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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

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

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

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Application

Trioxsalen has been used for mutagenesis of N2 worms4,5.
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.
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.

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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Isolation of deletion mutants by reverse genetics in Caenorhabditis elegans
Park BJ, et al.
Korean Journal of Biological Sciences, 5(1), 65-69 (2001)
UHRF1 is a sensor for DNA interstrand crosslinks and recruits FANCD2 to initiate the Fanconi anemia pathway
Liang CC, et al.
Cell Reports, 10(12), 1947-1956 (2015)
Chunru Lin et al.
Molecular and cellular biology, 25(17), 7484-7493 (2005-08-19)
We have previously demonstrated that p68 RNA helicase, as an essential human splicing factor, acts at the U1 snRNA and 5' splice site (5'ss) duplex in the pre-mRNA splicing process. To further analyze the function of p68 in the spliceosome
Eriko Kage-Nakadai et al.
BMC biotechnology, 12, 1-1 (2012-01-06)
Transgenic strains of Caenorhabditis elegans are typically generated by injecting DNA into the germline to form multi-copy extrachromosomal arrays. These transgenes are semi-stable and their expression is silenced in the germline. Mos1 transposon or microparticle bombardment methods have been developed
Methodological considerations for mutagen exposure in C. elegans
Kessler Z and Yanowitz J
Methods, 68(3), 441-449 (2014)

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