Trichome

thcscience_admin
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
JimRenge (talk | contribs)
Extended confirmed users
19,983 edits
Undid revision 1092419658 by JimRenge (talk)self-rvt
Tag: Undo
217.149.170.34 (talk)
 
(11 intermediate revisions by 9 users not shown)
Line 1: Line 1:
{{Chembox
{{Chembox
| Verifiedfields = changed
|Verifiedfields = changed
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 476994181
|verifiedrevid = 476994181
| Name = Cinnamic acid
|Name = Cinnamic acid
| ImageFile = Zimtsäure - Cinnamic acid.svg
|ImageFile = Zimtsäure - Cinnamic acid.svg
| ImageAlt = Skeletal formula of cinnamic acid
|ImageName = Skeletal formula of trans-cinnamic acid
| ImageFile1 = Cinnamic acid 3D ball.png
|ImageFile1 = Cinnamic acid 3D ball.png
| ImageAlt1 = Ball-and-stick model of the cinnamic acid molecule
|ImageName1 = Ball-and-stick model of the trans-cinnamic acid molecule
| ImageFile2 = Cinnamic acid.jpg
|ImageFile2 = Cinnamic acid.jpg
| ImageAlt2 = Sample of compound
|ImageName2 = Sample of the compound cinnamic acid in powder form
| PIN = (2''E'')-3-Phenylprop-2-enoic acid
|PIN = (2''E'')-3-Phenylprop-2-enoic acid
|SystematicName = Cinnamic acid
| OtherNames = Cinnamic acid<br>''trans''-Cinnamic acid<br>Phenylacrylic acid<ref>{{cite EB1911|wstitle=Cinnamic Acid|volume=6|page=376|short=1}}</ref><br>Cinnamylic acid<br>3-Phenylacrylic acid<br />(''E'')-Cinnamic acid<br>Benzenepropenoic acid<br>Isocinnamic acid
|OtherNames = ''trans''-Cinnamic acid<br>Phenylacrylic acid<ref>{{cite EB1911|wstitle=Cinnamic Acid|volume=6|page=376|short=1}}</ref><br>Cinnamylic acid<br>3-Phenylacrylic acid<br />(''E'')-Cinnamic acid<br>Benzenepropenoic acid<br>Isocinnamic acid
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 3203
|IUPHAR_ligand = 3203
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 392447
|ChemSpiderID = 392447
| ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 27246
|ChEMBL = 27246
| InChI = 1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
|InChI = 1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
| ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 35697
|ChEBI = 35697
| SMILES = O=C(O)\C=C\c1ccccc1
|SMILES = O=C(O)\C=C\c1ccccc1
| InChIKey = WBYWAXJHAXSJNI-VOTSOKGWBT
|InChIKey = WBYWAXJHAXSJNI-VOTSOKGWBT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
|StdInChI = 1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WBYWAXJHAXSJNI-VOTSOKGWSA-N
|StdInChIKey = WBYWAXJHAXSJNI-VOTSOKGWSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
|CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 140-10-3
|CASNo = 140-10-3
| UNII_Ref = {{fdacite|changed|FDA}}
|UNII_Ref = {{fdacite|changed|FDA}}
| UNII = U14A832J8D
|UNII = U14A832J8D
| PubChem = 444539
|PubChem = 444539
| KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00423
|KEGG = C00423
| Gmelin = 3731
|Gmelin = 3731
| Beilstein = 1905952
|Beilstein = 1905952
| EINECS = 205-398-1
|EINECS = 205-398-1
| 3DMet = B00108
|3DMet = B00108
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=9 | H=8 | O=2
|C=9 | H=8 | O=2
| Appearance = White monoclinic crystals
|Appearance = White monoclinic crystals
| Odor = Honey-like<ref name="Cinnamic acid">{{cite web|url=http://www.flavornet.org/info/140-10-3.html|title=Cinnamic acid|website=flavornet.org}}</ref>
|Odor = Honey-like<ref name="Cinnamic acid">{{cite web|url=http://www.flavornet.org/info/140-10-3.html|title=Cinnamic acid|website=flavornet.org}}</ref>
| Solubility = 500 mg/L<ref name=GESTIS>{{GESTIS|ZVG=25910}}</ref>
|Solubility = 500 mg/L<ref name=GESTIS>{{GESTIS|ZVG=25910}}</ref>
| Density = 1.2475 g/cm<sup>3</sup><ref name=GESTIS/>
|Density = 1.2475 g/cm<sup>3</sup><ref name=GESTIS/>
| MeltingPtC = 133
|MeltingPtC = 133
| MeltingPt_ref = <ref name=GESTIS/>
|MeltingPt_ref = <ref name=GESTIS/>
| BoilingPtC = 300
|BoilingPtC = 300
| BoilingPt_ref = <ref name=GESTIS/>
|BoilingPt_ref = <ref name=GESTIS/>
| pKa = 4.44
|pKa = 4.44
| MagSus = {{val|-7.836e-5|u=cm<sup>3</sup>/mol}}
|MagSus = {{val|-7.836e-5|u=cm<sup>3</sup>/mol}}
}}
}}
|Section7={{Chembox Hazards
|Section3={{Chembox Hazards
| NFPA-H = 1
|NFPA-H = 1
| NFPA-F = 1
|NFPA-F = 1
| NFPA-R = 0
|NFPA-R = 0
⚫
|GHSPictograms = {{GHS07}}
| ExternalSDS =
⚫
|GHSSignalWord = Warning
⚫
| GHSPictograms = {{GHS07}}
⚫
|HPhrases = {{H-phrases|315|319|335}}
⚫
| GHSSignalWord = Warning
⚫
|PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
⚫
| HPhrases = {{H-phrases|315|319|335}}
|FlashPt = >
⚫
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| FlashPt = >
|FlashPtC = 100
⚫
|FlashPt_ref = <ref name=GESTIS/>
| FlashPtC = 100
⚫
}}
⚫
| FlashPt_ref = <ref name=GESTIS/>
⚫
|Section4={{Chembox Related
}}
⚫
|OtherCompounds = [[Benzoic acid]], [[Phenylacetic acid]], [[Phenylpropanoic acid]]
⚫
|Section8={{Chembox Related
⚫
}}
⚫
| OtherCompounds = [[Benzoic acid]], [[Phenylacetic acid]], [[Phenylpropanoic acid]]
⚫
}}
}}
}}


