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Home > Encyclopedia > 4′-Methoxyacetophenone

4′-Methoxyacetophenone

4′-Methoxyacetophenone structure

4′-Methoxyacetophenone 

structure
  • CAS No:

    100-06-1

  • Formula:

    C9H10O2

  • Chemical Name:

    4′-Methoxyacetophenone

  • Synonyms:

    Ethanone,1-(4-methoxyphenyl)-;Acetophenone,4′-methoxy-;1-(4-Methoxyphenyl)ethanone;p-Acetylanisole;Linarodin;Novatone;Vananote;4′-Methoxyacetophenone;p-Methoxyphenyl methyl ketone;p-Methoxyacetophenone;4-Methoxyphenyl methyl ketone;4-Acetylanisole;Methyl p-methoxyphenyl ketone;1-Acetyl-4-methoxybenzene;p-Anisyl methyl ketone;para-Methoxyacetophenone;Methyl 4-methoxyphenyl ketone;Acetoanisole;p-Methoxy(acetyl)benzene;NSC 209523;NSC 5601;4-Methoxyhypnone;1-(4-Methoxyphenyl)ethan-1-one;4-Methoxyphenylethanone

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

4′-Methoxyacetophenone is an organic compound with the chemical formula C9H10O2. At room temperature, 4′-Methoxyacetophenone is a solid with white to pale yellow crystals. When melted, the white crystals turn into a transparent liquid. It is light-sensitive, soluble in ethanol, ether and acetone, insoluble in water, and irritating. The melting point of 4′-Methoxyacetophenone is 37-40°C, the boiling point is 152-154 °C/26 mmHg, and the flash point is 138 °C. 4′-Methoxyacetophenone is an aromatic compound with a sweet, fruity, nutty and vanilla-like aroma similar to hawthorn flowers and anisealdehyde. In addition, 4′-Methoxyacetophenone sometimes smells like butter or caramel. 4′-Methoxyacetophenone can be found in natural castoreum (the glandular secretion of beavers). The compound is used as a cigarette additive, flavoring, and added to food flavoring.

4′-Methoxyacetophenone Basic Attributes

150.17

150.17

742313

202-815-9

0IRH2BR587

209523|5601

DTXSID2044347

Crystalline solid|Colorless to pale-yellow fused solid|Yellowish-white crystals

2914509090

Characteristics

26.3

1.7

White Crystals or Crystalline Powder

1.0818 g/cm3 @ Temp: 41 °C

38.5 °C

258 °C

>230 °F

1.5470 (estimate)

H2O: insoluble

Store below +30°C.

6.44X10-3 mm Hg at 25 deg C

The acute oral LD 50 value in rats was reported as 1.72 g/kg (1.47-1.97 g/kg) (Moreno, 1973). The acute dermal LD 50 value in rabbits was reported as > 5 g/kg (Moreno, 1973).

Pleasant odor

Bitter and unpleasant taste

Henry's Law constant = 8.88X10-6 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 2.05X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

2

22-38-36/38-20/21/22

37-37/39-26-36

AM9240000

Xn

Stable under recommended storage conditions.

P301 + P312 + P330

H302-H315

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents, strong bases

Acetanisole 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: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 1746 companies from 5 notifications to the ECHA C&L Inventory.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P321, P330, P332+P313, P362, and P501

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Flammable liquid.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Do not let product enter drains.|Precautions for safe handling: Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|For more Preventive Measures (Complete) data for 4-Acetylanisole (6 total), please visit the HSDB record page.

A skin irritant.

4-Acetylanisole has been reported as present in tobacco and tobacco smoke(1). The compound was detected in wood smoke from pine and oak and at 5.19 and 3.78 mg/kg of wood burnt but was not detected in smoke from synthetic logs(2).

Toxicity

IDENTIFICATION AND USE: 4-Acetylanisole is a colorless to pale-yellow fused solid. It is used in perfumery (for floral odors), and flavoring. HUMAN EXPOSURE AND TOXICITY: Human systemic effects by inhalation: pulse rate increase without fall in blood pressure and blood pressure elevation. ANIMAL STUDIES: In an experiment using isolated bovine eyes, 4-acetylanisole did not show an ocular severe irritant or corrosive potential.

