Α-Cyano-4-hydroxycinnamic acid: Difference between revisions

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			{{lowercase title}}
⚫	~~{{DISPLAYTITLE:''alpha''~~-Cyano-4-hydroxycinnamic acid}}
	{{chembox		{{chembox
			\|Verifiedfields = changed
⚫	\| verifiedrevid = ~~446533273~~
			\|Watchedfields = changed
⚫	\|~~Name~~=α-~~Cyano~~-4-hydroxycinnamic acid
		⚫	\|verifiedrevid = 446778754
	\|ImageFile=Cyanohydroxycinnamic acid.png
		⚫	\|Name =α-Cyano-4-hydroxycinnamic acid
	\|ImageSize=200px
		⚫	\|ImageFile =alpha-cyano-4-hydroxycinnamic acid.svg
⚫	\|~~IUPACName~~=(''E'')-2-~~cyano~~-3-(4-hydroxyphenyl)prop-2-~~enoate~~
	\|~~OtherNames~~=~~''alpha''~~-cyano-4-hydroxycinnamic acid~~<br>''alpha''-cyano-4-hydroxycinnamate<br>2-cyano-4-hydroxycinnamate~~		\|ImageAlt = Structural formula of α-cyano-4-hydroxycinnamic acid
			\|ImageFile1 = Alpha-Cyano-4-hydroxycinnamic acid 3D spacefill.png
	\|Section1= {{Chembox Identifiers
			\|ImageSize1 = 180
⚫	\| ~~CASNo~~=28166-41-8
			\|ImageAlt1 = Space-filling model of the α-cyano-4-hydroxycinnamic acid molecule
	\| PubChem=6931228
		⚫	\|PIN =(2''E'')-2-Cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
	\| SMILES=C1=CC(=CC=C1C=C(C#N)C(=O))O
			\|OtherNames =α-Cyano-''p''-hydroxycinnamic acid<br>2-Cyano-4-hydroxycinnamic acid<br>2-Cyano-3-(4-hydroxyphenyl)-2-propenoic acid<br>2-Cyano-3-(4-hydroxyphenyl)-2-acrylic acid<br>4-Hydroxy-α-cyanocinnamic acid
⚫	}}
	\|~~Section2~~= {{Chembox ~~Properties~~		\|Section1={{Chembox Identifiers
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
⚫	\| C=10\|H=7\|O=3\|N=1
		⚫	\|CASNo =28166-41-8
⚫	\| Appearance=Yellow powder

	\| Density=
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| MeltingPt=245-250 °C

	\| BoilingPt=
			\| UNII = NL5EEM9E2G
	\| Solubility=
			\|PubChem = 5328791
	}}
			\|ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\|Section3= {{Chembox Hazards
			\|ChemSpiderID = 4485953
	\| MainHazards=
			\|SMILES = c1cc(ccc1/C=C(\C#N)/C(=O)O)O
	\| FlashPt=
			\|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+
	\| Autoignition=
			\|InChIKey = AFVLVVWMAFSXCK-VMPITWQZBB
	}}
			\|StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\|StdInChI = 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+
			\|StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\|StdInChIKey = AFVLVVWMAFSXCK-VMPITWQZSA-N
			\|ChEBI_Ref = {{ebicite\|changed\|EBI}}
			\|ChEBI = 64340}}
			\|Section2={{Chembox Properties
		⚫	\|C=10 \| H=7 \| O=3 \| N=1
		⚫	\|Appearance = Yellow powder
			\|MeltingPtC = 245 to 250
		⚫	}}
	}}		}}

	'''α-Cyano-4-hydroxycinnamic acid''', also written as '''''alpha''-cyano-4-hydroxycinnamic acid''' and abbreviated '''CHCA''', is a ] derivative and is a member of the ] family. It is used as a matrix for ]s and ] in ] ] analyses.<ref>{{cite journal \|title=-α-Cyano-4-hydroxycinnamic acid as a matrix for matrix-assisted laser desorption mass spectrometry \|journal=Org. Mass Spectrom. \|volume=27 \|issue= 2\|pages=156–8 \|year=1992 \|doi=10.1002/oms.1210270217 \|author=Beavis, R. C. \|last2=Chaudhary \|first2=T. \|last3=Chait \|first3=B. T. }}</ref>		'''α-Cyano-4-hydroxycinnamic acid''', also written as '''''alpha''-cyano-4-hydroxycinnamic acid''' and abbreviated '''CHCA''' or '''HCCA''', is a ] derivative and is a member of the ] family. The ] form is '''α-cyano-4-hydroxycinnamate'''.

			==Matrix-assisted laser desorption/ionization==
			α-Cyano-4-hydroxycinnamic acid is used as a matrix for ]s and ] in ] ] analyses.<ref>{{cite journal \|title=-α-Cyano-4-hydroxycinnamic acid as a matrix for matrix-assisted laser desorption mass spectrometry \|journal=Org. Mass Spectrom. \|volume=27 \|issue= 2\|pages=156–8 \|year=1992 \|doi=10.1002/oms.1210270217 \|author=Beavis, R. C. \|last2=Chaudhary \|first2=T. \|last3=Chait \|first3=B. T.}}</ref><ref>{{cite book\|author1=Franz Hillenkamp\|author2=Jasna Peter-Katalinic\|title=MALDI MS: A Practical Guide to Instrumentation, Methods and Applications\|url=https://books.google.com/books?id=XZczAQAAQBAJ&pg=PA110\|date=3 October 2013\|publisher=Wiley\|isbn=978-3-527-67373-5\|pages=110–}}</ref>

	== See also ==		== See also ==
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	{{DEFAULTSORT:Cyano-4-hydroxycinnamic acid, alpha-}}		{{DEFAULTSORT:Cyano-4-hydroxycinnamic acid, alpha-}}
	]		]
	]		]
	]		]
	]		]
			]

	]
	]

Latest revision as of 18:41, 21 October 2024

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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:64340
ChemSpider	4485953
ECHA InfoCard	100.044.421
PubChem CID	5328791
UNII	NL5EEM9E2G
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+Key: AFVLVVWMAFSXCK-VMPITWQZSA-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
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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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.

Matrix-assisted laser desorption/ionization

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

References

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.
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.

Categories:

Latest revision as of 18:41, 21 October 2024

Matrix-assisted laser desorption/ionization

See also

References