3-(メチルチオ)プロピオンアルデヒド

Other Classes -> Aldehydes

Flammable agents - 2nd degree

Powerful, onion, meat-like odor

Cooked potato

Extremely foul and persistent odor

Relative density (water = 1): 1.03

1.037-1.052

Colorless to pale yellow liquid

Colorless to amber liquid

In water, 16.3% vol at 25 °C, pH 7

Solubility in water, g/100ml at 37.8 °C: 17.5

insoluble in water; soluble in alcohol, propylene glycol and oil

1 ml in 1 ml 95% alcohol (in ethanol)

142 °F (NFPA, 2010)

142 °F (61 °C) (closed cup)

58-63 °C

BP: 62 °C at 11 mm Hg

165 °C

165-166 °C

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1661) of reports.

Danger

H226 (14%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P332+P317, P333+P317, P361+P364, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1661 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: Propanal, 3-(methylthio)-

Regulation (EC) No 1831/2003 (amended)

Propanal, 3-(methylthio)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanal, 3-(methylthio)- 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: 28-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13720

3-(Methylthio)-propionaldehyde: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Combustible. Above 58 °C explosive vapour/air mixtures may be formed.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

Causes skin irritation and permanent injury to eyes in studies of rabbits; Shows skin sensitizing potential in guinea pig maximization tests; Mild hemolytic effects (reduced red blood cell counts and hemoglobin levels, increased blood bilirubin levels, and signs of increased hematopoiesis in the spleen) observed in 28-day oral study of rats; No evidence of adverse effects to male or female gonads or developmental toxicity in rats; [OECD SIDS: 3-(Methylthio) propionaldehyde - 2003] A severe skin, eye, and respiratory tract irritant; May cause skin sensitization; [ICSC] May cause mild irritation; [CAMEO] Safe when used as a flavoring agent in food; [JECFA] An irritant; Harmful by ingestion and inhalation; [Alfa Aesar MSDS]

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. Propanal, 3-(methylthio)- is included on this list. Effective date: 9/30/91; Sunset date: 6/30/98.

Organosulfides, such as 4-THIAPENTANAL, are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

General First Aid:

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. Further information: Use water spray to cool unopened containers.

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature 2 - 8 °C Handle and store under inert gas. Air sensitive. Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.

ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. 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: Contact a licensed professional waste disposal service to dispose of this material. This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.

Prostaglandin biosynthesis from eicosa-8, 11, 14-trienoic acid in microsomes from bovine seminal vesicles is inhibited by relatively high concentrations of hydroxyl radical scavengers: dimethyl sulfoxide, n- and t-butanol, and methional. Methional is a more effective scavenger than t-butanol and dimethyl sulfoxide, two compounds which are more miscible with water than methional. The synthesis of both PGE and PGF is inhibited with incubation systems that promote PGE formation and with incubation systems that promote PGF formation. Furthermore, dimethyl sulfoxide and methional inhibit arachidonic acid-induced platelet aggregation, a reaction involving endoperoxide biosynthesis. The water soluble alcohol, ethanol, stimulates PGF biosynthesis when it is added in the same concentration range as t-butanol. Thus hydroxyl radical scavengers inhibit biosynthesis when their effective concentrations are high and stimulate biosynthesis when their effective concentrations are low. The results of this study and other studies where low concentrations of hydroxyl radical scavengers stimulate both prostaglandin biosynthesis and lipid peroxidation are consistent with a mechanism involving the hydroxyl radical both in the generation of singlet oxygen and the elimination of hydrogen peroxide.

