sinapinic acid

{{cs1 config|name-list-style=vanc}}

{{chembox

| Watchedfields = changed

| verifiedrevid = 464391904

| Name = Sinapinic acid

| ImageFile = sinapic acid.png

| ImageName = Sinapinic acid

| PIN = (2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acid

| OtherNames = Sinapinic acid
Sinapic acid
3,5-Dimethoxy-4-hydroxycinnamic acid
4-Hydroxy-3,5-dimethoxycinnamic acid

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 553361

| 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+

| InChIKey = PCMORTLOPMLEFB-ONEGZZNKBS

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = PCMORTLOPMLEFB-ONEGZZNKSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 530-59-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 68A28V6010

| PubChem = 637775

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 109341

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB08587

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 15714

| SMILES = COc1cc(cc(c1O)OC)/C=C/C(=O)O

}}

|Section2={{Chembox Properties

| Formula = C₁₁H₁₂O₅

| MolarMass = 224.21 g/mol

| MeltingPtC = 203 to 205

| MeltingPt_notes = (decomposes)

}}

}}

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.{{cite journal |vauthors=Beavis RC, Chait BT |title=Matrix-assisted laser-desorption mass spectrometry using 355 nm radiation |journal=Rapid Commun. Mass Spectrom. |volume=3 |issue=12 |pages=436–9 |year=1989 |pmid=2520224 |doi=10.1002/rcm.1290031208|bibcode=1989RCMS....3..436B }}{{cite journal |vauthors=Beavis RC, Chait BT |title=Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins |journal=Rapid Commun. Mass Spectrom. |volume=3 |issue=12 |pages=432–5 |year=1989 |pmid=2520223 |doi=10.1002/rcm.1290031207|bibcode=1989RCMS....3..432B }} 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.{{cite journal |vauthors=Bunzel M, Ralph J, Kim H, Lu F, Ralph SA, Marita JM, Hatfield RD, Steinhart H |title=Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fibre |journal=J. Agric. Food Chem. |volume=51 |pages=1427–1434 |year=2003 |doi=10.1021/jf020910v |pmid=12590493 |issue=5}}

Sinapine is an alkaloidal amine found in black mustard seeds. It is considered a choline ester of sinapinic acid.{{Cite journal| last1=Tzagoloff| first1=A. |title = Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline| journal=Plant Physiology| volume = 38| issue = 2| pages = 202–206| year = 1963| pmid = 16655775| pmc = 549906| doi=10.1104/pp.38.2.202}}