Cinnamaldehyde
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Cinnamaldehyde
structure -
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CAS No:
104-55-2
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Formula:
C9H8O
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Chemical Name:
Cinnamaldehyde
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Synonyms:
2-Propenal,3-phenyl-;Cinnamaldehyde;3-Phenyl-2-propenal;Cassia aldehyde;Cinnamal;Cinnamic aldehyde;Phenylacrolein;3-Phenylpropenal;3-Phenyl-2-propene-1-al;Cinnamyl aldehyde;3-Phenylacrolein;Benzylideneacetaldehyde;3-Phenyl-2-propenaldehyde;Zimtaldehyde;3-Phenyl-2-propen-1-al;3-Phenylacrylaldehyde;Abion CA;β-Phenylacrolein;Cinnamite;NSC 16935;NSC 40346;Cinnacure;XC 800
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CAS No:
Description
Cinnamaldehyde is an aldehyde organic compound, a light yellow or colorless viscous liquid with a strong cinnamon aroma and a mild spicy smell. It is found in large quantities in plants such as cinnamon. Its molecular formula is C9H8O, molecular weight is 132.16, melting point is -7.5℃, boiling point is 253℃ (normal pressure), refractive index is 1.619-1.623 (20℃), and density is 1.046-1.052. Cinnamaldehyde is insoluble in water and glycerin, but easily soluble in organic solvents such as alcohol, ether and petroleum ether.
Cinnamaldehyde Basic Attributes
132.16
132.16
203-213-9
SR60A3XG0F
40346|16935
DTXSID6024834|DTXSID1024835
Yellowish oily liquid|GREENISH-YELLOW LIQUID
29122900
Characteristics
17.1
1.90
Cinnamaldehyde is a yellow oily liquid with a cinnamon odor and sweet taste. (NTP, 1992)
1.048-1.052 g/cm3 @ Temp: 25 °C
-7.5 °C
246 °C
160 °F
n 20/D 1.622(lit.)
H2O: Slightly soluble
Store below +30°C.
<0.1 hPa (20 °C)
4.6 (vs air)
Oral-Rat LD50 2220 mg/kg; Oral-Mouse LD50: 2225 mg/kg
Flammable, spicy and irritating smoke emitted from the fire
PUNGENT, SPICY NOTE
BURNING TASTE
4.80e-11 cm3/molecule*sec
Henry's Law constant = 3.5X10-6 atm-cu m/mol at 25 °C (est)
134.25 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|121.5 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|121.5 Ų [M+H]+
ACID VALUE: 5 MAXIMUM|CONVERSION FACTORS: 1 MG/L= 185 PPM, 1 PPM= 5.4 MG/CU M|Yellow liquid; MP: -7.5 °C; BP: 246 °C; density: 1.0497 g/cu cm at 20 °C; Index of refraction: 1.6195 at 20 °C/D; slightly soluble in water; soluble in ethanol, ethyl ether, chloroform; insoluble in ligroin /trans-Cinnamaldehyde/|MP: 7.5 °C; BP: 253 °C decomposes; 137 °C at 16 mm Hg; density 1.0497 at 20 °C; Index of refraction: 1.6195 at 20 °C/D; solubility: slightly soluble in water; soluble in ethanol, ethyl ether, chloroform; insoluble in ligroin (E-siomer)|UV: 424 (Sadtler Research Laboratories Spectral Collection) (E-isomer)|Raman: 148 (Sadtler Research Laboratories Spectral Collection) (E-isomer)|Hydroxyl radical reaction rate constant = 3.8X10-11 cu cm/molec-sec at 25 °C /cis-isomer/; 4.0X10-11 cu cm/molecule-sec /trans-isomers/ (est)|Ozone radical reaction rate constant = 1.7X10-18 cu cm/molec-sec at 25 °C /cis-isomer/; 3.4X10-18 cu cm/molec-sec at 25 °C /trans-isomer/ (est)
Thickens on exposure to air. May be unstable to prolonged exposure to air. Slightly water soluble (NTP, 1992).|May be sensitive to prolonged exposure to air and light. Insoluble in water.
