4-hydroxycinnamate
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| Names | |
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IUPAC name
(E)-3-(4-hydroxyphenyl)-2-propenoic acid
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| Other names
para-coumaric acid,
4-hydroxycinnamic acid, β-(4-hydroxyphenyl)acrylic acid |
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| Identifiers | |
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3D model (Jmol)
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| ChEBI | |
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| DrugBank | |
| ECHA InfoCard | 100.116.210 |
| EC Number | 231-000-0 |
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PubChem CID
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| Properties | |
| C9H8O3 | |
| Molar mass | 164.16 g·mol−1 |
| Melting point | 210 to 213 °C (410 to 415 °F; 483 to 486 K) |
| Hazards | |
| R-phrases (outdated) | R36/37/38 |
| S-phrases (outdated) | S24/25 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
4-hydroxycinnamic acid,
p-Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acid—o-coumaric acid, m-coumaric acid, and p-coumaric acid—that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. p-Coumaric acid exists in two forms trans-p-coumaric acid and cis-p-coumaric acid.
It is a crystalline solid that is slightly soluble in water, but well soluble in ethanol and diethyl ether.
Together with sinapyl alcohol and coniferyl alcohols, p-coumaric acid is a major component of lignin.
p-Coumaric acid can be found in Gnetum cleistostachyum.
p-Coumaric acid can be found in a wide variety of edible plants such as peanuts, navy beans, tomatoes, carrots, basil and garlic. It is found in wine and vinegar. It is also found in barley grain.
p-Coumaric acid from pollen is a constituent of honey.
p-Coumaric acid glucoside can also be found in commercial breads containing flaxseed.
Diesters of p-coumaric acid can be found in carnauba wax.
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