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5-O-Caffeoylshikimic acid

CAS# 73263-62-4

5-O-Caffeoylshikimic acid

Catalog No. BCN7929----Order now to get a substantial discount!

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Quality Control of 5-O-Caffeoylshikimic acid

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Chemical structure

5-O-Caffeoylshikimic acid

3D structure

Chemical Properties of 5-O-Caffeoylshikimic acid

Cas No. 73263-62-4 SDF Download SDF
PubChem ID 5281762 Appearance Powder
Formula C16H16O8 M.Wt 336.29
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
SMILES C1C(C(C(C=C1C(=O)O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O
Standard InChIKey QMPHZIPNNJOWQI-GDDAOPKQSA-N
Standard InChI InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 5-O-Caffeoylshikimic acid

The fruits of Illicium verum

Biological Activity of 5-O-Caffeoylshikimic acid

Description1. 5-O-Caffeoylshikimic acid shows moderate MDR reversal activity. 2. 5-O-Caffeoylshikimic acid shows anti-oxidative activity . 3. 5-O-Caffeoylshikimic acid can remarkably inhibit the macrophage migration and adhesion. 4. 5-O-Caffeoylshikimic acid has anti-inflammatory activity, the underlying mechanism was associated with downregulation of nuclear factor-κB.
TargetsNO | TNF-α | IL Receptor | COX | PGE | NF-kB

5-O-Caffeoylshikimic acid Dilution Calculator

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5-O-Caffeoylshikimic acid Molarity Calculator

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Preparing Stock Solutions of 5-O-Caffeoylshikimic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9736 mL 14.8681 mL 29.7362 mL 59.4725 mL 74.3406 mL
5 mM 0.5947 mL 2.9736 mL 5.9472 mL 11.8945 mL 14.8681 mL
10 mM 0.2974 mL 1.4868 mL 2.9736 mL 5.9472 mL 7.4341 mL
50 mM 0.0595 mL 0.2974 mL 0.5947 mL 1.1894 mL 1.4868 mL
100 mM 0.0297 mL 0.1487 mL 0.2974 mL 0.5947 mL 0.7434 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 5-O-Caffeoylshikimic acid

Antioxidant and Anti-Inflammatory Activities of Phenolic-Enriched Extracts of Smilax glabra.[Pubmed:25477999]

Evid Based Complement Alternat Med. 2014;2014:910438.

Smilax glabra Roxb. has been used for a long time as both food and folk medicine. In the present study, phenolic-enriched extract of S. glabra (PEESG) was extracted with 70% ethanol and purified by HP-20 column chromatography. Its antioxidant and anti-inflammatory activities were evaluated by radical scavenging assay, reducing power determination, and lipopolysaccharide (LPS)-induced RAW264.7 cells assays, respectively. PEESG exhibited obviously scavenging capacity for DPPH and ABTS radicals, as well as significant reducing power for ferric ion. Particularly, PEESG (12.5-50 mug/mL) showed a significantly higher efficiency for scavenging ABTS than that of ascorbic acid and no significant difference with ascorbic acid for DPPH scavenging. PEESG also possessed a significant suppression effect on proinflammatory mediators production, such as nitric oxide (NO), tumor necrosis factor-alpha (TNF-alpha), and interleukin-6 (IL-6), in LPS-induced RAW264.7 cells. In addition, the main ingredients of PEESG were identified using ultrahigh pressure liquid chromatography coupled to electrospray mass spectrometry (U-HPLC-ESI-MS). Seventeen components, including 5-O-Caffeoylshikimic acid, neoastilbin, astilbin, neoisoastilbin, isoastilbin, engetin and isoengeletin were identified. These findings strongly suggest the potential of PEESG as a natural antioxidant and anti-inflammatory agent.

Macrophage biospecific extraction and HPLC-ESI-MSn analysis for screening immunological active components in Smilacis Glabrae Rhizoma.[Pubmed:23384550]

J Pharm Biomed Anal. 2013 Apr 15;77:44-8.

