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.

α-Cyano-4-hydroxycinnamic acid

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
CAS Number	28166-41-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:64340 N
ChemSpider	4485953 N
ECHA InfoCard	100.044.421
PubChem CID	5328791
UNII	NL5EEM9E2G Y
InChI 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
SMILES c1cc(ccc1/C=C(\C#N)/C(=O)O)O
Properties
Chemical formula	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 ?) Infobox references

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

• Sinapinic acid

References

1. Beavis, R. C.; Chaudhary, T.; Chait, B. T. (1992). "-α-Cyano-4-hydroxycinnamic acid as a matrix for matrix-assisted laser desorption mass spectrometry". Org. Mass Spectrom. 27 (2): 156–8. doi:10.1002/oms.1210270217.
2. Franz Hillenkamp; Jasna Peter-Katalinic (3 October 2013). MALDI MS: A Practical Guide to Instrumentation, Methods and Applications. Wiley. pp. 110–. ISBN 978-3-527-67373-5.