9-methoxy-7H-furo[3,2-g]chromen-7-one

• ChemBase ID: 435
• Molecular Formular: C12H8O4
• Molecular Mass: 216.18952
• Monoisotopic Mass: 216.04225874
• SMILES: o1c2c(cc3c(oc(=O)cc3)c2OC)cc1
• Canonical SMILES: COc1c2oc(=O)ccc2cc2c1occ2
• InChI: InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
• InChIKey: QXKHYNVANLEOEG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-methoxy-7H-furo[3,2-g]chromen-7-one
• IUPAC Traditional name: methoxsalen
• Brand Name: Ammodin; Ammoidin; Meladinin; Meladinine; Meladoxen; Meloxine; Methoxa-Dome; Methoxalen; Methoxaten; New-Meladinin; Oxoralen; Oxsoralen; Oxsoralen Lotion; Oxsoralen-Ultra; Oxypsoralen; Proralone-Mop; Psoralen-Mop; Puvalen; Puvamet; Ultra Mop; Ultramop Lotion; Uvadex; Xanthotoxin; Xanthotoxine; Xanthoxin; Zanthotoxin
• Synonyms: Methoxsalen; Xanthotoxin; Metoxaleno; Dltasoralen; 8-MOP; 9-Methoxyfuro[3,2-g][1]benzopyran-7-one; Ammoidin; Methoxsalen; Xanthotoxin; 8-METHOXYPSORALEN; 8-Methoxypsoralen; Uvadex; Vitpso; Xanthotoxine; 8-Methoxy Psoralen; 9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one; 6-Hydroxy-7-methoxy-5-benzofuranacrylic Acid δ-Lactone; 8-MP; 8-Methoxy-6,7-furanocoumarin; 8-Methoxy[furano-3',2':6,7-coumarin]; 8-Methoxypsoralene; Ammodin; Deltapsoralen; Geroxalen; Meladinin; Meladinine; Meladoxen; Meloxine; Methoxa-Dome; Methoxsalene; NSC 45923; New-Meladinin; Oxsoralen; Oxsoralen Lotion; Oxsoralen-Ultra; Oxypsoralen; Puvalen; Puvamet; 9-methoxy-2H-furo[3,2-g]chromen-2-one; 8-Methoxypsoralen; Xanthotoxin; 8-METHOXYPSORALENE; 9-甲氧基呋喃并[3,2-g][1]苯并吡喃-7-酮; 甲氧沙林; 花椒毒内酯; 花椒毒素; 8-甲氧基补骨脂素; 8-甲氧基补骨脂素; 花椒毒素

Database IDs

• CAS Number: 298-81-7
• EC Number: 206-066-9
• MDL Number: MFCD00005009
• Beilstein Number: 196453
• Merck Index: 145988
• PubChem SID: 24896845; 46506275; 160963898
• PubChem CID: 4114

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.7848117
• LogD (pH = 7.4): 1.7848117
• Log P: 1.7848117
• Molar Refractivity: 56.8529 cm^3
• Polarizability: 22.598698 Å^3
• Polar Surface Area: 48.67 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.1
• LOG S: -3.12
• Solubility (Water): 1.64e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.0476 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; acetic acid: soluble; Chloroform; DMSO; H2O: slightly soluble
• Apperance: Powder; White Solid; white to yellow powder
• Melting Point: 131-133°C; 142-148 °C; 146-150°C; 148 - 150°C; 148°C; 148-150 °C(lit.); 148-150°C
• Hydrophobicity(logP): 1.7; 2.266

Safety Information

• Storage Condition: -20°C; -20°C Freezer, Under Inert Atmosphere; Room Temperature (15-30°C), Protect from light
• RTECS: LV1400000
• European Hazard Symbols: Corrosive (C); Toxic (T); Harmful (Xn)
• UN Number: 1759
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: II
• Australian Hazchem: 2X
• Risk Statements: 22-43; 45-46-22-41; R:22-34-45
• Safety Statements: 36/37; 53-20-26-36/39-45; S:27/28-29-36/37/39-45-53
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H340-H350-H318; H302-H334
• GHS Precautionary statements: P261-P342 + P311; P280-P301+P310-P305+P351+P338-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Maoa(29253)

Product Information

• Purity: ≥98% (GC); ≥99.0% (HPLC); 95%; 97.5; 99%
• Grade: analytical standard; for fluorescence
• Salt Data: Free Base
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤1% loss on drying
• Empirical Formula (Hill Notation): C12H8O4
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02103296

Purity: 99%

DrugBank - DB00553

• Drug Groups: approved
• Description: A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA adducts in the presence of ultraviolet A irradiation. [PubChem]
• Indication: For the treatment of psoriasis and vitiligo
• Pharmacology: Methoxsalen selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of Methoxsalen-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed.
• Affected Organisms: Humans and other mammals
• Half Life: Approximately 2 hours
• Elimination: In both mice and man, methoxsalen is rapidly metabolized. Approximately 95% of the drug is excreted as a series of metabolites in the urine within 24 hours (Pathak et al. 1977).
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1952

Research Area: Inflammation
Biological Activity:
Methoxsalen (Oxsoralen) a naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia, is a drug used to treat psoriasis, eczema, vitiligo and some cutaneous Lymphomas in conjunction with exposing the skin to sunlight. It is a photoactive substance that forms DNA adducts in the presence of ultraviolet an irradiation. After activation it binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function. [1]

Sigma Aldrich - 232726

Biochem/physiol Actions
8-methoxypsoralen (8-MOP) plus ultraviolet A (UVA) irradiation induces monoadducts and interstrand cross-links in DNA and therefore can be used to study DNA repair and recombination mechanisms. Cultured normal human melanocytes treated with 8-methoxypsoralen and irradiated with ultraviolet A (UVA) formed 8-methoxypsoralen-phospholipid photoadducts that could be substituted for diacylglycerol to activate protein kinase C in a cell-free system. 8-MOP is an inactivator of purified reconstituted cytochrome P450. It also inhibits substance P-induced histamine release from substance P-activated rat peritoneal mast cells by suppressing the rise in [Ca2+].

Sigma Aldrich - M3501

Biochem/physiol Actions
8-甲氧基补骨脂素 (8-MOP) 加 A 波紫外线 (UVA) 辐射可诱导单加合物形成和 DNA 链间交联，因此可用于研究 DNA 修复和重组机制。培养的正常人黑素细胞经 8-甲氧基补骨脂素处理和 A 波紫外线 (UVA) 照射后形成 8-甲氧基补骨脂素-磷脂光加成产物，经二酰甘油取代后可在无细胞体系中激活蛋白激酶 C。8-MOP 是纯化重组细胞色素 P450 的灭活剂。它还可以通过抑制 [Ca2+] 的升高，而抑制从 P 物质激活的大鼠腹膜肥大细胞的 P 物质诱导型组胺释放。
Caution
避光。
包装
1, 5 g in glass bottle

Sigma Aldrich - 56448

Biochem/physiol Actions
8-methoxypsoralen (8-MOP) plus ultraviolet A (UVA) irradiation induces monoadducts and interstrand cross-links in DNA and therefore can be used to study DNA repair and recombination mechanisms. Cultured normal human melanocytes treated with 8-methoxypsoralen and irradiated with ultraviolet A (UVA) formed 8-methoxypsoralen-phospholipid photoadducts that could be substituted for diacylglycerol to activate protein kinase C in a cell-free system. 8-MOP is an inactivator of purified reconstituted cytochrome P450. It also inhibits substance P-induced histamine release from substance P-activated rat peritoneal mast cells by suppressing the rise in [Ca2+].

Sigma Aldrich - 95560

Biochem/physiol Actions
8-methoxypsoralen (8-MOP) plus ultraviolet A (UVA) irradiation induces monoadducts and interstrand cross-links in DNA and therefore can be used to study DNA repair and recombination mechanisms. Cultured normal human melanocytes treated with 8-methoxypsoralen and irradiated with ultraviolet A (UVA) formed 8-methoxypsoralen-phospholipid photoadducts that could be substituted for diacylglycerol to activate protein kinase C in a cell-free system. 8-MOP is an inactivator of purified reconstituted cytochrome P450. It also inhibits substance P-induced histamine release from substance P-activated rat peritoneal mast cells by suppressing the rise in [Ca2+].
Other Notes
Properties1; Photochemical reactions of 8-methoxypsoralen with calf thymus DNA2

Toronto Research Chemicals - M260795

Naturally occurring analog of Psoralen (P839800). Use in treatment of psoriasis and mycosis fungoides.

REFERENCES

• http://www.drugbank.ca/drugs/DB00553
• Loutfy, M.A., et al.: Anal. Profiles Drug Subs., 9, 427 (1980)
• Parrish, J.A., et al.: Int. J. Dermatol., 19, 379 (1980)