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Cinnamaldehyde

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Cinnamaldehyde
Cinnamaldehyde new.png800px-Cinnamaldehyde-3D-pi-MO.png
General
Systematic name (E)-3-phenyl-2-propenal
Other names

Cinnamic aldehyde
trans-cinnamaldehyde

Molecular formula C9H8O
SMILES C1COC(O1)C=CC2=CC=CC=C2
Molar mass Molar mass::132.16 g/mol
Appearance Yellow oil
CAS number CAS number::104-55-2
Properties
Density and phase Density::1.05 g/ml, ?
Solubility in water 1.42 mg/100 ml (25°C)
Melting point Melting point::-7.5 °C
Boiling point Boiling point::248 °C
Acidity (pKa) 5.0 max
Viscosity 510 K to cP at 1130 K°C
Dipole moment 0.58 D
Hazards
MSDS Material safety data sheet
Main hazards Corrosive
NFPA 704

NFPA 704 svg.png

2
2
0
Flash point 71°C
R/S statement R: R36 R37 R38
S: S26 S36
RTECS number GD6475000
Related compounds
Related compounds Cinnamic acid
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Cinnamaldehyde is the organic compound that gives cinnamon its flavor and odor (also known as cinnamic aldehyde) The spice of Cinnamon is from the dried bark of the evergreen tree Cinnamomum zeylanicum which grows in South India. The bark of the trees is called "Ceylon cinnamon" or "true cinnamon". [1] Its molecular formula was determined in 1834 by French chemists Jean Baptiste André Dumas (1800–1884) and Eugène Melchior Péligot (1811–1890).

Primary uses of Cinnamaldehyde are food flavoring and a medical herb. It has been used for centuries to treat variety of disorders. Cinamaldehyde was mentioned in Chinese medical books which name is Tang Materia Medica. [2]

Properties

Chemical structure of Cinnamaldehyde

Cinnamaldehyde is a yellow oily liquid only a little stickier than water. It strongly smells like cinnamon. This compound is the main source of cinnamon oil that can be produced from [distillation]. Concentrated cinnamaldehyde can be harmful to your skin. Chemical is irritant when is in large doses. Both aromatic and an aldehyde, cinnamaldehyde has a mono-substituted [benzene] ring. A conjugated double bond (alkene) makes geometry of the compound planar. The molecule is in a phenyl group that is tied to an unsaturated aldehyde. The molecule can also be shown as a derivative of acrolein. Its melting point is -8.00 to -6.00 °C. @ 760.00 mm Hg and a boiling point of 249.00 to 252.00 °C. @ 760.00 mm Hg. In the Cinnamomum zeylanicum tree, Cinnamaldehyde makes up to 1 to 4 percent of essential oil.[3] Dumas and Péligot isolated Cinnamaldehyde from Cinnamon essential oil in 1834. The trans-cinnamaldehyde is a natural product. Its color is due to π → π* transition.[4]

Occurrences

Cinnamon Fern Osmunda cinnamonea at the Norfolk Botanical Garden

[5] Cinnamon is widely known and been used for many years Cinnamaldehyde can be synthetically made, but it is usually obtained from distillation of the oil of cinnamon bark and is much more efficient and fast. Cinnamaldehyde was made by dosing the bark of the Cinnamomum zeylanicum tree with steam. The natural Cinnamaldehyde which is from nature is called trans-cinnamaldehyde. the molecule is made of a phenyl group attached to an unsaturated aldehyde. [3] Cinnamic aldehyde is the main component of Cinnamaldehyde.

It can be produced from the synthesis of the related compounds like cinnamyl alcohol and the condensation of benzaldehyde and acetaldehyde. Cinnamaldehyde is a benzene ring substituent acrylic aldehyde having a carbon. The aldehyde melts in the steam and can be pulled out as the steam cools and condenses to form into cold water and in doing so, the compound becomes much less soluble. Benzaldehyde (C6H5CHO) and Acetaldehyde (CH3CHO) can have Cinnamaldehyde to be synthesized. The two compounds compress with the removal of water to form form cinnamaldhyde.[5]

Synthesis There are several ways of laboratory synthesis to obtain the compound. The compound can be produced from related compounds like cinnamyl alcohol. [6]

Biosynthesis Cinnamaldehyde takes place widely and closely related compounds give rise to lignin. Almost all compounds are biosynthesized starting from [phenylalanine], and then it endures conversion to cinnamoyl ester of coenzyme A. [6]

