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[ CAS No. 480-41-1 ] {[proInfo.proName]}

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Chemical Structure| 480-41-1
Chemical Structure| 480-41-1
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Product Citations

Product Citations      Expand+

Commey, Leslie ; Mechref, Yehia ; Burow, Mark , et al. DOI: PubMed ID:

Abstract: The peanut seed coat acts as a physical and biochemical barrier against Aspergillus flavus infection; however, the nature of the inhibitory chemicals in the peanut seed coat in general is not known. This study identified and characterized peanut seed coat metabolites that inhibit A. flavus growth and aflatoxin contamination. Selected peanut accessions grown under well-watered and water-deficit conditions were assayed for A. flavus resistance, and seed coats were metabolically profiled using liquid chromatography mass spectrometry. Kyoto Encyclopedia of Genes and Genome phenylpropanoid pathway reference analysis resulted in the identification of several seed coat metabolic compounds, and ten selected metabolites were tested for inhibition of A.flavus growth and aflatoxin contamination. Radial growth bioassay demonstrated that inhibited A. flavus growth (98.7%) and reduced the aflatoxin contamination estimate from 994 to 1 μg/kg. Scanning electron micrographs showed distorted hyphae and conidiophores in cultures of 2,5-dihydroxybenzaldehyde-treated A. flavus, indicating its potential use for field application as well as seed coat metabolic engineering.

Keywords: aflatoxin, A. flavus ; metabolomics ; seed coat ; liquid chromatography mass spectrometry (LC-MS) ; radial growth bioassay ; secondary metabolites

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Nasanjargal Dorjjugder ; Goro Taguchi ; DOI: PubMed ID:

Abstract: Flavonoid 7-O-glucosides exhibit various biological activities; however, some are not abundant in nature. Therefore, a method to produce flavonoid 7-O-glucosides was investigated. Escherichia coli expressing tobacco-derived glucosyltransferase (Ec-NtGT2) converted several flavonoids (apigenin, luteolin, quercetin, kaempferol, and naringenin) to their 7-O-glucosides with conversion rates of 67–98%. In scaled-up production, Ec-NtGT2 yielded 24 mg/L of apigenin 7-O-glucoside, 41 mg/L of luteolin 7-O-glucoside, 118 mg/L of quercetin 7-O-glucoside, 40 mg/L of kaempferol 7-O-glucoside, and 75 mg/L of naringenin 7-O-glucoside through sequential administration of substrates in 4–9 h. The conversion rates of apigenin, luteolin, quercetin, kaempferol, and naringenin were 97%, 72%, 77%, 98%, and 96%, respectively. These results indicated that Ec-NtGT2 is a simple and efficient bioconversion system for the production of flavonoid 7-O-glucosides.

Keywords: Escherichia coli bioconversion ; Flavonoid 7-O-glucoside ; Flavonoid ; 7-O-glucosyltransferase ; Sequential administration

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Dorjjugder, Nasanjargal ; Hatano, Mayu ; Taguchi, Goro DOI: PubMed ID:

Abstract: Objectives: To produce flavonol and flavone 6-C-glucosides by bioconversion using recombinant Escherichia coli expressing a C-glucosyltransferase from wasabi (WjGT1). Results: Escherichia coli expressing WjGT1 (Ec-WjGT1) converted flavones (apigenin and luteolin) and flavonols (quercetin and kaempferol) into their 6-C-glucosides in M9 minimal media supplemented with glucose, and released these products into the culture media. Ec-WjGT1 system also converts a flavanone (naringenin) into its C-glucoside at a conversion rate of 60% in 6 h. For scale-up production, apigenin, kaempferol, and quercetin were sequentially fed into the Ec-WjGT1 system at concentrations of 20-50 μM every 15-60 min, and the system was then able to produce isovitexin, kaempferol 6-C-glucoside, and quercetin 6-C-glucoside at an 89-99% conversion rate. Conclusions: The Ec-WjGT1 system quickly and easily produces flavone and flavonol 6-C-glucosides at high conversion rates when using sequential administration to avoid precipitation of substrates.

Keywords: C-glucosyltransferase ; Escherichia coli bioconversion ; Flavonol C-glucoside

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Product Details of [ 480-41-1 ]

CAS No. :480-41-1 MDL No. :MFCD00870553
Formula : C15H12O5 Boiling Point : -
Linear Structure Formula :- InChI Key :FTVWIRXFELQLPI-ZDUSSCGKSA-N
M.W : 272.25 Pubchem ID :439246
Synonyms :
NSC 34875;S-Dihydrogenistein;Salipurol;NSC 11855
Chemical Name :(S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

Calculated chemistry of [ 480-41-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 71.57
TPSA : 86.99 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 2.52
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 0.71
Log Po/w (SILICOS-IT) : 2.05
Consensus Log Po/w : 1.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.49
Solubility : 0.0874 mg/ml ; 0.000321 mol/l
Class : Soluble
Log S (Ali) : -3.99
Solubility : 0.0277 mg/ml ; 0.000102 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.42
Solubility : 0.104 mg/ml ; 0.000382 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.01

Safety of [ 480-41-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 480-41-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 480-41-1 ]
  • Downstream synthetic route of [ 480-41-1 ]

[ 480-41-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 480-41-1 ]
  • [ 578-74-5 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034
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