Aldehydes
Peroxidizable Compound
CINNAMALDEHYDE reacts with sodium hydroxide owing to aerobic oxidation. (NTP, 1992)|TRANS-CINNAMALDEHYDE is incompatible with strong oxidizing agents and strong bases. It can also react with sodium hydroxide. (NTP, 1992)
Cinnamaldehyde|D*: Other compounds that may form peroxides|Bretherick's|A mixture of cinnamaldehyde and sodium hydroxide over-heated and ignited upon extended exposure to air. Warrants caution. See Bretherick's.
Safety Information
UN1989 Aldehydes, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquidUN8027
3
36/37/38-43
26-36/37
GD6476000
Xi
Storeroom low temperature, ventilated, dry; fireproof; stored separately from oxidants, food ingredients
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
H315
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Do not use, pour, spill or store near heat or open flame. /Cinnacure A3005/
Rags soaked in sodium hydroxide and in /cinnamaldehyde/ overheated and ignited owing to aerobic oxidation when they came into contact in a waste bin.
Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Cinnamaldehyde 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. Cinnamaldehyde is included on this list.
EPA/Office of Pollution Prevention and Toxics; High Production Volume Information System (HPVIS) Detailed chemical results for 3-Phenyl-2-propenal (104-55-2).|WHO/FAO; Joint Expert Committee on Food Additives (JECFA) - Monographs and Evaluations; Nutrition Meetings Report Series 44a: 097. Cinnamaldehyde (August 1967). JEFCA Monographs are toxicological evaluations of food additives and contaminants and of residues of veterinary drugs in food used by the Codex Alimentarius Commission and national governments to set international food standards and safe levels for protection of the consumer.|European Chemicals Bureau; IUCLID Dataset, Cinnamaldehyde (104-55-2) (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of July 14, 2009: http://esis.jrc.ec.europa.eu/]|USEPA, Office of Pesticide Programs/ Ombudsman, Biopesticides and Pollution Prevention Division: Active Ingredient Fact Sheet for Cinnamaldehyde (040506) (December 2000).[Available from, as of July 13, 2009: http://www.epa.gov/pesticides/biopesticides/ingredients/index_p-s.htm]|EPA/Office of Pollution prevention and toxics; High production Volume Information System (HPVIS) Detailed chemical results for 3-Phenyl-2-propenal (104-55-2).[Available from, as of July 13, 2009: http://iaspub.epa.gov/oppthpv/quicksearch.chemical]
This chemical is combustible. (NTP, 1992)
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H312 (81.89%): Harmful in contact with skin [Warning Acute toxicity, dermal]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P312, P321, P322, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 2782 companies from 33 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|H312: Harmful in contact with skin [Warning Acute toxicity, dermal]|P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated 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)|SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)
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)|Agricultural use requirements. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, water, is: Coveralls, waterproof gloves, shoes plus socks./Cinnacure A3005/|Long-sleeved shirt and long pants, protective eyewear, shoes plus socks, waterproof gloves.
CO2, dry chemical, or appropriate foam.
May ignite after a delay period in contact with NaOH.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.|Do not contaminate water by cleaning of equipment or disposal of wastes. /Cinnacure A3005/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.|User should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /Cinnacure A3005/|Agricultural use requirements. Use this product only in accordance with its labeling and with Worker Protection Standard, 40 CFR part 170. ... Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 4 hours. /Cinnacure A3005/|Do not apply directly to water, or to areas where surface water is present or to intertidal areas below the nean high water mark. /Cinnacure A3005/
Primary eye irritant ... Dermal irritant.|No primary dermal irritation was observed in human subjects exposed for 48 hours to a solution of a 3% active ingredient, while severe primary dermal irritation was observed in human subjects after exposure to 8% active ingredient.
Fine particle cinnamaldehyde was detected in smoke emitted from burning Southern US wood species, expressed as mg/g Organic Carbon, at concentrations of 0.431, 0.355, 0.168, 0.108, 3.789 and 3.521 for Yellow Poplar, White Ash, Sweet-gum, Mockernut Hickory, Loblolly Pine and Slash Pine woods, respectively(1).
