4-Methylanisole
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4-Methylanisole
structure -
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CAS No:
104-93-8
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Formula:
C8H10O
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Chemical Name:
4-Methylanisole
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Synonyms:
Benzene,1-methoxy-4-methyl-;Anisole,p-methyl-;1-Methoxy-4-methylbenzene;p-Cresol methyl ether;p-Cresyl methyl ether;p-Methoxytoluene;4-Methoxytoluene;p-Methylanisole;O-Methyl-p-cresol;Methyl p-tolyl ether;p-Tolyl methyl ether;4-Methylanisole;Methyl p-methylphenyl ether;1-Methyl-4-methoxybenzene;4-Methyl-1-methoxybenzene;4-Cresol methyl ether;NSC 6254;4-Methoxy-1-methylbenzene;1071687-44-9
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CAS No:
Description
p-Methylanisole has a pungent odor suggestive of ylang-ylang. colourless liquidp-Methylanisole has a pungent odor suggestive of ylang-ylang. May be prepared by methylation of p-cresol.
p-Methoxytoluene is a building block that has been used as a reactant for the preparation of electrophilic fluorinating agents.
Liquid|Colourless liquid, Pungent sharp sweet aroma
1-Methoxy-4-methylbenzene is a member of methoxybenzenes.
4-Methylanisole Basic Attributes
122.16
122.16
1237336
203-253-7
10FAI0OR9W
6254
DTXSID9026710
COLORLESS LIQUID
29093090
Characteristics
9.2
2.7
Clear colorless to slightly yellow Liquid
0.969 g/cm3 @ Temp: 25 °C
-32 °C
175.5 °C @ Press: 760 Torr
128 °F
n 20/D 1.511(lit.)
H2O: slightly soluble ;1:3 IN 80% ALCOHOL, 1:7 IN 70% ALCOHOL
Flammables area
5.25 mm Hg ( 50 °C)
Oral-Rat LD50: 1920 mg/kg
Flammable; burning produces irritating fumes
1.1-8.3%(V)
STRONG FLORAL ODOR
NUTTY TASTE
Safety Information
III
3
UN 1993 3/PG 3
1
22-38-10-52/53-63
36/37-16-61
BZ8780000
Xn
Warehouse ventilated, low temperature and dry
Stable. Incompatible with strong oxidizing agents. Combustible.
P273-P281
H226-H302-H315-H361-H412
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.
p-Methylanisole is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.
THE FOOD CHEMICALS CODEX (1972) HAS A MONOGRAPH ON P-CRESYL METHYL ETHER.[Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon Press, 1979., p. 269]
UN 1993 3/PG 3
|Warning|H226 (86.54%): Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P264, P270, P273, P280, P281, P301+P312, P302+P352, P303+P361+P353, P305+P351+P338, P308+P313, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P235, P405, and P501|Aggregated GHS information provided by 1828 companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
1-Methoxy-4-methylbenzene has been detected at trace amounts (limit of detection = 0.1 ppb) in a product water sample from a coal gasification site in Hanna, WY(1). 1-Methoxy-4-methylbenzene was qualitatively detected in advanced waste treatment water in Pomona, CA on 9/25/74(2).
Toxicity
moderately toxic
FOUND IN OIL OF YLANG YLANG, CANAGA & OTHERS.
1-Methoxy-4-methylbenzene's production and use as an synthetic flavor(1), perfume ingredient(2), and as a starting material for the preparation of p-anisaldehyde(3) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 670(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that 1-methoxy-4-methylbenzene will have low mobility in soil(SRC). Volatilization of 1-methoxy-4-methylbenzene may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.7X10-3 atm-cu m/mole(4,SRC), and from dry soil surfaces(SRC) based on an estimated vapor pressure of 1.14 mm Hg(5,SRC). Insufficient data are available to determine the rate or importance of biodegradation of 1-methoxy-4-methylbenzene in soil(SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 670(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that 1-methoxy-4-methylbenzene may adsorb to suspended solids and sediment(SRC) in water. 1-Methoxy-4-methylbenzene may volatilize from water surfaces based on an estimated Henry's Law constant of 4.7X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 3.4 hours and 4.4 days, respectively(3,SRC). An estimated BCF value of 62(3,SRC), from an experimental log Kow(2), suggests that 1-methoxy-4-methylbenzene will only bioconcentrate moderately in aquatic organisms(SRC) according to a recommended classification scheme(5). Insufficient data are available to determine the rate or importance of biodegradation of 1-methoxy-4-methylbenzene in water(SRC).|ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 1.1 mm Hg at 25 °C(2,SRC) indicates that 1-methoxy-4-methylbenzene will exist in the vapor phase in the ambient atmosphere. Vapor-phase 1-methoxy-4-methylbenzene 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 about 14 hours(3,SRC).
The rate constant for the vapor-phase reaction of 1-methoxy-4-methylbenzene with photochemically produced hydroxyl radicals has been estimated as 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
An estimated BCF value of 62 was calculated for 1-methoxy-4-methylbenzene(SRC), using an experimental log Kow of 2.66(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that 1-methoxy-4-methylbenzene will bioconcentrate moderately in aquatic organisms(SRC).
The Koc of 1-methoxy-4-methylbenzene is estimated as approximately 670(SRC), using an experimental log Kow of 2.66(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 1-methoxy-4-methylbenzene has low mobility in soil(SRC).
