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4-O-Caffeoylshikimic acid

CAS# 180842-65-3

4-O-Caffeoylshikimic acid

Catalog No. BCN7931----Order now to get a substantial discount!

Product Name & Size Price Stock
4-O-Caffeoylshikimic acid:5mg Please Inquire In Stock
4-O-Caffeoylshikimic acid:10mg Please Inquire In Stock
4-O-Caffeoylshikimic acid:20mg Please Inquire In Stock
4-O-Caffeoylshikimic acid:50mg Please Inquire In Stock

Quality Control of 4-O-Caffeoylshikimic acid

Number of papers citing our products

Chemical structure

4-O-Caffeoylshikimic acid

3D structure

Chemical Properties of 4-O-Caffeoylshikimic acid

Cas No. 180842-65-3 SDF Download SDF
PubChem ID 49821869 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,4S,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,5-dihydroxycyclohexene-1-carboxylic acid
SMILES C1C(C(C(C=C1C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O
Standard InChIKey VTURJKQJEXSKNY-GDDAOPKQSA-N
Standard InChI InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(21)24-15-12(19)6-9(16(22)23)7-13(15)20/h1-6,12-13,15,17-20H,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 4-O-Caffeoylshikimic acid

The fruits of Illicium verum

Biological Activity of 4-O-Caffeoylshikimic acid

Description4-O-Caffeoylshikimic acid is a natural product from Illicium verum.

Protocol of 4-O-Caffeoylshikimic acid

Structure Identification
Journal of the Agricultural Chemical Society of Japan, 1997, 61(8):1397-1398.

4-O-Caffeoylshikimic and 4-O-(p-Coumaroyl)shikimic Acids from the Dwarf Tree Fern, Dicksonia antarctica[Reference: WebLink]

Two derivatives of shikimic acid were isolated from croziers of the dwarf tree fern, Dicksonia antarctica, and their structures were elucidated as 4-O-Caffeoylshikimic acid and 4-O-(p-coumaroyl)-shikimic acid on the basis of mass spectrometric and NMR spectroscopic evidence.

4-O-Caffeoylshikimic acid Dilution Calculator

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4-O-Caffeoylshikimic acid Molarity Calculator

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Preparing Stock Solutions of 4-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 4-O-Caffeoylshikimic acid

Crop Domestication Alters Floral Reward Chemistry With Potential Consequences for Pollinator Health.[Pubmed:30319666]

Front Plant Sci. 2018 Sep 26;9:1357.

Crop domestication can lead to weakened expression of plant defences, with repercussions for herbivore and pathogen susceptibility. However, little is known about how domestication alters traits that mediate other important ecological interactions in crops, such as pollination. Secondary metabolites, which underpin many defence responses in plants, also occur widely in nectar and pollen and influence plant-pollinator interactions. Thus, domestication may also affect secondary compounds in floral rewards, with potential consequences for pollinators. To test this hypothesis, we chemically analysed nectar and pollen from wild and cultivated plants of highbush blueberry (Vaccinium corymbosum L.), before conducting an artificial diet bioassay to examine pollinator-pathogen interactions. Our results indicated that domestication has significantly altered the chemical composition of V. corymbosum nectar and pollen, and reduced pollen chemical diversity in cultivated plants. Of 20 plant metabolites identified in floral rewards, 13 differed significantly between wild and cultivated plants, with a majority showing positive associations with wild compared to cultivated plants. These included the amino acid phenylalanine (4.5 times higher in wild nectar, 11 times higher in wild pollen), a known bee phagostimulant and essential nutrient; and the antimicrobial caffeic acid ester 4-O-Caffeoylshikimic acid (two times higher in wild nectar). We assessed the possible biological relevance of variation in caffeic acid esters in bioassays, using the commercially available 3-O-caffeoylquinic acid. This compound reduced Bombus impatiens infection by a prominent gut pathogen (Crithidia) at concentrations that occurred in wild but not cultivated plants, suggesting that domestication may influence floral traits with consequences for bee health. Appreciable levels of genetic variation and heritability were found for most floral reward chemical traits, indicating good potential for selective breeding. Our study provides the first assessment of plant domestication effects on floral reward chemistry and its potential repercussions for pollinator health. Given the central importance of pollinators for agriculture, we discuss the need to extend such investigations to pollinator-dependent crops more generally and elaborate on future research directions to ascertain wider trends, consequences for pollinators, mechanisms, and breeding solutions.

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