Toxicity
moderately
The Japanese medaka (Oryzias latipes) was used in the medaka embryo-larval assay (MELA) to determine possible adverse developmental effects of ethanol and the spice component, cinnamaldehyde (CAD) ... Medaka were exposed to ethanol at 100 mM, CAD at 10, 1.0, 0.67 or 0.50 mM, to ethanol and CAD combined, or were non-treated controls. Ethanol at 100 mM was without effect. CAD alone at 10 mM and 1.0 mM was lethal by 1 dpf. Embryos exposed to 100 mM ethanol and 0.67 mM CAD exhibited cardiovascular and pigmentation defects and delayed hatching. Embryos exposed to 0.50 mM CAD alone had less severe cardiovascular problems as compared to the combined ethanol and CAD treatment. Taken together the results indicate that the combined effects of ethanol and CAD are greater than the individual effects and indicate the need to monitor effluents in fish nursery areas to protect natural fish populations.
LD50 Rat oral 3400 mg/kg|LD50 Mouse oral 200 mg/kg|LD50 Mouse ip 200 mg/kg|LD50 Mouse iv 75 mg/kg|For more Non-Human Toxicity Values (Complete) data for CINNAMALDEHYDE (8 total), please visit the HSDB record page.
Groups of 50 male and 50 female B6C3F1 mice were fed diets containing 1,000, 2,100, or 4,100 ppm microencapsulated trans-cinnamaldehyde for 2 years. Additional groups of 50 male and 50 female mice received untreated feed (untreated controls) or feed containing placebo microcapsules (vehicle controls). Dietary concentrations of 1,000, 2,100, or 4,100 ppm delivered average daily doses of approximately 125, 270, or 550 mg/kg to males and females. Survival of males in the 2,100 ppm group was less than that of the vehicle control group. Mean body weights of 2,100 and 4,100 ppm males and females were generally less than those of the vehicle controls throughout the study, and mean body weights of 1,000 ppm males were less after week 74. Feed consumption by exposed mice was similar to that by the vehicle controls. The incidences of olfactory epithelial pigmentation in 4,100 ppm males and in 2,100 and 4,100 females were significantly greater than those in vehicle controls. There were no neoplasms that were attributed to exposure to trans-cinnamaldehyde. /trans-Cinnamaldehyde/|Groups of 50 male and 50 female F344/N rats were fed diets containing 1,000, 2,100, or 4,100 ppm microencapsulated trans-cinnamaldehyde for 2 years. Additional groups of 50 male and 50 female rats received untreated feed (untreated controls) or feed containing placebo microcapsules (vehicle controls). Dietary concentrations of 1,000, 2,100, or 4,100 ppm delivered average daily doses of approximately 50, 100, or 200 mg/kg to males and females. Survival of 4,100 ppm males was greater than that of the vehicle controls. Mean body weights of 4,100 ppm males and females were generally less than those of the vehicle controls throughout the study. Feed consumption by 2,100 and 4,100 ppm males and 4,100 ppm females was less than that by the vehicle controls at the beginning and end of the study. There were no neoplasms or nonneoplastic lesions that were attributed to exposure to trans-cinnamaldehyde. /trans-Cinnamaldehyde/|trans-Cinnamaldehyde was mutagenic in S. typhimurium strain TA100 in the presence of induced mouse liver S9 activation enzymes only. All other strain and activation combinations, including the standard rat and hamster derived liver S9 fractions yielded negative results. trans-cinnamaldehyde induced sister chromatid exchanges in Chinese hamster ovary cells with and without induced rat liver S9 activation. No significant increase in the frequency of chromosomal aberrations occurred in Chinese hamster ovary cells cultured with trans-cinnamaldehyde, with or without induced rat liver S9. In tests for induction of germ cell genetic damage in male Drosophila melanogaster, trans-cinnamaldehyde induced a significant increase in the frequency of sex-linked recessive lethal mutations when administered by abdominal injection; however, no induction of reciprocal translocations occurred in germ cells of treated males. No increase in the frequency of micronucleated erythrocytes was observed in peripheral blood of male or female mice administered trans-cinnamaldehyde in dosed feed for 3 months. /trans-Cinnamaldehyde/|Groups of 10 male and 10 female F344/N rats were fed diets containing 4,100, 8,200, 16,500, or 33,000 ppm microencapsulated trans-cinnamaldehyde (equivalent to average daily doses of approximately 275, 625, 1,300, or 4,000 mg trans-cinnamaldehyde/kg body weight to males and 300, 570, 1,090, or 3,100 mg/kg to females) for 3 months. Additional groups of 10 male and 10 female rats received untreated feed (untreated controls) or feed containing placebo microcapsules (vehicle controls). All rats survived to the end of the study. Mean body weights of all exposed groups of males and 16,500 and 33,000 ppm females were significantly less than those of the vehicle controls, and 33,000 ppm males lost weight during the study. Feed consumption by exposed groups of males and females was less than that by the vehicle controls throughout the study. Clinical chemistry results