| Identification | Back Directory | [Name]
3,4-O-Isopropylidene shikimic acid | [CAS]
183075-03-8 | [Synonyms]
4-O-Isopropylidene shikimic acid
3,4-O-Isopropylidene shikimic acid
3,4-O-Isopropylidene shikimic acid USP/EP/BP
7-Hydroxy-2,2-diMethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylic acid
1,3-Benzodioxole-5-carboxylic acid, 3a,6,7,7a-tetrahydro-7-hydroxy-2,2-dimethyl-, (3aR,7R,7aS)- | [Molecular Formula]
C10H14O5 | [MDL Number]
MFCD17214943 | [MOL File]
183075-03-8.mol | [Molecular Weight]
214.22 |
| Chemical Properties | Back Directory | [Boiling point ]
404.831±45.00 °C(Press: 760.00 Torr)(predicted) | [density ]
1.325±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted) | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
4.189±0.60(predicted) | [color ]
Off-white to light yellow |
| Hazard Information | Back Directory | [Description]
3,4-Oxo- isopropylidene-shikimic acid has significant anti-inflammatory effect which may be related to inhibiting the production of prostaglandin E2 and protecting free radical against oxidation.
3,4-Oxo-isopropylidene-shikimic acid has protective effects on experimental colitis induced by trinitrobenzenesulfonic acid in rats, probably due to an antioxidant action.
3. 3,4-Oxo-isopropylidene-shikimic acid has anti-thrombosis effect, it inhibits thrombosis by anti-platelet-aggregation.
4. 3,4-Oxo-isopropylidene shikimic acid relieves the brain edema of rats subjected to MCAT by improving the energy metabolism and Na +, K +-ATPase activity in rat brain tissue.
5. 3,4-Oxo-isopropylidene-shikimic acid can inhibit adhesion of polymorphonuclear leukocyte to TNF-alpha-induced endothelial cells in vitro.
6. 3,4-Oxo-isopropylidene-shikimic acid has analgesic and antioxidant activities, it exhibits moderate antioxidant activity by scavenging the superoxide radical and hydroxyl radical with IC50 values of 0.214 and 0.450 ug/mL, respectively.
7. 3,4-Oxo-isopropylidene-shikimic acid has exhibited ameliorative effect on cognitive impairment in experimental animal models of dementia, it can promote adipogenesis by up-regulating expressions of C/EBP β, PPAR γ, C/EBP α, aP2 and FAS, and also stimulate adipokines during adipocyte differentiation, suggests that stimulation of adipokines and cognitive enhancing effect of 3,4-oxo-isopropylidene-shikimic acid have some relationship. | [Uses]
3,4-O-Isopropylidene-shikimicn acid is a natural product that can be isolated from the whole plants of Hypericum wightianum. 3,4-O-Isopropylidene-shikimic acid has anti-inflammatory effect and antioxidant activities[1][2]. | [target]
NO | NOS | PGE | TNF-α | PPAR | Sodium Channel | ATPase | Potassium Channel | [References]
[1] Shu-Hong Tao, et al. Note: A New Flavone from Hypericum Wightianum. Journal of Asian Natural Products Research. 2004. 6(4), 307-310.
[2] Jianfeng Xing, et al. Anti-inflammatory effect of 3,4-oxo-isopropylidene-shikimic acid on acetic acid-induced colitis in rats. Inflammation. 2012 Dec;35(6):1872-9. DOI:10.1007/s10753-012-9509-7 |
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