Reactivities of o-phenylphenol and its metabolites (2,5-dihydroxybiphenyl, 2-phenyl-1,4-benzoquinone) with DNA were investigated by a DNA sequencing technique, and the reaction mechanism was studied by UV-visible and ESR spectroscopies. In the presence of Cu(II), 2,5-dihydroxybiphenyl caused strong DNA damage even without piperidine treatment. Catalase, methionine, and methional inhibited the DNA damage completely, whereas mannitol, sodium formate, ethanol, tert-butyl alcohol, and superoxide dismutase did not. 2,5-Dihydroxybiphenyl plus Cu(II) frequently induced a piperidine-labile site at thymine and guanine residues. The addition of Fe(III), Mn(II), Co(II), Ni(II), Zn(II), Cd(II), or Pb(II) did not induce DNA damage with 2,5-dihydroxybiphenyl. When H2O2 was added, 2-phenyl-1,4-benzoquinone also induced DNA damage in the presence of Cu(II). Cu(II) accelerated the autoxidation of 2,5-dihydroxybiphenyl to quinone. An ESR study revealed that the semiquinone radical is an intermediate of the autoxidation. Catalase had no inhibitory effect on the acceleration by Cu(II). Superoxide dismutase promoted both the autoxidation of 2,5-dihydroxybiphenyl and the initial rate of semiquinone radical production. ESR spin trapping experiments showed that the addition of Fe(III) produced hydroxyl radical during the autoxidation of 2,5-dihydroxybiphenyl, whereas the addition of Cu(II) hardly did so. The results suggest that DNA damage by 2,5-dihydroxybiphenyl plus Cu(II) is due to active species other than hydroxyl free radical.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a structure estimation method(2), indicates that 4-thiapentanal is expected to have very high mobility in soil(SRC). Volatilization of 4-thiapentanal from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.0X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). 4-Thiapentanal has a vapor pressure of 0.397 mm Hg(3) and exists as a liquid under environmental conditions; therefore, 4-thiapentanal may volatilize from dry soil(SRC). Utilizing a domestic sewage inoculum, 92% biodegradation was reached in 28 days(3) indicating that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a structure estimation method(2), indicates that 4-thiapentanal is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.0X10-7 atm-cu m/mole(4)(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.41(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing a domestic sewage inoculum, 92% biodegradation was reached in 28 days(5) indicating that biodegradation may be 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), 4-thiapentanal, which has a vapor pressure of 0.397 g at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-thiapentanal 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 7 hrs(SRC), calculated from its rate constant of 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 4-Thiapentanal contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Reported found in potato, potato chips, asparagus, tomato, tomato paste, wheat and rye bread, many cheeses, boil egg, meats, hop oil, beer, malt whiskey, cocoa, coffee, roasted filberts and peanuts, popcorn, baked potato, cooked chicken, oatmeal, passion fruit, beans, mushroom, macadamia nut, tamarind, parsnip root, jackfruit, pumpkin, sweet corn

4-Thiapentanal was detected in slow fermented sausage after 3 months storage under vacuum, producing a cooked potato odor(1). 4-Thiapentanal was identified in the head space volatiles emitted from oaked Chardonnay wine following long-term storage(2). 4-Thiapentanal concentrations in lager beer flavor contribute to the flavor aged beer concentrations of 0.5 and 1.3 ug/L were reported in beer stored for 180 days at 4 °C and 7 days at 37 °C, respectively(3). Steam treatment of defective Brazilian coffee beans (Coffea canephora) and then added to Coffea arabica blends resulted in an increase in 4-thiapentanal in the volatile profile, as a means for improving flavor(4). Analysis of peel and pulp of Chinese quince (Pseudocydonia sinensis) identified 4-thiapentanal as one of the potent aroma-active compounds present(5). 4-Thiapentanal was identified as one of the key aroma-active volatiles of Gouda cheese(6). Concentrations of 10 and 5 ppb were reported in volatiles from 2 super market rice cakes made with whole grain brown rice(7), in popcorn at 14 ug/kg dry wt and 12 ug/kg wet wt(8), and <1 ppb in different forms (creamed, canned, frozen kernel, fresh kernel) of sweet corn(9).

Typical high-temperature, short-time (HTST) pasteurization encompasses a lower heat treatment and shorter refrigerated shelf life compared with ultra-pasteurization (UP) achieved by direct steam injection (DSI-UP) or indirect heat (IND-UP). A greater understanding of the effect of different heat treatments on flavor and flavor chemistry of milk is required to characterize, understand, and identify the sources of flavors. The objective of this study was to determine the differences in the flavor and volatile compound profiles of milk subjected to HTST, DSI-UP, or IND-UP using sensory and instrumental techniques. Raw skim and raw standardized 2% fat milks (50 L each) were processed in triplicate and pasteurized at 78 °C for 15 sec (HTST) or 140 °C for 2.3 sec by DSI-UP or IND-UP. Milks were cooled and stored at 4 °C, then analyzed at day 0, 3, 7, and 14. Sensory attributes were determined using a trained panel, and aroma active compounds were evaluated by solid-phase micro-extraction or stir bar sorptive extraction followed by gas chromatography-mass spectrometry, gas chromatography-olfactometry, and gas chromatography-triple quad mass spectrometry. The UP milks had distinct cooked and sulfur flavors compared with HTST milks. The HTST milks had less diversity in aroma active compounds compared with UP milks. Flavor intensity of all milks decreased by days 14 of storage. Aroma active compound profiles were affected by heat treatment and storage time in both skim and 2% milk. High-impact aroma active compounds were hydrogen sulfide, dimethyl trisulfide, and methional in DSI-UP and 2 and 3-methylbutanal, furfural, 2-heptanone, 2-acetyl-1-pyrroline, 2-aminoacetophenone, benzaldehyde, and dimethyl sulfide in IND-UP. These results provide a foundation knowledge of the effect of heat treatments on flavor development and differences in sensory quality of UP milks.

