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3-Ethoxy-4-hydroxybenzaldehyd
3-ETHOXY-4-HYDROXYBENZALDEHYDE · ETHYL VANILIN · Benzaldehyde, 3-ethoxy-4-hydroxy- · Vanirom · FEMA 2464 · Rhodiarome · VANILLAL · FEMA 3107
Identifikatoren & physikalische Daten
| CAS No. | 121-32-4 |
|---|---|
| Summenformel | C9H10O3 |
| Durchschnittliche Molmasse | 166,17 g/mol |
| Monoisotopische Masse | 166,06299418 g/mol |
| SMILES | CCOc1cc(C=O)ccc1O |
| InChIKey | CBOQJANXLMLOSS-UHFFFAOYSA-N |
| PubChem CID | 8467 |
| ChEMBL | CHEMBL508676 |
| ChEBI | CHEBI:48408 |
| EC No. | 204-464-7 |
| DTXSID | DTXSID5021968 |
| Lokaler Name | 3-Ethoxy-4-hydroxybenzaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 147 |
| Stoffklassen | Other Classes -> Benzaldehydes |
| Kosmetika | SoothingMasking |
| pH | Solutions are acid to litmus |
| SpringerMaterials Properties | Boiling point |
| Duftstoffe | Fragrance Ingredient (Ethyl vanillin) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | log Kow = 1.58 |
| Geruch | Finer and more intense vanillaResembles that of vanillin but approximately 3 times as strong. |
| Geschmack | SweetFiner and more intense taste than vanillin |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT, PH CONTROL AGENT -> FDA Substance added to food |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Fine, crystalline needlesWhite or slightly yellowish crystalsColorless flakes |
| Löslichkeit | Slightly soluble (NTP, 1992)In water, 2,822 mg/L at 25 °CSlightly soluble in water (1 g in 100 mL at 50 °C)Soluble in ethanol, ether, benzene, chloroformFreely soluble in ... solutions of alkali hydroxidessoluble in glycerol, propylene glycolSolubility in 95% alcohol about 1 g/2 mL2.82g/l |
| Schmelzpunkt | 74-77 °C (lit.) |
| Siedepunkt | 285°C |
| Dichte | 1.1097 (rough estimate) |
| Dampfdruck | <0.01 mm Hg ( 25 °C) |
| Brechungsindex | 1.4500 (estimate) |
| FEMA | 2464 | ETHYL VANILLIN |
| Flammpunkt | 127°C |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 7.91±0.18(Predicted) |
| Aggregatzustand | Fine Crystalline Powder |
| Farbe | White to off-white |
| Geruch | at 10.00 % in dipropylene glycol. sweet creamy vanilla caramel |
| Geruchsart | vanilla |
| Biologische Quelle | synthetic |
| Merck | 14,3859 |
| JECFA Number | 893 |
| BRN | 1073761 |
| Henry-Konstante | 1.2×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Hygroscopic |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | SOOTHINGFRAGRANCE |
| InChI | 1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 |
| InChIKey | CBOQJANXLMLOSS-UHFFFAOYSA-N |
| SMILES | [H]C(=O)c1ccc(O)c(OCC)c1 |
| LogP (Verteilungskoeffizient) | 1.58 at 25℃ |
| CAS Datenbank | 121-32-4(CAS DataBase Reference) |
| NIST chemische Informationen | 3-Ethoxy-4-hydroxybenzadehyde(121-32-4) |
| EPA chemische Informationen | Ethyl vanillin (121-32-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 78.7% (1611 of 2046) of all reports.WarningH319 (20.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)Aggregated GHS information provided per 2046 reports by companies from 15 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: Benzaldehyde, 3-ethoxy-4-hydroxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Benzaldehyde, 3-ethoxy-4-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzaldehyde, 3-ethoxy-4-hydroxy- 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: 30-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13700Ethylvanillin: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible (NTP, 1992) |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: Toxic. May cause irritation on contact. (NTP, 1992) |
| Gefahrenübersicht | A skin irritant[HSDB] Causes liver injury in high-dose feeding studies of rats[RTECS] Safe when used as a flavoring agent in food[JECFA] May cause irritation[CAMEO] An irritant[MSDSonline] See Vanillin. |
| FDA-Anforderungen | Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, withn the meaning of section 409 of the Act. Ethyl vanillin is included on this list.Substances migrating to food from paper and paperboard products used in food packaging that are generally recognized as safe for their intended use, within section 409 of the Act. Ethyl vanillin is included on this list.Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Ethyl vanillin is included on this list. |
| Reaktive Gruppe | Aldehydes |
| Special Reports | REVIEW WITH 13 REFERENCES.[OPDYKE DL JFRAGRANCE RAW MATERIALS. ETHYL VANILLINFOOD COSMET TOXICOL 13(1) 103 (1975)]BIBRA working group, Ethyl vanillin, Toxicity profileThe British Industrial Biological Research Association4 (1967). In a volunteer study, ethyl vanillin (EV) demonstrated no sensitizing potential but was a skin irritant. |
| TSCA-Anforderungen | 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: 9/30/91Reporting 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, 3-ethoxy-4-hydroxy- is included on this list. Effective date: 9/30/91Sunset date: 6/30/98. |
| Reactivity Profile | Protect from light. (NTP, 1992) Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. |
| Air and Water Reactions | Slightly water soluble (NTP, 1992). |
| Hazard Classes and Categories | Eye Irrit. 2A (20.7%) |
| Skin, Eye, and Respiratory Irritations | A human skin irritant.... Highly irritating action on the eyes and mucous membranes of the respiratory tract. /Aldehydes/ |
