4-Methoxybenzaldehyde

log Kow = 1.76

1.76

1.61

Hawthorn odor

Odor resembles that of coumarin

Sweet powdery, spicy creamy, fruity, vanilla and hay-like. Coumarin, almond, anisic with berry nuances.

Sweet powdery, spicy creamy, spice anise, nutty, cherry pit and almond-like nuances.

It has a bitter flavor above 30 to 40 ppm.

1.1191 g/cu cm at 15 °C

1.115-1.123

Oily liquid

Colorless to pale yellow liquid

In water, 4.29X10+3 mg/L at 25 °C

Insoluble in water

Miscible with ethanol, diethyl ether; very soluble in acetone, chloroform; soluble in benzene.

Soluble in 5 volumes of 5% alcohol

4.29 mg/mL at 25 °C

poorly soluble in water, glycols, glycerol; soluble in organic solvents, oils

This chemical does not meet GHS hazard criteria for 57% (2268 of 3980) of all reports.

Warning

H302 (40.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3980 reports by companies from 23 notifications to the ECHA C&L Inventory.

Warning

Chemical: Benzaldehyde, 4-methoxy-

Commission Regulation (EC) No 1565/2000 (Repealed by Com.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

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

Status: Active Update: 30-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13682

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

A mutagen and moderate skin irritant; Causes somnolence in lethal-dose feeding studies of rats; Causes GI necrosis and fatty liver in high-dose feeding studies of mice; [RTECS] In humans at 10% in petrolatum, there was no irritation after 48 hours closed-patch testing; [HSDB] Safe when used as a flavoring agent in food; [JECFA] An irritant; May cause damage to GI tract and liver; [MSDSonline]

Synthetic flavoring substances and adjuvants may be safely used in food 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. (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. p-Anisaldehyde is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Benzaldehyde, 4-methoxy- is included on this list. Effective date: 9/30/91; Sunset date: 6/30/98.

Acute Tox. 4 (40.1%)

Reproductive toxicity - Category 2

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 breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

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.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains.

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.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Eye/face protection: 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: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

It has been suggested that aromatic aldehydes may reduce cytochrome c. Therefore, interaction of the aromatic aldehydes, p-anisaldehyde, benzaldehyde, p-tolualdehyde, p-carboxybenzaldehyde, p-chlorobenzaldehyde and p-nitrobenzaldehyde, with rat liver mitochondria was examined in vitro. Although both pyruvate/malate- and succinate-mediated respiration, as well as that mediated by other citric acid cycle intermediates, were inhibited by the aromatic aldehydes (0.5 to 1.0 mM), cytochrome c oxidase was not inhibited by aromatic aldehydes (1.0 to 20 mM). There was a marked inhibition of succinic dehydrogenase and both ADP- and DNP-stimulated respiration by benzaldehyde (2 to 20 mM). Since both pyruvate/malate- and succinate-mediated respiration were inhibited by the aromatic aldehydes without inhibition of cytochrome c oxidase, several sites of inhibition, possibly both at the site of transport of substrates and the active enzymes, may exist. Benzaldehyde, 300 uM, inhibited pyruvate/malate-mediated state 3 respiration by 50% which suggests that no additional functional group or metabolism to another species is required for these inhibitory effects.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 53(SRC), determined from a log Kow of 1.76(2) and a regression-derived equation(3), indicates that p-anisaldehyde is expected to high mobility in soil(SRC). Volatilization of p-anisaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 3.29X10-2 mm Hg(4), and water solubility, 4.29X10+3 mg/L(5). p-Anisaldehyde has a vapor pressure of 3.29X10-2 mm Hg at 25 °C(4) and exists as a liquid under environmental conditions; therefore, p-anisaldehyde may volatilize from dry soil. A 99% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 53(SRC), determined from a log Kow of 1.76(2) and a regression-derived equation(3), indicates that p-anisaldehyde is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.4X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 3.29X10-2 mm Hg(5), and water solubility, 4.29X10+3 mg/L(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 20 days and 230 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 6.7(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 99% of theoretical BOD using activated sludge in the Japanese MITI test(7) suggests that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-anisaldehyde, which has a vapor pressure of 3.29X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase p-anisaldehyde 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 15 hours(SRC), calculated from its rate constant of 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). p-Anisaldehyde absorbs UV light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: p-Anisaldehyde is oily liquid. It is used in perfumery and toilet soaps. It is also used in organic syntheses. p-Anisaldehyde is also an intermediate in many industrial processes. HUMAN STUDIES: When tested at 10% in petrolatum, it produced no irritation after a 48 hr closed-patch test on human subjects. A maximization test was carried out on 25 volunteers. The material was tested at a concentration of 10% in petrolatum and produced no sensitization reactions. p-Anisaldehyde was positive for sister chromatid exchange in human lymph oocytes but not Chinese Hamster Ovary (CHO) cells in vitro. ANIMAL STUDIES: In a combined oral repeated-dose/reproductive/developmental toxicity screening test in rats, decreased body weights, decreased platelets and hypertrophy of hepatocytes were noted at 100 mg/kg/day. In reproduction studies, it showed significantly reduced fertility index, number of pups/litter, delivery index and number of live pups at 500 mg/kg/day. It was not mutagenic in bacteria but it was mutagenic in mouse lymphoma cells in vitro.

