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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 of SINAPIC ACID, (Z)-

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-

HIDE SMILES / InChI

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

Curator's Comment: CNS active in animal model of anxiety

Originator

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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline.
1963 Mar
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

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 Sat Dec 16 09:42:30 GMT 2023
Edited
by admin
on Sat Dec 16 09:42:30 GMT 2023
Record UNII
64J2B0K41V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SINAPIC ACID, (Z)-
Common Name English
CIS-SINAPINIC ACID
Common Name English
CINNAMIC ACID, 4-HYDROXY-3,5-DIMETHOXY-, (Z)-
Systematic Name English
CIS-SINAPIC ACID
Systematic Name English
Z-SINAPINIC ACID
Common Name English
2-PROPENOIC ACID, 3-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, (2Z)-
Systematic Name English
2-PROPENOIC ACID, 3-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, (Z)-
Systematic Name English
Code System Code Type Description
PUBCHEM
1549091
Created by admin on Sat Dec 16 09:42:30 GMT 2023 , Edited by admin on Sat Dec 16 09:42:30 GMT 2023
PRIMARY
CAS
7361-90-2
Created by admin on Sat Dec 16 09:42:30 GMT 2023 , Edited by admin on Sat Dec 16 09:42:30 GMT 2023
PRIMARY
FDA UNII
64J2B0K41V
Created by admin on Sat Dec 16 09:42:30 GMT 2023 , Edited by admin on Sat Dec 16 09:42:30 GMT 2023
PRIMARY