| Brandbekämpfung | To extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguishera water spray may also be used. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. |
| Lagerbedingungen | ... Should not be stored near powerful oxidizers or in areas of high fire hazard. They should be kept cool and the containers electrically grounded to avoid sparks. /Ethers/ |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Entsorgungsverfahren | 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 qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand 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. |
| Preventive Measures | 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. |
| Personal Protective Equipment (PPE) | MINIMUM PROTECTIVE CLOTHING: When working with this chemical, you should wear impervious coveralls, shoe covers and gloves. |
| Ökotoxizitätswerte | EC50Species: Pimephales promelas (Fathead Minnow) age 28 days, length 14.2 mmConditions: freshwater, flow through, 24 (22.7-25.2) °C, pH 7.65 (7.19-8.10), hardness 52.2 (51.4-53.0) mg/L CaCO3, alkalinity 46.6 (46.0-47.0) mg/L CaCO3, dissolved oxygen 77.4 (71.5-90.1) mg/LConcentration: 90600 ug/L for 24 hrEffect: behavior, decreased equilibrium /97% purity/Concentration: 84300 ug/L for 48 hrLC50Concentration: 98000 ug/L for 24 hr /97% purity/Concentration: 90400 ug/L for 48 hr /97% purity/Species: Pimephales promelas (Fathead Minnow) age 28 days, length 14.3 mm. weight 0.034 gConditions: freshwater, flow through, 24.1 °C, pH 7.7, hardness 52.2 mg/L CaCO3, alkalinity 46.4 mg/L CaCO3, dissolved oxygen 6.5 mg/LConcentration: 87600 ug/L for 96 hr (95% confidence limit: 81400-94300 ug/L) /97% purity/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a log Kow of 1.58(2) and a regression-derived equation(3), indicates that ethyl vanillin is expected to have high mobility in soil(SRC). Volatilization of ethyl vanillin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.1X10-10 atm-cu m/mole(4) derived from its vapor pressure, 1.04X10-5 mm Hg(5), and water solubility, 2,820 mg/L(6). Ethyl vanillin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). Utilizing the Japanese MITI test, 88% of the Theoretical BOD was reached in 2 weeks(7) 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 60(SRC), determined from a log Kow of 1.58(2) and a regression-derived equation(3), indicates that ethyl vanillin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 8.1X10-10 atm-cu m/mole(5), derived from its vapor pressure, 1.04X10-5 mm Hg(6), and water solubility, 2,820 mg/L(7). According to a classification scheme(8), an estimated BCF of 5(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Ethyl vanillin contains chromophores that absorb at wavelengths >290 nm(9) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Utilizing the Japanese MITI test, 88% of the Theoretical BOD was reached in 2 weeks(10) 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), ethyl vanillin, which has a vapor pressure of 1.04X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase ethyl vanillin 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 3.3X10-11 cu cm/molecule-sec at 25 °C(SRC). Particulate-phase ethyl vanillin may be removed from the air by wet and dry deposition(SRC). Ethyl vanillin contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| Lebensmitteluntersuchungswerte | Ethyl vanillin was detected in artificial vanilla extracts purchased from local and internet retail stores at concentrations ranging from 0.13 to 2.39 ng/mL(1). Ethyl vanillin was detected in samples of 23 domestic and imported vanilla extract products at concentrations ranging from 0.4 to 2.2 mg/g(2). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Milk Concentrations | Ethyl vanillin was detected in 2 out of 5 powdered milk samples from a local supermarket in Xi'an, China(1). |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Ethyl vanillin forms fine crystalline needles and is used in fragrances for its vanilla odor. It is also used as a replacement of or to strengthen the flavor of vanilla in a variety of foods. Ethyl vanillin is a widely used food additive and spice in foods, beverages, cosmetics and drugs. HUMAN EXPOSURE AND TOXICITY: Research in humans showed that ethyl vanillin had no significant effect on the activity of five human CYP450 enzymes with concentration ranged from 8 to 128 uM. A 2% concentration of ethyl vanillin caused mild irritation on the skin of humans after 48 hours of direct contact. ANIMAL STUDIES: In animal studies, ethyl vanillin was found to be mostly non-toxic except when given at high doses for longer than 6 weeks. Rabbits were given ethyl vanillin orally in 10% aqueous glycerin 49 mg/kg bw/day for 43 days. At this dose level anemia, diarrhea and lack of weight gain were observed. Rats (20/sex/group) were fed ethyl vanillin of > 99.9% purity (nature of diet e.g., semi-synthetic/chow diet, not specified) at dose levels of 0, 500, 1000 or 2000 mg/kg bw/day for 13 weeks. Clinical biochemistry showed statistically significant higher values in the high-dose group compared to control for ALAT, ALP, cholesterol and total plasma protein. Histological examination revealed a dose-related increased incidence of hepatic peribiliary inflammatory change in both males and females of the