MilliporeSigma
All Photos(4)

Documents

T6137

Sigma-Aldrich

Trioxsalen

≥98% (HPLC), powder

Sign Into View Organizational & Contract Pricing

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:
Molecular Weight:
228.24
Beilstein/REAXYS Number:
221723
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
A4330P8399E1379
Trioxsalen ≥98% (HPLC), powder

T6137

Trioxsalen

Psoralen ≥99% (HPLC)

P8399

Psoralen

7-Ethoxycoumarin

E1379

7-Ethoxycoumarin

assay

≥98% (HPLC)

assay

-

assay

≥99% (HPLC)

assay

≥99.45% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

solubility

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

solubility

H2O: 1 mg/mL, DMSO: 2 mg/mL

solubility

-

solubility

95% ethanol: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

originator

Valeant

originator

-

originator

-

originator

-

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. 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.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Dam. 1 - Muta. 2 - Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 4

1 of 4

5-Methoxypsoralen 99%

Sigma-Aldrich

275727

5-Methoxypsoralen

Methoxsalen United States Pharmacopeia (USP) Reference Standard

USP

1417001

Methoxsalen

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)
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
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)

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.

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service