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Scopoletin information


Scopoletin
Chemical structure of scopoletin
Names
Preferred IUPAC name
7-Hydroxy-6-methoxy-2H-1-benzopyran-2-one
Other names
7-Hydroxy-6-methoxy-2H-chromen-2-one
7-Hydroxy-6-methoxychromen-2-one
Gelseminic acid
Chrysatropic acid
Scopoletine
6-Methylesculetin
Murrayetin
Scopoletol
Escopoletin
Methylesculetin
6-O-Methylesculetin
Esculetin-6-methyl ether
7-Hydroxy-5-methoxycoumarin
6-Methoxyumbelliferone
Identifiers
CAS Number
  • 92-61-5 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4444113 ☒N
ECHA InfoCard 100.001.975 Edit this at Wikidata
PubChem CID
  • 5280460
UNII
  • KLF1HS0SXJ checkY
CompTox Dashboard (EPA)
  • DTXSID0075368 Edit this at Wikidata
InChI
  • InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3 ☒N
    Key: RODXRVNMMDRFIK-UHFFFAOYSA-N ☒N
  • InChI=1/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3
    Key: RODXRVNMMDRFIK-UHFFFAOYAG
SMILES
  • COC1=C(C=C2C(=C1)C=CC(=O)O2)O
Properties
Chemical formula
C10H8O4
Molar mass 192.16 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Scopoletin is a coumarin found in the root of plants in the genus Scopolia such as Scopolia carniolica and Scopolia japonica, in chicory, in Artemisia scoparia, in the roots and leaves of stinging nettle (Urtica dioica), in the passion flower, in Brunfelsia, in Viburnum prunifolium, in Solanum nigrum,[1] in Datura metel,[2] in Mallotus resinosus,[3] or and in Kleinhovia hospita. It can also be found in fenugreek,[4] vinegar,[5][4] some whiskies or in dandelion coffee. A similar coumarin is scoparone. Scopoletin is highly fluorescent when dissolved in DMSO or water and is regularly used as a fluorimetric assay for the detection of hydrogen peroxide in conjunction with horseradish peroxidase. When oxidized, its fluorescence is strongly suppressed.

  1. ^ Zhao Y; Liu F; Lou HX (2010). "[Studies on the chemical constituents of Solanum nigrum]". Zhong Yao Cai (in Chinese). 33 (4): 555–556. PMID 20845784.
  2. ^ Han XL, Wang H, Zhang ZH, Tan Y, Wang JH (August 2015). "[Study on Chemical Constituents in Seeds of Datura metel from Xinjiang]". Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials (in Chinese). 38 (8): 1646–8. PMID 26983236.
  3. ^ Ma J; Jones SH; Hecht SM (2004). "A coumarin from Mallotus resinosus that mediates DNA cleavage". J Nat Prod. 67 (9): 1614–1616. doi:10.1021/np040129c. PMID 15387675.
  4. ^ a b Ouzir, M; El Bairi, K; Amzazi, S (October 2016). "Toxicological properties of fenugreek (Trigonella foenum graecum)". Food and Chemical Toxicology. 96: 145–54. doi:10.1016/j.fct.2016.08.003. PMID 27498339.
  5. ^ Analysis of polyphenolic compounds of different vinegar samples. Miguel Carrero Gálvez, Carmelo García Barroso and Juan Antonio Pérez-Bustamante, Zeitschrift für Lebensmitteluntersuhung und -Forschung A, Volume 199, Number 1, pages 29-31, doi:10.1007/BF01192948

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Scopoletin

Last Update:

Scopoletin is a coumarin found in the root of plants in the genus Scopolia such as Scopolia carniolica and Scopolia japonica, in chicory, in Artemisia...

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Scopoletin glucosyltransferase

Last Update:

enzymology, a scopoletin glucosyltransferase (EC 2.4.1.128) is an enzyme that catalyzes the chemical reaction UDP-glucose + scopoletin ⇌{\displaystyle...

Word Count : 186

Fenugreek

Last Update:

prevalent alkaloid is trigonelline and coumarins include cinnamic acid and scopoletin. Research into whether fenugreek reduces biomarkers in people with diabetes...

Word Count : 2190

Scopolia japonica

Last Update:

of the nightshade family Solanaceae. The coumarins umbelliferone and scopoletin have been isolated from the roots of Scopolia japonica. The hairy roots...

Word Count : 152

Ruta graveolens

Last Update:

coumarins and limonoids. Cell cultures produce the coumarins umbelliferone, scopoletin, psoralen, xanthotoxin, isopimpinellin, rutamarin and rutacultin, and...

Word Count : 2060

Morinda citrifolia

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flavonoids, iridoids such as deacetylasperulosidic acid, fatty acids, scopoletin, catechin, beta-sitosterol, damnacanthal, and alkaloids. M. citrifolia...

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C10H8O4

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mass: 192.17 g/mol, exact mass: 192.0423 u) may refer to: Anemonin Furoin Scopoletin, a coumarin the monomer of polyethylene terephthalate This set index page...