Uses

Cinnamon

Cinnamon has been known for many years and been used in many countries. It is mostly used as spices and according to Biblical times, it was also used for bed and perfume. The fragrance f cinnamon is also believed to be used by Egyptians for processing mummies. The Romans also considered the spice very valuable. The Roman Emperor, Neo burned a year supply of the spices on his wife's funeral. The Cinnamon is also used in medical world. Cinnamon is believed to treat diarrhea and arthritis.[7] The Cinnamaldehyde, in predominant form, is used as favoring in chewing gum, ice cream, and beverages. The aldehyde melts in the steam and can be pull out as the steam cools and condenses to form into cold water in doing that compound become much less soluble. [1]

As an agrichemical and a antimicrobial

Cinnamaldehyde is also being used in fungicide. It is scientificly proven that it affects on more than 40 crops. It is also known to be very effective on insecticide for mosquitoes. As an amount of 29 ppm of cinnamaldehyde kills half of Aedes aegypti mosquito larvae in 24 hours. Also, University of Illinois at Chicago found that Cinnamic aldehyde is antimicrobial. When it is used in Big Red, it prevents your oral from bacterial growt above 50 percent. It especially is effective of preventing bacteria from tongue. The recent research also found the fact that cinnamaldehyde/cinnamic aldehyde shows anti-cancer activity. [8]

As a flavorant

Cinnamaldehyde is used in perfume to create fruit scents. Cinnamon odor is also needed to put smells in soaps and household products. The laurel plant family includes the cinnamon tree. [5]


Miscellaneous uses

Cinnamaldehyde can also be used as a corrosion inhibitor metal and other ferrous alloys in corrosive fluids. It is also known to combine two components solvents and other surfactants.[4]

Derivatives of cinnamaldehyde

Many of derivatives of cinnamaldehyde could commercially be useful. Dihydrocinnamic alcohol which is naturally produced by hydrogenation of cinnamaldehyde is being used to consult smell of hyacinth and lilac. Cinnamic alcohol also occurs naturally, but has the smell of lilac. The chosen hydrogenation of the alkene subunit can produce Dihydrocinnamaldehyde. α-Amyl- and α-hexylcinnamaldehyde are important smell but are not sufficient for Cinnamaldehyde. [6]

Other

This morning's breakfast: Numerous supplements + organic Scottish oatmeal with cinnamon, no sugar, (not pictured, non fat milk) and herb tea, no sugar.

Cinnamaldehyde is non toxic, but it can irritate your skin if in contact for too long.[9] Cinnamon capsules are sold as food supplements or as dietetic foods to reduce blood sugar levels in type II Diabetes mellitus, a serious chronic disease. Doctors recommend only a daily long-term dose of the product, although safety of of a cinnamon dose of this amount has not yet been demonstrated. The cinnamon that is thought to reduce the blood sugar has not been proven yet. However, Federal Institute for Risk Assessment was asked for a research. Small amounts of Cinnamaldehyde has been used for a long time as a spice without any reports of hazards. cassia cinnamon Ceylon cinnamon hardly has any coumarin which can cause you liver problem when digested in a large amount. [9]

References

  1. 1.0 1.1 Cinnamaldehyde by Thomson Learning, book Raggs, 2008.
  2. Cinnamaldehyde (040506) Fact Sheet by unknown Author, Ombudsman, Biopesticides and Pollution Prevention Division, February 16, 2011.
  3. 3.0 3.1 CINNAMALDEHYDE: The smell and flavour of cinnamon by Paul M. Burnham, Hillsborough College, Sheffield, Uk, in unknown Date.
  4. 4.0 4.1 eNote by Unknown author, eNote, 2011.
  5. 5.0 5.1 5.2 Cinnamaldehyde by Unknown Author, Chemicalland21, Unknown date.
  6. 6.0 6.1 6.2 Cinnamaldehyde by Unknown author, Wikipedia, 2 March 2011.
  7. CINNAMALDEHYDE by Paul M. Burnham, by Hillsborough College, Sheffield, UK, Unknown Date.
  8. Mubychem Group By unknown Author, "REACH" Pre-registered, 1976 .
  9. 9.0 9.1 Cinnamon By Gesamtverband der Deutschen Versicherungswirtschaft , Transport Information Service, 2007-10-23.