SCOPOLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H18O9
Molecular Weight	354.3087
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C3OC(=O)C=CC3=C1

InChI

InChIKey=SGTCGCCQZOUMJJ-YMILTQATSA-N

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

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Studies on the constituents of the leaves of Morus alba L.	2001 Feb	11217100
Molecular cloning and heterologous expression of novel glucosyltransferases from tobacco cultured cells that have broad substrate specificity and are induced by salicylic acid and auxin.	2001 Jul	11454003
[Nonpolar components of the leaves of Philadelphus coronarius L].	2001 Nov	11797195
Study on the determination of polyphenols in tobacco by HPLC coupled with ESI-MS after solid-phase extraction.	2003 Jan	12597595
Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products.	2004 Dec 2	15566295
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.	2004 Jan	15159640
Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity.	2004 Jan	14750192
Phenylpropanoids, phenylalanine ammonia lyase and peroxidases in elicitor-challenged cassava (Manihot esculenta) suspension cells and leaves.	2004 Jul	15145789
Cytotoxic activity of five compounds isolated from Colombian plants.	2004 Mar	15030931
Molecular phenotyping of the pal1 and pal2 mutants of Arabidopsis thaliana reveals far-reaching consequences on phenylpropanoid, amino acid, and carbohydrate metabolism.	2004 Oct	15377757
Ectopic expression of a UDP-glucose:phenylpropanoid glucosyltransferase leads to increased resistance of transgenic tobacco plants against infection with Potato Virus Y.	2004 Sep	15509841
A new bisabolane sesquiterpenoid from Euphorbia chrysocoma.	2005 Dec	16308205
Morning glory systemically accumulates scopoletin and scopolin after interaction with Fusarium oxysporum.	2005 Jan-Feb	15787250
Accumulation of coumarins in Arabidopsis thaliana.	2006 Feb	16405932
Growth at elevated CO2 concentrations leads to modified profiles of secondary metabolites in tobacco cv. SamsunNN and to increased resistance against infection with potato virus Y.	2006 Jan	17086759
A new C9 nor-isoprenoid glucoside from Rantherium suaveolens.	2007 Aug	17680498
Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.	2007 Aug	17599369
Regulation of arbuscular mycorrhization by apoplastic invertases: enhanced invertase activity in the leaf apoplast affects the symbiotic interaction.	2007 Aug	17521407
Antifungal activity of a new phenolic compound from capitulum of a head rot-resistant sunflower genotype.	2007 Dec	18034282
Identification and determination of glycosides in tobacco leaves by liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry.	2007 Feb	17396585
Structures, biogenesis, and biological activities of pyrano[4,3-c]isochromen-4-one derivatives from the Fungus Phellinus igniarius.	2007 Feb	17279797
[Studies on the chemical constituents from Inula cappa (II)].	2007 Jan	17539299
Rare biscoumarins and a chlorogenic acid derivative from Erycibe obtusifolia.	2007 Jul	17570448
Evaluation of natural substances from Evolvulus alsinoides L. with the purpose of determining their antioxidant potency.	2008 Aug	18666003
Biosynthesis of scopoletin and scopolin in cassava roots during post-harvest physiological deterioration: the E-Z-isomerisation stage.	2008 Dec	19004461
Investigation of biosynthetic pathways to hydroxycoumarins during post-harvest physiological deterioration in Cassava roots by using stable isotope labelling.	2008 Dec 15	19035613
On the extent and origins of genic novelty in the phylum Nematoda.	2008 Jul 2	18596977
[Studies on chemical constituents of Saussurea laniceps].	2008 May	18652351
A high-performance liquid chromatographic method for determination of scopolin in rat plasma: application to pharmacokinetic studies.	2008 Oct	18506740
Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana.	2008 Sep	18547395
Novel sesquiterpene and coumarin constituents from the whole herbs of Crossostephium chinense.	2009	19177244
Scopolin isolated from Erycibe obtusifolia Benth stems suppresses adjuvant-induced rat arthritis by inhibiting inflammation and angiogenesis.	2009 Jul	19327410
[Effects of chemical constituents of Crossostephium chinense on insulin secretion in rat islets in vitro].	2009 Jun	19771872
Diterpene esters and phenolic compounds from Sapium insigne (ROYLE) BENTH. ex HOOK. fil.	2009 Nov	19881284
[Bioactivity guided isolation of alpha-glucosidase inhibitor from whole herbs of Crossostephium chinense].	2009 Sep	19943487
Cassava: an appraisal of its phytochemistry and its biotechnological prospects.	2010 Dec	20943239
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.	2010 Dec 13	21144003
[Chemical constituents from Hydrangea paniculata].	2010 Nov	21355271
Method development and validation for the simultaneous determination of four coumarins in Saussurea superba by capillary zone electrophoresis.	2010 Sep-Oct	21140650

Patents

Name

Type

Language

SCOPOLIN

Common Name

English

6-METHOXYCOUMARIN 7-O-.BETA.-D-GLUCOSIDE

Common Name

English

SCOPOLETIN 7-GLUCOSIDE

Common Name

English

SCOPOLETIN 7-O-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

NSC-404560

Code

English

SCOPOLOSIDE

Common Name

English

SCOPOLETIN 7-O-GLUCOSIDE

Common Name

English

2H-1-BENZOPYRAN-2-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-6-METHOXY-

Systematic Name

English

7-O-.BETA.-GLUCOPYRANOSYLSCOPOLETIN

Common Name

English

7-(.BETA.-D-GLUCOPYRANOSYLOXY)-6-METHOXYCOUMARIN

Common Name

English

6-METHOXY-7-(.BETA.-D-GLUCOPYRANOSYLOXY)COUMARIN

Common Name

English

SCOPOLIN [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

439514