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of November 16, 2017: http://actor.epa.gov/dashboard/]

The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for p-anisaldehyde is available.[Available from, as of November 3, 2017: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]

In 1999, ortho-, meta-, and para-anisaldehyde, had a reported combined emission factor of 0.38 mg/L for light duty passenger vehicles, emissions were measured in inside the Caldecott tunnel on Highway 24 near San Francisco Bay, California(1); a study conducted in July and August 2006, measuring emissions from inside the Caldecott tunnel omitted isomers of anisaldehyde due to analytical method limitations(2). Anisaldehyde (as the combined isomers ortho-, meta-, and para-) was detected in light- and heavy-duty vehicle exhaust at the Pennsylvania Tuscarora Mountain Tunnel inlet at 0.0058 ug/m cu and outlet at 0.014 ug/m cu with a calculated emission factor of 0.017 mg/km(3).

The Koc of p-anisaldehyde is estimated as 53(SRC), using a log Kow of 1.76(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that p-anisaldehyde is expected to have high mobility in soil.

p-Anisaldehyde is a metabolic product of odoriferous fungus Lentinus Lepidus; of wood rotting fungus Polyporus benzoinus; of Daldaldea juniperina(1). p-Anisaldehyde occurs in many essential oils, often together with anethole(2). The compound is reportedly found in essential oils and extracts of vanilla, acacia farnesiana, magnolia salicifolia maxim, eric arborea, pirus communis, and boswellia serrata; also in anise, fennel and star anise (especially when aged due to oxidation of anethol), cranberry, black current, cinnamon and basil(3).

Synthetic flavoring substances and adjuvants may be safely used in food 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. (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. p-Anisaldehyde is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Benzaldehyde, 4-methoxy- is included on this list. Effective date: 9/30/91; Sunset date: 6/30/98.

Metabolite of Lentinus lepidus (oderiforous fungus), Polyporus benzoinus (wood rotting fungus), and Daldalea juniperina; [Merck Index] Found in various essential oils and extracts; Used to make insect attractants (especially for cockroaches); Also used in electroplating and in fragrances and flavors; [HSDB]

Electroplating [Category: Plate]

Perfumery and toilet soaps; ... also used in organic syntheses.

p-Anisaldehyde is an intermediate in many industrial processes.

Reported uses (ppm):

Intermediate for antihistamines, electroplating.

(1972) No Data

(1975) No Data

(1972) No Data

(1975) No Data

2023: 8,500,000 - <10,000,000 lb

(1972) 4.8X10+8 GRAMS

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: p-Anisaldehyde:

p-Methoxybenzaldehyde

p-Methoxybenzaldehyde; Anisaldehyde; p-Anisaldehyde; Anisic aldehyde; Anisyl aldehyde; Benzaldehyde, 4-methoxy; 4-Methoxybenzaldehyde; Aubepine P Cresol (commercial name); Aubepine liquid (commercial name)

IFRA_STD_054.pdf

51

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Restriction: This material should be used only in the limited quantity as stated in the Standard

By methylation and oxidation of p-cresol and also by oxidation of anethole.

OXIDATION OF ANETHOLE WITH CHROMIC ACID; METHYLATION OF P-CRESOL TO P-CRESYL METHYL ETHER, FOLLOWED BY OXIDATION WITH MANGANESE DIOXIDE

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

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Benzaldehyde, 4-methoxy-: ACTIVE