'''Cinnamic acid''' is an [[organic compound]] with the formula [[phenyl|C<sub>6</sub>H<sub>5</sub>]]-CH=CH-[[Carboxylic acid|COOH]]. It is a white crystalline compound that is slightly [[soluble]] in water, and freely soluble in many organic solvents.<ref name=Merck/> Classified as an unsaturated [[carboxylic acid]], it occurs naturally in a number of plants. It exists as both a [[Cis–trans isomerism|''cis'' and a ''trans'' isomer]], although the latter is more common.<ref name=Ullmann/>
'''Cinnamic acid''' is an [[organic compound]] with the formula [[phenyl|C<sub>6</sub>H<sub>5</sub>]]-CH=CH-[[Carboxylic acid|COOH]]. It is a white crystalline compound that is slightly [[soluble]] in water, and freely soluble in many organic solvents.<ref name=Merck/> Classified as an unsaturated [[carboxylic acid]], it occurs naturally in a number of plants. It exists as both a [[Cis–trans isomerism|''cis'' and a ''trans'' isomer]], although the latter is more common.<ref name=Ullmann/>


==Occurrence and production==
==Occurrence and production==
Line 77: Line 77:


===Natural occurrence===
===Natural occurrence===
It is obtained from oil of [[cinnamon]], or from [[balsam]]s such as [[storax]].<ref name=Merck>{{Merck12th}}</ref> It is also found in [[shea butter]]. Cinnamic acid has a [[honey]]-like odor;<ref name="Cinnamic acid">{{cite web|url=http://www.flavornet.org/info/140-10-3.html|title=Cinnamic acid|website=flavornet.org}}</ref> 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.
It is obtained from oil of [[cinnamon]], or from [[balsam]]s such as [[storax]].<ref name=Merck>{{Merck12th}}</ref> It is also found in [[shea butter]].{{cn|date=June 2023}} Cinnamic acid has a [[honey]]-like odor;<ref name="Cinnamic acid">{{cite web|url=http://www.flavornet.org/info/140-10-3.html|title=Cinnamic acid|website=flavornet.org}}</ref> 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.<ref>{{cite web |last1=Oldach |first1=Laurel |title=Forensic researchers use mass spectrometry to identify smuggled wood |url=https://cen.acs.org/analytical-chemistry/mass-spectrometry/Forensic-researchers-use-mass-spectrometry-to-identify-smuggled-wood/101/i7 |website=Chemical and Engineering News |publisher=American Chemical Society |date=February 22, 2023}}</ref>


