2) Contraindications: unprotected airway (increases risk/severity of aspiration) , nonfunctioning gastrointestinal tract, uncontrolled vomiting, and ingestion of most hydrocarbons (Chyka et al, 2005).
    6.5.2) PREVENTION OF ABSORPTION
    A) ACTIVATED CHARCOAL
    1) CHARCOAL ADMINISTRATION
    a) Consider administration of activated charcoal after a potentially toxic ingestion (Chyka et al, 2005). Administer charcoal as an aqueous slurry; most effective when administered within one hour of ingestion.
    2) CHARCOAL DOSE
    a) Use a minimum of 240 milliliters of water per 30 grams charcoal (FDA, 1985). Optimum dose not established; usual dose is 25 to 100 grams in adults and adolescents; 25 to 50 grams in children aged 1 to 12 years (or 0.5 to 1 gram/kilogram body weight) ; and 0.5 to 1 gram/kilogram in infants up to 1 year old (Chyka et al, 2005).
    1) Routine use of a cathartic with activated charcoal is NOT recommended as there is no evidence that cathartics reduce drug absorption and cathartics are known to cause adverse effects such as nausea, vomiting, abdominal cramps, electrolyte imbalances and occasionally hypotension (None Listed, 2004).
    b) ADVERSE EFFECTS/CONTRAINDICATIONS
    1) Complications: emesis, aspiration (Chyka et al, 2005). Aspiration may be complicated by acute respiratory failure, ARDS, bronchiolitis obliterans or chronic lung disease (Golej et al, 2001; Graff et al, 2002; Pollack et al, 1981; Harris & Filandrinos, 1993; Elliot et al, 1989; Rau et al, 1988; Golej et al, 2001; Graff et al, 2002). Refer to the ACTIVATED CHARCOAL/TREATMENT management for further information.
    2) Contraindications: unprotected airway (increases risk/severity of aspiration) , nonfunctioning gastrointestinal tract, uncontrolled vomiting, and ingestion of most hydrocarbons (Chyka et al, 2005).
    B) GASTRIC LAVAGE
    1) Significant esophageal or gastrointestinal tract irritation or burns may occur following ingestion. The possible benefit of early removal of some ingested material by cautious gastric lavage must be weighed against potential complications of bleeding or perforation.
    2) INDICATIONS: Consider gastric lavage with a large-bore orogastric tube (ADULT: 36 to 40 French or 30 English gauge tube {external diameter 12 to 13.3 mm}; CHILD: 24 to 28 French {diameter 7.8 to 9.3 mm}) after a potentially life threatening ingestion if it can be performed soon after ingestion (generally within 60 minutes).
    a) Consider lavage more than 60 minutes after ingestion of sustained-release formulations and substances known to form bezoars or concretions.
    3) PRECAUTIONS:
    a) SEIZURE CONTROL: Is mandatory prior to gastric lavage.
    b) AIRWAY PROTECTION: Place patients in the head down left lateral decubitus position, with suction available. Patients with depressed mental status should be intubated with a cuffed endotracheal tube prior to lavage.
    4) LAVAGE FLUID:
    a) Use small aliquots of liquid. Lavage with 200 to 300 milliliters warm tap water (preferably 38 degrees Celsius) or saline per wash (in older children or adults) and 10 milliliters/kilogram body weight of normal saline in young children(Vale et al, 2004) and repeat until lavage return is clear.
    b) The volume of lavage return should approximate amount of fluid given to avoid fluid-electrolyte imbalance.
    c) CAUTION: Water should be avoided in young children because of the risk of electrolyte imbalance and water intoxication. Warm fluids avoid the risk of hypothermia in very young children and the elderly.
    5) COMPLICATIONS:
    a) Complications of gastric lavage have included: aspiration pneumonia, hypoxia, hypercapnia, mechanical injury to the throat, esophagus, or stomach, fluid and electrolyte imbalance (Vale, 1997). Combative patients may be at greater risk for complications (Caravati et al, 2001).
    b) Gastric lavage can cause significant morbidity; it should NOT be performed routinely in all poisoned patients (Vale, 1997).
    6) CONTRAINDICATIONS:
    a) Loss of airway protective reflexes or decreased level of consciousness if patient is not intubated, following ingestion of corrosive substances, hydrocarbons (high aspiration potential), patients at risk of hemorrhage or gastrointestinal perforation, or trivial or non-toxic ingestion.
    6.5.3) TREATMENT
    A) SUPPORT
    1) Exposed individuals should have a careful, thorough medical history and physical examination performed, looking for any abnormalities. Exposure to chemicals with a strong odor often results in such nonspecific symptoms as headache, dizziness, weakness, and nausea.
    B) OBSERVATION REGIMES
    1) Carefully observe patients with ingestion exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary.

Inhalation Exposure

    6.7.1) DECONTAMINATION
    A) Move patient from the toxic environment to fresh air. Monitor for respiratory distress. If cough or difficulty in breathing develops, evaluate for hypoxia, respiratory tract irritation, bronchitis, or pneumonitis.
    B) OBSERVATION: Carefully observe patients with inhalation exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary.
    C) INITIAL TREATMENT: Administer 100% humidified supplemental oxygen, perform endotracheal intubation and provide assisted ventilation as required. Administer inhaled beta-2 adrenergic agonists, if bronchospasm develops. Consider systemic corticosteroids in patients with significant bronchospasm (National Heart,Lung,and Blood Institute, 2007). Exposed skin and eyes should be flushed with copious amounts of water.
    6.7.2) TREATMENT
    A) OBSERVATION REGIMES
    1) Carefully observe patients with inhalation exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary.
    B) IRRITATION SYMPTOM
    1) If respiratory tract irritation or respiratory depression is evident, monitor arterial blood gases, chest x-ray, and pulmonary function tests.
    C) Treatment should include recommendations listed in the ORAL EXPOSURE section when appropriate.

