Cinnamaldehyde

Cinnamaldehyde Basic information
Product Name:Cinnamaldehyde
Synonyms:abionca;Acrolein, 3-phenyl-;Aldehyd skoricovy;aldehydskoricovy;Benzylideneacetaldehyde;beta-phenylacrolein;beta-phenylcrolein;(E)-3-phenylprop-2-enal
CAS:104-55-2
MF:C9H8O
MW:132.16
EINECS:203-213-9
Product Categories:chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Aromatic Aldehydes & Derivatives (substituted);Alphabetical Listings;C-DFlavors and Fragrances;Certified Natural Products;Flavors and Fragrances;Pharmaceutical Intermediates;Cosmetics;104-55-2
Mol File:104-55-2.mol
Cinnamaldehyde Structure
Cinnamaldehyde Chemical Properties
Melting point −9-−4 °C(lit.)
Boiling point 248 °C (lit.)
density 1.05 g/mL at 25 °C (lit.)
vapor density 4.6 (vs air)
vapor pressure <0.1 hPa (20 °C)
FEMA 2286 | CINNAMALDEHYDE
refractive index n20/D 1.622(lit.)
Fp 160 °F
storage temp. Store below +30°C.
solubility 1g/l soluble
form Liquid
pka0[at 20 ℃]
color Clear yellow
Specific Gravity1.05
OdorStrong odor of cinnamon
Odor Typespicy
Water Solubility Slightly soluble
Merck 13,2319
JECFA Number656
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
InChIKeyKJPRLNWUNMBNBZ-QPJJXVBHSA-N
LogP1.83-2.1 at 25-27℃
CAS DataBase Reference104-55-2(CAS DataBase Reference)
NIST Chemistry ReferenceCinnamylaldehyde(104-55-2)
EPA Substance Registry SystemCinnamaldehyde (104-55-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38-43
Safety Statements 26-36/37
RIDADR UN8027
WGK Germany 3
RTECS GD6476000
10-23
HS Code 29122900
Hazardous Substances Data104-55-2(Hazardous Substances Data)
ToxicityLD50 in rats (mg/kg): 2220 orally (Jenner)
MSDS Information
ProviderLanguage
Cinnamaldehyde English
SigmaAldrich English
ACROS English
ALFA English
Cinnamaldehyde Usage And Synthesis
DescriptionCinnamic aldehyde is used as a flavoring agent, ingredient of fragrance in soft drinks, ice creams, dentifrices, pastries, chewing-gum, etc. It can induce both contact urticaria and delayed-type reactions. It can be implicated in contact dermatitis in those who work in the perfume industry or food handlers. Cinnamic aldehyde is contained in the "fragrance mix".
Chemical PropertiesCinnamaldehyde exists as yellowish to greenish-yellow oily liquid with a Strong pungent, spicy, cinnamon odor. It is normally insoluble in water and many organic solvents but is miscible with alcohol and other flavoring oils. Exposure to air will result in thickening and oxidation.
Cinnamaldehyde
Cinnamaldehyde (cinnamic aldehyde, benzylideneactaldehyde, phenylacrolein, 3-phenylpropenal, 3-phenyl-2-propenal) is a saturated aldehyde with an aromatic ring that is a yellowish, oily liquid at room temperature. It is used as a flavoring and aromatic agent in a variety of food products, perfumes, and household products. It has also seen use as a rubber reinforcing agent. A burning taste that produces the odor and flavor of the spice may be found with this aromatic aldehyde. Cinnamaldehyde has also been used as an attractant for insect control, in the preparation of corrosion inhibitors, and as a coating for metals. Although extensively used in industry, it is also a natural constituent of cinnamon leaves and bark, some essential oils, and other plant products.