The Henry's Law constant for 1-methoxy-4-methylbenzene is estimated as 4.7X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 1-methoxy-4-methylbenzene will volatilize from water surfaces(2,SRC). 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) is estimated as approximately 3.4 hours(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 4.4 days(2,SRC). 1-Methoxy-4-methylbenzene's vapor pressure, 1.1 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil may occur(SRC).
SURFACE WATER: 1-Methoxy-4-methylbenzene was a major compound found in Spirit Lake and in Smith Creek located within the blast zone of Mount St. Helens, Washington(1). 1-Methoxy-4-methylbenzene was also identified in the South Fork of Castle Lake also located within the blast zone of Mount St. Helens in Washington(1).
Methoxymethylbenzene (isomer unspecified) has been detected as a natural component of the aroma fraction of blue cheese(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 6,583 workers are potentially exposed to 1-methoxy-4-methylbenzene in the USA(1).
Drug Information
LIVER MICROSOMES...INDUCE MIGRATION OF AN AROMATIC METHYL GROUP /BY WAY OF NIH SHIFT/, SINCE ONE OF THE HYDROXYLATED METABOLITES OF PARA-METHYLANISOLE WAS FOUND TO BE META-METHYL-PARA-HYDROXYANISOLE.|P-METHYLANISOLE IS METAB TO ANISIC ACID & P-CRESOL IN RABBITS. 2-METHOXY-5-METHYLPHENOL & 5-METHOXY-2-METHYLPHENOL ARE METABOLITES PRODUCED IN RATS & RABBITS. /FROM TABLE/
...TESTED AT 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 HUMAN VOLUNTEERS...AT CONCN OF 2% IN PETROLATUM & PRODUCED NO SENSITIZATION REACTIONS.
4-methoxytoluene
4-Methylanisole Use and Manufacturing
By methylation of p-cresol.
Perfumery, flavoring.
(1979) 1.36X10+7 GRAMS|(1981) 2.86X10+7 GRAMS
GRADES: FCC; TECHNICAL.
Benzene, 1-methoxy-4-methyl-: ACTIVE|APPLICATIONS: FLAVOR USEFUL IN BLACK WALNUT, MAPLE, BERRY.|IN PUBLIC USE SINCE 1920S. USE IN FRAGRANCES IN USA AMOUNTS TO LESS THAN 10000 LB/YR. CONCN IN FINAL PRODUCT (%): SOAP (0.03 USUAL, 0.15 MAX), DETERGENT (0.003 USUAL, 0.015 MAX), CREAMS, LOTIONS (0.01 USUAL, 0.05 MAX), PERFUME (0.2 USUAL, 0.2 MAX).|REPORTED USED IN NON-ALCOHOLIC BEVERAGES 2.7 PPM; ICE CREAMS, ICES, ETC 2.7 PPM; CANDY 4.8 PPM; BAKED GOODS 7.6 PPM; GELATINS & PUDDINGS 0.50-4.0 PPM; CONDIMENTS 2.0 PPM; SYRUPS 8.0 PPM.|...GRANTED GRAS STATUS BY FEMA (1965)... THE COUNCIL OF EUROPE (1970) INCLUDED .../IT/ IN LIST OF ADMISSIBLE ARTIFICIAL FLAVORING SUBSTANCES AT LEVEL OF 5 PPM.
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index
Flavoring Agents
Analysis Methods
| Name | Column Shape | Active Phase(℃) | Retention index | Temperature Control | Method | Comments | Reference |
|---|---|---|---|---|---|---|---|
| Kovats' RI, non-polar column, isothermal | Capillary | SE-30 | 986.6 | 100. | isothermal | 40. m/0.35 mm/0.35 μm | Tudor, E.Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equationsJ. Chromatogr. A1997, 779, 1-2, 287-297. |
| Kovats' RI, non-polar column, isothermal | Packed | Apiezon L | 1020. | 100. | isothermal | Chromatone N AW DNCS | Bogoslovsky, Yu.N.Anvaer, B.I.Vigdergauz, M.S.Chromatographic constants in gas chromatography (in Russian)Standards Publ. House, Moscow, 1978, 192. |
| Kovats' RI, non-polar column, isothermal | Packed | Apiezon L | 1036. | 150. | isothermal | Chromatone N AW DNCS | Bogoslovsky, Yu.N.Anvaer, B.I.Vigdergauz, M.S.Chromatographic constants in gas chromatography (in Russian)Standards Publ. House, Moscow, 1978, 192. |
| Kovats' RI, non-polar column, isothermal | Capillary | CP Sil 5 CB | 1005. | temperature ramp | He, 3. K/min; Column length: 25. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 230. C | Kasali, A.A.Adio, A.M.Oyedeji, A.O.Eshilokun, A.O.Adefenwa, M.Volatile constituents of Boswellia serrata Roxb. (Burseraceae) barkFlavour Fragr. J.2002, 17, 6, 462-464. | |
| Kovats' RI, non-polar column, isothermal | Capillary | OV-101 | 1003. | temperature ramp | 100. m/0.3 mm/0.15 μm, H2, 2. K/min; Tstart: 90. C; Tend: 220. C | Gaydou, E.M.Randriamiharisoa, R.Bianchini, J.-P.Composition of the essential oil of ylang-ylang (Canaga odorata Hook Fil. et Thomson forma genuina) from MadagascarJ. Agric. Food Chem.1986, 34, 3, 481-487. |
Computed Properties
Molecular Weight:122.16
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:122.073164938
Monoisotopic Mass:122.073164938
Topological Polar Surface Area:9.2
Heavy Atom Count:9
Complexity:72.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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