4,8-dimethyl-7-<(β-bromoallyl)oxy>coumarin
trioxsalen
Conditions | Yield |
---|---|
With N,N-diethylaniline at 225℃; for 24h; | 60% |
4,8-dimethyl-7-<(β-chloroalllyl)oxy>coumarin
trioxsalen
Conditions | Yield |
---|---|
With N,N-diethylaniline at 220 - 225℃; for 24h; | 14% |
6-allyl-7-hydroxy-4,8-dimethyl-2H-chromen-2-one
A
trioxsalen
B
4,10-Dimethyl-pyrano[3,2-g]chromene-2,8-dione
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 12h; Heating; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / acetone 2: N,N-diethylaniline / 218 °C 3: 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / benzene / 12 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 77 percent / potassium carbonate / acetone / 24 h / Heating 2: 14 percent / N,N-diethylaniline / 24 h / 220 - 225 °C View Scheme | |
Multi-step reaction with 2 steps 1: 91 percent / potassium carbonate / acetone / 6 h / Heating 2: 60 percent / N,N-diethylaniline / 24 h / 225 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N,N-diethylaniline / 218 °C 2: 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / benzene / 12 h / Heating View Scheme |
Conditions | Yield |
---|---|
Stage #1: 1,3,5-Trioxan; trioxsalen With hydrogenchloride at 20℃; for 16h; Stage #2: With sodium azide; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 80℃; for 24h; | 94% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran 1.) 15 min, 2.) 10 h; | 92% |
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 16h; | 86% |
With hydrogenchloride In water at 25℃; for 12h; | 70% |
trioxsalen
4'-bromotrioxsalen
Conditions | Yield |
---|---|
With bromine In dichloromethane at 25℃; for 3h; | 82% |
trioxsalen
ethyl chloromethyl ether
4'-hydroxymethyl-4,5',8-trimethylpsoralen
Conditions | Yield |
---|---|
In acetic acid at 20℃; for 15h; Protected from light; | 75% |
trioxsalen
A
4',5'-dihydro-4,5',8-trimethylpsoralen
B
6,7-dihydro-4,10-dimethyl-2H,8H-benzo<1,2-b;5,4-b'>dipyran-2-one
Conditions | Yield |
---|---|
With cyclohexene; palladium on activated charcoal In ethanol for 3h; Heating; | A 74% B 12% |
trioxsalen
C14H11IO3
Conditions | Yield |
---|---|
With N-iodo-succinimide In chloroform; trifluoroacetic acid at 20℃; for 3h; | 71% |
trioxsalen
4',5'-dihydro-4,5',8-trimethylpsoralen
Conditions | Yield |
---|---|
With palladium on activated charcoal In ethanol for 0.5h; Heating; | 70% |
trioxsalen
chloromethyl methyl ether
4'-chloromethyl-4,5',8-trimethylpsoralen
Conditions | Yield |
---|---|
With acetic acid | 62% |
In acetic acid for 48h; Ambient temperature; | 55% |
With acetic acid | |
With acetic acid at 20℃; for 72h; |
Conditions | Yield |
---|---|
With tin(IV) chloride at 25℃; for 72h; | 62% |
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione
trioxsalen
4'-N-Phthalimidomethyl-4,5',8-trimethylpsoralen
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; trifluoroacetic acid In dichloromethane for 6h; Ambient temperature; | 61% |
trioxsalen
Conditions | Yield |
---|---|
With piperidine; tetraphosphorus decasulfide In benzene at 70℃; for 12h; | 60% |
trioxsalen
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 120℃; for 24h; | 50% |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 120℃; for 24h; | 50% |
Conditions | Yield |
---|---|
at 15℃; Quantum yield; Irradiation; |
Methyl oleate
trioxsalen
8-((1S,2R,2aR,9bS)-5,7,9b-Trimethyl-2-octyl-3-oxo-1,2a,3,9b-tetrahydro-2H-4,6-dioxa-cyclobuta[a]cyclopenta[g]naphthalen-1-yl)-octanoic acid methyl ester
8-((1S,2S,2aR,9bS)-5,7,9b-Trimethyl-2-octyl-3-oxo-1,2a,3,9b-tetrahydro-2H-4,6-dioxa-cyclobuta[a]cyclopenta[g]naphthalen-1-yl)-octanoic acid methyl ester
8-((1S,2R,2aR,9bS)-5,7,9b-Trimethyl-1-octyl-3-oxo-1,2a,3,9b-tetrahydro-2H-4,6-dioxa-cyclobuta[a]cyclopenta[g]naphthalen-2-yl)-octanoic acid methyl ester
8-((1S,2S,2aR,9bS)-5,7,9b-Trimethyl-1-octyl-3-oxo-1,2a,3,9b-tetrahydro-2H-4,6-dioxa-cyclobuta[a]cyclopenta[g]naphthalen-2-yl)-octanoic acid methyl ester
Conditions | Yield |
---|---|
at 15℃; Product distribution; Mechanism; Quantum yield; Irradiation; |
trioxsalen
benzyl chloride
(Z)-3-(6-Benzyloxy-2,7-dimethyl-benzofuran-5-yl)-but-2-enoic acid
Conditions | Yield |
---|---|
With potassium hydroxide 1.) DMSO, 1 h, 2.) (4,2',8-trimethylpsoralen : C6H5CH2Cl = 1:1) 12 h; Yield given. Multistep reaction; |
