SINAPIC ACID, (E)-

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

Structure Search

SMILES

COC1=CC(=CC(OC)=C1O)\C=C\C(O)=O

InChI

InChIKey=PCMORTLOPMLEFB-ONEGZZNKSA-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+

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Description
Sources: http://onlinelibrary.wiley.com/doi/10.1111/1541-4337.12041/full

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17570441	Activator 1430
NF-kappa B signaling pathway 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18841975	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Bacterial infections 234 Sources: http://onlinelibrary.wiley.com/doi/10.1002/lipi.19920940406/abstract	Primary	Basic research	Unknown Approved Use Unknown
Drug-induced liver injury 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23494565	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14979919	Primary	Basic research	Unknown Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17570441	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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	18841975

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Name

Type

Language

SINAPIC ACID, (E)-

Common Name

English

DEGLY SINA

Brand Name

English

2-PROPENOIC ACID, 3-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, (2E)-

Common Name

English

(E)-SINAPIC ACID

Systematic Name

English

2-PROPENOIC ACID, 3-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-

Common Name

English

CINNAMIC ACID, 4-HYDROXY-3,5-DIMETHOXY-, (E)-

Common Name

English

TRANS-SINAPINIC ACID

Brand Name

English

TRANS-SINAPIC ACID

Systematic Name

English

Code System Code Type Description

MESH

C073734