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Sinapinic acid

Chemical compound From Wikipedia, the free encyclopedia

Sinapinic acid

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.

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Sinapinic acid
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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
3D model (JSmol)
ChEBI
ChEMBL
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DrugBank
UNII
  • 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
  • COc1cc(cc(c1O)OC)/C=C/C(=O)O
Properties
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).
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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]

Natural occurrences

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

Metabolism

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.

Related compounds

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

See also

References

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