of these studies indicated that trans-cinnamaldehyde administration, at the doses selected, induced an increase in serum bile acid concentration that suggests a hepatic effect in both male and female rats. Gross lesions observed at necropsy included multifocal to diffuse white nodules of the forestomach mucosa in 8,200 ppm or greater males and females. Increased incidences of nonneoplastic lesions of the forestomach included squamous epithelial hyperplasia in 8,200 ppm or greater males and females and chronic active inflammation in 33,000 ppm males and 16,500 and 33,000 ppm females. /trans-Cinnamaldehyde/|Groups of 10 male and 10 female B6C3F1 mice were fed diets containing 4,100, 8,200, 16,500, or 33,000 ppm microencapsulated trans-cinnamaldehyde (equivalent to average daily doses of approximately 650, 1,320, 2,550, and 5,475 mg/kg to males and 625, 1,380, 2,680, and 5,200 mg/kg to females) for 3 months. Additional groups of 10 male and 10 female mice received untreated feed (untreated controls) or feed containing placebo microcapsules (vehicle controls). One vehicle control male, one 4,100 ppm male, and one 33,000 ppm male died during the first week of the study due to inanition that resulted from difficulty with the feeder. Five 16,500 ppm and eight 33,000 ppm male mice died during weeks 2 and 3 due to unpalatability of the dosed feed. Mean body weights of all exposed groups of males and of females exposed to 8,200 ppm or greater were significantly less than those of the vehicle controls. Feed consumption by 16,500 and 33,000 ppm mice was less than that by the vehicle controls during weeks 1 and 2. The incidence of squamous epithelial hyperplasia of the forestomach mucosa in 33,000 ppm females was significantly increased, and olfactory epithelial degeneration of the nasal cavity occurred in 16,500 and 33,000 ppm males and females. /trans-Cinnamaldehyde/
The main component of Sri Lanka cinnamon bark oil (75%).|It has been identified in essential oils of: Ceylon and Madagascar cinnamon leaves, Ceylon, Seychelles, and Japanese (cinnamon laureirii) cinnamon bark, and in other cinnamon species in varying amt (0.1-76%) ... Also in essential oils of: hyacinth, myrrh, Bulgarian rose, patchouli, and others.|... Reported found in grapefruit, celery seed, clove bud and lemon balm (Melissa officinalis L).
Cinnamaldehyde's production and use in the flavor and perfume industry(1) may result in its release to the environment through various waste streams. Its use as a pesticide(2) will result in its direct release to the environement.(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a log Kow of 1.9(2) and a regression-derived equation(3), indicates that cinnamaldehyde is expected to have very high mobility in soil(SRC). Volatilization of cinnamaldehyde from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.89X10-2 mm Hg(4), and water solubility, 1,420 mg/L(5). Cinnamaldehyde is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data were not available(SRC, 2009).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a log Kow of 1.9(2) and a regression-derived equation(3), indicates that cinnamaldehyde is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.89X10-2 mm Hg(4), and water solubility, 1,420 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 290 hours and 91 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 8(SRC), from its log Kow (2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2009).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cinnamaldehyde, which has a vapor pressure of 2.89X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cinnamaldehyde 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 10 hours and 9.5 hours for the cis- and trans-isomers, respectively(SRC), calculated from its rate constant of 3.8X10-11 and 4.0X10-11 cu cm/molecule-sec at 25 °C for cis- and trans-isomers, respectively(SRC). Cinnamaldehyde does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of cinnamaldehyde with photochemically-produced hydroxyl radicals has been estimated as 3.8X10-11 and 4.0X10-11 cu cm/molecule-sec for the cis- and trans-isomers, respectively, at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 and 9.5 hours for cis- and trans-isomers, respectively, at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of cinnamaldehyde with ozone has been estimated as 1.7X10-18 and 3.4X10-18 cu cm/molecule-sec for cis- and trans-isomers, respectively, at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6.8 and 3.4 days for cis- and trans-isomers, respectively, at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Cinnamaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Cinnamaldehyde does not contain chromophores that absorb at wavelengths >290 nm(3)and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 8 was calculated in fish for cinnamaldehyde(SRC), using a log Kow of 1.9(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The Koc of cinnamaldehyde is estimated as 37(SRC), using a log Kow of 1.9(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cinnamaldehyde is expected to have very high mobility in soil.