LD50 Rat oral 1720 mg/kg|LD50 Mouse oral 820 mg/kg

4-Acetylanisole occurs naturally in European cranberry (Vaccinium oxycoccus), guava fruit (Psidium guajava), Vitis labrusca, tomato, anise (Pimpinella anisum), mentha oils, cloudberry (Rubus chamaemorus), Illicium verum and black chokeberry (Aronia melanocarpa ell.).

4-Acetylanisole's production and use in perfumery and synthetic flavoring(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a log Koc value of 2.43(2) indicates that 4-acetylanisole is expected to have moderate mobility in soil(SRC). Volatilization of 4-acetylanisole from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 8.9X10-6 atm-cu m/mole(3). 4-Acetylanisole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.44X10-3 mm Hg at 25 °C(4). Biodegradation data in soil were not available(SRC, 2016).|AQUATIC FATE: Based on a classification scheme(1), a log Koc value of 2.43(2) indicates that 4-acetylanisole is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may be expected(3) based upon an estimated Henry's Law constant of 8.9X10-6 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 3 days and 42 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 1.74(6) and a regression-derived equation(4), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation data in water were not available(SRC, 2016). An environmental half-life of 12 days was measured in sunlit surface waters at 40 °C(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-acetylanisole, which has a vapor pressure of 6.44X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-acetylanisole 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 1 day(SRC), calculated from its rate constant of 2.05X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 4-Acetylanisole contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). An environmental half-life of 12 days was measured in sunlit surface waters at 40 °C(5).

The rate constant for the vapor-phase reaction of 4-acetylanisole with photochemically-produced hydroxyl radicals has been estimated as 2.05X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). 4-Acetylanisole is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 4-Acetylanisole contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). An environmental half-life of 12 days was measured in sunlit surface waters at 40 °C(4).

An estimated BCF of 3 was calculated in fish for 4-acetylanisole (SRC), using a log Kow of 1.74(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

A log Koc of 2.43 for 4-acetylanisole was measured in a black agricultural soil (silty loam, pH 5.86, 27.2% clay content, 4.78% soil organic matter, 4.01% water content) obtained from Northeastern China(1). This corresponds to a Koc of 270(SRC). According to a classification scheme(2), this Koc value suggests that 4-acetylanisole is expected to have moderate mobility in soil.

The Henry's Law constant for 4-acetylanisole is estimated as 8.9X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-acetylanisole is expected to volatilize 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 3 days(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 42 days(SRC). 4-Acetylanisole's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 4-Acetylanisole is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.44X10-3 mm Hg at 25 °C(3).

SURFACE WATER: 4-Acetylanisole was detected but not quantified in water samples from Spirit Lake, WA on September 11, 1980(1).

4-Acetylanisole has been detected in grilled and roast beef, sherry, salted and picked plums(1).

Occupational exposure to 4-acetylanisole may occur through inhalation and dermal contact with this compound at workplaces where 4-acetlanisole is produced or used. Limited monitoring and use data indicate that the general population may be exposed to 4-acetylanisole via smoking cigarettes, inhalation of wood smoke, ingestion of food, and dermal contact with and inhalation of consumer products containing 4-acetylanisole. (SRC)

Name Type of Test Exposure Route Species Observed Dose/Duration Toxic Effects Reference
SKIN/EYE IRRITATION DATA Standard Draize test Administration onto the skin Rodent - rabbit 500 mg/24H -- Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 12,927,1974
SKIN/EYE IRRITATION DATA TCLo - Lowest published toxic concentration Inhalation Human 1700 ug/m3/39W-I Cardiac--pulse rate increase, without fall in BP
Vascular--BP elevation not characterized in autonomic section
Gigiena i Sanitariya. For English translation, see HYSAAV. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1936- Volume(issue)/page/year: 50(4),86,1985
SKIN/EYE IRRITATION DATA LD50 - Lethal dose, 50 percent kill Oral Rodent - rat 1720 mg/kg Details of toxic effects not reported other than lethal dose value-- Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 12,927,1974

Drug Information

/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 as 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. /Aromatic hydrocarbons and related compounds/|/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 necessary. 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. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|/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. Consider drug therapy for pulmonary edema ... . 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 if necessary ... Start IV administration of D5W /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 or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

/SIGNS AND SYMPTOMS/ Human systemic effects by inhalation: pulse rate increase without fall in blood pressure and blood pressure elevation.

