T6137

Trioxsalen

≥98% (HPLC), powder, photochemical DNA crosslinker

• Synonym(s): 2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one, 4,5′,8-Trimethylpsoralen, TMP, Trisoralen
• Empirical Formula (Hill Notation): C₁₄H₁₂O₃
• CAS Number: 3902-71-4
• Molecular Weight: 228.24
• Beilstein: 221723
• EC Number: 223-459-0
• MDL number: MFCD00005010
• UNSPSC Code: 12352200
• PubChem Substance ID: 24900351
• NACRES: NA.77

Properties

• product name: Trioxsalen, ≥98% (HPLC), powder
• Assay: ≥98% (HPLC)
• form: powder
• color: white
• mp: 229-231 °C (lit.)
• solubility: chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow
• fluorescence: λ_ex 269 nm; λ_em 445 nm in methanol; λ_ex 321 nm; λ_em 445 nm (bound to DNA in Tris, pH 8.1)
• originator: Valeant
• storage temp.: −20°C
• SMILES string: Cc1cc2cc3C(C)=CC(=O)Oc3c(C)c2o1
• InChI: 1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3
• InChI key: FMHHVULEAZTJMA-UHFFFAOYSA-N

Description

Application

Trioxsalen has been used for mutagenesis of N2 worms^4,5.

Trioxsalen has been used:

• to induce small deletion mutations in worms
• in combination with ultraviolet A (UVA)
• to induce interstrand crosslinks (ICLs) in DNA
• for the preparation and photoactivation of trimethyl psoralen

Biochem/physiol Actions

Photochemical crosslinker of DNA that has been used as a probe for nucleic acid structure and function. Trioxsalen has also been used to crosslink DNA onto mica surfaces.

Trioxsalen (TRX) is a 4,5′,8-trimethylated psoralen analog, which belongs to the family of furocoumarins. It is mostly used to treat psoriasis.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Valeant. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Trioxsalen is soluble in chloroform at 50 mg/ml and yields a clear, colorless to faint yellow solution.

Safety Information

• Pictograms: GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H312 + H332,H314,H341
• Precautionary Statements: P202 - P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Dam. 1 - Muta. 2 - Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves