p-Coumaric acid

Names
Preferred IUPAC name

(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid

Other names

(E)-3-(4-Hydroxyphenyl)-2-propenoic acid
(E)-3-(4-Hydroxyphenyl)acrylic acid
para-Coumaric acid
4-Hydroxycinnamic acid
β-(4-Hydroxyphenyl)acrylic acid

Identifiers

CAS Number

* 501-98-4 Y

3D model (JSmol)

* Interactive image
* Interactive image

Beilstein Reference

| 2207383
ChEBI |

* CHEBI:32374 Y

ChEMBL |

* ChEMBL66879 Y

ChemSpider |

* 553148 Y

DrugBank |

* DB04066 Y

ECHA InfoCard | 100.116.210
EC Number |

* 231-000-0

Gmelin Reference

| 2245630

IUPHAR/BPS

* 5787

KEGG |

* C00811

PubChem CID

* 637542

UNII |

* IBS9D1EU3J

CompTox Dashboard (EPA)

* DTXSID30901076

InChI

* InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ Y

Key: NGSWKAQJJWESNS-ZZXKWVIFSA-N Y

* InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11, 12)/b6-3+/f/h11H

* InChI=1/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+

Key: NGSWKAQJJWESNS-ZZXKWVIFBJ

SMILES

* C1=CC(=CC=C1\C=C\C(=O)O)O

* c1cc(ccc1/C=C/C(=O)O)O

Properties

Chemical formula

| C9H8O3
Molar mass | 164.160 g·mol−1
Melting point | 210 to 213 °C (410 to 415 °F; 483 to 486 K)
Hazards
GHS labelling:

Pictograms

Signal word

| Danger

Hazard statements

| H301, H302, H311, H314, H315, H317, H319, H335

Precautionary statements

| P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

p-Coumaric acid is an organic compound with the formula HOC6H4CH=CHCO2H. It is one of the three isomers of hydroxycinnamic acid. It is a white solid that is only slightly soluble in water but very soluble in ethanol and diethyl ether.

## Natural occurrences

[edit]

It is a precursor to many natural products, especially lignols, precursors to the woody mass that comprise many plants.[1] Of the myriad occurrences, p-coumaric acid can be found in Gnetum cleistostachyum.[2]

### In food

[edit]

p-Coumaric acid can be found in a wide variety of edible plants and fungi such as peanuts, navy beans, tomatoes, carrots, basil and garlic.[citation needed] It is found in wine and vinegar.[3] It is also found in barley grain.[4]

p-Coumaric acid from pollen is a constituent of honey.[5]

### Derivatives

[edit]

p-Coumaric acid glucoside can also be found in commercial breads containing flaxseed.[6] Diesters of p-coumaric acid can be found in carnauba wax.

### Biosynthesis

[edit]

It is biosynthesized from cinnamic acid by the action of the P450-dependent enzyme 4-cinnamic acid hydroxylase (C4H).

-> C 4 H {\displaystyle {\begin{matrix}{}\\\\{\xrightarrow {\mathrm {C4H} }}\\\\{}\end{matrix}}}

It is also produced from L-tyrosine by the action of tyrosine ammonia lyase (TAL).

-> T A L {\displaystyle {\xrightarrow {\mathrm {TAL} }}} \+ NH3 \+ H+

### Biosynthetic building block

[edit]

p-Coumaric acid is the precursor of 4-ethylphenol produced by the yeast Brettanomyces in wine. The enzyme cinnamate decarboxylase catalyzes the conversion of p-coumaric acid into 4-vinylphenol.[7] Vinyl phenol reductase then catalyzes the reduction of 4-vinylphenol to 4-ethylphenol. Coumaric acid is sometimes added to microbiological media, enabling the positive identification of Brettanomyces by smell.

The conversion of p-coumaric acid to 4-ethyphenol by Brettanomyces

cis-p-Coumarate glucosyltransferase is an enzyme that uses uridine diphosphate glucose and cis-p-coumarate to produce 4′-O-β-D-glucosyl-cis-p-coumarate and uridine diphosphate (UDP). This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases.[8]

Phloretic acid, found in the rumen of sheep fed with dried grass, is produced by hydrogenation of the 2-propenoic side chain of p-coumaric acid.[9]

The enzyme, resveratrol synthase, also known as stilbene synthase, catalyzes the synthesis of resveratrol ultimately from a tetraketide derived from 4-coumaroyl CoA.[10]

p-Coumaric acid is a cofactor of photoactive yellow proteins (PYP), a homologous group of proteins found in many eubacteria.[11]

p-Coumaric acid is found as the base moiety of Caleicine, one of many sesquiterpenes in Calea ternifolia.

