Ethylvanillin
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Ethylvanillin
structure -
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CAS No:
121-32-4
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Formula:
C9H10O3
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Chemical Name:
Ethylvanillin
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Synonyms:
Benzaldehyde,3-ethoxy-4-hydroxy-;3-Ethoxy-4-hydroxybenzaldehyde;Bourbonal;Ethavan;Ethovan;Ethylprotal;Protocatechuic aldehyde ethyl ether;Quantrovanil;Vanillal;Ethylvanillin;4-Hydroxy-3-ethoxybenzaldehyde;Vanirom;2-Ethoxy-4-formylphenol;Rhodiarome;NSC 1803;NSC 67240;Arovanillon;3-Ethylvanillin;YS 065
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CAS No:
Description
Ethylvanillin is a flavorant, about three times as potent as vanillin and is used in the production of chocolate.
Ethyl vanillin appears as colorless crystals. More intense vanilla odor and taste than vanillin. (NTP, 1992)|DryPowder; Liquid; PelletsLargeCrystals|Solid|colourless or slightly yellow crystal flakes with an intense vanilla odour
Ethyl vanillin appears as colorless crystals. More intense vanilla odor and taste than vanillin. (NTP, 1992)|Ethyl vanillin is a member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group. It has a role as an antioxidant and a flavouring agent. It is a member of benzaldehydes, a member of phenols and an aromatic ether. It derives from a vanillin.
Ethylvanillin Basic Attributes
166.17400
166.17
204-464-7
YC9ST449YJ
67240|1803
DTXSID5021968
Fine, crystalline needles|White or slightly yellowish crystals|Colorless flakes
2912420000
Characteristics
46.53000
1.6
Ethyl vanillin appears as colorless crystals. More intense vanilla odor and taste than vanillin. (NTP, 1992)
1.2±0.1 g/cm3
77.5 °C
285 °C
119ºC
1.434
H2O: slightly soluble
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protect
<0.01 mm Hg ( 25 °C)
Finer and more intense vanilla
Sweet
Solutions are acid to litmus
Henry's law constant = 8.1X10-10 atm cu-m/mole at 25 °C (est)
Conversion factors: 1 ppm is equiv to 6.78 mg/cu m; 1 mg/L is equiv to 147.2 ppm at 25 °C, 760 mm Hg|Odor detection in water: 1.00X10-1 ppm|Hydroxyl radical reaction rate constant = 3.3X10-11 cu cm/mole-sec at 25 °C (est)
Slightly water soluble (NTP, 1992).
Aldehydes
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.
Safety Information
I; II; III
NONH for all modes of transport
1
R22; R36/37/38
S26-S36
CU6125000
Xn
AFFECTED BY LIGHT
P261-P305 + P351 + P338
H302-H315-H319-H335
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.
Incompatible with oxidizing materials, BI3. /Ethers/
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.
REVIEW WITH 13 REFERENCES.[OPDYKE DL J; FRAGRANCE RAW MATERIALS. ETHYL VANILLIN; FOOD COSMET TOXICOL 13(1) 103 (1975)]|BIBRA working group, Ethyl vanillin, Toxicity profile; The British Industrial Biological Research Association; 4 (1967). In a volunteer study, ethyl vanillin (EV) demonstrated no sensitizing potential but was a skin irritant.
Combustible (NTP, 1992)
|Warning|H302 (19.82%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 1948 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
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. STORAGE PRECAUTIONS: You should keep this material in a tightly-closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: When working with this chemical, you should wear impervious coveralls, shoe covers and gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
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.
A human skin irritant.|... Highly irritating action on the eyes and mucous membranes of the respiratory tract. /Aldehydes/
SEDIMENT: Ethyl vanillin was identified but not quantified in suspended sediment of the freshwater lake, Singletary Lake, in eastern North Carolina(1).
Ethyl vanillin is a component of tobacco, tobacco smoke, and tobacco substitute smoke(1).
Toxicity
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.
LD50 Dog iv 760 mg/kg|LD50 Rat sc 1800 mg/kg|LD50 Rabbit oral 3000 mg/kg|LD50 Rat oral >2000 mg/kg|For more Non-Human Toxicity Values (Complete) data for ETHYL VANILLIN (7 total), please visit the HSDB record page.
