Cinnamic acid

Cinnamic acid
Cinnamic acid
Identifiers
CAS number 140-10-3 YesY
PubChem 444539
ChemSpider 392447 YesY
KEGG C00423 N
ChEBI CHEBI:35697 N
ChEMBL CHEMBL27246 N
Jmol-3D images Image 1
Properties
Molecular formula C9H8O2
Molar mass 148.16 g mol−1
Exact mass 148.05243
Appearance White monoclinic crystals
Density 1.2475 g/cm3[1]
Melting point

133 °C, 406 K, 271 °F ([1])

Boiling point

300 °C, 573 K, 572 °F ([1])

Solubility in water 500 mg/L[1]
Acidity (pKa) 4.44
Hazards
EU classification Irritant (Xi)
R-phrases R36
S-phrases S25
Flash point >100 °C (212 °F)[1]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cinnamic acid is a white crystalline hydroxycinnamic acid, which is slightly soluble in water.

It is obtained from oil of cinnamon, or from balsams such as storax.[2] It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions. It can also be made synthetically.

Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals, though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry.[2] Cinnamic acid has a honey-like odor;[3] it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent. Cinnamic acid is also part of the biosynthetic shikimate and phenylpropanoid pathways. Its biosynthesis is performed by action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine.

Cinnamic acid is freely soluble in benzene, diethyl ether, acetone, and acetic acid;[2] it is insoluble in hexane.

Cinnamic acid is also a kind of self-inhibitor produced by fungal spore to prevent germination.

Chemical synthesis

Rainer Ludwig Claisen (1851–1930), German chemist, described for the first time in 1890 the synthesis of cinnamates by reacting aromatic aldehydes with esters. The reaction is known as the Claisen reaction.

References

  1. ^ a b c d e Record in the GESTIS Substance Database from the IFA
  2. ^ a b c Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123 
  3. ^ Cinnamic acid], flavornet.org



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Look at other dictionaries:

  • Cinnamic acid — Cinnamic Cin*nam ic, a. [From {Cinnamon}.] (Chem.) Pertaining to, or obtained from, cinnamon. [1913 Webster] {Cinnamic acid} (Chem.), a white, crystalline, odorless substance. {C6H5.C2H2C2H2.CO2H}, formerly obtained from storax and oil of… …   The Collaborative International Dictionary of English

  • cinnamic acid — sə̇ˈnamik also ˈsinəmik noun Etymology: French cinnamique, from cinnam + ique ic : a white crystalline odorless acid C6H5CH:CHCOOH found especially in cinnamon oil and storax and made synthetically for preparing esters for perfumes * * * Chem. a… …   Useful english dictionary

  • cinnamic acid — Obtained from cinnamon oil, Peruvian and tolu balsams, or storax. It has been used in lupus as paint and in infectious diseases to promote leukocytosis. SYN: cinnamylic acid, phenylacrylic acid. * * * cinnamic acid n a white crystalline odorless… …   Medical dictionary

  • cinnamic acid — cinamono rūgštis statusas T sritis chemija formulė C₆H₅CH=CHCOOH atitikmenys: angl. cinnamic acid rus. коричная кислота ryšiai: sinonimas – (E) 3 fenilpropeno rūgštis …   Chemijos terminų aiškinamasis žodynas

  • cinnamic acid — noun Etymology: French cinnamique of cinnamon, from cinname cinnamon, from Latin cinnamomum Date: circa 1864 a white crystalline odorless acid C9H8O2 found especially in cinnamon oil and storax …   New Collegiate Dictionary

  • cinnamic acid — noun The aromatic carboxylic acid CH CH=CH COOH obtained from cinnamon; it is used in perfumery etc …   Wiktionary

  • cinnamic acid — n. (Chemistry) white crystalline acid that has no odor and is used in the perfume industry …   English contemporary dictionary

  • cinnamic acid — /səˌnæmɪk ˈæsəd/ (say suh.namik asuhd) noun an aromatic, unsaturated acid, C6H5CH=CHCOOH, derived from cinnamon, balsams, etc., or by synthesis …  

  • cinnamic acid — Chem. a white, crystalline, water insoluble powder, C9H8O2, usually obtained from cinnamon or synthesized: used chiefly in the manufacture of perfumes and medicines. [1880 85] * * * …   Universalium

  • Cinnamic — Cin*nam ic, a. [From {Cinnamon}.] (Chem.) Pertaining to, or obtained from, cinnamon. [1913 Webster] {Cinnamic acid} (Chem.), a white, crystalline, odorless substance. {C6H5.C2H2C2H2.CO2H}, formerly obtained from storax and oil of cinnamon, now… …   The Collaborative International Dictionary of English

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