isopsoralen (CAS 523-50-2) — formula C11H6O3, molecular weight 186.16; category organic chemicals.
Documented applications: Uses: Found in many plants traditionally used as herbal remedies, Highly fluorescent, [HSDB] Present in plants of the Umbelliferae family, Clinically tested in combination with ultraviolet A radiation for the treatment of psoriasis, [IARC], MEDICATION, Angelicin is used as tranquilliser, sedative, or anticonvulsant. (L579), Methods of Manufacturing: We have developed two practical one-step syntheses of 2, 3-dihydro-3-hydroxy-2-hydroxyalkylbenzofurans from readily available optically pure alpha, beta-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH, CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy iodocoumarins 35d and 40 and acetoxy bromonaphthalene 41 add to epoxy aldehyde (S)-26 to complete the first syntheses of vaginidiol (7c), vaginol (7t), smyrindiol (8c), xanthoarnol (8t), and avicenol A (9t). Acid-catalyzed fragmentation of vaginidiol or vaginol provides angelicin, while that of smyrindiol or xanthoarnol affords psoralen. In both cases, the trans isomers fragment only twice as fast as the cis isomers, possibly through the intermediacy of a common benzylic cation. This may have implications for the biosynthesis of angelicin and psoralen., General Manufacturing Information: Psoralens are natural furocoumarins well-known for their photosensitizing potential. Porphyrins, including hematoporphyrin derivatives (HPD), are also potent photosensitizers. ... Psoralens ... have an action spectrum in the UV-A range., Psoralens.
isopsoralen is a carbon-based organic compound with CAS registry number 523-50-2 and molecular formula C11H6O3 (molecular weight 186.16), belonging to the organic chemicals segment of chemical raw materials.
CAS number: 523-50-2
Its molecular formula C11H6O3 comprises 11 C, 6 H, 3 O atoms.
Also known as: isopsoralen · angelicin
Category: organic chemicals
The CAS registry number of isopsoralen is 523-50-2.
Molecular formula C11H6O3, molecular weight 186.16.
It is also registered under: isopsoralen, angelicin.
Recorded applications: Uses: Found in many plants traditionally used as herbal remedies, Highly fluorescent, [HSDB] Present in plants of the Umbelliferae family, Clinically tested in combination with ultraviolet A radiation for the treatment of psoriasis, [IARC], MEDICATION, Angelicin is used as tranquilliser, sedative, or anticonvulsant. (L579), Methods of Manufacturing: We have developed two practical one-step syntheses of 2, 3-dihydro-3-hydroxy-2-hydroxyalkylbenzofurans from readily available optically pure alpha, beta-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH, CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy iodocoumarins 35d and 40 and acetoxy bromonaphthalene 41 add to epoxy aldehyde (S)-26 to complete the first syntheses of vaginidiol (7c), vaginol (7t), smyrindiol (8c), xanthoarnol (8t), and avicenol A (9t). Acid-catalyzed fragmentation of vaginidiol or vaginol provides angelicin, while that of smyrindiol or xanthoarnol affords psoralen. In both cases, the trans isomers fragment only twice as fast as the cis isomers, possibly through the intermediacy of a common benzylic cation. This may have implications for the biosynthesis of angelicin and psoralen., General Manufacturing Information: Psoralens are natural furocoumarins well-known for their photosensitizing potential. Porphyrins, including hematoporphyrin derivatives (HPD), are also potent photosensitizers. ... Psoralens ... have an action spectrum in the UV-A range., Psoralens.
Category: Organic Chemicals.
Public-database records for isopsoralen (CAS 523-50-2), reproduced here for independent cross-checking.
| Reported hazard statements | H302 (100%), H312 (90.5%), H315 (100%), H319 (100%), H332 (90.5%), H335 (97.6%), H351 (90.5%) |
|---|
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (90.5%): Harmful in contact with skin [Warning Acute toxicity, dermal]
| 沸点 | 360.00 to 362.00 °C. @ 760.00 mm Hg |
|---|---|
| 熔点 | 140 °C |
| 熔点 | 138 - 139.5 °C |
| 溶解度 | In water, 20 mg/L |
| 蒸气压 | 0.0000224 [mmHg] |
| LogP | log Kow = 2.08 |
| LogP | 2.08 |
| CAS Registry Number | 523-50-2 |
|---|---|
| PubChem CID | 10658 |
| 分子式 | C11H6O3 |
| IUPAC 名称 | furo[2,3-h]chromen-2-one |
| UNII（FDA） | CZZ080D7BD |
Angelicin; 523-50-2; ISOPSORALEN; Angecin; Furo(2,3-h)coumarin; 2H-Furo[2,3-H]-1-benzopyran-2-one; Angelicin (coumarin derivative); 2H-Furo(2,3-H)-1-benzopyran-2-one; Furo(5',4':7,8)coumarin; 4-Hydroxy-5-benzofuranacrylic acid gamma-lactone; CZZ080D7BD; DTXSID00200321; 3-(4-Hydroxy-5-benzofuranyl)-2-propenoic acid gamma-lactone; Angelicin plus ultraviolet A radiation; NSC-404563; Furo[5',4':7,8]coumarin
| 分子量 | 186.16 |
|---|---|
| XLogP3 | 2 |
| 氢键供体数 | 0 |
| 氢键受体数 | 3 |
| 可旋转键数 | 0 |
| 精确质量 | 186.031694049 |
| 单同位素质量 | 186.031694049 |
| 拓扑极性表面积 | 39.4 |
| 重原子数 | 14 |
| 形式电荷 | 0 |
isopsoralen · CAS 523-50-2 · C11H6O3. UNII CZZ080D7BD. 沸点: 360.00 to 362.00 °C. @ 760.00 mm Hg; 熔点: 140 °C; 熔点: 138 - 139.5 °C.
Source: PubChem / Wikidata; the batch COA governs where values differ.
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