Ethyl vanillin does not occur in nature(1,2).
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).
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).
The rate constant for the vapor-phase reaction of ethyl vanillin with photochemically-produced hydroxyl radicals has been estimated as 3.3X10-11 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(1). Ethyl vanillin is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Ethyl vanillin contains chromophores that absorb at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 5 was calculated in fish for ethyl vanillin(SRC), using a log Kow of 1.58(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
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).
The Henry's Law constant for ethyl vanillin is estimated as 8.1X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 1.04X10-5 mm Hg mm Hg(1), and water solubility, 2,820 mg/L(2). This Henry's Law constant indicates that ethyl vanillin is expected to be essentially nonvolatile from water surfaces(3). Ethyl vanillin's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected(SRC). Ethyl vanillin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
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).
Ethyl vanillin was detected in 2 out of 5 powdered milk samples from a local supermarket in Xi'an, China(1).
According to the 2012 TSCA Inventory Update Reporting data, 7 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of ethyl vanillin in the United States may be as low as <10 workers and as high as 99 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 53,949 workers (31,080 of these are female) were potentially exposed to ethyl vanillin in the US(1). Occupational exposure to ethyl vanillin may occur through dermal contact with this compound at workplaces where ethyl vanillin is produced or used. Use data indicate that the general population may be exposed to ethyl vanillin via ingestion of food and dermal contact with consumer products containing ethyl vanillin(SRC).
Drug Information
Ethyl (14C)-vanillin was administered to male and female Sprague-Dawley CD rats by gavage in polyethylene glycol solution at single doses of 50, 100, or 200 mg/kg bw. Ethyl vanillin was rapidly absorbed and peak plasma radioactivity occurred within 2 hr after dosing at all dose levels, falling rapidly to undetectable levels within 96 hr. Plasma radioactivity tended to be higher in female than male rats and it was postulated that this might reflect a lower metabolic capacity of female rats. Urinary excretion of radioactivity was rapid and more than 94% of the dose was excreted by this route within 24 hr. Only 1-5% of the dose was excreted in faeces. After 5 days, more than 99% of the administered dose was excreted. No radioactivity was detected in expired air, indicating that the aromatic ring was in a metabolically stable position.
A healthy adult male volunteer drank a 235 ml aliquot of a liquid dietary supplement containing an unknown quantity of ethyl vanillin. A concentration of 13 mg ethyl vanillic acid/g creatinine was found in a 12-hour urine sample. The compound was not present in urine collected before exposure.|Ethyl vanillic acid was identified by GC/MS in the urine of a 9-year old female patient who had received liquid dietary supplementation flavored with vanilla. Other patients excreting this acid were also known to have consumed foodstuffs flavored with ethyl vanillin. Eight different urine samples containing more than 50 mg ethyl vanillic acid/g creatinine were also found to contain small amounts of vanillylmandelic acid. Unchanged ethyl vanillin was not detected in any of the urine samples.|During urinary organic acid profiling in human subjects, several patients excreted high concentrations of ethyl vanillic acid (3-ethoxy-4-hydroxybenzoic acid) and traces of 3-ethoxy-4-hydroxy- mandelic acid.|Ethyl (14C)-vanillin was administered to male and female Sprague Dawley CD rats at single oral doses of 50, 100, or 200 mg/kg bw. Rapid metabolism occurred and the principal metabolite at all dose levels was ethyl vanillic acid. Analysis of urine after hydrolysis with glucuronidase and/or sulfatase indicated that the major metabolites were glucuronide or sulfate conjugates of ethyl vanillic acid (56-62%), ethyl vanillyl alcohol (15-20%), and ethyl vanillin (7-12%). A minor proportion of the dose (2-8%) was excreted as the glycine conjugate of vanillic acid (ethyl vanilloyl glycine).|Early reports indicated that ethyl vanillin was probably metabolized to glucuroethyl vanillin and ethyl vanillic acid, of which some was conjugated with glucuronic and sulfuric acids.
