530-14-3 , L-Picein,
CAS:530-14-3
C14H18O7 / 298.29
MFCD00016916
4-Acetylphenyl-b-D-glucopyranoside
Picein, also known as piceoside, is a phytochemical compound that belongs to the class of flavonoids. It is primarily found in coniferous trees, such as spruce and pine, and has been identified in various parts of these trees, including the bark, needles, and wood. The compound was first isolated and identified in the late 19th century, and since then, several studies have investigated its various properties and potential applications.
Synthesis and Characterization:
Picein can be synthesized through several methods, including extraction from natural sources, chemical synthesis, and microbial synthesis. The compound is characterized using various analytical methods, such as high-performance liquid chromatography (HPLC), mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy.
Analytical Methods:
HPLC is the most commonly used method for the analysis and quantification of picein in plant extracts and other samples. MS and NMR spectroscopy are used for the identification and structural characterization of the compound. Other analytical methods, such as infrared (IR) spectroscopy and X-ray crystallography, may also be used.
Biological Properties:
Picein has been reported to possess several biological properties, including antioxidant, anti-inflammatory, and antimicrobial activities. Additionally, the compound has been shown to exhibit anticancer and neuroprotective effects, making it an attractive candidate for potential therapeutic applications.
Toxicity and Safety in Scientific Experiments:
Several studies have investigated the toxicity and safety of picein in scientific experiments. Most of these studies have reported no significant adverse effects at therapeutic doses. However, further research is required to fully assess the toxicity and safety of this compound, particularly in long-term studies and at higher doses.
Applications in Scientific Experiments:
Picein has potential applications in various fields of research, including pharmacology, food science, and materials science. In pharmacology, the compound has been investigated for its potential therapeutic applications, including anticancer, neuroprotective, and anti-inflammatory effects. In food science, picein has been identified as a potential natural food preservative due to its antioxidant and antimicrobial properties. In materials science, the compound has been investigated for its potential use in developing biodegradable materials.
Current State of Research:
The current state of research on picein is characterized by a growing interest in the compound's potential therapeutic applications, particularly in cancer and neuroprotection. Additionally, increasing attention is being paid to the compound's potential applications in food science and materials science.
Potential Implications in Various Fields of Research and Industry:
Picein has numerous potential implications in various fields of research and industry. In pharmacology, the compound has the potential to be developed into a new class of drugs for the treatment of cancer, neurodegenerative diseases, and other conditions. In food science, picein has potential applications as a natural preservative in food products, reducing the need for synthetic preservatives. In materials science, the compound has potential applications in developing biodegradable materials, reducing waste and environmental pollution.
Limitations and Future Directions:
Despite its potential, there are several limitations and future directions for research on picein. One major limitation is the lack of large-scale clinical studies to fully assess the compound's therapeutic potential and safety. Additionally, further research is needed to fully understand the compound's mechanisms of action and its potential interactions with other drugs. Future research directions may also include investigating new synthesis methods for the compound and identifying potential new applications in various fields.
Some possible future directions for research on picein include:
1. Investigating the compound's potential applications in the field of nanotechnology, particularly in developing new drug delivery systems.
2. Further investigating the compound's anticancer and anti-inflammatory effects and exploring its potential as a new class of drugs for these conditions.
3. Assessing the compound's potential as a natural colorant in food products, reducing the need for synthetic colorants.
4. Investigating the compound's potential as a natural preservative in cosmetics, reducing the need for synthetic preservatives.
5. Further investigating the compound's neuroprotective effects and exploring its potential as a new treatment for neurodegenerative diseases such as Alzheimer's and Parkinson's disease.
6. Developing new synthetic methods for the compound that are more environmentally friendly and sustainable.
Overall, picein is a promising compound with numerous potential applications in various fields of research and industry. However, further research is needed to fully understand its therapeutic potential, safety, and mechanisms of action.
