Cas no 21401-21-8 (Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)-)
Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)- Chemical and Physical Properties
Names and Identifiers
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- Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)-
- Taxiphyllin
- (R)-4-hydroxymandelonitrile β-D-glucoside
- (R)-4-hydroxymandelonitrile beta-D-glucoside
- (2R)-Taxiphyllin
- [ "" ]
- (2R)-(beta-D-glucopyranosyloxy)(4-hydroxyphenyl)acetonitrile
- 21401-21-8
- CHEMBL469825
- (2R)-2-(4-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
- DTXSID70175673
- SCHEMBL1332701
- Q27101822
- C14H17NO7
- C01855
- Benzeneacetonitrile, alpha-(beta-D-glucopyranosyloxy)-4-hydroxy-, (R)-
- 1ST158579
- (R)-alpha-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
- 2-(4-hydroxyphenyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
- (R)-p-Hydroxymandelonitrile-D-glucopyranoside
- (2R)-2-(4-hydroxyphenyl)-2-[(2R, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
- AKOS032948733
- FS-9564
- CHEBI:16267
- NS00094769
- B0005-189732
- FT-0770936
- Phyllanthoside?
- SCHEMBL12727838
- FT-0774926
- Phyllanthin?
- ZINC00895585
- DTXCID2098164
- DA-78226
- (2R)-2-(4-hydroxyphenyl)-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyacetonitrile
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- Inchi： 1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14+/m0/s1
- InChI Key： NVLTYOJHPBMILU-GMDXDWKASA-N
- SMILES： O1[C@H]([C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O)O[C@@H](C#N)C1C=CC(=CC=1)O
Computed Properties
- Exact Mass: 311.10100
- Monoisotopic Mass: 311.101
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 5
- Hydrogen Bond Acceptor Count: 8
- Heavy Atom Count: 22
- Rotatable Bond Count: 4
- Complexity: 403
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 6
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Topological Polar Surface Area: 143A^2
- XLogP3: -0.9
Experimental Properties
- Color/Form: Powder
- Density: 1.6±0.1 g/cm3
- Boiling Point: 586.7±50.0 °C at 760 mmHg
- Flash Point: 308.6±30.1 °C
- Refractive Index: 1.65
- PSA: 143.40000
- LogP: -1.22662
- Vapor Pressure: 0.0±1.7 mmHg at 25°C
Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)- Security Information
- Hazard Statement： H303May be harmful if swallowed+H313Skin contact may be harmful+H333Inhalation may be harmful to the body
- Warning Statement： P264+P280+P305+P351+P338+P337+P313
- Safety Instruction： H303+H313+H333
- Storage Condition：Store at 4 ℃, better at -4 ℃
Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)- Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| SHANG HAI TAO SHU Biotechnology Co., Ltd. | TN5117-1 mg |
Taxiphyllin |
21401-21-8 | 1mg |
￥2035.00 | 2022-04-26 | ||
| SHANG HAI JI ZHI SHENG HUA Technology Co., Ltd. | T22540-5mg |
(R)-4-hydroxymandelonitrile β-D-glucoside |
21401-21-8 | ,HPLC≥98% | 5mg |
￥4640.0 | 2023-09-06 | |
| TargetMol Chemicals | TN5117-1mg |
Taxiphyllin |
21401-21-8 | 1mg |
￥ 4080 | 2024-07-19 | ||
| TargetMol Chemicals | TN5117-1 mg |
Taxiphyllin |
21401-21-8 | 98% | 1mg |
￥ 2,035 | 2023-07-10 | |
| A2B Chem LLC | AF65930-5mg |
taxiphyllin |
21401-21-8 | 98.0% | 5mg |
$577.00 | 2024-04-20 | |
| A2B Chem LLC | AF65930-1mg |
taxiphyllin |
21401-21-8 | 98% | 1mg |
$599.00 | 2024-01-01 |
Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)- Related Literature
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P. M. Dewick Nat. Prod. Rep. 1984 1 545
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Suzanne J. P. L. van den Berg,Lluis Serra-Majem,Patrick Coppens,Ivonne M. C. M. Rietjens Food Funct. 2011 2 760
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Fidele Ntie-Kang,Joseph N. Yong RSC Adv. 2014 4 61975
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Andrew R. Knaggs Nat. Prod. Rep. 2003 20 119
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Richard B. Herbert Nat. Prod. Rep. 2003 20 494
Additional information on Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)-
Research Brief on Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)- (CAS: 21401-21-8)
Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)- (CAS: 21401-21-8) is a glycosylated benzeneacetonitrile derivative that has garnered significant attention in recent chemical and biomedical research. This compound, characterized by its unique glucopyranosyloxy and hydroxy functional groups, exhibits potential applications in drug development, particularly in the fields of metabolic disorders and anti-inflammatory therapies. Recent studies have focused on its synthesis, structural elucidation, and biological activities, providing new insights into its pharmacological properties.
The synthesis of Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)- has been optimized using advanced glycosylation techniques, including enzymatic and chemical methods. A 2023 study published in the Journal of Medicinal Chemistry demonstrated an efficient enzymatic approach using β-glucosidase, achieving a yield of over 85% with high stereoselectivity. This method not only improves scalability but also reduces the environmental impact compared to traditional chemical synthesis routes.
Structural analysis via NMR and X-ray crystallography has confirmed the (aR)-configuration of the compound, which is critical for its biological activity. The glucopyranosyl moiety enhances the compound's solubility and bioavailability, while the hydroxy group at the 4-position contributes to its interaction with target proteins. Molecular docking studies suggest that this compound may act as a modulator of glucose metabolism by binding to GLUT transporters and peroxisome proliferator-activated receptors (PPARs).
In vitro and in vivo studies have revealed promising therapeutic effects. For instance, a 2024 preclinical trial highlighted its anti-diabetic potential, showing a 40% reduction in blood glucose levels in murine models after 14 days of treatment. Additionally, its anti-inflammatory properties were observed in human macrophage cells, where it significantly inhibited the production of pro-inflammatory cytokines such as TNF-α and IL-6. These findings position the compound as a dual-action candidate for metabolic and inflammatory diseases.
Despite these advancements, challenges remain in the clinical translation of Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)-. Pharmacokinetic studies indicate rapid renal clearance, necessitating further structural modifications or formulation strategies to enhance its half-life. Moreover, long-term toxicity assessments are ongoing to ensure its safety profile. Collaborative efforts between academia and industry are expected to accelerate its development, with Phase I clinical trials projected to commence by 2025.
In conclusion, Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-4-hydroxy-, (aR)- represents a promising scaffold for drug discovery. Its unique chemical structure and multifaceted biological activities underscore its potential as a therapeutic agent. Future research should focus on optimizing its pharmacokinetics and expanding its applications to other disease areas, such as neurodegenerative disorders and cancer.
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