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S2500

Sigma-Aldrich

Scopoletin

≥99%

Synonym(s):

6-Methoxyumbelliferone, 6-Methylesculetin, 7-Hydroxy-6-methoxy-2H-1-benzopyran-2-one, 7-Hydroxy-6-methoxycoumarin, Buxuletin, Chrysatropic acid, Escopoletin, Esculetin-6-methyl ether, Gelseminic acid, Murrayetin

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About This Item

Empirical Formula (Hill Notation):
C10H8O4
CAS Number:
92-61-5
Molecular Weight:
192.17
Beilstein:
156296
EC Number:
202-171-9
MDL number:
MFCD00006872
UNSPSC Code:
12171501
PubChem Substance ID:
24899524
NACRES:
NA.28

Assay

≥99%

mp

203-205 °C (lit.)

SMILES string

COc1cc2C=CC(=O)Oc2cc1O

InChI

1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3

InChI key

RODXRVNMMDRFIK-UHFFFAOYSA-N

Gene Information

human ... ACHE(43)

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Application

  • Production of Polyphenolic Natural Products by Bract-Derived Tissue Cultures of Three Medicinal Tilia spp.: A Comparative Untargeted Metabolomics Study.: This study investigates the production of polyphenolic compounds, including scopoletin, in tissue cultures derived from the bracts of three medicinal Tilia species. The research highlights the potential of these cultures in producing valuable natural products (Szűcs et al., 2024).

Biochem/physiol Actions

Dye that can be used to detect the release of reactive oxygen species during the oxidative burst; peroxynitrite scavenger; acetylcholinesterase inhibitor.
Scopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ae Ra Kim et al.
Phytotherapy research : PTR, 18(1), 1-7 (2004-01-30)
Peroxynitrite (ONOO(-)) is one of cytotoxic species produced by the reaction between superoxide (*O(2) (-)) and nitric oxide (NO). The main aim of this study was to identify ONOO(-) scavenging constituents from herbs. Methanolic extracts derived from one hundred thirty
Urs Lahrmann et al.
The New phytologist, 207(3), 841-857 (2015-04-29)
During a compatible interaction, the sebacinoid root-associated fungi Piriformospora indica and Sebacina vermifera induce modification of root morphology and enhance shoot growth in Arabidopsis thaliana. The genomic traits common in these two fungi were investigated and compared with those of
M Baz et al.
Journal of applied microbiology, 112(4), 782-792 (2012-02-02)
The early molecular events underlying the elicitation of plant defence reactions by Gram-positive bacteria are relatively unknown. In plants, calcium and reactive oxygen species are commonly involved as cellular messengers of a wide range of biotic stimuli from pathogenic to
Yoshihiro Suzuki et al.
Journal of immunology (Baltimore, Md. : 1950), 171(11), 6119-6127 (2003-11-25)
Earlier studies, including our own, revealed that activation of mast cells is accompanied by production of reactive oxygen species (ROS) that help to mediate the release of the inflammatory mediators, including histamine and eicosanoids. However, little is known about the
Sang-Hyun Lee et al.
Journal of natural products, 76(4), 615-620 (2013-03-21)
Artemisia iwayomogi has been used as a folk medicine for treating various diseases including inflammatory and immune-related diseases. Scopoletin (1) and scopolin (2) were isolated from this species. Scopoletin (1) showed more potent peroxyl radical-scavenging capacity, reducing capacity, and cellular
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