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Basic Information
CAS No.: 3902-71-4
Name: TRIOXSALEN
Article Data: 8
Molecular Structure:
Molecular Structure of 3902-71-4 (TRIOXSALEN)
Formula: C14H12O3
Molecular Weight: 228.247
Synonyms: 5-Benzofuranacrylicacid, 6-hydroxy-b,2,7-trimethyl-,d-lactone (6CI,7CI);4,2',8-Trimethylpsoralen;4,5',8-Trimethylpsoralen;NSC 71047;Trimethylpsoralen;
EINECS: 223-459-0
Density: 1.236 g/cm3
Melting Point: 229-231 °C(lit.)
Boiling Point: 389 °C at 760 mmHg
Flash Point: 189.1 °C
Appearance: White to slightly beige crystalline powder
Hazard Symbols: CorrosiveC
Risk Codes: 34-40
Safety: 26-36/37/39-45
Transport Information: UN 1759 8/PG 1
PSA: 43.35000
LogP: 3.46440
Synthetic route
72478-66-1

4,8-dimethyl-7-<(β-bromoallyl)oxy>coumarin

3902-71-4

trioxsalen

Conditions
ConditionsYield
With N,N-diethylaniline at 225℃; for 24h;60%
69897-63-8

4,8-dimethyl-7-<(β-chloroalllyl)oxy>coumarin

3902-71-4

trioxsalen

Conditions
ConditionsYield
With N,N-diethylaniline at 220 - 225℃; for 24h;14%
3993-44-0

6-allyl-7-hydroxy-4,8-dimethyl-2H-chromen-2-one

A

3902-71-4

trioxsalen

B

141536-65-4

4,10-Dimethyl-pyrano[3,2-g]chromene-2,8-dione

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 12h; Heating; Yield given. Yields of byproduct given;
4115-76-8

4,8-dimethyl-7-hydroxycoumarin

3902-71-4

trioxsalen

Conditions
ConditionsYield
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
3993-43-9

7-allyloxy-4,8-dimethyl-2H-chromen-2-one

3902-71-4

trioxsalen

Conditions
ConditionsYield
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
110-88-3

1,3,5-Trioxan

3902-71-4

trioxsalen

1489190-74-0

4′-azidomethyl-4,5′,8-trimethylpsoralen

Conditions
ConditionsYield
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%
3902-71-4

trioxsalen

74-88-4

methyl iodide

(Z)-3-(6-Methoxy-2,7-dimethyl-benzofuran-5-yl)-but-2-enoic acid

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) 15 min, 2.) 10 h;92%
110-88-3

1,3,5-Trioxan

3902-71-4

trioxsalen

62442-57-3

4'-chloromethyl-4,5',8-trimethylpsoralen

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 16h;86%
With hydrogenchloride In water at 25℃; for 12h;70%
3902-71-4

trioxsalen

21902-49-8

4'-bromotrioxsalen

Conditions
ConditionsYield
With bromine In dichloromethane at 25℃; for 3h;82%
3902-71-4

trioxsalen

3188-13-4

ethyl chloromethyl ether

62442-59-5

4'-hydroxymethyl-4,5',8-trimethylpsoralen

Conditions
ConditionsYield
In acetic acid at 20℃; for 15h; Protected from light;75%
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2462-84-2
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Chemistry

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

Uses

 6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid γ-lactone (CAS NO.3902-71-4) is a furanocoumarin and a psoralen derivative.

Production

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.

Toxicity Data With Reference

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.

 

Consensus Reports

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.

Safety Profile

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 CodesCorrosiveC
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

Specification

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.