ISOPIMPINELLIN Chemical Properties

Melting point:

150-151°C

Boiling point:

448.7±45.0 °C(Predicted)

Density 

1.352±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Soluble in acetone and chloroform;

form 

powder to crystal

color 

Light yellow to Yellow to Green

Water Solubility 

practically insoluble in water

λmax

268nm(MeOH)(lit.)

BRN 

262337

InChI

InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3

InChIKey

DFMAXQKDIGCMTL-UHFFFAOYSA-N

SMILES

C1(=O)OC2=C(OC)C3OC=CC=3C(OC)=C2C=C1

LogP

1.407 (est)

CAS DataBase Reference

482-27-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

T+

Risk Statements 

20/21/22-28

Safety Statements 

22-36/37/39-45-36/37-28

RIDADR 

UN 2811 6.1 / PGII

WGK Germany 

3

RTECS 

LV1049200

HS Code 

2932202000

Hazardous Substances Data

482-27-9(Hazardous Substances Data)

ISOPIMPINELLIN Usage And Synthesis

Description

Psoralens are natural photoactivable compounds in plants and can cause phototoxic contact dermatitis. For example, Cachrys libanotis contains 5,8-dimethoxypsoralen.

Chemical Properties

Pale Yellow Solid

Uses

Antiviral, anti HIV

Uses

antineoplastic, antifungal, insect antifeedant

Definition

ChEBI: Isopimpinellin is a member of psoralens.

Hazard

A poison by ingestion.

Contact allergens

Psoralens are natural photoactivable compounds in plants and can cause phototoxic contact dermatitis. For example, Cachrys libanotis L., Apiaceae-Umbelliferae family, contains 5,8-dimethoxypsoralen.

Synthesis

General procedure for the synthesis of 4,9-dimethoxyfuro[3,2-g]benzopyran-7-one (Isopimpinellin, 29) from the compound (CAS:14348-23-3) and iodomethane: To a solution of 200 mg (0.9 mmol) of compound 25 in anhydrous DMF (30 mL) was added K2CO3 (286 mg. 2.07 mmol) and CH3I (167 μL, 3.6 mmol). The reaction mixture was heated to reflux under argon protection; after 1 h of reaction, the mixture was poured into cold water (100 mL) and acidified with 1 M aqueous HCl. The product was extracted with ethyl acetate (3 x 50 mL), the organic layers were combined, and the solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by column chromatography (eluent: ethyl acetate/hexane, 1:1). The fraction containing the target compound was collected, concentrated and dried to give 29 as a pale yellow powder (182 mg, 82% yield).

References

[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 784 - 788

ISOPIMPINELLIN(482-27-9)Related Product Information

• ISOXANTHOHUMOL
• 2-(3-Methoxy-4-hydroxyphenyl)-6-α-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one
• Alpinetin
• Panaxatriol
• Brassinolide
• HOMOORIENTIN
• Folic acid
• Panaxadiol
• Tectorigenin
• Diacerein
• Securinol A
• morusin
• ISOPIMPINELLIN(SH)
• BYAKANGELICIN
• ISOPIMPINELLIN
• NEOBYAKANGELICOL
• BYAKANGELICOL
• phellopterin