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Cinnamic acid

October 18, 2023

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents.[4] Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.[5]

Cinnamic acid
Names
Preferred IUPAC name
(2E)-3-Phenylprop-2-enoic acid
Systematic IUPAC name
Cinnamic acid
Other names
trans-Cinnamic acid
Phenylacrylic acid[1]
Cinnamylic acid
3-Phenylacrylic acid
(E)-Cinnamic acid
Benzenepropenoic acid
Isocinnamic acid
Identifiers
  • 140-10-3 Y
3D model (JSmol)
  • Interactive image
3DMet
  • B00108
1905952
ChEBI
  • CHEBI:35697 Y
ChEMBL
  • ChEMBL27246 Y
ChemSpider
  • 392447 Y
ECHA InfoCard 100.004.908
EC Number
  • 205-398-1
3731
  • 3203
KEGG
  • C00423 Y
  • 444539
UNII
  • U14A832J8D N
  • DTXSID5022489
  • InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ Y
    Key: WBYWAXJHAXSJNI-VOTSOKGWSA-N Y
  • InChI=1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
    Key: WBYWAXJHAXSJNI-VOTSOKGWBT
  • O=C(O)\C=C\c1ccccc1
Properties
C9H8O2
Molar mass 148.161 g·mol−1
Appearance White monoclinic crystals
Odor Honey-like[2]
Density 1.2475 g/cm3[3]
Melting point 133 °C (271 °F; 406 K)[3]
Boiling point 300 °C (572 °F; 573 K)[3]
500 mg/L[3]
Acidity (pKa) 4.44
−7.836×10−5 cm3/mol
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point > 100 °C (212 °F; 373 K)[3]
Related compounds
Related compounds
 Benzoic acid, Phenylacetic acid, Phenylpropanoic 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 YN ?)

Occurrence and production Edit

Biosynthesis Edit

Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine.[6]

Natural occurrence Edit

It is obtained from oil of cinnamon, or from balsams such as storax.[4] It is also found in shea butter.[citation needed] Cinnamic acid has a honey-like odor;[2] it and its more volatile ethyl ester, ethyl cinnamate, is a 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 of trees.[7]

Synthesis Edit

Cinnamic acid was first synthesized by the base-catalysed condensation of acetyl chloride and benzaldehyde, followed by hydrolysis of the acid chloride product.[5] In 1890, Rainer Ludwig Claisen described the synthesis of ethyl cinnamate via the reaction of ethyl acetate with benzaldehyde in the presence of sodium as base.[8] Another way of preparing cinnamic acid is by the Knoevenagel condensation reaction.[9] The reactants for this are benzaldehyde and malonic acid in the presence of a weak base, followed by acid-catalyzed decarboxylation. It can also be prepared by oxidation of cinnamaldehyde, condensation of benzal chloride and sodium acetate (followed by acid hydrolysis), and the Perkin reaction. The oldest commercially used route to cinnamic acid involves the Perkin reaction, which is given in the following scheme[5]

 
Synthesis of cinnamic acid via the Perkin reaction.[10]

Metabolism Edit

Cinnamic acid, obtained from autoxidation of cinnamaldehyde, is metabolized into sodium benzoate in the liver.[11]

Uses Edit

Cinnamic acid is used in flavorings, synthetic indigo, and certain pharmaceuticals. A major use is as a precursor to produce methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for the perfume industry.[4] Cinnamic acid is a precursor to the sweetener aspartame via enzyme-catalysed amination to give phenylalanine.[5] Cinnamic acid can dimerize in non-polar solvents resulting in different linear free energy relationships.[12]