The Henry's Law constant for cinnamaldehyde is estimated as 3.5X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 2.89X10-2 mm Hg(1), and water solubility, 1,420 mg/L(2). This Henry's Law constant indicates that cinnamaldehyde is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 290 hours (SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 91 days(SRC). Cinnamaldehyde's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Cinnamaldehyde is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
DRINKING WATER: Cinnamaldehyde was detected in tapwater from bank-filtered Rhine River water in The Netherlands at a maximum concentration 300 ng/L(1). Cinnamaldehyde was detected in drinking water after dune in-filtration and slow sand-filtration of polluted Rhine River water in The Netherlands, at concentrations greater than 10 mg/L(2).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 111,108 workers (43,381 of these were female) were potentially exposed to cinnamaldehyde in the US(1). Occupational exposure to cinnamaldehyde may occur through inhalation and dermal contact with this compound at workplaces where cinnamaldehyde is produced or used. Use and limited monitoring data indicate that the general population may be exposed to cinnamaldehyde via ingestion contaminated drinking water, and ingestion and dermal contact with this compound or other consumer products containing cinnamaldehyde(SRC).
Drug Information
Cinnamaldehyde is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.
/EXPL THER/ Cinnamonum zeylanicum (cinnamon) is widely used in traditional system of medicine to treat diabetes in India. The present study was carried out to isolate and identify the putative antidiabetic compounds ... Cinnamaldehyde was administered at different doses (5, 10 and 20 mg/kg bw) for 45 days to streptozotocin (STZ) (60 mg/kg bw)-induced male diabetic wistar rats. It was found that plasma glucose concentration was significantly (p<0.05) decreased in a dose-dependent manner (63.29%) compared to the control. In addition, oral administration of cinnamaldehyde (20 mg/kg bw) significantly decreased glycosylated hemoglobin (HbA(1C)), serum total cholesterol, triglyceride levels and at the same time markedly increased plasma insulin, hepatic glycogen and high-density lipoprotein-cholesterol levels. Also cinnamaldehyde restored the altered plasma enzyme (aspartate aminotransferase, alanine aminotransferase, lactate dehydrogenase, alkaline phosphatase and acid phosphatase) levels to near normal. Administration of glibenclamide, a reference drug (0.6 mg/kg bw) also produced a significant (p < 0.05) reduction in blood glucose concentration in STZ-induced diabetic rats. The results of this experimental study indicate that cinnamaldehyde possesses hypoglycemic and hypolipidemic effects in STZ-induced diabetic rats.
The probable oral lethal dose for humans is 0.5 to 5 g/kg for a 70-kg person. Both the oil and pure aldehyde are irritants, especially if undiluted. They can also cause inflammation and erosion of gastrointestinal mucosa. Prolonged skin contact (more than 48 hr) can produce superficial partial thickness burns|3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)|Agents that reduce the frequency or rate of spontaneous or induced mutations independently of the mechanism involved. (See all compounds classified as Antimutagenic Agents.)|Substances added to foods and medicine to improve the taste. (See all compounds classified as Flavoring Agents.)
