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Cinnamaldehyde information


Cinnamaldehyde
Skeletal formula of cinnamaldehyde
Ball-and-stick model of the cinnamaldehyde molecule
sample
Names
Preferred IUPAC name
(2E)-3-Phenylprop-2-enal
Other names
  • Cihinnamaldehyde
  • Cinnamal
  • Cinnamic aldehyde
  • trans-Cinnamaldehyde
Identifiers
CAS Number
  • 14371-10-9 ☒N
3D model (JSmol)
  • Interactive image
3DMet
  • B00198
Beilstein Reference
1071571
ChEBI
  • CHEBI:16731 checkY
ChEMBL
  • ChEMBL293492 checkY
ChemSpider
  • 553117 checkY
DrugBank
  • DB14184
ECHA InfoCard 100.111.079 Edit this at Wikidata
EC Number
  • 203-213-9
IUPHAR/BPS
  • 2423
KEGG
  • C00903 checkY
PubChem CID
  • 637511
RTECS number
  • GD6475000
UNII
  • SR60A3XG0F checkY
CompTox Dashboard (EPA)
  • DTXSID6024834 Edit this at Wikidata
InChI
  • InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+ checkY
    Key: KJPRLNWUNMBNBZ-QPJJXVBHSA-N checkY
  • InChI=1/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
    Key: KJPRLNWUNMBNBZ-QPJJXVBHBH
SMILES
  • c1ccc(cc1)/C=C/C=O
Properties
Chemical formula
C9H8O
Molar mass 132.16 g/mol
Appearance Yellow oil
Odor Pungent, cinnamon-like
Density 1.0497 g/mL
Melting point −7.5 °C (18.5 °F; 265.6 K)
Boiling point 248 °C (478 °F; 521 K)
Solubility in water
Slightly soluble
Solubility
  • Soluble in ether, chloroform
  • Insoluble in petroleum ether
  • Miscible with alcohol, oils
Magnetic susceptibility (χ)
−7.48×10−5 cm3/mol
Refractive index (nD)
1.6195
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H317, H319, H335
Precautionary statements
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
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 71 °C (160 °F; 344 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
3400 mg/kg (rat, oral)
Related compounds
Related compounds
Cinnamic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Cinnamaldehyde is an organic compound with the formula or C₆H₅CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor.[1] It is a phenylpropanoid that is naturally synthesized by the shikimate pathway.[2] This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde.[3] Cinnamaldehyde decomposes to styrene because of oxidation as a result of bad storage or transport conditions. Styrene especially forms in high humidity and high temperatures. This is the reason why cinnamon contains small amounts of styrene.[4]

  1. ^ "Cinnamon". Transport Information Service. Gesamtverband der Deutschen Versicherungswirtschaft e.V. Retrieved 2007-10-23.
  2. ^ Gutzeit, Herwig (2014). Plant Natural Products: Synthesis, Biological Functions and Practical Applications. Wiley. pp. 19–21. ISBN 978-3-527-33230-4.
  3. ^ PubChem. "Cinnamaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-10-18.
  4. ^ "High daily intakes of cinnamon: Health risk cannot be ruled out" (PDF). Federal Institute for Risk Assessment (BfR). 18 August 2006. Archived (PDF) from the original on 7 March 2022. Retrieved 20 May 2022.

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Cinnamaldehyde

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Hexyl cinnamaldehyde

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Hexyl cinnamaldehyde (hexyl cinnamal) is a common additive in the perfume and cosmetic industry as aroma substance. It is found naturally in the essential...

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Cinnamon

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of cinnamon derive from its essential oil and principal component, cinnamaldehyde, as well as numerous other constituents including eugenol. Cinnamon...

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flavor component in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent. It is also found in wood from all species...

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benzaldehyde is produced from cinnamaldehyde obtained from cassia oil by the retro-aldol reaction: the cinnamaldehyde is heated in an aqueous/alcoholic...

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Aldehyde

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(5) glucose (pyranose form as α-D-glucopyranose), (6) the flavorant cinnamaldehyde, (7) retinal, which forms with opsins photoreceptors, and (8) the vitamin...

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Cinnamyl alcohol

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industrial demand is usually fulfilled by chemical synthesis starting from cinnamaldehyde. The compound is a solid at room temperature, forming colourless crystals...

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Hydrocinnamaldehyde

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with the formula C6H5CH2CH2CHO. It is produced by the hydrogenation of cinnamaldehyde. The compound is used in many mechanistic studies. It is a common substrate...

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Cinnamon challenge

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and mucous membranes in cinnamon. As cinnamon is rich in the compound cinnamaldehyde that can irritate skin and tissues, the challenge often results in considerable...

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Coniferyl aldehyde

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compound with the formula HO(CH3O)C6H3CH=CHCHO. It is a derivative of cinnamaldehyde, featuring 4-hydroxy and 3-methoxy substituents. It is a major precursor...

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Saigon cinnamon

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genus as both. Saigon cinnamon has 1-5% essential oil content and 25% cinnamaldehyde in essential oil. Consequently, among the species, Saigon cinnamon commands...

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Curry tree

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Compounds found in curry tree leaves, stems, bark, and seeds include cinnamaldehyde, and numerous carbazole alkaloids, including mahanimbine, girinimbine...

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Cinnamonitrile

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conditions, an elimination reaction of various oximes derived from cinnamaldehyde, and oxidative coupling of benzene to acrylonitrile. "Cinnamonitrile"...

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Cinnamomum osmophloeum

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It is native to broad-leaved forests of central and northern Taiwan. Cinnamaldehyde, an essential oil extracted from C. osmophloeum, has numerous commercial...

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Cinnamomum cassia

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compounds found in the bark, powder and essential oils of C. cassia are cinnamaldehyde and styrene. In high doses, these substances can also be toxic to humans...

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Laundry detergent

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their esters (linalyl acetate), aromatic aldehydes (helional, hexyl cinnamaldehyde, lilial) and synthetic musks (galaxolide). Worldwide, while liquid and...

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Thyme

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Cannabichromene (cannabis) Cannabidiol (cannabis) Cannabigerol (cannabis) Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile)...

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Onion

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Cannabichromene (cannabis) Cannabidiol (cannabis) Cannabigerol (cannabis) Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile)...

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Oil of clove

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constituents phenylpropanoids (primarily eugenol), carvacrol, thymol, and cinnamaldehyde, with smaller quantities of polyphenols, carbohydrates, lipids, oleanolic...

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Cinnamomum citriodorum

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It has a characteristic smell of lemon grass. C. citriodorum has 45% Cinnamaldehyde compared to 80% for C. cassia. de Kok, R. (2021). "Cinnamomum citriodorum"...

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Stomatitis

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that may cause allergic contact stomatitis in some individuals include cinnamaldehyde, Balsam of Peru, peppermint, mercury, gold, pyrophosphates, zinc citrate...

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Sinapaldehyde

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compound with the formula HO(CH3O)2C6H2CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents...

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Paracetamol

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Coumarin

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flavor is generally cassia bark steam-distilled to concentrate the cinnamaldehyde, for example, to about 93%. Clear cinnamon-flavored alcoholic beverages...

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C9H8O

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Acrylophenone, an organic compound Benzopyran, a polycyclic organic compound Cinnamaldehyde, an organic compound with the formula C6H5CH=CHCHO 1-Indanone, the organic...

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Formaldehyde

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