| Stereochemistry | ABSOLUTE |
| Molecular Formula | C7H10O5 |
| Molecular Weight | 174.1513 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
InChI
InChIKey=JXOHGGNKMLTUBP-HSUXUTPPSA-N
InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
| Molecular Formula | C7H10O5 |
| Molecular Weight | 174.1513 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Shikimic acid (SA), an active metabolite of polyphenol-rich food intake, originally extracted from Illicium verum Hook. fil. is an indispensable starting material for the synthesis of the antiviral drug oseltamivir and others useful compounds. In the biological studies, SA has been reported to have anti-inflammatory, analgesia, antioxidant, antithrombotic, and antibacterial activities. SA can play an important role in reducing platelet activation, aggregation related thrombus formation and biomarkers of thrombogenesis in sedentary individuals. In addition, was investigated antibacterial activity of SA against S. aureus, which could be caused by the interactions of SA with S. aureus membrane proteins and lipids, resulting in causing cell membrane dysfunction and bacterial damage or even death.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
in mice: shikimic acid at 50, 100, and 200mg/kg decreased formalin-induced nociceptive behavior (around 50%) and inhibited the inflammatory nociception induced by TNF-α and PGE2 (50 to 75% each).
Route of Administration:
Oral
It was evaluated neuroprotective actions of Shikimic acid (SA) against oxidative stress-induced toxicity on human neuronal-like cells (SH-SY5Y). In vitro antioxidant activity of SA without exerting cytotoxic effects on SH-SY5Y cells at tested concentrations of 10 nM, 10 μM, and 10 mM. In addition, SA protected the cells against H2O2-induced toxicity; effect that could be related, at least in part, with decreased intracellular RS production and its antioxidant potential. The present study shows evidence for neuroprotective actions of SA against oxidative stress-induced toxicity on SH-SY5Y.