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p-Kresol-methylether

4-Methylanisole

HCID 7731
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Grundinformationen

CAS
104-93-8
Standard-SMILES
COc1ccc(C)cc1
InChIKey
CHLICZRVGGXEOD-UHFFFAOYSA-N
Summenformel
C8H10O
Durchschnittliche Molmasse
122,16 g/mol
Monoisotopische Masse
122,07316494

Überblick

1-Methoxy-4-methylbenzene is a member of methoxybenzenes.

Namen und Bezeichner

Bevorzugter Name
4-Methylanisole
IUPAC
1-methoxy-4-methylbenzene
Lokaler Name
p-Kresol-methylether
Englischer Name
4-Methylanisole
Summenformel
C8H10O
Molmasse
122.16

Namen und Synonyme

4-Methylanisole1-METHOXY-4-METHYLBENZENE104-93-84-MethoxytolueneBenzene, 1-methoxy-4-methyl-p-Cresol methyl etherp-methyl anisoleAnisole, p-methyl-Methyl p-tolyl ether4-Methyl anisoleMethyl p-cresolp-Tolyl methyl ether
Weitere Namen anzeigen
MSOPARA CRESYL METHYL ETHERP-CRESYL METHYL ETHERP-METHYLANISOLEFEMA 2681P-METHOXYTOLUENEBenzene,1-methoxy-4-methyl-
para-MethylanisoleMethyl p-cresyl ether4-Methyl-1-methoxybenzene4-Methylphenol methyl etherMethyl-para-cresolpara-Methoxytoluenepara-Cresyl methyl etherToluene, 4-methoxy-

Datenbank-Bezeichner

CAS
104-93-8
PubChem CID
7731
DTXSID
DTXSID9026710
ChEMBL
CHEMBL154155
ChEBI
CHEBI:89728
UNII
10FAI0OR9W
EC Number
203-253-7
Nikkaji
J10.114A

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
2,7
Polarare Oberfläche (TPSA)
9,2 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
1
Schwere Atome
9
Formalladung
0
Komplexität
72,6

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Other Aromatic Compounds
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (p-Methylanisole) -> IFRA transparency List
LogP · 3 Einträge

log Kow = 2.66

2.66

2.56

Odor · 3 Einträge

STRONG FLORAL ODOR

PUNGENT ODOR SUGGESTIVE OF YLANG-YLANG

SHARP, FRUITY SWEET ODOR

TasteNUTTY TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 Einträge

0.969 AT 25 °C/25 °C

0.996-1.004

Flavoring AgentsEU Flavoring substances

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1843) of reports.

Warning

H226 (86%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P303+P361+P353, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1843 reports by companies from 32 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Benzene, 1-methoxy-4-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzene, 1-methoxy-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1-methoxy-4-methyl- 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)

REACH registered substance: 4-methylanisole (EC: 203-253-7)

4-Methylanisole: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryEmergency treatment: Anisole. [HSDB] Safe when used as a flavoring agent in food; [JECFA] A moderate irritant on rabbit skin; [RTECS] An irritant; [MSDSonline] See Anisole.
FDA Requirements · 1 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

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/

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 6 Einträge

Used as a flavor, fragrance, and starting material for the preparation of p-anisaldehyde; [HSDB]

SYNTHETIC FLAVOR

PERFUME INGREDIENT

FRAGRANCE, EG, FOR PERFUMES, SOAPS & DETERGENTS

FLAVORING AGENT, EG, FOR SYRUPS, BAKED GOODS & CANDIES

Starting material for the preparation of p-anisaldehyde.

U.S. Production · 3 Einträge

2023: 8,451,246 lb

(1979) 1.36X10+7 GRAMS

(1981) 2.86X10+7 GRAMS

Consumer UsesFragrance
Industry UsesFragrance
Methods of Manufacturing · 2 Einträge

BY METHYLATION OF P-CRESOL.

REACTION OF P-CRESOL WITH METHYL SULFATE IN THE PRESENCE OF SODIUM HYDROXIDE (WILLIAMSON SYNTHESIS)

Formulations/PreparationsGRADES: FCC; TECHNICAL.
Household ProductsInformation on 7 consumer products that contain P-Cresyl Methylether in the following categories is provided:

Zugehörige Reaktionen

84
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 104761
HRID 104761als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 108812
HRID 108812als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 134265
HRID 134265als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 149313
HRID 149313als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 161569
HRID 161569als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 167674
HRID 167674als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 173065
HRID 173065als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 192354
HRID 192354als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
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Color/Form
COLORLESS LIQUID
Solubility · 4 Einträge

INSOL IN WATER; SOL IN ETHER, ETHANOL, AND CHLOROFORM.