A cell-permeable membrane, as typified by Transwell insert Permeable Supports, permit accurate repeatable invasion assays, has been developed as a tool for screening immunological active components in Smilacis Glabrae Rhizoma (SGR). In this research, components in the water extract of SGR (ESGR) might conjugate with the receptors or other targets on macrophages which invaded Transwell inserts, and then the eluate which contained components biospecific binding to macrophages was identified by HPLC-ESI-MS(n) analysis. Six compounds, which could interact with macrophages, were detected and identified. Among these compounds, taxifolin (2) and astilbin (4) were identified by comparing with the chromatography of standards, while the four others including 5-O-Caffeoylshikimic acid (1), neoastilbin (3), neoisoastilbin (5) and isoastilbin (6), were elucidated by their structure clearage characterizations of tandem mass spectrometry. Then compound 1 was isolated and purified from SGR, along with 2 and 4, was applied to the macrophage migration and adhesion assay in HUVEC (Human Umbilical Vein Endothelial Cells) -macrophages co-incultured Transwell system for immunological activity assessment. The results showed that compounds 1, 2 and 4 with concentration of 5muM (H), 500nM (M) and 50nM (L) could remarkably inhibit the macrophage migration and adhesion (Vs AGEs (Advanced Glycation End Produces) group, 1-L, 2-H and 4-L groups: p<0.05; other groups: p<0.01). Moreover, 1 and 4 showed satisfactory dose-effect relationship. In conclusion, the application of macrophage biospecific extraction coupled with HPLC-ESI-MS(n) analysis is a rapid, simple and reliable method for screening immunological active components from Traditional Chinese Medicine.

Screening of some saponins and phenolic components of Tribulus terrestris and Smilax excelsa as MDR modulators.[Pubmed:19567388]

In Vivo. 2009 Jul-Aug;23(4):545-50.

BACKGROUND: Cytotoxic activity of saponins and phenolic compounds have been described in the literature, but no reports were found on their multidrug resistance (MDR)-modulating effects on human mdr1 gene-transfected mouse lymphoma cell line. MATERIALS AND METHODS: Methylprototribestin, structurally related compounds and a mixture of 3 acetylated isomers of methylprotodioscin were investigated for antiproliferative effect and modulation of drug accumulation. RESULTS: The growth inhibitory dose (ID50) of the compounds ranged from 12.64 to 20.62 mug/ml. Methylprototribestin was the most effective resistance modifier. However, methylprotodioscin, pseudoprotodioscin, prosapogenin A of dioscin, tribestin and 5-O-Caffeoylshikimic acid showed moderate MDR reversal activity. In a checkerboard method, methyloprototribestin and the mixture of the 3 acetylated isomers enhanced the antiproliferative effects on MDR cells in combination with doxorubicin. CONCLUSION: Based on these results, methylprototribestin and the mixture of the 3 acetylated isomers can be recommended for further in vivo experiments in combination with anthracyclines in human MDR-cancer xenograft transplanted mice.

Secondary metabolites isolated from Castilleja rubra exert anti-inflammatory effects through NF-kappaB inactivation on lipopolysaccharide-induced RAW264.7 macrophages.[Pubmed:24062082]

Arch Pharm Res. 2014 Jul;37(7):947-54.

8-Epiloganin (1), mussaenoside (2), and 5-O-Caffeoylshikimic acid (3) have been isolated from Castilleja rubra, and the anti-inflammatory properties of these metabolites in a cell culture system were investigated. Compounds 1-3 suppressed not only the production of nitric oxide (NO) and prostaglandin E2, but also the expression of inducible NO synthase and cyclooxygenase-2 induced by lipopolysaccharide (LPS) in the RAW264.7 murine macrophage cell line. Compounds 1-3 also inhibited the release of pro-inflammatory cytokines induced by LPS, namely, tumor necrosis factor-alpha and interleukin-1beta. The underlying mechanism of the anti-inflammatory action of compounds 1-3 was associated with downregulation of nuclear factor-kappaB.

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