Title: Picein
CAS Registry Number: 530-14-3
CAS Name: 1-[4-(b-D-Glucopyranosyloxy)phenyl]ethanone
Additional Names: p-(acetylphenyl)-b-D-glucopyranoside; 4'-(b-D-glucopyranosyloxy)acetophenone; p-hydroxyacetophenone-D-glucoside; piceoside; salinigrin; salicinerein; ameliaroside
Molecular Formula: C14H18O7
Molecular Weight: 298.29
Percent Composition: C 56.37%, H 6.08%, O 37.55%
Literature References: In needles and sprouts of Pinus picea L., Picea excelsa Link., Picea glehnii Mast., Coniferae: Tanret, Bull. Soc. Chim. [3] 11, 944 (1894); Kariyone et al., Yakugaku Zasshi 79, 394 (1959), C.A. 53, 14096i (1953). In various willow barks, especially in bark of Salix discolor Muhl., S. nigra Marsh., Salicaceae: Jowett, J. Chem. Soc. 77, 707 (1900); Nonomura, J. Pharm. Soc. Jpn. 75, 80 (1955). In English mistletoe, Amelanchier vulgaris Moench., Rosaceae: Bridel et al., Compt. Rend. 187, 56 (1928). Synthesis: Mauthner, J. Prakt. Chem. [2] 85, 564 (1912).
Properties: Needles or prisms from methanol; mp 195-196°. [a]D23 -88° (c = 1). One gram dissolves in 50 ml water at 15°, in 1 ml boiling water, in ~650 ml abs alc at 15°, in ~40 ml boiling abs alc, in 140 ml ethyl acetate at 15°. Sol in hot glacial acetic acid. Practically insol in ether, chloroform. Hydrolysis with dil mineral acids or with emulsin yields D-glucose and p-hydroxyacetophenone (Piceol). Alkaline hydrolysis yields levoglucosan and p-hydroxyacetophenone: Montgomery et al., J. Org. Chem. 10, 194 (1945).
Melting point: mp 195-196°
Optical Rotation: [a]D23 -88° (c = 1)
CAS Number | 530-14-3 |
Product Name | Picein |
IUPAC Name | 1-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone |
Molecular Formula | C14H18O7 |
Molecular Weight | 298.29 g/mol |
InChI | InChI=1S/C14H18O7/c1-7(16)8-2-4-9(5-3-8)20-14-13(19)12(18)11(17)10(6-15)21-14/h2-5,10-15,17-19H,6H2,1H3/t10-,11-,12+,13-,14-/m1/s1 |
InChI Key | GOZCEKPKECLKNO-RKQHYHRCSA-N |
SMILES | CC(=O)C1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O |
Synonyms | 1-[4-(β-D-Glucopyranosyloxy)phenyl]ethanone; Picein; Ameliaroside; Piceoside; Salicinerein; Salinigrin; p-Hydroxyacetophenone-D-glucoside |
Canonical SMILES | CC(=O)C1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O |
Isomeric SMILES | CC(=O)C1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O |
CAS No: 530-14-3 Synonyms: PiceinAmeliarosidePiceosidep-Hydroxyacetophenone-D-glucosideSalinigrin MDL No: MFCD00016916 Chemical Formula: C14H18O7 Molecular Weight: 298.29 |
COA:
Name: L-Picein; 4-Acetylphenyl-beta-D-glucopyranoside CAS: 530-14-3
M.F.: C14H18O7 M.W.: 298.29 Batch No: 20131021 Quantity:17g
Items | Standards | Results |
Appearance | White or off-white powder | Complies |
MS and NMR | Should comply | Complies |
Identification | IR and TLC | Complies |
Loss weight on dryness | Max. 1% | 0.2% |
Residue on ignition | Max. 0.1% | 0.01% |
Heavy Metals | Max. 50ppm | Complies |
TLC | One spot | One spot |
Assay (HPLC) | Min. 98% | 99.2% |
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