## See also

[edit]

* o-coumaric acid
* m-coumaric acid
* Coumarin
* Coumaroyl-Coenzyme A
* Ferulic acid
* Cinnamic acid
* Phenolic content in wine
* p-Coumaroylated anthocyanins

## References

[edit]

1. ^ Wout Boerjan, John Ralph, Marie Baucher "Lignin Biosynthesis" Annu. Rev. Plant Biol. 2003, vol. 54, pp. 519–46. doi:10.1146/annurev.arplant.54.031902.134938
2. ^ Yao CS, Lin M, Liu X, Wang YH (April 2005). "Stilbene derivatives from Gnetum cleistostachyum". Journal of Asian Natural Products Research. 7 (2): 131–7. doi:10.1080/10286020310001625102. PMID 15621615. S2CID 37661785.
3. ^ Gálvez MC, Barroso CG, Pérez-Bustamante JA (1994). "Analysis of polyphenolic compounds of different vinegar samples". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 199: 29–31. doi:10.1007/BF01192948. S2CID 91784893.
4. ^ Quinde-Axtell Z, Baik BK (December 2006). "Phenolic compounds of barley grain and their implication in food product discoloration". Journal of Agricultural and Food Chemistry. 54 (26): 9978–84. doi:10.1021/jf060974w. PMID 17177530.
5. ^ Mao W, Schuler MA, Berenbaum MR (May 2013). "Honey constituents up-regulate detoxification and immunity genes in the western honey bee Apis mellifera". Proceedings of the National Academy of Sciences of the United States of America. 110 (22): 8842–6. Bibcode:2013PNAS..110.8842M. doi:10.1073/pnas.1303884110. PMC 3670375. PMID 23630255.
6. ^ Strandås C, Kamal-Eldin A, Andersson R, Åman P (October 2008). "Phenolic glucosides in bread containing flaxseed". Food Chemistry. 110 (4): 997–9. doi:10.1016/j.foodchem.2008.02.088. PMID 26047292.
7. ^ "Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol". etslabs.com. Archived from the original on 2008-02-19.
8. ^ Rasmussen S, Rudolph H (1997). "Isolation, purification and characterization of UDP-glucose: cis-p-coumaric acid-β-D-glucosyltransferase from sphagnum fallax". Phytochemistry. 46 (3): 449–453. doi:10.1016/S0031-9422(97)00337-3.
9. ^ Chesson A, Stewart CS, Wallace RJ (September 1982). "Influence of plant phenolic acids on growth and cellulolytic activity of rumen bacteria". Applied and Environmental Microbiology. 44 (3): 597–603. Bibcode:1982ApEnM..44..597C. doi:10.1128/aem.44.3.597-603.1982. PMC 242064. PMID 16346090.
10. ^ Wang, Chuanhong; Zhi, Shuang; Liu, Changying; Xu, Fengxiang; Zhao, Aichun; Wang, Xiling; Ren, Yanhong; Li, Zhengang; Yu, Maode (2017). "Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli". Journal of Agricultural and Food Chemistry. 65 (8): 1659–1668. doi:10.1021/acs.jafc.6b05212. PMID 28168876.
11. ^ Hoff WD, Düx P, Hård K, Devreese B, Nugteren-Roodzant IM, Crielaard W, Boelens R, Kaptein R, van Beeumen J, Hellingwerf KJ (November 1994). "Thiol ester-linked p-coumaric acid as a new photoactive prosthetic group in a protein with rhodopsin-like photochemistry". Biochemistry. 33 (47): 13959–62. doi:10.1021/bi00251a001. PMID 7947803.