Eye Exposure

    6.8.1) DECONTAMINATION
    A) EYE IRRIGATION, ROUTINE: Remove contact lenses and irrigate exposed eyes with copious amounts of room temperature 0.9% saline or water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist after 15 minutes of irrigation, an ophthalmologic examination should be performed (Peate, 2007; Naradzay & Barish, 2006).

Dermal Exposure

    6.9.1) DECONTAMINATION
    A) DERMAL DECONTAMINATION
    1) DECONTAMINATION: Remove contaminated clothing and wash exposed area thoroughly with soap and water for 10 to 15 minutes. A physician may need to examine the area if irritation or pain persists (Burgess et al, 1999).
    6.9.2) TREATMENT
    A) SKIN IRRITATION
    1) Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines.
    B) Treatment should include recommendations listed in the ORAL EXPOSURE section when appropriate.

Enhanced Elimination

    A) SUMMARY
    1) No studies have addressed the utilization of extracorporeal elimination techniques in poisoning with this agent.

Range Of Toxicity

Summary

    A) Anisole can be moderately toxic if ingested or inhaled. Anisole is an ether-type compound that can cause irritation in the nose, throat, skin, and eyes, along with dizziness and unconsciousness. A potential risk for chemical pneumonitis exists should liquid anisole be ingested and aspirated into the lungs .
    B) The minimum lethal human dose to this agent has not been delineated.
    C) The maximum tolerated human exposure to this agent has not been delineated.

Minimum Lethal Exposure

    A) GENERAL / SUMMARY
    1) The minimum lethal human dose to this agent has not been delineated.
    B) ANIMAL DATA
    1) Oral doses of 1230 mg/kg four times daily resulted in death in 1 of 6 rats. No macroscopic liver damage was seen (Taylor et al, 1964).
    2) A minimum lethal (LDLo) intraperitoneal dose to rats of 500 mg/kg is reported (RTECS, 2004).

Maximum Tolerated Exposure

    A) GENERAL / SUMMARY
    1) The maximum tolerated human exposure to this agent has not been delineated.
    B) ANIMAL DATA
    1) Mice who had a 10% solution applied to one third of the body surface did not experience toxic effects (Lebedev, 1969).
    2) A calf who had a whole body application of a 10% solution did not experience toxic effects (Lebedev, 1969).

Workplace Standards

    A) ACGIH TLV Values for CAS100-66-3 (American Conference of Governmental Industrial Hygienists, 2010):
    1) Not Listed

    B) NIOSH REL and IDLH Values for CAS100-66-3 (National Institute for Occupational Safety and Health, 2007):
    1) Not Listed

    C) Carcinogenicity Ratings for CAS100-66-3 :
    1) ACGIH (American Conference of Governmental Industrial Hygienists, 2010): Not Listed
    2) EPA (U.S. Environmental Protection Agency, 2011): Not Listed
    3) IARC (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004): Not Listed
    4) NIOSH (National Institute for Occupational Safety and Health, 2007): Not Listed
    5) MAK (DFG, 2002): Not Listed
    6) NTP (U.S. Department of Health and Human Services, Public Health Service, National Toxicology Project ): Not Listed

    D) OSHA PEL Values for CAS100-66-3 (U.S. Occupational Safety, and Health Administration (OSHA), 2010):
    1) Not Listed

Toxicity Information

    7.7.1) TOXICITY VALUES
    A) LD50- (ORAL)MOUSE:
    1) 2800 mg/kg -- tremor; convulsions or effect on threshold of seizure; excitement (Lewis, 2000; RTECS, 2004)
    B) LD50- (INTRAPERITONEAL)RAT:
    1) 1950 mg/kg (Grubner et al, 1972)
    C) LD50- (ORAL)RAT:
    1) 3700 mg/kg (Jenner et al, 1964; Taylor et al, 1964; Lewis, 1996)
    D) LD50- (SUBCUTANEOUS)RAT:
    1) 3500-4000 mg/kg (Hake & Rowe, 1963)
    E) TCLo- (INHALATION)RAT:
    1) 200 mg/m(3) for 122D - intermittent -- hepatitis, diffuse; changes in kidney tubules; weight loss or decreased weight gain (RTECS, 2004)

Pharmacology Toxicology

Toxicologic Mechanism

    A) Anisole antagonized hexenal sleep (Lupandin & Mar'yanovskii, 1972).
    B) In vitro, anisole has been studied as an inhibitor of bovine alpha chymotrypsin catalysed hydrolysis of acetyl-L-valine methyl ester (Wallace et al, 1963).
    C) When rats were given 195 mg/kg IP, decreased hexobarbital sleeping time was noted (Grubner et al, 1972).

Physicochemical

Physical Characteristics

    A) Anisole is a mobile liquid that possesses an aromatic, agreeable, anise-like odor and a clear to yellowish, straw color (HSDB, 2003; Budavari, 2001; Lewis, 2000; Sittig, 1991).

Molecular Weight

    A) 108.14

Other

    A) ODOR THRESHOLD
    1) 0.05 mg/kg (0.2 mg/L) (detection) (Verschueren, 2001)

References

General Bibliography

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    2) 40 CFR 372.65: Environmental Protection Agency - Toxic Chemical Release Reporting, Community Right-To-Know, Chemicals and Chemical Categories to which this part applies. National Archives and Records Association (NARA) and the Government Printing Office (GPO), Washington, DC. Final rules current as of Apr 3, 2006.
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