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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

Pricing and availability is not currently available.

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

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

SMILES string

Cc1cc2cc3C(C)=CC(=O)Oc3c(C)c2o1

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This Item
171450610006121044662
manufacturer/tradename

USP

manufacturer/tradename

USP

manufacturer/tradename

USP

manufacturer/tradename

USP

format

neat

format

neat

format

neat

format

neat

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

API family

vinorelbine

API family

vinorelbine

API family

acebutolol

API family

atovaquone

storage temp.

−20°C

storage temp.

−70°C

storage temp.

-

storage temp.

2-8°C

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

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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)
    Erin K Schwartz et al.
    PLoS genetics, 16(5), e1008816-e1008816 (2020-05-30)
    Alternative lengthening of telomeres (ALT) in human cells is a conserved process that is often activated in telomerase-deficient human cancers. This process exploits components of the recombination machinery to extend telomere ends, thus allowing for increased proliferative potential. Human MUS81

    Articles

    DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

    Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

    Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

    Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

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