Cinnamaldehyde is 52% absorbed through the skin and shown to be rapidly absorbed from the gut.|Cinnamaldehyde is metabolized and excreted primarily in the urine and, to a minor extent, in the feces. After oral or intraperitoneal administration to rats and mice, 69–98% of the dose of cinnamaldehyde was recovered in the urine and feces within 24 h.|The bioavailability of microencapsulated cinnamaldehyde (CNMA) was investigated in male F344 rats. Rats were gavaged with CNMA in corn oil using either microencapsulated or the neat chemical at doses of 50, 250, and 500 mg/kg. No differences between the two formulations at any of the doses were found in either CNMA blood concentration profiles or in the rate of urinary hippuric acid excretion. Both formulations showed a low bioavailability (< 20%) at 250 and 500 mg/kg. Regardless of the formulation used, oral gavage of CNMA significantly increased the urinary excretion of hippuric acid. About 75% of the dose of CNMA was metabolized to hippuric acid and recovered in the urine. The total amount of hippuric acid recovered in a 50-hr urinary collection correlated well with the CNMA dose. The data suggest that there was complete release of CNMA from the microcapsules and that microencapsulation of CNMA does not affect its bioavailability or its metabolism ...|/Cinnamaldehyde is/ presumably oxidized in vivo to cinnamic acid, which is excreted in urine as benzoic and hippuric acids.|After ip admin of cinnamic aldehyde to rats, urinary thio ether excretion amounted to 6.5% of dose.|Cinnamaldehyde administered intraperitoneally to a rabbit was excreted in the urine as cinnamic acid, cinnamoylglycine, benzoic acid and hippuric acid.|For more Absorption, Distribution and Excretion (Complete) data for CINNAMALDEHYDE (7 total), please visit the HSDB record page.
The metabolism of trans-[3-14C]cinnamaldehyde was investigated in male and female Fischer 344 rats and CD1 mice at doses of 2 and 250 mg/kg bw given by ip injection and in males at 250 mg/kg by oral gavage. Some 94% of the administered dose was recovered in the excreta in 72 hr in both species with most (75-81%) present in the 0-24-hr urine. Less than 2% of the administered dose was found in the carcasses at 72 hr after dosing. Urinary metabolites were identified by their chromatographic characteristics. In both species the major urinary metabolite was hippuric acid accompanied by 3-hydroxy-3-phenylpropionic acid, benzoic acid and benzoyl glucuronide. The glycine conjugate of cinnamic acid was formed to a considerable extent only in the mouse. The oxidative metabolism of cinnamaldehyde essentially follows that of cinnamic acid, by beta-oxidation analogous to that of fatty acids. Apart from the metabolites common to cinnamic acid and cinnamaldehyde, 7% of 0-24-hr urinary 14C was accounted for by two new metabolites in the rat and three in the mouse, which have been shown in other work to arise from a second pathway of cinnamaldehyde metabolism involving conjugation with glutathione. The excretion pattern and metabolic profile of cinnamaldehyde in rats and mice are not systematically affected by sex, dose size and route of administration. The data are discussed in terms of their relevance to the safety evaluation of trans-cinnamaldehyde, particularly the validity or otherwise of extrapolation of toxicity data from high to low dose. /trans-Cinnamaldehyde/|To evaluate the extent of cinnamaldehyde and cinnamic alcohol metabolism in human skin and provide evidence for the role of cutaneous alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) in such metabolism ... the extent of cinnamic alcohol and aldehyde metabolism was investigated in human skin homogenates and sub-cellular fractions ... Studies were conducted in the presence and absence of the ADH/cytochrome P450 inhibitor 4-methylpyrazole and the cytosolic ALDH inhibitor, disulfiram. Differential metabolism of cinnamic alcohol and cinnamaldehyde was observed in various subcellular fractions: skin cytosol was seen to be the major site of cinnamic compound metabolism. Significant metabolic inhibition was observed using 4-methylpyrazole and disulfiram in whole skin homogenates and cytosolic fractions only ... This study has demonstrated that cutaneous ADH and ALDH activities, located within defined subcellular compartments, play important roles in the activation and detoxification of CAlc and CAld in skin ...|Cinnamaldehyde administered intraperitoneally to a rabbit was excreted in the urine as cinnamic acid, cinnamoylglycine, benzoic acid and hippuric acid.|Identification of 2 sulfur containing urinary metabolites of cinnamic aldehyde in rat which are 3-S-(N-acetylcysteinyl)-3-phenylpropyl alcohol and 3-S-(N-acetylcysteinyl)-3-phenylpropionic acid.|For more Metabolism/Metabolites (Complete) data for CINNAMALDEHYDE (6 total), please visit the HSDB record page.|Cinnamaldehyde is a known human metabolite of cinnarizine.
