Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H12O5 |
Molecular Weight | 224.21 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(=CC(OC)=C1O)\C=C/C(O)=O
InChI
InChIKey=PCMORTLOPMLEFB-ARJAWSKDSA-N
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-
Molecular Formula | C11H12O5 |
Molecular Weight | 224.21 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Sinapic acid is one of the most common hydroxycinnamic acids and is widespread in the plant kingdom. It has been identified in various fruits, vegetables, cereal grains, oilseed crops, some spices, and medicinal plants. Sinapic acid and its derivatives possess antimicrobial, antioxidant, anti-inflammatory, anticancer and anti-anxiety activities.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17570441
Curator's Comment: CNS active in animal model of anxiety
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16655775
Curator's Comment: Sinapine was first isolated in 1825 from black mustard seeds. Its structure, a choline ester of sinapic acid, was proposed by Gadamer in 1897.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17570441 |
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Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18841975 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline. | 1963 Mar |
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Anti-inflammatory effects of sinapic acid through the suppression of inducible nitric oxide synthase, cyclooxygase-2, and proinflammatory cytokines expressions via nuclear factor-kappaB inactivation. | 2008 Nov 12 |
Patents
Sample Use Guides
Sinapic acid is widespread in the plant kingdom (fruits, vegetables, cereal grains, oilseed crops, and some spices and medicinal plants) and as such is common in the human diet.
Route of Administration:
Oral
Sinapic acid fraction isolated from the ethanolic extract of rapeseed was found to be highly effective against the growth of Gram-negative (Escherichia coli, Enterobacter aerogens, and Pseudomonas fluorescens) and Gram-positive (Bacillus subtilis, Bacillus cereus, Streptococcus lactis, and Streptococcus cremoris) bacteria. Antibacterial properties were determined on a solid foundation by the tile method and in liquid cultures. After 48 h of incubation with sinapic acid on a solid foundation, no growth of cells was observed. In the case of liquid cultures, the introduction of 0.6% sinapic acid caused a decrease in the numbers of live cells by 97.7% to 99.1% after 48 h of incubation. For B. cereus, S. lactis, and P. fluorescens it caused total inhibition of their growth.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:42:30 GMT 2023
by
admin
on
Sat Dec 16 09:42:30 GMT 2023
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Record UNII |
64J2B0K41V
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Record Status |
Validated (UNII)
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Record Version |
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