Anethole

148.20200

148.20

203-205-5

Q3JEK5DO4K

758626|209529|4018

1993

DTXSID4020086|DTXSID9020087

White crystals

2909309090

9.23000

3.3

Anethole appears as white crystals or a liquid. Odor of anise oil and a sweet taste. (NTP, 1992)

0.9878 g/cm³ @ Temp: 20 °C

21.3 °C

234 °C

90ºC

n20/D 1.561(lit.)

Water solubility = 1.110E-1 g/l @ 25 deg C

2-8ºC

5.45 Pa @ 294 deg K

SPECIFIC OPTICAL ROTATION: +0.08 DEG

ANISE OIL ODOR

SWEET TASTE

MAX ABSORPTION (ISOOCTANE): 258 NM (LOG E= 4.25); MELTING POINT 21.35 °C; BP: 234.5 DEG @ 763 MM HG /TRANS-ISOMER/|INDEX OF REFRACTION: 1.55455 @ 20 °C/D; MAX ABSORPTION (ETHANOL): 253 NM (E= 18,500); MELTING POINT -22.5 °C; BOILING POINT 79-79.5 °C @ 23 MM HG /CIS-ISOMER/|DISTILLATION RANGE: 234-237 °C

Slightly water soluble (NTP, 1992).

Ethers

Protect from light (NTP, 1992).

1993

2

R43

S24/25

BZ9275000

Xi

Stable. Combustible. Incompatible with strong oxidizing agents.

P261, P272, P280, P302+P352, P321, P333+P313, P363, P501

H317

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Anethole used as a synthetic flavoring substance or adjuvant in food for human consumption is generally recognized as safe when used in accordance with good manufacturing practice.|Anethole used as a synthetic flavoring substance or adjuvant in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

This compound is combustible. (NTP, 1992)

|Warning|H317 (97.29%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 1750 companies from 18 notifications to the ECHA C&L Inventory.|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 248 companies from 4 notifications to the ECHA C&L Inventory.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

To extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguisher; a water spray may also be used. (NTP, 1992)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail 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)

SMALL SPILLS AND LEAKAGE: Use absorbent paper to pick up spill material. Contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with alcohol followed by washing with a strong soap and water solution. STORAGE PRECAUTIONS: You should keep this material in a tightly-closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: When working with this chemical, you should wear impervious coveralls, shoe covers and gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

In a monitoring study of organic constituents of kraft mill aerated stabilization basins in Oregon, anethole was detected at trace quantities (detection limits were not reported)(1). Another study of kraft mill aerated lagoons also identified anethole in four samples of an unbleached kraft aerated lagoon influent and effluent in the following concentrations (ppb): 30-60, 20-10, 30-trace (detection limit not reported), and 20-10; influents and effluents respectively(2). A third study of unbleached treated kraft paper mill wastewater in Georgia found anethole at approximately 0.007 mg/l(3).

MEAN SLEEPING TIME IN MICE TREATED WITH 50 MG/KG NA-PENTOBARBITAL ABOUT DOUBLED WITH 20 & 50 MG OF SOME COMPD; ANETHOLE WAS LESS ACTIVE.

Anethole occurs naturally in anise, star anise, and fennel oils(1) and chickpea seed(2).

Chloronitrobenzenes are produced by nitration of chlorobenzene. The crude chloronitrobenzene obtained from the nitration process contains about 34% o-chloronitrobenzene, 65% p-chloronitrobenzene, and 1% m-chloronitrobenzene. The isomers are separated by a combination of crystallization and distillation.

TERRESTRIAL FATE: Anethole will have a medium to low mobility(3) in soil based on estimated Koc values ranging from 327 to 680(1,2). Insufficient data are available to predict the relative importance or rate of biodegradation in soil conditions(SRC).|AQUATIC FATE: Volatilization of anethole from water is not rapid but could possibly be significant based upon estimated Henry's Law constant of 7.18X10-5 atm cu m/mol(1,2,SRC). Volatilization half-lives from a model river (1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec) and a model lake (1 meter deep) can be estimated to be about 18 hours and 9 days respectively(2). Insufficient data are available to predict the relative importance or rate of biodegradation from natural waters(SRC). Aquatic bioconcentration is not expected to be an important fate process, however, based on a Koc value of 680(3), some absorption to sediment may occur(SRC).|ATMOSPHERIC FATE: Based on an extrapolated vapor pressure of approximately 0.005 mm Hg at 25 °C(1), anethole will exist in the atmosphere in the vapor phase(2). It will degrade in the atmosphere by reaction with photochemically produced hydroxyl radicals with estimated half-lives of 4.9 and 4.5 hrs for the cis and trans isomers, respectively(3). Anethole will also degrade in the atmosphere by reaction with atmospheric ozone with estimated half-lives of 4.03 and 2.02 hrs for the cis and trans isomers, respectively(3).