SYMPTOMS: Symptoms of exposure to this compound may include inflammation and erosion of gastrointestinal mucous. ACUTE/CHRONIC HAZARDS: Exposure to this chemical may cause irritation of the skin, eyes, upper respiratory tract and mucous membranes. (NTP, 1992)|SYMPTOMS: Symptoms of exposure to this compound may include inflammation and erosion of gastrointestinal mucosa. The vapor or mist causes irritation of the eyes, mucous membranes and upper respiratory tract. ACUTE/CHRONIC HAZARDS: This chemical may be harmful by inhalation, ingestion or skin absorption. It may cause irritation of the skin, eyes, upper respiratory tract, and mucous membranes. When heated to decomposition it may emit toxic fumes of carbon monoxide and carbon dioxide. (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)
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aldehydes and Related Compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Aggressive airway management may be necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and treat if necessary ... . Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aldehydes and Related Compounds/|/SRP:/ Advanced treatment: Consider Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Intubation should be considered at the first sign of upper airway obstruction caused by edema. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . 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 ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aldehydes and Related Compounds/
/HUMAN EXPOSURE STUDIES/ The objective of this study was to determine the frequency of reactivity to a series of commonly used fragrances in dermatological patients. A total of 48 fragrances (FF) were chosen ... In a pilot study on a total of 1069 patients in 11 centers, the appropriate test concentration and vehicle were examined. For most fragrances, 1% and 5% were chosen, and petrolatum proved to be the best vehicle ... In the main study, a set of 5 to 10 fragrances at 2 concentrations was patch tested in each center on a minimum of 100 consecutive patients seen in the patch test clinic. These patients were also patch tested to a standard series with the 8% fragrance mix (FM) and its 8 constituents. In patients with a positive reaction to any of the 48 FF, a careful history with regard to past or present reactions to perfumed products was taken. A total of 1323 patients were tested in 11 centers. The 8% FM was positive in 89 patients (8.3% of 1072 patients). Allergic reactions to the constituents were most frequent to oak moss (24), isoeugenol (20), eugenol (13), cinnamic aldehyde (10) and geraniol (8) ...|/HUMAN EXPOSURE STUDIES/ ... The skin response to serial dilution patch tests and 6-week graded use tests with 0.02, 0.1 and 0.8% cinnamic aldehyde in ethanol was studied in a group of cinnamic-aldehyde-sensitive eczema patients. The minimum effect level demonstrated was 0.02% cinnamic aldehyde on patch testing and 0.1% cinnamic aldehyde on use testing, which are allowed usage concentrations in different kind of cosmetics. 72% (13/18) developed eczema in the use test performed with an alcoholic solution of cinnamic aldehyde on healthy upper arm skin. 6 of the 13 use-test-positive subjects (46%) reacted later than day 7, indicating that the standard exposure period of 7 days in use testing may not be sufficient, if low concentrations or volatile substances are used. A significant correlation between patch test sensitivity and the outcome of use testing was found (1, < 0.001), which should be considered in designing future use test studies and advising patients. Detailed exposure information is needed to evaluate more fully the consequences of cinnamic aldehyde sensitivity.|/HUMAN EXPOSURE STUDIES/ The authors followed the frequency of fragrance contact sensitization in Hungary in a multicentre study in the years 1998 and 1999. A total of 3,604 patients were tested with fragrance mix (FM), and positive reactions were observed in 294 (8.2%). In 160 FM hypersensitive patients, the study was continued with patch testing of the mix constituents (cinnamic alcohol, cinnamic aldehyde, eugenol, amyl cinnamic aldehyde, hydroxycitronellal, geraniol, isoeugenol, oak moss absolute). Of the patients tested, 70.6% produced positive reactions to the constituents. FM contact sensitization was mainly observed in female patients (74.4%). The incidence of contact urticaria in FM hypersensitive patients was 6.1%. Simultaneous patch test trials of other environmental contact allergens, in both early and late evaluations, mainly confirmed hypersensitivity reactions to balsams. Female dominance of hypersensitivity reactions observed during testing the individual components of the mix was striking (82.4%). In positive skin reactions, cinnamic alcohol, isoeugenol and oak moss provoked skin symptoms most frequently ...