OccurrenceReported found in celery seed, cinnamon, cinnamon leaf, cassia leaf, clove stem and lemon balm.
UsesCinnamaldehyde is used in flavor and perfumes.It occurs in cinnamon oils.
UsesCinnamic aldehyde is a common ingredient in perfumes for household products like deodorizers, detergents, and soap; flavor in toothpaste, sweets, ice cream, soft drinks, chewing gums, and cakes; in balsam of Tolu and Peru, hyacinth plant, spices, cinnamon, Ceylon and cassia oil; some perfumery uses (Canoe; hyacinth; bubblegum; Balsam; Cassia); natural occurrence (cinnamon).
UsesIn the flavor and perfume industry.
DefinitionChEBI: (E)-cinnamaldehyde is the E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes. It has a role as a hypoglycemic agent, an EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor, a vasodilator agent, an antifungal agent, a flavouring agent, a plant metabolite and a sensitiser. It is a 3-phenylprop-2-enal and a member of cinnamaldehydes.
Aroma threshold valuesDetection at 50 to 750 ppb.
Taste threshold valuesTaste characteristics at 0.5 ppm: spicy, cinnamon and cinnamon bark.
General DescriptionYellow oily liquid with a cinnamon odor and sweet taste.
Air & Water ReactionsThickens on exposure to air. May be unstable to prolonged exposure to air. Slightly water soluble .
Reactivity ProfileCinnamaldehyde reacts with sodium hydroxide owing to aerobic oxidation.
Health HazardCinnamaldehyde can cause moderate to severeskin irritation. Exposure to 40 mg in48 hours produced a severe irritation effecton human skin. The toxicity of this compoundwas low to moderate on test subjects,depending on the species and the toxicroutes. However, when given by oral routein large amounts, its poisoning effect wassevere. Amounts greater than 1500 mg/kghave produced a wide range of toxic effectsin rats, mice, and guinea pigs. The symptomswere respiratory stimulation, somnolence,convulsion, ataxia, coma, hypermotility, anddiarrhea.
LD50 value, oral (guinea pigs): 1150 mg/kg
Cinnamaldehyde is a mutagen. Its carcinogeniceffect is not established.

Fire HazardCinnamaldehyde is combustible.
Agricultural UsesFungicide, Insecticide: Used as an antifungal agent, corn rootworm attractant, and dog and cat repellent. Can be used on soil casing for mushrooms, row crops, turf and all food commodities. Not listed for use in EU countries.
Trade nameADIOS®; ZIMTALDEHYDE®; ZIMTALDEHYDE® LIGHT
Contact allergensThis perfumed molecule is used as a fragrance in perfumes, a flavoring agent in soft drinks, ice creams, dentifrices, pastries, chewing-gum, etc. It can induce both contact urticaria and delayed-type reactions. It can be responsible for dermatitis in the perfume industry or in food handlers. Cinnamic aldehyde is contained in “fragrance mix.” As a fragrance allergen, it has to be mentioned by name in cosmetics within the EU.
Anticancer ResearchThis is promising in antitumor activity against NSCLC cells. The cells were inducedin apoptosis and also the epithelial-mesenchymal transition was reversed affectingthe Wnt/b-catenin pathway (Bouyahya et al. 2016).
Safety ProfilePoison by intravenous and parenteral routes. Moderately toxic by ingestion and intraperitoneal routes. A severe human skin irritant. Mutation data reported. Combustible liquid. May ipte after a delay period in contact with NaOH. When heated to decomposition it emits acrid smoke and fumes. See also ALDEHYDES.
SynthesisBy isolation from natural sources; synthetically, by condensation of benzaldehyde with acetaldehyde in the presence of sodium or calcium hydroxide.
Potential ExposureBotanical fungicide and insecticide. Used as an antifungal agent, corn rootworm attractant, and dog and cat repellent. Can be used on soil casing for mushrooms, row crops, turf, and all food commodities. Not listed for use in EU countries.
ShippingUN1989 Aldehydes, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid
IncompatibilitiesAldehydes are frequently involved in selfcondensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. 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. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, ketones, azo dyes, caustics, boranes, hydrazines
Waste DisposalIncineration. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.
alpha-Methylcinnamic acid ALPHA-BROMO-1,1-DIMETHOXY-CINNAMALDEHYDE CINNAMALDEHYDE,3,4,5-TRIMETHOXY- alpha-Hexylcinnamaldehyde 4-Fluorocinnamaldehyde 1-Nonanal 3,4-dihydro-5,6,7-trimethoxy-2-naphthoic acid 1,1-dimethoxy cinnamaldehyde 2,5-Dimethyl-3,4-diphenylcyclopentadienone PHENYL RESIN CinnamicAldehyde(Cinnamaldehyde) 2-(Benzoylamino)cinnamaldehyde Cinnamaldehyde diphenyl hydrazone ALPHA-BROMO-ETHYLENE GLYCOL CINNAMALDEHYDE PHENYL VALERATE β-Methyl-cis-cinnamaldehyde A-BROMO-ETHYLENE GLYCOL CINNAMALDEHYDE Cinnamaldehyde tosylhydrazone

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