ACUTE/CHRONIC HAZARDS: Toxic. May cause irritation on contact. (NTP, 1992)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
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. /Phenols and related compounds/|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 ... . Administer activated charcoal ... . Dilution may be contraindicated because if may increase absorption. Do not use emetics. Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and related compounds/|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. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . 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. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... Treat seizures with diazepam or lorazepam. ... Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/
/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....
3-ethoxy-4-hydroxybenzaldehyde
Ethylvanillin Use and Manufacturing
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.|By reacting o-ethoxyphenol with formaldehyde and p-nitrosodimethylaniline in the presence of aluminum and water.
It is widely used in food, chocolate, ice cream, beverages and daily cosmetics to enhance and fix the fragrance. The purpose is basically the same as vanillin. It can be used as a sweetener and fixative. It can be used for sweet floral fragrance and fruit lipstick fragrance. It can also be used as a fixative for formulas that require sweet milk fragrance. It can cause discoloration, so avoid using it in white creams and soaps. It is widely used in vanilla bean and chocolate flavors. It is also used in cream, fruity, smoked sugar, caramel, nuts, rum and other flavors, as a sweetener and fixative.
Odor agents
Air care products
1,000,000 - 10,000,000 lb|(1972) 1.27X10+7 GRAMS|(1975) GREATER THAN 4.5X10+7 GRAMS|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzaldehyde, 3-ethoxy-4-hydroxy-. Aggregated National Production Volume: 1 to < 10 million pounds.|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzaldehyde, 3-ethoxy-4-hydroxy-. National Production Volume: 1,000,000 - 10,000,000 lb/yr.
100% AS A FLAVORING AGENT (1976)
Grades: National Formulary; Food Chemical Codex
Soap, cleaning compound, and toilet preparation manufacturing|Benzaldehyde, 3-ethoxy-4-hydroxy-: ACTIVE|The flavoring power is two to four times stronger than vanillin.
...ETHYL VANILLIN CAN BE TRAPPED FROM THE AIR BY SCRUBBING WITH METHANOL. ... SOLUTIONS CAN BE ANALYZED BY ULTRAVIOLET SPECTROPHOTOMETRY. STRONG ABSORPTION BANDS OCCUR FROM...310 AND 278 NM. ...IN THE RANGE 0.01 MG/100 ML METHANOL CAN BE MEASURED ACCURATELY WHEN A 10-CM CELL IS USED.|AOAC 966.13. Vanillin and ethyl vanillin in vanilla extract. Paper chromatographic method.|AOAC 955.31. Vanillin, ethyl vanillin and coumarin in vanilla extract. Chromatographic separation method.|The easiest way to tell real and synthetic vanilla essence apart is to use Gas-Liquid Chromatography, which can spot the impurities like 4-hydroxybenzaldehyde present in natural vanilla essence, but the fakers can simply add these molecules. Another way is to look at the radiocarbon content, the amount of radioactive carbon-14. Natural plant-sourced vanillin contains a certain level of carbon-14, but since the half life of carbon-14 is 5730 years, vanillin derived from crude oil has no radiocarbon, since it has decayed away over the millions of years the oil was trapped underground. But determined forgers started putting some carbon-14 adulterated molecules into their fake vanilla extract. To counter that, the analysts started looking at the ratio of the natural isotopes, carbon-12 and carbon-13. Because the vanilla orchid uses a different biosynthetic pathway to other plants, orchid-derived vanillin has a greater ratio of carbon-13 to carbon-12 than synthetic vanillin. The fraudsters hit back by doping their synthetic vanillin with molecules containing extra carbon-13. However, the fraudsters cannot get a uniform level of carbon-13 at all the carbons. Instead they tend to concentrate it at the aldehyde and methyl groups, and this can be spotted by chemists who use the aptly named site-specific natural isotope fractionation NMR (SNIF-NMR)
EPA Safer Chemical Functional Use Classes -> Fragrances|Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern|Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Masking; Soothing
Flavoring Agents
Computed Properties
Molecular Weight:166.17
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:166.062994177
Monoisotopic Mass:166.062994177
Topological Polar Surface Area:46.5
Heavy Atom Count:12
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
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