1:3 IN 80% ALCOHOL, 1:7 IN 70% ALCOHOL

Insoluble in water, soluble in oils

soluble (in ethanol)

Flash Point60 °C

Physikochemische Eigenschaften

Schmelzpunkt
-32 °C · -32°C
Siedepunkt
174 °C · 174 °C(lit.)
Dichte
0.969 g/mL · 0.969 g/mL at 25 °C(lit.)
Dampfdruck
5.25 mm · 5.25 mm Hg ( 50 °C)
Brechungsindex
20 · n20/D 1.511(lit.)
FEMA
2681 · 2681 | P-METHYLANISOLE
Flammpunkt
128 °F · 128 °F
storage temp.
Sealed in dry,Room Temperature
Löslichkeit
Chloroform (Soluble), Ethyl Acetate (Slightly)
Aggregatzustand
Liquid
Farbe
Clear colorless to slightly yellow
Geruch (Odor)
1 % · at 1.00 % in dipropylene glycol. naphthyl cresol ylang powdery nutty
Geruchsart
naphthyl
Biologische Quelle
synthetic
Explosionsgrenze
1.1 · 1.1-8.3%(V)
Odor Threshold
0.0012 ppm · 0.0012ppm
Wasserlöslichkeit
slightly soluble
JECFA Number
1243 · 1243
BRN
1237336 · 1237336
Henry's Law Constant
2.1 · 2.1×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
Dielectric constant
4.03 · 4.0300000000000002
Stabilität
Stable. Incompatible with strong oxidizing agents. Combustible.
Major Application
cleaning productscosmeticsfood and beveragespersonal care
Kosmetik-Inhaltsstoffe Funktionen
PERFUMING
InChI
1S/C8H10O/c1-7-3-5-8(9-2)6-4-7/h3-6H,1-2H3
InChIKey
CHLICZRVGGXEOD-UHFFFAOYSA-N
SMILES
COc1ccc(C)cc1
LogP
2.74 · 2.74-2.8 at 25-35℃
CAS Datenbank
104 · 104-93-8(CAS DataBase Reference)
NIST chemische Informationen
1 · Benzene, 1-methoxy-4-methyl-(104-93-8)
EPA chemische Informationen
p-Methylanisole (104-93-8)
Special ReportsTHE 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]
Hazard Classes and CategoriesFlam. Liq. 3 (86%)

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Environmental Fate · 3 Einträge

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).

Food Survey ValuesMethoxymethylbenzene (isomer unspecified) has been detected as a natural component of the aroma fraction of blue cheese(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Plant Concentrations1-Methoxy-4-methylbenzene is released to the atmosphere in emissions from vegetation(1,2).
Effluent Concentrations · 1 Eintrag

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).

Soil Adsorption/Mobility · 1 Eintrag

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).

Natural Pollution SourcesFOUND IN OIL OF YLANG YLANG, CANAGA & OTHERS.
Human Toxicity Excerpts...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.
Artificial Pollution Sources · 1 Eintrag

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).

Environmental Bioconcentration · 1 Eintrag

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).

Volatilization from Water/Soil · 1 Eintrag

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).

Non-Human Toxicity Excerpts · 2 Einträge

ACUTE DERMAL LD50 IN RABBITS WAS REPORTED AS GREATER THAN 5 G/KG. ...APPLIED FULL STRENGTH ON INTACT OR ABRADED RABBIT SKIN WAS MODERATELY IRRITATING.

4-Methoxytoluene was given by gavage to 4 groups of 20 rats at dosage levels of 0, 40, 120 or 240 mg/kg body wt/day for 4 wk. There was a statistically significant decr in serum creatinine and urea in the intermediate and high dose group for both sexes. Among males, a statistically significant decr in the packed cell volume was observed in the high and intermediate dose group. A no observed effect level of 40 mg/kg body wt/day was determined.

Regulatorische Informationen

FDA Requirements · 1 Eintrag

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.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 1993 3/PG 3
hs_code
29093090
RTECS-Nr.
BZ8780000
risk_code
22-38-10-52/53-63
Toxizität
The acute oral LD50 in rats was reported as 1.92 (1.51-2.45) g/kg (Hart, 1971). The acute dermal LD50 in rabbits was reported as > 5 g/kg (Hart, 1971).
hazard_code
Xn
safety_code
36/37-16-61
hazard_class
3
packing_group
III
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
104-93-8(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 OralFlam. Liq. 3Repr. 2Skin Irrit. 2
Use Classification · 6 Einträge

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 6 Einträge

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

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.

Anwendungen · 3 Einträge

Beschreibungp-Methylanisole has a pungent odor suggestive of ylang-ylang. May be prepared by methylation of p-cresol.

OccurrenceReported found in the oils of ylang-ylang, cananga and flowers of Mimusops elengi L. Also reported found in tomato, blue and Camembert cheese, starfruit, buckwheat, rooibus tea (Aspalathus linearis) and tapereba (Spondias lutea).

Verwenden4-Methylanisole was used to prepare 5-methoxy-1,8-dimethyltetralin. It was also used as the solubilizate molecule to study the site of incorporation of solubilizates in sodium dodecyl sulfate (SDS) micellar systems.

Darstellung

synthetischeBy methylation of p-cresol.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

p-Kresol2-MethylanisolBenzene, 1,1'-[thiobis(methylene)]bis[4-methoxy-TRIBUTYL(4-METHOXYPHENYL)STANNANE4-Methoxy-α-toluolthiolTetramethylzinnNatriummethylsulfat4-Methoxybenzylalkohol4-MethoxyphenylacetonitrilBenzoic acid, 4-broMo-, phenyl ester

Nachgelagerte Produkte

Natrium-4-((5-methoxy-4-((4-metho-xyphenyl)azo)-2-methylphenyl)azo)-benzolsulfonat5-Methyl-o-anisidinVESNARINONEAnisaldehydBenzene, 1-methyl-4-(1-methylethoxy)-Trinitromethanp-(Dimethoxymethyl)anisol