Scopoletin

Base Information

• Chemical Name: Scopoletin
• CAS No.: 92-61-5
• Molecular Formula: C10H8O4
• Molecular Weight: 192.171
• Hs Code.: 29322090
• European Community (EC) Number: 202-171-9
• UNII: KLF1HS0SXJ
• ChEMBL ID: CHEMBL71851
• DSSTox Substance ID: DTXSID0075368
• Metabolomics Workbench ID: 46493
• NCI Thesaurus Code: C126100
• Nikkaji Number: J4.658B
• NSC Number: 405647
• Pharos Ligand ID: 49UFWTUZ8W94
• Wikidata: Q2472366
• Wikipedia: Scopoletin
• Mol file: 92-61-5.mol

Synonyms:Acid, Chrysotropic;Acid, Gelseminic;Chrysotropic Acid;Gelseminic Acid;Methylesculetin;Scopoletin

Chemical Property of Scopoletin

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 2E-07mmHg at 25°C
• Melting Point: 203-205 °C(lit.)
• Refractive Index: 1.609
• Boiling Point: 413.5 °C at 760 mmHg
• PKA: 7.91±0.20(Predicted)
• Flash Point: 172.4 °C
• PSA: 59.67000
• Density: 1.377 g/cm³
• LogP: 1.50720
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Sightly, Heated), Ethyl Acetate (Slightly, Heated), Methanol (Sightl
• Water Solubility.: Slightly soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 192.04225873
• Heavy Atom Count: 14
• Complexity: 261

Purity/Quality:

more than 98% ^*data from raw suppliers

Scopoletin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: COC1=C(C=C2C(=C1)C=CC(=O)O2)O
• Uses: Scopoletin can be used for cosmetics, topical formulations, and foods. Scopoletin is the aglucone of Scopolin. Used for cosmetics, topical formulations, and foods. Dyes and metabolites.

Technology Process of Scopoletin

There total 46 articles about Scopoletin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

7-acetoxy-6-methoxycoumarin (56795-51-8) → 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one (92-61-5)

Guidance literature:

With silica-supported phosphomolybdic acid; In methanol; at 20 ℃; for 3h;

DOI:10.1002/adsc.200700292

Reference yield: 93.7%

2,4-dihydroxy-5-methoxybenzaldehyde (51061-83-7) + malonic acid (141-82-2) → 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one (92-61-5)

Guidance literature:

With N,N-dimethyl-aniline; for 4h; Reflux;

Reference yield: 91.6%

2,4-dihydroxy-5-methoxybenzaldehyde (51061-83-7) + Malonic acid monomethyl ester (16695-14-0) → 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one (92-61-5)

Guidance literature:

With N,N-dimethyl-aniline; at 180 ℃; for 6h;

upstream raw materials:

aesculetin

dimethyl sulfate

7-hydroxy-6-methoxy-2-oxo-2H-benzopyran-3-carboxylic acid

7-acetoxy-6-methoxycoumarin

Downstream raw materials:

Scoparone

2,4-dihydroxy-5-methoxybenzoic acid

braylin

aesculetin

Refernces

• 1、 Yalcin, Dilek,Bayraktar, Oguz. "Inhibition of catechol-O-methyltransferase (COMT) by some plant-derived alkaloids and phenolics". . p. 162 - 166. Retrieved 2010.
• 2、 Alaniya et al.. "-". . . Retrieved 1972.
• 3、 Matkarimov, A. D.,Batirov, E. Kh.,Malikov, V. M.,Seitmuratov, E.. "OBTUSININ - A NEW COUMARIN FROM Haplophyllum obtusifolium". . p. 240 - 242. Retrieved 1980.
• 4、 Kitajima, Junichi,Kamoshita, Akane,Ishikawa, Toru,Takano, Akihito,Fukuda, Tatsuo,Isoda, Susumu,Ida, Yoshiteru. "Glycosides of Atractylodes ovata.". . p. 1106 - 1108. Retrieved 2003.
• 5、 Xia, Yang-Liu,Wang, Jing-Jing,Li, Shi-Yang,Liu, Yong,Gonzalez, Frank J.,Wang, Ping,Ge, Guang-Bo. "Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment". . . Retrieved 2020/11/25.
• 6、 Chen, Cheng,Chen, Li,Lei, Zhichao,Li, Na,Shi, Zhixian,Sun, Jianbo,Wang, Yujin. "Novel NO-releasing scopoletin derivatives induce cell death via mitochondrial apoptosis pathway and cell cycle arrest". . . Retrieved 2020/05/19.