IDENTIFICATION AND USE: 4-Thiapentanal is a colorless to amber liquid. The chemical is used as intermediate in chemical industry for the production of the amino acid methionine and methionine-hydroxyl analog. A minor use as a food flavoring agent and tobacco ingredient has been identified. HUMAN STUDIES: The activities of butyryl and acetylchoninesterase decreased with increases of occupational service time in the blood of apparently healthy workers exposed to the chemical. ANIMAL STUDIES: 4-Thiapentanal was irritating to the skin and mucous membranes. It had demonstrated a skin sensitizing potential in a guinea pig test. With regard to respiratory irritation it is unclear from the existing studies whether the observed local effects in inhalation studies are attributable to 4-thiapentanal or acrolein that can be enriched in the vapor phase under the test conditions. Exposure of rats to a statically generated saturated atmosphere killed all 5 males with a 40 min exposure and all 5 females with a 24 min exposure. In contrast, a 4-hr exposure of rats to a dynamically generated saturated vapor atmosphere did not produce any mortalities or signs of toxicity. After 28 days oral administration of 4-thiapentanal by gavage to rats a slight hemolytic effect with reduced red blood cell counts and hemoglobin levels, increases in blood bilirubin levels and indications of increased hematopoiesis in the spleen observed at 521 mg/kg bw/d. Dermal exposure of rats for 9 days (6 hr occluded exposure per day) resulted in a slight decrease in body weight gain at a dose of 527 mg/kg bw/d. No effects on the sex organs of rats (male or female) have been observed in the 9-day inhalation study and the 28-day oral study. 4-Thiapentanal did not reveal any developmental toxicity in a study with rats by the inhalation route at exposure concentrations that were clearly maternally toxic. 4-Thiapentanal did not produce mutagenic activity either in the absence or presence of metabolic activation with a Salmonella typhimurium reverse mutation assay using strains TA98, TA100, TA1535, TA1537 and TA1538. In a mouse lymphoma cell assay, it produced concentration-related increases in mutant colonies, both in the absence and presence of metabolic activation. However, in an in vivo mouse micronucleus study 4-thiapentanal showed a negative result, indicating that the clastogenesis that was demonstrated in an in vitro study does not occur in vivo.

4-Thiapentanal is reported present at a maximum concentration of 1700 ppm in the fruit essential oil of Indian tamarind (Tamarindus indica; Fabaceae)(1). Methional was identified as one of the odor volatiles from three varieties of hawthorne (Crataegus pinnatifida spp.)(2).

Cough. Sore throat.

Redness.

Redness. Pain.

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 4-thiapentanal is available.[Available from, as of February 1, 2019: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]

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 February 4, 2019: http://actor.epa.gov/dashboard/]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 4-thiapentanal can be estimated to be 3(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4-thiapentanal is expected to have very high mobility in soil(SRC).

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. Propanal, 3-(methylthio)- is included on this list. Effective date: 9/30/91; Sunset date: 6/30/98.

Four commonly used food antioxidants, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), propyl gallate and octyl gallate, were tested for their ability to inhibit the formation of ethylene from methional in NADPH-oxidizing rat liver microsomes. It is assumed that the action of the antioxidants on ethylene formation reflects their free radical scavenging activity. Only propyl gallate and octyl gallate are efficient inhibitors of ethylene formation. BHT is inhibitory only at very high concentrations, and BHA tends to increase ethylene formation. It is concluded that gallic acid ester antioxidants may possess a protective potential during chemical-induced microsomal oxidations.

Naturally present in plants and aquatic animals; Used nearly exclusively as an intermediate in chemical synthesis; Also used in small quantities as a flavoring agent; [OECD SIDS: 3-(Methylthio) propionaldehyde - 2003]

Reported uses (ppm):

The vast majority of 3-(methylthio) propionaldehyde is used as intermediate in chemical industry for the production of the amino acid methionine and methionine-hydroxyl analoge. A minor use of 3-(methylthio) propionaldehyde as a food flavoring agent has been identified.

3-(Methylthio) propionaldehyde is a colorless to light yellow organic liquid with a purity of > 97 % (w/w). Impurities are water (</= 2.5 %), acetaldehyde (0.1 to 0.8 %), methanol (0.1 - 0.3 %), methanethiol (</= 0.6 %), acrylaldehyde (</= 0.3 %) (Qualities used and tested in the past may have had higher amounts of impurities in particular acrylaldehyde and acetaldehyde).

2023: 150,000,000 - <500,000,000 lb

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Propanal, 3-(methylthio)-:

The production of 3-(methylthio) propionaldehyde by reaction of acrolein with methylmercaptan is conducted in a closed reaction vessel followed by a distillative purification. The separated light and high boiler products are fed into a thermal oxidizer.

By transamination and decarboxylation of various amino acids; by oxidation of alcohol.

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

All Other Basic Organic Chemical Manufacturing

Propanal, 3-(methylthio)-: ACTIVE

Methional alone smells like boiled potatoes ... potato characteristic disappears when methional becomes a component of Cheddar cheese flavor