The rate constant for the vapor-phase reaction of anethole with photochemically produced hydroxyl radicals has been estimated to be approximately 78.6X10-12 and 86.3X10-12 cu cm/molecule-sec at 25 °C for the cis and trans isomers, respectively, which corresponds to atmospheric half-lives of about 4.9 and 4.5 hours, respectively at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Alkylphenyl ethers are generally resistant to aqueous environmental hydrolysis(2); therefore, anethole is not expected to hydrolyze in environmental media(SRC). The rate constant for the vapor-phase reaction of anethole with atmospheric ozone has been estimated to be approximately 6.82X10-17 and 13.6X10-17 cu cm/mol sec for the cis and trans isomers, respectively, which corresponds to atmospheric half-lives of 4.03 and 2.02 hours, respectively, at an atmospheric conc of 7X10+11 molecules of ozone per cu cm(1).

Based upon an experimental water solubility of 111 mg/l(1), the BCF of anethole can be estimated to be approximately 43.4 from a regression-derived equation(2). This estimated BCF value suggests that bioconcentration in aquatic organisms is not expected to be an important fate process(SRC).

Using a structure estimation method based on molecular connectivity indexes, the Koc for anethole can be estimated to be about 680(1). The Koc for anethole can be estimated to be about 327 based on an experimental water solubility of 111 mg/L(3) and a regression derived equation(2). According to a suggested classification scheme(4), these estimated Koc values suggest that anethole has medium to low soil mobility.

The Henry's Law constant for anethole can be estimated to be 7.18X10-5 atm-cu m/mole using a structure estimation method(1). This value of Henry's Law constant indicates that volatilization from water is not rapid but possibly significant(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec) can be estimated to be about 18 hours(2). The volatilization half-life from a model environmental lake (1 meter deep) can be estimated to be about 9 days(3).

An analysis of chickpea seed, found a 0.9% constituent of anethole(1).

Anethole occurs naturally in anise, star anise, and fennel oils(1) and Chickpea Seed(2), and is used as a flavor ingredient(3). Therefore, the general population is exposed to anethole through consumption of foodstuffs(SRC).

Anethole was discovered in one out of 46 samples of human adipose tissue (age class: 0-14 yrs and North Central region(1).

Substances added to foods and medicine to improve the taste. (See all compounds classified as Flavoring Agents.)

/IN BIOTRANSFORMATION OF ANETHOLE/...ANISIC ACID...CONSTITUTED THE MAJOR URINARY METABOLITE. ...THERE WAS A QUANTITATIVE RECOVERY OF THE DOSE ADMIN.|TRANS-ANETHOLE WAS AMONG 4 FOOD ADDITIVES STUDIED & FOUND LARGELY ABSORBED FROM DIGESTIVE TRACT BY PASSIVE DIFFUSION. ABSORPTION KINETICS VARY PARTIALLY BY DIFFERENCES OF COMPD IN COEFFICIENTS OF LIPOSOLUBILITY.|...TRANS-ANETHOLE USED IN PREPN OF ANIS-FLAVORED ALCOHOLIC BEVERAGES WAS STUDIED IN THE RABBIT & RAT AFTER IV & ORAL ADMIN. IT WAS EXCRETED RAPIDLY FROM THE ANIMAL REGARDLESS OF /ROUTE/ OF ADMIN. AFTER IV INJECTION, IT WAS FOUND CONCENTRATED IN LIVER, LUNGS & BRAIN; AFTER ORAL ADMIN...MOST OF IT REMAINED IN STOMACH.|TRANS-ANETHOLE IS ONE OF THE COMPOUNDS LARGELY ABSORBED FROM THE DIGESTIVE TRACT BY MECHANISM OF PASSIVE DIFFUSION.|THE METABOLITES OF ANETHOLE IN RATS WERE IDENTIFIED AND DETERMINED. MOST OF THE URINARY METABOLITES WERE ALSO DETECTED IN THE BILE.

ANETHOLE YIELDS PARA-PROPENYLPHENOL IN RABBIT, MOUSE, GUINEA PIG, & DOG. ANETHOLE YIELDS PARA-PROPENYLPHENOL IN RAT. /FROM TABLE/|ANETHOLE YIELDS ANISIC ACID IN MAN, RABBIT, & RAT. ANETHOLE YIELDS PARA-METHOXYCINNAMYL ALCOHOL IN RAT.|OXIDATIVE O-DEMETHYLATION LEADING TO P-HYDROXYPROPENYLBENZENE & P-HYDROXYCINNAMIC ACID WAS FOUND TO BE A MAJOR BIOTRANSFORMATION OF ANETHOLE. METABOLISM VIA CINNAMOYL DERIV WAS MORE EXTENSIVE WITH THE PROPENYL SUBSTITUENT THAN FOR THE ALLYL COMPD; & FURTHER METABOLISM BY BETA-OXIDATION ALSO OCCURRED.

