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92-61-5

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92-61-5 Usage

Description

Scopoletin, also known as 6-methoxyumbelliferone, is a pharmacologically active coumarin compound found in various plant species. It is the aglucone of Scopolin and exhibits a crystalline solid form. Scopoletin possesses a wide range of applications due to its unique chemical properties and biological activities.

Uses

Used in Cosmetics:
Scopoletin is used as an active ingredient in cosmetics for its beneficial properties. It is incorporated into skincare products to provide various benefits, such as improving skin health and appearance.
Used in Topical Formulations:
Scopoletin is utilized in topical formulations for its therapeutic effects. It can be found in creams, ointments, and other topical applications to treat various skin conditions and promote healing.
Used in Foods:
Scopoletin is also used in the food industry, where it serves as a natural preservative and flavoring agent. Its presence in food products helps maintain freshness and enhance taste.
Used in Dyes and Metabolites:
Scopoletin has applications in the dye industry, where it is used as a natural dye due to its color-producing properties. Additionally, it is involved in the synthesis of various metabolites, which have potential applications in pharmaceutical and chemical research.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 3083, 1962 DOI: 10.1021/jo01056a023

Biochem/physiol Actions

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.

Purification Methods

Crystallise it from water, acetic acid or *C6H6/MeOH. It is dimorphic with a second m at 193-195o. It sublimes at 120-130o/12mm. [Beilstein 18 H 99, 18 I 348, 18 II 68, 18 III/IV 1323, 18/3 V 203.]

Check Digit Verification of cas no

The CAS Registry Mumber 92-61-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 2 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 92-61:
(4*9)+(3*2)+(2*6)+(1*1)=55
55 % 10 = 5
So 92-61-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3

92-61-5 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (S0367)  Scopoletin  >98.0%(HPLC)(T)

  • 92-61-5

  • 100mg

  • 1,160.00CNY

  • Detail
  • TCI America

  • (S0367)  Scopoletin  >98.0%(HPLC)(T)

  • 92-61-5

  • 1g

  • 6,500.00CNY

  • Detail
  • Sigma-Aldrich

  • (38332)  Scopoletin  analytical standard

  • 92-61-5

  • 38332-10MG

  • 1,100.97CNY

  • Detail
  • USP

  • (1610090)  Scopoletin  United States Pharmacopeia (USP) Reference Standard

  • 92-61-5

  • 1610090-20MG

  • 4,662.45CNY

  • Detail

92-61-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name scopoletin

1.2 Other means of identification

Product number -
Other names 7-hydroxy-6-methoxychromen-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:92-61-5 SDS

92-61-5Relevant articles and documents

-

Braymer et al.

, p. 163 (1960)

-

Coumarins from Astragalus asper

Guzhva

, p. 767 - 768 (2008)

-

COUMARIN COMPOSITION OF Haplophyllum bungei

Abyshev, A. Z.,Gashimov, N. F.

, p. 615 - 616 (1982)

-

A COUMARIN GLUCOSIDE FROM XEROMPHIS OBOVATA

Sibanda, S.,Ndengu, B.,Multari, G.,Pompi, V.,Galeffi, C.

, p. 1550 - 1552 (1989)

From root bark of Xeromphis obovata three coumarins have been isolated: scopoletin, its 7-β-D-glucopyranoside (scopolin) and the new β-D-apiosyl-(1" -> 6)-β-D-glucopyranoside of scopoletin, named xeroboside.Also two iridoids, deacetylasperulosidic acid methyl ester and gardenoside, have been isolated and identified as the corresponding acetyl derivetives. Key Word Index-Xeromphis obovata; Rubiaceae; coumarins; iridoids; xeroboside.

COUMARINS OF Ptarmica bisserata

Davidyats, E. S.

, p. 233 (1982)

-

Novel NO-releasing scopoletin derivatives induce cell death via mitochondrial apoptosis pathway and cell cycle arrest

Chen, Cheng,Chen, Li,Lei, Zhichao,Li, Na,Shi, Zhixian,Sun, Jianbo,Wang, Yujin

, (2020/05/19)

A series of phenylsulfonyfuroxan-based NO-releasing scopoletin derivatives were designed and synthesized in the study. All target compounds showed significantly improved antiproliferative activity against four cancer cell lines (MDA-MB-231, MCF-7, HepG2 and A459) and lower cytotoxicity toward normal liver LO2 cells. Derivative 47 concentration-dependently inhibited the colony formation of MDA-MB-231 cells. NO-releasing assessment indicated that the intracellular NO level was almost positively correlated with the antiproliferative ability. Compound 47, which released the highest amounts of NO, showed the best potency (IC50 = 1.23 μM) against MDA-MB-231 cells. Mechanism research revealed for the first time that 47 blocked the proliferation of MDA-MB-231 cells by activating mitochondrial apoptosis pathway and arresting cell cycle at G2/M phase. Taken together, as a novel scopoletin derivative, 47 exhibited excellent inhibitory effects against malignant cancer cells and lower toxicity on normal cells. Thus, an in-depth evaluation of 47 to explore its complete therapeutic potential for cancer treatment is warranted.

Preparation method of scopoletin

-

Paragraph 0048-0052, (2019/10/04)

The invention discloses a preparation method of scopoletin, which comprises the following steps: 1) with 2,4-dihydroxy-5-methoxybenzaldehyde as an initial raw material, adding a solvent and a catalyst, adding a malonic acid compound within a reaction temperature range of 0-300 DEG C, and carrying out a heat preservation reaction for 2-10 hours to obtain a reaction solution, the usage amount of the malonic acid compound being 1-10 equivalents; 2) cooling the reaction solution at a cooling temperature of -10 DEG C to 35 DEG C, wherein a large amount of solids is separated after the reaction solution is cooled, and carrying out reduced pressure suction filtration on the reaction solution from which the large amount of solids are separated out to obtain a crude product of the scopoletin and filtrate; and 3) recrystallizing the crude product of the scopoletin with ethyl acetate to obtain a pure product of the scopoletin. The method has the advantages of high yield, low cost and low pollution.

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