|/HUMAN EXPOSURE STUDIES/ ... The records of patients patch tested to the European standard series/were analyzed retrospectively/ during the 15-yr period 1984-98 for positive reactions to Fragrance Mix I (FM I). In a subset of patients tested to the constituents of FM I, positive reactions to cinnamal, cinnamic alcohol, isoeugenol and eugenol were sought. Data were analysed using 2x2 contingency tables (Fisher's exact test). During this period, 23,660 patients were tested to the European standard series, of whom 1811 (7.7%) had positive reactions to FM I. Of the 1112 patients tested to the constituents of FM I, 934 had positive reactions to at least one constituent (total 1324 positive reactions to constituents). Of these 934, 826 also had positive reactions to FM I itself; 108 were negative to FM I but reacted to one or more of its constituents. One hundred and seventy-eight patients did not react to any of the breakdown constituents of FM I; 34 of these had positive reactions to FM I itself. Of 139 patients allergic to cinnamic alcohol, 87 were also allergic to cinnamal (63%), compared with 108 (11.1%) of 973 cinnamic alcohol-negative patients (P < 0.00001) ...|For more Human Toxicity Excerpts (Complete) data for CINNAMALDEHYDE (18 total), please visit the HSDB record page.
3-phenyl-2-propenal
Cinnamaldehyde Use and Manufacturing
For the synthesis, only the base-catalyzed condensation of benzaldehyde with acetaldehyde has been adopted on an industrial scale.|Cinnamaldehyde has been efficiently isolated in high purity by fractional distillation from cassia and cinnamon bark essential oils.|Preparation by condensation of benzaldehyde and acetaldehyde.|... Oxidation of cinnamyl alcohol
Cinnamaldehyde is a naturally occurring organic compound primarily responsible for the flavor and aroma of cinnamon. In the food and beverage industry, cinnamaldehyde is extensively used as a flavoring agent in products such as candies, baked goods, chewing gum, and beverages due to its warm, spicy-sweet profile. In perfumery and cosmetics, it serves as a fragrance component in soaps, lotions, and perfumes. Cinnamaldehyde also exhibits antimicrobial and antifungal properties, making it valuable in pharmaceutical and personal care formulations. Additionally, it is employed as a corrosion inhibitor in metalworking fluids and as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agricultural chemicals, and polymers. In agriculture, it is used as a natural pesticide and fungicide due to its bioactivity against a broad spectrum of pests and pathogens.
1,000,000 - 10,000,000 lb|(1972) 7.11X10+8 G|(1973) 8.0X10+8 GRAMS|2-Propenal, 3-phenyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#820]|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#821]
Greater than 95% of the consumption of cinnamaldehyde occurs in flavor applications where a spicy, cinnamon character is required.
Perfume grade, FCC, 98% min purity.|Chief ingredient (up to 90%) of oil of cinnamon.|Cinnacure A3005; Active ingredient 30.00% Cinnamaldehyde|Cinnacure Ready to Use; Active ingredient 0.255% Cinnamaldehyde
All other basic organic chemical manufacturing|2-Propenal, 3-phenyl-: ACTIVE|Controls/repels a variety of pests including aphids, sharpshooter aphids, mites, spider mites (including two-spotted mites, Pacific mites and Williamette mites), leafhoppers, whiteflies (including sifverleaf and greenhouse), thrips (including western flower), algae, moss, and liverworts/hornworts/pearlworts. /Cinnacure A3005/|Method of purification: rectification
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Denaturant
Flavoring Agents
Computed Properties
Molecular Weight:132.16
XLogP3:1.9
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:132.057514874
Monoisotopic Mass:132.057514874
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:121
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Analgesic, anti-inflammatory, detumescence
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