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Artemisia vulgaris

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others. Examples of the phytochemicals include vulgarin, artemisinin, scopoletin, camphene, camphor, sabinene, and some derivatives of quercetin and kaempferol...

Word Count : 1030

Viburnum prunifolium

Last Update:

the part of the plant used in treatments. The active components include scopoletin, aesculetin, salicin, 1-methyl-2,3 dibutyl hemimellitate, and viburnin...

Word Count : 1128

Lycium barbarum

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linoleic acid, and myristic acid. Other compounds include β-sitosterol, scopoletin, and p-coumaric acid. The alkaloid atropine, common in plants of the family...

Word Count : 1357

Dandelion coffee

Last Update:

glycoside) Lactupircin Carotenoids Lutein Violaxanthin Coumarins Esculin Scopoletin Flavonoids Apigenin-7-glucoside Luteolin-7-glucoside Isorhamnetin 3-glucoside...

Word Count : 824

Aesculetin

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fluorescence of bovine serum albumin. Aesculetin can be transformed into scopoletin (7-hydroxy-6-methoxycoumarin) and isoscopoletin (6-hydroxy-7-methoxycoumarin)...

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List of poisonous plants

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Non-alkaloid constituents included sitosterol and beta-methylesculetin (scopoletin).[citation needed] The alkaloids make the plant, in particular the root...

Word Count : 4901

Allamanda

Last Update:

allamandicin did not have activity. The lignan pinoresinol and coumarins such as scopoletin and scoparone have been isolated from A. schottii. Allamanda species have...

Word Count : 820

Tobacco smoke

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or flavor. Tobacco polyphenols (e. g., caffeic acid, chlorogenic acid, scopoletin, rutin) determine the taste and quality of the smoke. Freshly cured tobacco...

Word Count : 1101

Scopolia

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hyoscyamine, and atroscine. The coumarin phenylpropanoids umbelliferone and scopoletin have been isolated from the roots of Scopolia japonica. The existence...

Word Count : 677

Noni juice

Last Update:

absent scientific evidence for health benefits of the noni phytochemicals scopoletin and damnacanthal, neither of which has been confirmed with biological...

Word Count : 1054

Coumarin derivatives

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auraptene ensaculin phenprocoumon (Marcoumar) PSB-SB-487 PSB-SB-1202 scopoletin can be isolated from the bark of Shorea pinanga warfarin (Coumadin) Coumarin...

Word Count : 881

Mandragora officinarum

Last Update:

Non-alkaloid constituents included sitosterol and beta-methylesculetin (scopoletin). The alkaloids make the plant, in particular the root and leaves, poisonous...

Word Count : 2583

Senra incana

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genus Senra. The plant produces the phenolic compounds coniferaldehyde, scopoletin, sinapaldehyde and syringaldehyde "Senra incana". Tropicos. Missouri Botanical...

Word Count : 63

Passiflora

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warmingii. Other compounds found in passion flowers are coumarins (e.g. scopoletin and umbelliferone), maltol, phytosterols (e.g. lutenin) and cyanogenic...

Word Count : 3675

Whisky

Last Update:

compounds. One study identified 40 different phenolic compounds. The coumarin scopoletin is present in whisky, with the highest level reported in Bourbon whiskey...

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Phenylpropanoids metabolism

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for antibiotic purposes. Scopoletin glucosyltransferase, the enzyme that transforms scopoletin into scopolin 4-Coumaroyl-CoA can be combined...

Word Count : 573

Artemisia scoparia

Last Update:

7-Methylesculetin Sabandin A Sabandin B Scoparone (6,7-dimethoxycoumarin) Scopoletin β-Sitosterol Capillin Tropicos search for Artemisia scoparia Roxb. Hort...

Word Count : 370

Scopolin

Last Update:

Scopolin is a glucoside of scopoletin formed by the action of the enzyme scopoletin glucosyltransferase. It occurs in Chamaemelum nobile. Hino F, Okazaki...

Word Count : 151

Gelsemium

Last Update:

(gelsemicine, gelsedine, etc). Other compounds found in the plant include scopoletin (also called gelsemic acid), a small amount of volatile oil, fatty acid...

Word Count : 934

6O

Last Update:

6-O-arabinopyranosylglucopyranoside; see Vicianin 6-O-Methylesculetin; see Scopoletin 6-O-palmitoylascorbic acid; see Ascorbyl palmitate...

Word Count : 105

Chicory

Last Update:

Other components are aesculetin, aesculin, cichoriin, umbelliferone, scopoletin, 6,7-dihydrocoumarin, and further sesquiterpene lactones and their glycosides...

Word Count : 3953

Evolvulus alsinoides

Last Update:

medically verified. Chemical compounds isolated from E. alsinoides include scopoletin, umbelliferone, scopolin and 2-methyl-1,2,3,4-butanetetrol. "Evolvulus...

Word Count : 422

Mandragora autumnalis

Last Update:

Non-alkaloid constituents included sitosterol and beta-methylesculetin (scopoletin). The alkaloids make the plant, particularly the root and leaves, poisonous...

Word Count : 1360

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