4-acetylanisole

4′-Methoxyacetophenone Use and Manufacturing

Methods of Manufacturing

From anisole and acetic acid in the presence of boron trifluoride. It is derived from the reaction of anisole and acetyl chloride in the presence of aluminum chloride and carbon disulfide.

Uses

4′-Methoxyacetophenone is a chemical substance commonly used as an intermediate for flavors, fragrances, medicines, and cosmetics. It can be used to synthesize p-methoxyphenylacetic acid through the preparation of 4′-Methoxyacetophenone, thus serving as an intermediate for puerarin. Puerarin is an important medical raw material that has not yet been artificially synthesized. 4′-Methoxyacetophenone can be used in the production of liquid crystal monomers. In the synthesis of high-grade acetylene liquid crystals, 4′-Methoxyacetophenone is used as an initial synthetic raw material. It is still in the research and development stage, but this fine chemical product has market prospects in the field of sunscreen intermediates. The synthesis method of 4′-Methoxyacetophenone includes the following steps: acetonitrile, under the action of protonic acid, first generates an intermediate product called pinner salt, which reacts with phenol. The above product is hydrolyzed to generate phenyl acetate and ammonium salt. Phenyl acetate is rearranged under the action of alkyl sulfonate. After separating and purifying the para-product, it reacts with dimethyl sulfate to finally generate 4′-Methoxyacetophenone.

Production

< 25,000 lb

Grade: Technical, FCC /Food Chemicals Codex/.

Ethanone, 1-(4-methoxyphenyl)-: ACTIVE

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 1337.0 100. 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 OV-101 1310.9 120. isothermal N2, Chromosorb G HP; Column length: 5. m Righezza, M.Hassani, A.Meklati, B.Y.Chrétien, J.R.Quantitative structure-retention relationships (QSRR) of congeneric aromatics series studied on phenyl OV phases in gas chromatographyJ. Chromatogr. A1996, 723, 1, 77-91.
Kovats' RI, non-polar column, isothermal Packed OV-101 1314.3 130. isothermal N2, Chromosorb G HP; Column length: 5. m Righezza, M.Hassani, A.Meklati, B.Y.Chrétien, J.R.Quantitative structure-retention relationships (QSRR) of congeneric aromatics series studied on phenyl OV phases in gas chromatographyJ. Chromatogr. A1996, 723, 1, 77-91.
Kovats' RI, non-polar column, isothermal Packed OV-101 1325.8 140. isothermal N2, Chromosorb G HP; Column length: 5. m Righezza, M.Hassani, A.Meklati, B.Y.Chrétien, J.R.Quantitative structure-retention relationships (QSRR) of congeneric aromatics series studied on phenyl OV phases in gas chromatographyJ. Chromatogr. A1996, 723, 1, 77-91.
Kovats' RI, non-polar column, isothermal Packed OV-3 1392.4 120. isothermal N2, Chromosorb G HP; Column length: 5. m Righezza, M.Hassani, A.Meklati, B.Y.Chrétien, J.R.Quantitative structure-retention relationships (QSRR) of congeneric aromatics series studied on phenyl OV phases in gas chromatographyJ. Chromatogr. A1996, 723, 1, 77-91.

Computed Properties

Molecular Weight:150.17
XLogP3:1.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:150.068079557
Monoisotopic Mass:150.068079557
Topological Polar Surface Area:26.3
Heavy Atom Count:11
Complexity:135
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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