Sinapic acid

Structural formula
General
Surname	Sinapic acid
other names	trans -3,5-dimethoxy-4-hydroxycinnamic acid; ( E ) -3,5-dimethoxy-4-hydroxycinnamic acid; ( 2E ) -3- (4-Hydroxy-3,5-dimethoxyphenyl) -2-propenoic acid;
Molecular formula	C 11 H 12 O 5
External identifiers / databases
PubChem	637775
ChemSpider	553361
DrugBank	DB08587
Wikidata	Q417527
properties
Molar mass	224.21 g mol −1
Physical state	firmly
Melting point	202 ° C
boiling point	decomposition
solubility	poorly soluble in water; soluble in methanol (1.04 mol / l), ethanol (0.79 mol / l), THF (0.446 mol / l).;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sinapic acid ( trans -3,5-dimethoxy-4-hydroxycinnamic acid) belongs to the group of phenylpropanoids or phenolic acids , more precisely the cinnamic acid derivatives. With bases it forms partly crystallizable salts which decompose in the air.

Occurrence in nature

Rapeseed fields

Sinapic acid occurs naturally in rapeseed . The total content of phenolic acids in rapeseed meal is significantly higher than in other oil crops (e.g. peanut : 63.6 mg / 100 g, rapeseed: 639.9 mg / 100 g). Sinapic acid and its esters make up the largest proportion of phenolic acids in rapeseed with 70 to 85% . Sinapic acid is produced in the plant as a product of cinnamic acid biosynthesis . Starting from the amino acid phenylalanine is produced by deamination using the enzyme phenylalanine ammonia lyase ( EC 4.3.1.5 ), the cinnamic acid . Sinapic acid is produced from this via caffeic acid , ferulic acid and 5-hydroxyferulic acid.

In plants, sinapic acid esters prevent the short-wave UV-B radiation from penetrating deeper into the leaves and, in the worst case, damage the plant DNA.

use

In analytical chemistry , in addition to α-cyano-4-hydroxycinnamic acid ( HCCA ) and 2,5-dihydroxybenzoic acid (DHB), it is used as an organic matrix substance in MALDI-MS (Matrix assisted laser desorption ionization mass spectrometry).

Individual evidence

↑ ^a ^b ^c ^d data sheet Sinapic acid from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).
↑ Data sheet sinapinic acid (PDF) from Carl Roth , accessed on February 19, 2010.
↑ Solubility of sinapic acid in non-aqueous solvents ( Memento of July 20, 2011 in the Internet Archive )
↑ Sinapic acid . In: Heinrich August Pierer , Julius Löbe (Hrsg.): Universal Lexicon of the Present and the Past . 4th edition. tape 16 . Altenburg 1863, p. 122 ( zeno.org ).
↑ Dissertation Genetic variation and inheritance of sinapic acid compounds in oilseed rape (Brassica napus L.) , Thomas zum Felde, University of Göttingen, 2005.
↑ Daniela Zeibig: UV radiation: Why plants don't get sunburn
↑ University of Bonn: mass spectrometry, interpretation aids ( memento from July 17, 2012 in the web archive archive.today ).
↑ Beavis, RC; Chait, BT: Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins , Rapid Commun. Mass Spectrom. , 1989 , 3 (12), pp. 432-435 ( PMID 2520223 ).

[SIGMA-1] ta sheet Sinapic acid from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).

[2] Data sheet sinapinic acid (PDF) from Carl Roth , accessed on February 19, 2010.

[3] Solubility of sinapic acid in non-aqueous solvents ( Memento of July 20, 2011 in the Internet Archive )

[4] Sinapic acid . In: Heinrich August Pierer , Julius Löbe (Hrsg.): Universal Lexicon of the Present and the Past . 4th edition. tape 16 . Altenburg 1863, p. 122 ( zeno.org ).

[5] Dissertation Genetic variation and inheritance of sinapic acid compounds in oilseed rape (Brassica napus L.) , Thomas zum Felde, University of Göttingen, 2005.

[6] Daniela Zeibig: UV radiation: Why plants don't get sunburn

[7] University of Bonn: mass spectrometry, interpretation aids ( memento from July 17, 2012 in the web archive archive.today ).

[8] Beavis, RC; Chait, BT: Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins , Rapid Commun. Mass Spectrom. , 1989 , 3 (12), pp. 432-435 ( PMID 2520223 ).