References Edit

  1. ^ "Cinnamic Acid" . Encyclopædia Britannica. Vol. 6 (11th ed.). 1911. p. 376.
  2. ^ a b "Cinnamic acid". flavornet.org.
  3. ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ^ a b c Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
  5. ^ a b c d Garbe, Dorothea (2012). "Cinnamic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_099.
  6. ^ Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3 (1): 2–20. doi:10.1093/mp/ssp106. PMID 20035037.
  7. ^ Oldach, Laurel (February 22, 2023). "Forensic researchers use mass spectrometry to identify smuggled wood". Chemical and Engineering News. American Chemical Society.
  8. ^ Claisen, L. (1890). "Zur Darstellung der Zimmtsäure und ihrer Homologen" [On the preparation of cinnamic acid and its homologues]. Berichte der Deutschen Chemischen Gesellschaft. 23: 976–978. doi:10.1002/cber.189002301156.
  9. ^ Tieze, L. (1988). Reactions and Synthesis in the Organic Chemistry Laboratory. Mill Vall, CA. p. 1988.{{cite book}}: CS1 maint: location missing publisher (link)
  10. ^ F. K. Thayer (1925). "m-Nitrocinnamic Acid". Organic Syntheses. 5: 83. doi:10.15227/orgsyn.005.0083.
  11. ^ Jana A, Modi KK, Roy A, Anderson JA, van Breemen RB, Pahan K (June 2013). "Up-regulation of neurotrophic factors by cinnamon and its metabolite sodium benzoate: therapeutic implications for neurodegenerative disorders". Journal of Neuroimmune Pharmacology. 8 (3): 739–55. doi:10.1007/s11481-013-9447-7. PMC 3663914. PMID 23475543.
  12. ^ Bradley, J.-C.; Abraham, M. H.; Acree, W. E.; Lang, A.; Beck, S. N.; Bulger, D. A.; Clark, E. A.; Condron, L. N.; Costa, S. T.; Curtin, E. M.; Kurtu, S. B.; Mangir, M. I.; McBride, M. J. (2015). "Determination of Abraham model solute descriptors for the monomeric and dimeric forms of trans-cinnamic acid using measured solubilities from the Open Notebook Science Challenge". Chemistry Central Journal. 9: 11. doi:10.1186/s13065-015-0080-9. PMC 4369286. PMID 25798191.