* v
* t
* e

Types of hydroxycinnamic acids

Aglycones|

| Precursor|

* Cinnamic acid

|

Monohydroxycinnamic acids
(Coumaric acids)|

* p-Coumaric acid
* o-Coumaric acid
* m-Coumaric acid

Dihydroxycinnamic acids|

* Caffeic acid (3,4-dihydroxycinnamic acid)
* Umbellic acid (2,4-dihydroxycinnamic acid)
* 2,3-Dihydroxycinnamic acid
* 2,5-Dihydroxycinnamic acid
* 3,5-Dihydroxycinnamic acid

Trihydroxycinnamic acids|

* 2,4,5-Trihydroxycinnamic acid
* 3,4,5-Trihydroxycinnamic acid

O-methylated forms|

* Ferulic acid
* 5-Hydroxyferulic acid
* Isoferulic acid
* Sinapinic acid

others|

* Plicatin A
* Plicatin B

Esters|

| glycoside-likes|

| Esters of
caffeic acid
with cyclitols|

| esters of
quinic acid|

* Chlorogenic acid (3-caffeoylquinic acid)
* Cryptochlorogenic acid (4-O-caffeoylquinic acid)
* Neochlorogenic acid (5-O-Caffeoylquinic acid)
* Cynarine (1,5-dicaffeoylquinic acid)
* 3,4-dicaffeoylquinic acid
* 3,5-dicaffeoylquinic acid

|

esters of
shikimic acid|

* Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides|

* Ferulic acid glucoside
* p-Coumaric acid glucoside
* 1-Sinapoyl-D-glucose

Tartaric acid esters|

* Caftaric acid
* Chicoric acid (dicaffeoyltartaric acid)
* Coutaric acid
* Fertaric acid
* Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid|

* Caffeoylmalic acid
* Ethyl caffeate
* Methyl caffeate
* Caffeic acid phenethyl ester (CAPE)
* Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)

Caffeoyl phenylethanoid
glycoside (CPG)|

* Echinacoside
* Calceolarioside A, B, C, F
* Chiritoside A, B, C
* Cistanoside A, B, C, D, E, F, G, H
* Conandroside
* Myconoside
* Pauoifloside
* Plantainoside A
* Plantamajoside
* Tubuloside B
* Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)

Oligomeric forms|

| Dimers|

* Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-O-4′-Diferulic acid, 8,5′-Diferulic acid, 8,5′-DiFA (DC), 8,5′-DiFA (BF), 8,8′-Diferulic acid

|

Trimers|

* Triferulic acids : 5-5′,8′-O-4″-Triferulic acid

Tetramers|

* Tetraferulic acids

Conjugates with
coenzyme A (CoA)|

* Caffeoyl-CoA
* Cinnamoyl-CoA
* Coumaroyl-CoA

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H301]: H301: Toxic if swallowed
*[H302]: H302: Harmful if swallowed
*[H311]: H311: Toxic in contact with skin
*[H314]: H314: Causes severe skin burns and eye damage
*[H315]: H315: Causes skin irritation
*[H317]: H317: May cause an allergic skin reaction
*[H319]: H319: Causes serious eye irritation
*[H335]: H335: May cause respiratory irritation
*[P260]: P260: Do not breathe dust/fume/gas/mist/vapours/spray.
*[P261]: P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
*[P264]: P264: Wash ... thoroughly after handling.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P271]: P271: Use only outdoors or in a well-ventilated area.
*[P272]: P272: Contaminated work clothing should not be allowed out of the workplace.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P301+P310]: P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
*[P301+P312]: P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P301+P330+P331]: P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[P303+P361+P353]: P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].
*[P304+P340]: P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
*[P305+P351+P338]: P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
*[P310]: P310: Immediately call a POISON CENTER or doctor/physician.
*[P312]: P312: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P321]: P321: Specific treatment (see ... on this label).
*[P322]: P322: Specific measures (see ... on this label).
*[P330]: P330: Rinse mouth.
*[P332+P313]: P332+P313: If skin irritation occurs: Get medical advice/attention.
*[P333+P313]: P333+P313: If skin irritation or a rash occurs: Get medical advice/attention.
*[P337+P313]: P337+P313: If eye irritation persists: Get medical advice/attention.
*[P361]: P361: Remove/Take off immediately all contaminated clothing.
*[P362]: P362: Take off contaminated clothing.
*[P363]: P363: Wash contaminated clothing before reuse.
*[P403+P233]: P403+P233: Store in a well ventilated place. Keep container tightly closed.
*[P405]: P405: Store locked up.
*[P501]: P501: Dispose of contents/container to ...
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