intermediate- and high-dose groups, and minor bile duct hyperplasia affecting 1/20 intermediate- and 4/20 high-dose males. There were no changes observed in the liver parenchyma and no degenerative or inflammatory changes of the bile duct epithelium. Increased white pulp cellularity and prominence of germinal centers in the spleen, and increased prominence of germinal centers and lymphoid proliferation in cervical lymph nodes were seen in the intermediate- and high-dose groups. Groups of 12 male and 12 female rats were fed diets containing 0, 0.5, 1 and 2% ethyl vanillin for 2 years or 2% and 5% for one year without any adverse effects on growth, organ weights of major organs, hematology and histology of major tissues. In genotoxicity studies, ethyl vanillin did not induce genetic changes in vitro but was reported to enhance the ability of mitomycin C to cause sister chromatid exchanges. Ethyl vanillin has shown to have anti-angiogenic, anti-inflammatory and anti-nociceptive properties that are based on its suppressive effect on the production of nitric oxide possibly via decreasing the reactive oxygen species level. The in vivo results revealed that drug interaction between vanillin/ethyl vanillin and drugs metabolized by CYP2E1 or CYP1A2 might be possible, and also suggested that the application of the above additives in foods and drugs should not be unlimited so as to avoid the adverse interaction. The thermal tolerance Cronobacter sakazakii was examined in sterile powdered infant formula (PIF) rehydrated at 58 °C in water or apple juice supplemented with vanillin, ethyl vanillin, or vanillic acid. All three compounds decreased thermal tolerance during-rehydration. Supplementation of PIF with vanillin, ethyl vanillin, or vanillic acid could enhance the safety of PIF or other dehydrated foods contaminated with C. sakazakii. |
| Ongoing Test Status | EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of 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 assaysClick on the "Chemical Explorer" button on the tool bar to see the data./[USEPAICSS Dashboard ApplicationAvailable from, as of April 22, 2015: http://actor.epa.gov/dashboard/] |
| Soil Adsorption/Mobility | The Koc of ethyl vanillin is estimated as 60(SRC), using a log Kow of 1.58(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that ethyl vanillin is expected to have high mobility in soil. The pKa of the related compound vanillin is 7.4(3). By analogy, this value suggests that ethyl vanillin will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). |
| Natural Pollution Sources | Ethyl vanillin does not occur in nature(1,2). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ ... A maximization test was carried out on 25 volunteers. The material /ethyl vanillin/ was tested at a concentration of 2% in petrolatum and produced no sensitization reactions./HUMAN EXPOSURE STUDIES/ ... When tested as 2% in petrolatum, ethyl vanillin produced mild irritation after a 48 hr closed-patch test in 25 human subjects./ALTERNATIVE and IN VITRO TESTS/ ... The objective of the present work was to evaluate the impact of vanillin and ethyl vanillin on the activities of CYP2C9, CYP2E1, CYP3A4, CYP2B6 and CYP1A2 in human liver microsomes (HLM) in vitro.... The in vitro results demonstrated that vanillin and ethyl vanillin had no significant effect on the activity of five human CYP450 enzymes with concentration ranged from 8 to 128 uM.... |
| Artificial Pollution Sources | Ethyl vanillin's production and use in flavoring and perfumery(1) may result in its release to the environment through various waste streams(SRC). It is used in tobacco flavor formulations(2). |
| Environmental Biodegradation | AEROBIC: Ethyl vanillin reached 52.9% of its theoretical BOD in 5 days using an acclimated mixed microbial culture in the Closed Bottle test(1). Ethyl vanillin, present at 100 mg/L, reached 88% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(2). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29124200 |
| RTECS-Nr. | CU6125000 |
| R-Sätze (R) | 22-36/37/38 |
| Toxizität | LD50 orally in rats: >2000 mg/kg, P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964) |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Harmful/Irritant/Light Sensitive |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 121-32-4(Hazardous Substances Data) |
| Gefahrenklasse | Eye Irrit. 2 |
Anwendungen & Verwendung
Occurrence
Not reported found in nature; it can be distinguished from vanillin because of the yellow color developed in the presence of concentrated H2SO4.
Verwenden
Ethyl Vanillin is a flavoring agent that is a synthetic vanilla flavor with approximately three and one-half times the flavoring power of vanillin. it has a solubility of 1 g in 100 ml of water at 50°c. it is used in ice cream, beverages, and baked goods.
Herstellung & Synthese
synthetische
From safrole by isomerization to isosafrole and subsequent oxidation to piperonal; the methylene linkage is then broken by heating piperonal in an alcoholic solution of KOH; finally the resulting protocatechualdehyde is reacted with ethyl alcohol. From guaethol by condensation with chloral to yield 3-ethoxy-4-hydroxyphenyl trichloromethyl carbinol; this is then boiled with an alcoholic solution of KOH or NaOH, acidified, and extracted with chloroform to yield ethyl vanillin.