Α-Cyano-4-hydroxycinnamic acid

Chemical compound From Wikipedia, the free encyclopedia

Α-Cyano-4-hydroxycinnamic acid

α-Cyano-4-hydroxycinnamic acid, also written as alpha-cyano-4-hydroxycinnamic acid and abbreviated CHCA or HCCA, is a cinnamic acid derivative and is a member of the phenylpropanoid family. The carboxylate form is α-cyano-4-hydroxycinnamate.

Quick Facts Names, Identifiers ...
α-Cyano-4-hydroxycinnamic acid
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Names
Preferred IUPAC name
(2E)-2-Cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
Other names
α-Cyano-p-hydroxycinnamic acid
2-Cyano-4-hydroxycinnamic acid
2-Cyano-3-(4-hydroxyphenyl)-2-propenoic acid
2-Cyano-3-(4-hydroxyphenyl)-2-acrylic acid
4-Hydroxy-α-cyanocinnamic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.044.421
UNII
  • InChI=1S/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)/b8-5+ N
    Key: AFVLVVWMAFSXCK-VMPITWQZSA-N N
  • InChI=1/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)/b8-5+
    Key: AFVLVVWMAFSXCK-VMPITWQZBB
  • c1cc(ccc1/C=C(\C#N)/C(=O)O)O
Properties
C10H7NO3
Molar mass 189.170 g·mol−1
Appearance Yellow powder
Melting point 245 to 250 °C (473 to 482 °F; 518 to 523 K)
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 ?)
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Matrix-assisted laser desorption/ionization

α-Cyano-4-hydroxycinnamic acid is used as a matrix for peptides and nucleotides in MALDI mass spectrometry analyses.[1][2]

See also

References

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