===Synthesis===
===Synthesis===
Line 87: Line 87:


==Uses==
==Uses==
Cinnamic acid is used in flavorings, [[Indigo dye#Chemical synthesis|synthetic indigo]], and certain [[pharmaceutical]]s. A major use is as a precursor to produce [[methyl cinnamate]], [[ethyl cinnamate]], and [[benzyl cinnamate]] for the perfume industry.<ref name=Merck/> Cinnamic acid is a precursor to the sweetener [[aspartame]] via enzyme-catalysed amination to give [[phenylalanine]].<ref name=Ullmann/> Cinnamic acid can [[Dimer (chemistry)|dimerize]] in non-polar solvents resulting in different [[Free-energy relationship|linear free energy relationships]].<ref>{{cite journal | doi = 10.1186/s13065-015-0080-9 | pmid = 25798191 | pmc = 4369286 | title = 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 | journal = Chemistry Central Journal | volume = 9 | pages = 11 | year = 2015 | last1 = Bradley | first1 = J.-C. | last2 = Abraham | first2 = M. H. | last3 = Acree | first3 = W. E. | last4 = Lang | first4 = A. | last5 = Beck | first5 = S. N. | last6 = Bulger | first6 = D. A. | last7 = Clark | first7 = E. A. | last8 = Condron | first8 = L. N. | last9 = Costa | first9 = S. T. | last10 = Curtin | first10 = E. M. | last11 = Kurtu | first11 = S. B. | last12 = Mangir | first12 = M. I. | last13 = McBride | first13 = M. J. }}</ref>
Cinnamic acid is used in flavorings, [[Indigo dye#Chemical synthesis|synthetic indigo]], and certain [[pharmaceutical]]s. A major use is as a precursor to produce [[methyl cinnamate]], [[ethyl cinnamate]], and [[benzyl cinnamate]] for the perfume industry.<ref name=Merck/> Cinnamic acid is a precursor to the sweetener [[aspartame]] via enzyme-catalysed amination to give [[phenylalanine]].<ref name=Ullmann/> Cinnamic acid can [[Dimer (chemistry)|dimerize]] in non-polar solvents resulting in different [[Free-energy relationship|linear free energy relationships]].<ref>{{cite journal | doi = 10.1186/s13065-015-0080-9 | pmid = 25798191 | pmc = 4369286 | title = 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 | journal = Chemistry Central Journal | volume = 9 | pages = 11 | year = 2015 | last1 = Bradley | first1 = J.-C. | last2 = Abraham | first2 = M. H. | last3 = Acree | first3 = W. E. | last4 = Lang | first4 = A. | last5 = Beck | first5 = S. N. | last6 = Bulger | first6 = D. A. | last7 = Clark | first7 = E. A. | last8 = Condron | first8 = L. N. | last9 = Costa | first9 = S. T. | last10 = Curtin | first10 = E. M. | last11 = Kurtu | first11 = S. B. | last12 = Mangir | first12 = M. I. | last13 = McBride | first13 = M. J. | doi-access = free }}</ref>


==References==
==References==
Line 98: Line 98:
[[Category:Flavors]]
[[Category:Flavors]]
[[Category:Enoic acids]]
[[Category:Enoic acids]]
[[Category:Phenylpropanoids| ]]
[[Category:Phenylpropanoids]]

Latest revision as of 21:09, 30 October 2023

Cinnamic acid
Skeletal formula of trans-cinnamic acid
Ball-and-stick model of the trans-cinnamic acid molecule
Sample of the compound cinnamic acid in powder form
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
3D model (JSmol)
3DMet
1905952
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.908 Edit this at Wikidata
EC Number
  • 205-398-1
3731
KEGG
UNII
  • InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ checkY
    Key: WBYWAXJHAXSJNI-VOTSOKGWSA-N checkY
  • 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:
GHS07: Exclamation mark
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)
NFPA 704 four-colored diamondHealth 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 checkY☒N ?)

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]

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] 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. ISBN 978-3527306732.
  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.
source: https://en.wikipedia.org/w/index.php?title=Cinnamic_acid&diff=1182697855&oldid=1092419746

Leave a Reply