October 18, 2023
cinnamic, acid, organic, compound, with, formula, c6h5, cooh, white, crystalline, compound, that, slightly, soluble, water, freely, soluble, many, organic, solvents, classified, unsaturated, carboxylic, acid, occurs, naturally, number, plants, exists, both, tr. Cinnamic acid is an organic compound with the formula C6H5 CH CH COOH It is a white crystalline compound that is slightly soluble in water and freely soluble in many organic solvents 4 Classified as an unsaturated carboxylic acid it occurs naturally in a number of plants It exists as both a cis and a trans isomer although the latter is more common 5 Cinnamic acid NamesPreferred IUPAC name 2E 3 Phenylprop 2 enoic acidSystematic IUPAC name Cinnamic acidOther names trans Cinnamic acidPhenylacrylic acid 1 Cinnamylic acid3 Phenylacrylic acid E Cinnamic acidBenzenepropenoic acidIsocinnamic acidIdentifiersCAS Number 140 10 3 Y3D model JSmol Interactive image3DMet B00108Beilstein Reference 1905952ChEBI CHEBI 35697 YChEMBL ChEMBL27246 YChemSpider 392447 YECHA InfoCard 100 004 908EC Number 205 398 1Gmelin Reference 3731IUPHAR BPS 3203KEGG C00423 YPubChem CID 444539UNII U14A832J8D NCompTox Dashboard EPA DTXSID5022489InChI InChI 1S C9H8O2 c10 9 11 7 6 8 4 2 1 3 5 8 h1 7H H 10 11 b7 6 YKey WBYWAXJHAXSJNI VOTSOKGWSA N YInChI 1 C9H8O2 c10 9 11 7 6 8 4 2 1 3 5 8 h1 7H H 10 11 b7 6 Key WBYWAXJHAXSJNI VOTSOKGWBTSMILES O C O C C c1ccccc1PropertiesChemical formula C 9H 8O 2Molar mass 148 161 g mol 1Appearance White monoclinic crystalsOdor Honey like 2 Density 1 2475 g cm3 3 Melting point 133 C 271 F 406 K 3 Boiling point 300 C 572 F 573 K 3 Solubility in water 500 mg L 3 Acidity pKa 4 44Magnetic susceptibility x 7 836 10 5 cm3 molHazardsGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P264 P271 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501NFPA 704 fire diamond 110Flash point gt 100 C 212 F 373 K 3 Related compoundsRelated compounds Benzoic acid Phenylacetic acid Phenylpropanoic acidExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Occurrence and production 1 1 Biosynthesis 1 2 Natural occurrence 1 3 Synthesis 2 Metabolism 3 Uses 4 ReferencesOccurrence and production EditBiosynthesis Edit Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols precursors to lignin and lignocellulose flavonoids isoflavonoids coumarins aurones stilbenes catechin and phenylpropanoids Its biosynthesis involves the action of the enzyme phenylalanine ammonia lyase PAL on phenylalanine 6 Natural occurrence Edit It is obtained from oil of cinnamon or from balsams such as storax 4 It is also found in shea butter citation needed Cinnamic acid has a honey like odor 2 it and its more volatile ethyl ester ethyl cinnamate is a 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 of trees 7 Synthesis Edit Cinnamic acid was first synthesized by the base catalysed condensation of acetyl chloride and benzaldehyde followed by hydrolysis of the acid chloride product 5 In 1890 Rainer Ludwig Claisen described the synthesis of ethyl cinnamate via the reaction of ethyl acetate with benzaldehyde in the presence of sodium as base 8 Another way of preparing cinnamic acid is by the Knoevenagel condensation reaction 9 The reactants for this are benzaldehyde and malonic acid in the presence of a weak base followed by acid catalyzed decarboxylation It can also be prepared by oxidation of cinnamaldehyde condensation of benzal chloride and sodium acetate followed by acid hydrolysis and the Perkin reaction The oldest commercially used route to cinnamic acid involves the Perkin reaction which is given in the following scheme 5 nbsp Synthesis of cinnamic acid via the Perkin reaction 10 Metabolism EditCinnamic acid obtained from autoxidation of cinnamaldehyde is metabolized into sodium benzoate in the liver 11 Uses EditCinnamic acid is used in flavorings synthetic indigo and certain pharmaceuticals A major use is as a precursor to produce methyl cinnamate ethyl cinnamate and benzyl cinnamate for the perfume industry 4 Cinnamic acid is a precursor to the sweetener aspartame via enzyme catalysed amination to give phenylalanine 5 Cinnamic acid can dimerize in non polar solvents resulting in different linear free energy relationships 12 References Edit Cinnamic Acid Encyclopaedia Britannica Vol 6 11th ed 1911 p 376 a b Cinnamic acid flavornet org a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health a b c Budavari Susan ed 1996 The Merck Index An Encyclopedia of Chemicals Drugs and Biologicals 12th ed Merck ISBN 0911910123 a b c d Garbe Dorothea 2012 Cinnamic Acid Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a07 099 Vogt T 2010 Phenylpropanoid Biosynthesis Molecular Plant 3 1 2 20 doi 10 1093 mp ssp106 PMID 20035037 Oldach Laurel February 22 2023 Forensic researchers use mass spectrometry to identify smuggled wood Chemical and Engineering News American Chemical Society Claisen L 1890 Zur Darstellung der Zimmtsaure und ihrer Homologen On the preparation of cinnamic acid and its homologues Berichte der Deutschen Chemischen Gesellschaft 23 976 978 doi 10 1002 cber 189002301156 Tieze L 1988 Reactions and Synthesis in the Organic Chemistry Laboratory Mill Vall CA p 1988 a href Template Cite book html title Template Cite book cite book a CS1 maint location missing publisher link F K Thayer 1925 m Nitrocinnamic Acid Organic Syntheses 5 83 doi 10 15227 orgsyn 005 0083 Jana A Modi KK Roy A Anderson JA van Breemen RB Pahan K June 2013 Up regulation of neurotrophic factors by cinnamon and its metabolite sodium benzoate therapeutic implications for neurodegenerative disorders Journal of Neuroimmune Pharmacology 8 3 739 55 doi 10 1007 s11481 013 9447 7 PMC 3663914 PMID 23475543 Bradley J C Abraham M H Acree W E Lang A Beck S N Bulger D A Clark E A Condron L N Costa S T Curtin E M Kurtu S B Mangir M I McBride M J 2015 Determination of Abraham model solute descriptors for the monomeric and dimeric forms of trans cinnamic acid using measured solubilities from the Open Notebook Science Challenge Chemistry Central Journal 9 11 doi 10 1186 s13065 015 0080 9 PMC 4369286 PMID 25798191 Retrieved from https en wikipedia org w index php title Cinnamic acid amp oldid 1176201553, wikipedia, wiki, book, books, library,

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