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scopolin

CAS No.:
531-44-2
Catalog Number:
AG00DCCU
Molecular Formula:
Molecular Weight:
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Product Description
Catalog Number:
AG00DCCU
Chemical Name:
scopolin
CAS Number:
531-44-2
MDL Number:
MFCD02259444
IUPAC Name:
6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
InChI:
InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
InChI Key:
SGTCGCCQZOUMJJ-YMILTQATSA-N
UNII:
1Y49270PY8
Properties
Complexity:
510  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
354.095g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
354.311g/mol
Monoisotopic Mass:
354.095g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
135A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.1  
Literature
Title Journal
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The cyclic nucleotide cGMP is involved in plant hormone signalling and alters phosphorylation of Arabidopsis thaliana root proteins. Journal of experimental botany 20120501
Anti-inflammatory changes of gene expression by Artemisia iwayomogi in the LPS-stimulated human gingival fibroblast: microarray analysis. Archives of pharmacal research 20120301
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Identification and functional characterization of cDNAs coding for hydroxybenzoate/hydroxycinnamate glucosyltransferases co-expressed with genes related to proanthocyanidin biosynthesis. Journal of experimental botany 20120201
The coumarin scopoletin potentiates acetylcholine release from synaptosomes, amplifies hippocampal long-term potentiation and ameliorates anticholinergic- and age-impaired memory. Neuroscience 20111201
Unique defense strategy by the endoplasmic reticulum body in plants. Plant & cell physiology 20111201
Phenolic glycosides from sugar maple (Acer saccharum) bark. Journal of natural products 20111128
Changes in scopoletin concentration in cassava chips from four varieties during storage. Journal of the science of food and agriculture 20111001
Inhibition of 5-lipoxygenase and skin inflammation by the aerial parts of Artemisia capillaris and its constituents. Archives of pharmacal research 20110901
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Predicting cyclooxygenase inhibition by three-dimensional pharmacophoric profiling. Part II: Identification of enzyme inhibitors from Prasaplai, a Thai traditional medicine. Phytomedicine : international journal of phytotherapy and phytopharmacology 20110115
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The differential spatial distribution of secondary metabolites in Arabidopsis leaves reacting hypersensitively to Pseudomonas syringae pv. tomato is dependent on the oxidative burst. Journal of experimental botany 20100701
Constituents and secondary metabolite natural products in fresh and deteriorated cassava roots. Phytochemistry 20100401
Coumarins from the leaves of Bambusa pervariabilis McClure. Journal of Asian natural products research 20100301
Scopolin-hydrolyzing beta-glucosidases in roots of Arabidopsis. Plant & cell physiology 20100101
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints. International journal of molecular sciences 20100101
Method development and validation for the simultaneous determination of four coumarins in Saussurea superba by capillary zone electrophoresis. Journal of AOAC International 20100101
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal. Journal of ethnobiology and ethnomedicine 20100101
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[Non-alkaloid constituents of Gelsemium elegans]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090901
Scopolin isolated from Erycibe obtusifolia Benth stems suppresses adjuvant-induced rat arthritis by inhibiting inflammation and angiogenesis. International immunopharmacology 20090701
Protein and metabolite analysis reveals permanent induction of stress defense and cell regeneration processes in a tobacco cell suspension culture. International journal of molecular sciences 20090701
[Effects of chemical constituents of Crossostephium chinense on insulin secretion in rat islets in vitro]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090601
Novel sesquiterpene and coumarin constituents from the whole herbs of Crossostephium chinense. Journal of Asian natural products research 20090101
Investigation of biosynthetic pathways to hydroxycoumarins during post-harvest physiological deterioration in Cassava roots by using stable isotope labelling. Chembiochem : a European journal of chemical biology 20081215
Biosynthesis of scopoletin and scopolin in cassava roots during post-harvest physiological deterioration: the E-Z-isomerisation stage. Phytochemistry 20081201
A high-performance liquid chromatographic method for determination of scopolin in rat plasma: application to pharmacokinetic studies. Biomedical chromatography : BMC 20081001
Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana. The Plant journal : for cell and molecular biology 20080901
Evaluation of natural substances from Evolvulus alsinoides L. with the purpose of determining their antioxidant potency. Journal of enzyme inhibition and medicinal chemistry 20080801
On the extent and origins of genic novelty in the phylum Nematoda. PLoS neglected tropical diseases 20080701
[Studies on chemical constituents of Saussurea laniceps]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080501
Antifungal activity of a new phenolic compound from capitulum of a head rot-resistant sunflower genotype. Journal of chemical ecology 20071201
Regulation of arbuscular mycorrhization by apoplastic invertases: enhanced invertase activity in the leaf apoplast affects the symbiotic interaction. The Plant journal : for cell and molecular biology 20070801
Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L. Phytochemistry 20070801
A new C9 nor-isoprenoid glucoside from Rantherium suaveolens. Natural product research 20070801
Rare biscoumarins and a chlorogenic acid derivative from Erycibe obtusifolia. Phytochemistry 20070701
Structures, biogenesis, and biological activities of pyrano[4,3-c]isochromen-4-one derivatives from the Fungus Phellinus igniarius. Journal of natural products 20070201
Identification and determination of glycosides in tobacco leaves by liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry. Journal of separation science 20070201
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Morning glory systemically accumulates scopoletin and scopolin after interaction with Fusarium oxysporum. Zeitschrift fur Naturforschung. C, Journal of biosciences 20050101
Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. Journal of medicinal chemistry 20041202
Molecular phenotyping of the pal1 and pal2 mutants of Arabidopsis thaliana reveals far-reaching consequences on phenylpropanoid, amino acid, and carbohydrate metabolism. The Plant cell 20041001
Ectopic expression of a UDP-glucose:phenylpropanoid glucosyltransferase leads to increased resistance of transgenic tobacco plants against infection with Potato Virus Y. Plant & cell physiology 20040901
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Cytotoxic activity of five compounds isolated from Colombian plants. Fitoterapia 20040301
Agrobacterium tumefaciens AK-6b gene modulates phenolic compound metabolism in tobacco. Phytochemistry 20040101
Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity. Phytotherapy research : PTR 20040101
Phytochemical constituents from Diodia teres. Archives of pharmacal research 20040101
Over-expression of a scopoletin glucosyltransferase in Nicotiana tabacum leads to precocious lesion formation during the hypersensitive response to tobacco mosaic virus but does not affect virus resistance. Plant molecular biology 20040101
Scaphopetalone and scaphopetalumate, a lignan and a triterpene ester from Scaphopetalum thonneri. Phytochemistry 20030201
Study on the determination of polyphenols in tobacco by HPLC coupled with ESI-MS after solid-phase extraction. Journal of chromatographic science 20030101
Resistance of transgenic tobacco seedlings expressing the Agrobacterium tumefaciens C58-6b gene, to growth-inhibitory levels of cytokinin is associated with elevated IAA levels and activation of phenylpropanoid metabolism. Plant & cell physiology 20020801
Downregulation of a pathogen-responsive tobacco UDP-Glc:phenylpropanoid glucosyltransferase reduces scopoletin glucoside accumulation, enhances oxidative stress, and weakens virus resistance. The Plant cell 20020501
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Patterns of phenylpropanoids in non-inoculated and potato virus Y-inoculated leaves of transgenic tobacco plants expressing yeast-derived invertase. Phytochemistry 20010301
Studies on the constituents of the leaves of Morus alba L. Chemical & pharmaceutical bulletin 20010201
Properties