Contents

Sinapinic acid

Sinapinic acid

Names
Preferred IUPAC name (2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid
Other names Sinapinic acid Sinapic acid 3,5-Dimethoxy-4-hydroxycinnamic acid 4-Hydroxy-3,5-dimethoxycinnamic acid
Identifiers
CAS Number	530-59-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15714 Y
ChEMBL	ChEMBL109341 Y
ChemSpider	553361 Y
DrugBank	DB08587 Y
PubChem CID	637775
UNII	68A28V6010 Y
CompTox Dashboard (EPA)	DTXSID201355800 DTXSID40862129, DTXSID201355800
InChI InChI=1S/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+ Y Key: PCMORTLOPMLEFB-ONEGZZNKSA-N Y InChI=1/C11H12O5/c1-15-8-5-7(3-4-10(12)13)6-9(16-2)11(8)14/h3-6,14H,1-2H3,(H,12,13)/b4-3+ Key: PCMORTLOPMLEFB-ONEGZZNKBS
SMILES COc1cc(cc(c1O)OC)/C=C/C(=O)O
Properties
Chemical formula	C11H12O5
Molar mass	224.21 g/mol
Melting point	203 to 205 °C (397 to 401 °F; 476 to 478 K) (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Chemical compound

Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family. It is a commonly used matrix in MALDI mass spectrometry.^[1][2] It is a useful matrix for a wide variety of peptides and proteins. It serves well as a matrix for MALDI due to its ability to absorb laser radiation and to also donate protons (H⁺) to the analyte of interest.

Sinapic acid can form dimers with itself (one structure) and ferulic acid (three different structures) in cereal cell walls and therefore may have a similar influence on cell-wall structure to that of the diferulic acids.^[3]

Sinapine is an alkaloidal amine found in black mustard seeds. It is considered a choline ester of sinapinic acid.^[4]

Sinapinic acid can be found in wine,^[5] vinegar,^[6] and black plums.^[7]

Sinapate 1-glucosyltransferase is an enzyme that uses UDP-glucose and sinapate to produce UDP and 1-sinapoyl-D-glucose.

Sinapoylglucose—malate O-sinapoyltransferase is an enzyme that uses 1-O-sinapoyl-beta-D-glucose and (S)-malate to produce D-glucose and sinapoyl-(S)-malate.

Canolol is a phenolic compound found in crude canola oil. It is produced by decarboxylation of sinapic acid during canola seed roasting.^[8]