ACUTE/CHRONIC HAZARDS: Toxic. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

A CASE OF STOMATITIS HAS BEEN REPORTED AFTER USE OF DENTURE CREAM CONTAINING OIL OF ANISE (80-90% ANETHOLE). APPLIED TO SKIN ANETHOLE CAUSES ERYTHEMA, SCALING & VESICULATION.|COMPARED WITH RESULTS OF TESTS WITH BALSAMS & OTHER ESSENTIAL OILS, STAR OF ANISE OIL DOES NOT GIVE CROSS-REACTION & PSEUDO CROSS-SENSITIVITY. PT POSITIVE TO THIS OIL ARE FREQUENTLY POSITIVE TO ANETHOLE.|ANETHOLE TESTED @ 2% IN PETROLATUM PRODUCED NO IRRITATION AFTER A 48-HR CLOSED PATCH TEST IN 25 HUMAN SUBJECTS. A MAXIMIZATION TEST WAS CARRIED OUT ON 25 VOLUNTEERS. MATERIAL WAS TESTED @ 2% CONCN IN PETROLATUM & PRODUCED NO REACTIONS.|ANETHOLE WAS THE MOST SENSITIZING OF APPROX 8 SENSITIZING COMPONENTS. SYNERGISM MAY HAVE BEEN INVOLVED IN THE IRRITATING & SENSITIZING PROPERTIES.

1-(4-methoxyphenyl)propene

GRADES: USP (TECHNICAL); FCC (FOOD CHEMICALS CODEX).

All other chemical product and preparation manufacturing|Benzene, 1-methoxy-4-(1E)-1-propen-1-yl-: ACTIVE|All other basic organic chemical manufacturing|Benzene, 1-methoxy-4-(1-propen-1-yl)-: ACTIVE|...THERE IS REGULAR USE OF COMPOUNDED ESSENTIAL OILS CONSISTING...OF...ANETHOL /IN MFR OF SWEET LIQUEURS/. ... THE EFFECTIVE YIELD OF ANETHOL, BASED ON THE FINISHED LIQUEUR "AS IS" IS APPROX 1:2000.|CHIEF CONSTITUENT...ANISE, STAR ANISE & FENNEL OILS: MONAD, DE DORTAN, IND PARFUM 5: 401 (1950); NAVES, TUCAKOV, COMPT REND 248: 843 (1959).|ANISE SEED YIELDS UP TO 3% OF ESSENTIAL OIL HAVING UP TO 90% ANETHOL AS PRINCIPAL CONSTITUENT.|FEMA NUMBER 2086. NON-ALCOHOLIC BEVERAGES 11 PPM, ALCOHOLIC BEVERAGES 1,400 PPM, ICE CREAMS, ICES, ETC 26 PPM, CANDY 340 PPM, BAKED GOODS 150 PPM, & CHEWING GUM 1,500 PPM.|...PRESENT IN...OIL OF ILLICIUM ANISATUM L...OIL FROM LEAVES OF PIPER PELIPER PELTATUM SUR...ROOTS OF OSMORRHIZA LONGISTYLIS EBERH... OILS OF COMMON FENNEL & BASIL...OILS FROM LEAVES OF CLAUSENA ANISATA HOOK, BACKHOUSIA ANISATA, & MAGNOLIA SALICIFOLIA.

CHEMICAL COMPOSITION OF OIL FROM FRESH SEEDS OF F VULGARE WAS DETERMINED BY GAS CHROMATOGRAPHY.|SPECTROPHOTOMETRIC DETERMINATION OF ANETHOLE IN VOLATILE OILS OF ANISE & FENNEL @ 258 NM.|USE OF THERMOMICROANALYTICAL METHOD OF STAHL FOR THE EXAM OF DRUGS & VOLATILE OILS. ANETHOLE WAS DETECTED AT 80 DEGREES AND VAPORS WERE ANALYZED BY THIN LAYER CHROMATOGRAPHY.|GLC DETERMINATIONS OF SELECTED ORGANIC COMPOUNDS IN WASTEWATER (SENSITIVE TO LOW PPB RANGE). 11 COMPOUNDS, INCL ANETHOLE, WERE STUDIED.|THE METABOLITES OF ANETHOLE IN RATS WERE DETECTED BY GLC & BY COMBINED GLC-MASS SPECTROMETRY.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Denaturant

Flavoring Agents