| Identification | More | [Name]
ISOPIMPINELLIN | [CAS]
482-27-9 | [Synonyms]
4,9-DIMETHOXYPSORALEN
5,9-DIMETHOXYPSORALEN
AKOS 243-24
DIMETHYLPSORALEN
ISOPIMPINELLIN
4,9-Dimethoxy-7H-furo[3,2-g]chromen-7-one
4,9-Dimethoxy-furo[3,2-g]chromen-7-one
5,8-Dimethoxy-6,7-furanocoumarin
5,8-Dimethoxypsoralen
5,8-Dimethoxypsoralene
7H-Furo[3,2-g][1]benzopyran-7-one, 4,9-dimethoxy-
7H-Furo[3,2-g][1]benzopyran-7-one,4,9-dimethoxy-
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one
DIMETHYLPSORALEN hplc
ISOPIMPINELLIN WITH HPLC
4,9-Dimethoxy-7H-furo[3,2-γ],[1]benzopyran-7-one
4,9-Dimethoxy-furo[3,2-γ],chromen-7-one | [Molecular Formula]
C13H10O5 | [MDL Number]
MFCD00017407 | [Molecular Weight]
246.22 | [MOL File]
482-27-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
150-151°C | [Boiling point ]
448.7±45.0 °C(Predicted) | [density ]
1.352±0.06 g/cm3(Predicted) | [storage temp. ]
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 | [Usage]
Antiviral, anti HIV | [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 | [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. | [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) |
| Hazard Information | Back Directory | [Chemical Properties]
Pale Yellow Solid | [Uses]
antineoplastic, antifungal, insect antifeedant | [Uses]
Antiviral, anti HIV | [Hazard]
A poison by ingestion. | [Description]
Psoralens are natural photoactivable compounds in
plants and can cause phototoxic contact dermatitis.
For example, Cachrys libanotis contains 5,8-dimethoxypsoralen.
| [Definition]
ChEBI: Isopimpinellin is a member of psoralens. | [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 |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1 / PGII | [WGK Germany ]
3 | [RTECS ]
LV1049200 | [HS Code ]
2932202000 | [Hazardous Substances Data]
482-27-9(Hazardous Substances Data) |
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