Angelicin

Base Information

• Chemical Name: Angelicin
• CAS No.: 523-50-2
• Deprecated CAS: 39310-13-9
• Molecular Formula: C11H6O3
• Molecular Weight: 186.167
• Hs Code.: 29322090
• European Community (EC) Number: 637-055-0
• NSC Number: 404563
• UNII: CZZ080D7BD
• DSSTox Substance ID: DTXSID00200321
• Nikkaji Number: J1.579B
• Wikipedia: Angelicin
• Wikidata: Q2849857
• Pharos Ligand ID: 6N8PHP1GLD1D
• Metabolomics Workbench ID: 46287
• ChEMBL ID: CHEMBL53569
• Mol file: 523-50-2.mol

Synonyms:angelicin;isopsoralen

Chemical Property of Angelicin

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.91E-05mmHg at 25°C
• Melting Point: 132-134 °C
• Refractive Index: 1.667
• Boiling Point: 362.621 °C at 760 mmHg
• Flash Point: 173.107 °C
• PSA: 43.35000
• Density: 1.389 g/cm³
• LogP: 2.53920
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 186.031694049
• Heavy Atom Count: 14
• Complexity: 284

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Angelicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-40
• Safety Statements: 26-36/37/39-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C1=CC2=C(C=CO2)C3=C1C=CC(=O)O3
• Description: Angelicin is a furanocoumarin typically isolated from the seeds of P. corylifolia. Like other furanocoumarins, angelicin has antibacterial activities against a number of Gram (+) and Gram (-) bacteria. It has also been shown to prevent tacrine-induced cytotoxicity in human liver-derived HepG2 cells (EC50 = 47 μg/ml) and vascular relaxation in phenylephrine-precontracted rat aorta. Angelicin also weakly inhibits topoisomerase II (IC50 = 404 μM).
• Uses: Antifungal
• Clinical Use: Angelicin derivatives are used to treat psoriasis and cancer. One way of treating these diseases is by photochemotherapy (PUVA) which combines UV irradiation with photosensitizing chemical. Also, it was shown that it is actively inhibits the synthesis of nucleic acids in tumor cells thereby decreasing their growth.

Technology Process of Angelicin

There total 3 articles about Angelicin 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: 100.0%

cis-8,9-dihydro-9-hydroxy-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]-1-benzopyran-2-one (26992-52-9,46954-39-6,56815-93-1,62624-87-7,86851-58-3) → angelicin (523-50-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1021/jo047974k

Reference yield: 71.0%

2-[(2-oxo-2H-chromen-7-yl)oxy]acetaldehyde (16851-02-8) → psoralen (66-97-7) + angelicin (523-50-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 4h; Heating;

DOI:10.1016/S0040-4020(02)00441-6

Reference yield:

tetrachloromethane (56-23-5) + 7-hydroxy-2H-chromen-2-one (93-35-6) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 7-ethoxycoumarin (31005-02-4) + angelicin (523-50-2)

Guidance literature:

at 180 ℃;

upstream raw materials:

tetrachloromethane

7-hydroxy-2H-chromen-2-one

Bromoacetaldehyde diethyl acetal

2-[(2-oxo-2H-chromen-7-yl)oxy]acetaldehyde

Downstream raw materials:

8-(1,2-diphenyl-ethyl)-7-hydroxy-chromen-2-one

Refernces

• 1、 Chimichi, Stefano,Boccalini, Marco,Cosimelli, Barbara,Viola, Giampietro,Vedaldi, Daniela,Dall'Acqua, Francesco. "A convenient synthesis of psoralens". . p. 4859 - 4863. Retrieved 2007/10/03.