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Merck

T6137

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C14H12O3
CAS Number:
Molecular Weight:
228.24
Beilstein:
221723
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

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product name

Trioxsalen, ≥98% (HPLC), powder

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white

mp

229-231 °C (lit.)

solubility

chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow

fluorescence

λex 269 nm; λem 445 nm in methanol
λex 321 nm; λem 445 nm (bound to DNA in Tris, pH 8.1)

originator

Valeant

storage temp.

−20°C

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Show Differences

1 of 4

This Item
U2625AG974286842
Uric acid ≥99%, crystalline

U2625

Uric acid

mp

30-34 °C (lit.)

mp

>300 °C (lit.)

mp

-

mp

60-61 °C (lit.)

bp

330 °C (lit.)

bp

-

bp

-

bp

-

form

crystalline, waxy solid, liquid

form

crystalline

form

powder

form

-

density

0.786 g/mL at 25 °C (lit.)

density

-

density

-

density

-

vapor density

9.27 (vs air)

vapor density

-

vapor density

-

vapor density

-

Application

Trioxsalen has been used for mutagenesis of N2 worms4,5.
Trioxsalen has been used:
  • to induce small deletion mutations in worms[1]
  • in combination with ultraviolet A (UVA)
  • to induce interstrand crosslinks (ICLs) in DNA[2]
  • for the preparation and photoactivation of trimethyl psoralen[3]

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.[4]

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.

Signal Word

Danger

Hazard Statements

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Filippo Doria et al.
Journal of medicinal chemistry, 50(26), 6570-6579 (2007-12-01)
Mild photoactivation of new BINOL-amino acid and -amino ester conjugates (BINOLAMs) yielded alkylating and DNA cross-linking agents with high photoefficiency and superior cytotoxicity. Detection of the transient electrophile, by laser flash photolysis (LFP), suggests that BINOL-quinone methides (QMs) are key
Aurèle Piazza et al.
Methods in molecular biology (Clifton, N.J.), 2153, 535-554 (2020-08-26)
DNA double-strand breaks (DSBs) are genotoxic lesions that can be repaired in a templated fashion by homologous recombination (HR). HR is a complex pathway that involves the formation of DNA joint molecules (JMs) containing heteroduplex DNA. Various types of JMs
Methodological considerations for mutagen exposure in C. elegans
Kessler Z and Yanowitz J
Methods, 68(3), 441-449 (2014)
Isolation of deletion mutants by reverse genetics in Caenorhabditis elegans
Park BJ, et al.
Korean Journal of Biological Sciences, 5(1), 65-69 (2001)
Anna Tamanini et al.
American journal of physiology. Lung cellular and molecular physiology, 300(3), L380-L390 (2010-12-15)
Chronic inflammatory response in the airway tract of patients affected by cystic fibrosis is characterized by an excessive recruitment of neutrophils to the bronchial lumina, driven by the chemokine interleukin (IL)-8. We previously found that 5-methoxypsoralen reduces Pseudomonas aeruginosa-dependent IL-8

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