trioxsalen
benzyl chloride
(Z)-3-(6-Benzyloxy-2,7-dimethyl-benzofuran-5-yl)-but-2-enoic acid benzyl ester
Conditions | Yield |
---|---|
With potassium hydroxide 1.) DMSO, 1 h, 2.) (4,2',8-trimethylpsoralen : C6H5CH2Cl = 1:2) 12 h; Yield given. Multistep reaction; |
trioxsalen
3-methoxymethyl-2,5,9-trimethyl-furo[3,2-g]chromen-7-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetic acid 2: 6 h / Heating View Scheme |
trioxsalen
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetic acid 2: 82 percent / 6 h / Heating View Scheme |
trioxsalen
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetic acid 2: 91 percent / 6 h / Heating View Scheme |
trioxsalen
4-
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 55 percent / acetic acid / 48 h / Ambient temperature 2: CHCl3 / 20 h / Heating View Scheme |
trioxsalen
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 55 percent / acetic acid / 48 h / Ambient temperature 2: benzene / 216 h / Heating View Scheme |
trioxsalen
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 55 percent / acetic acid / 48 h / Ambient temperature 2: benzene / 216 h / Heating View Scheme |
trioxsalen
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 55 percent / acetic acid / 48 h / Ambient temperature 2: benzene / 216 h / Heating View Scheme |
IUPAC Name: 2,5,9-Trimethylfuro[3,2-g]chromen-7-one
Synonyms:2 ,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one ; 2,5,9-Trimethyl-7H-furo[3,2-g]chromen-7-one ; 6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic Acid d-Lactone ; 7H-Furo(3,2-g)(1)benzopyran-7-one, 2,5,9-trimethyl-
CAS NO: 3902-71-4
Molecular Formula of 6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid γ-lactone (CAS NO.3902-71-4) : C14H12O3
Molecular Weight of 6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid γ-lactone (CAS NO.3902-71-4) : 228.24
Molecular structure of 6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid γ-lactone (CAS NO.3902-71-4) :
EINECS: 223-459-0
Index of Refraction: 1.613
Surface Tension: 45.2 dyne/cm
Density: 1.236 g/cm3
Flash Point: 189.1 °C
Enthalpy of Vaporization: 63.83 kJ/mol
Boiling Point: 389 °C at 760 mmHg
Vapour Pressure: 2.93E-06 mmHg at 25°C
Melting point: 229-231 °C(lit.)
Storage temp: 2-8°C
Solubility: DMSO: soluble
Appearance:White to slightly beige crystalline powder
6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid γ-lactone (CAS NO.3902-71-4) is a furanocoumarin and a psoralen derivative.
Raw materials :Etanol-->Sodium hydroxide-->Methanol-->Potassium carbonate-->Magnesium sulfate-->Acetone-->Ethyl acetoacetate-->Sulfamic acid -->N,N-Diethylaniline-->Potassium bisulfate -->1,2,3-Tribromopropane-->2-Methylresorcinol
It is obtained from several plants, mainly Psoralea corylifolia.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 3gm/kg (3000mg/kg) | Drugs in Japan Vol. -, Pg. 740, 1990. | |
mouse | LD50 | oral | > 7gm/kg (7000mg/kg) | Drugs in Japan Vol. 6, Pg. 520, 1982. | |
mouse | LD50 | subcutaneous | > 4gm/kg (4000mg/kg) | Drugs in Japan Vol. -, Pg. 740, 1990. | |
rat | LD50 | oral | > 22gm/kg (22000mg/kg) | Drugs in Japan Vol. 6, Pg. 520, 1982. |
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 366.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 40 , 1986,p. 357.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 40 , 1986,p. 357.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.
Moderately toxic by intraperitoneal and subcutaneous routes. Low toxicity by ingestion. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard CodesC
Risk Statements 34-40
R34:Causes burns.
R40:Limited evidence of a carcinogenic effect.
Safety Statements 26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR UN 1759 8/PG 1
WGK Germany 2
RTECS LV1576000
F 8-10
Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo and hand eczema.After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellular mechanisms. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage.The compound is also being explored for development of antisense oligonucleotides that can be cross-linked specifically to a mutant mRNA sequence without affecting normal transcripts differing at even a single base pair.
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