4-O-Caffeoylshikimic acidCAS# 180842-65-3 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| 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. |
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| 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. |
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| 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. | ||
| Description | 4-O-Caffeoylshikimic acid is a natural product from Illicium verum. |
| 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
4-O-Caffeoylshikimic acid Molarity Calculator
| 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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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.
