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Trioxsalen (Standard)

CAT: 0804-HY-B1157R-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B1157R-01Size:10 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Trioxsalen (Standard) is the analytical standard of Trioxsalen. This product is intended for research and analytical applications. Trioxsalen (Trisoralen), a psoralen derivative, is a photochemical DNA crosslinker. Trioxsalen only works after photoactivation with near ultraviolet light. Trioxsalen is a photosensitizer that can be used for the research of vitiligo and hand eczema. Trioxsalen is used for visualization of genomic interstrand cross-links localized by laser photoactivation[1][2][3].
CAS Number
3902-71-4
Product Name Alternative
Trisoralen (Standard) ; Trioxysalen (Standard) ; TMP (Standard)
UNSPSC
12352005
Target
DNA Alkylator/Crosslinker; Reference Standards
Type
Reference Standards
Related Pathways
Cell Cycle/DNA Damage; Others
Field of Research
Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/trioxsalen-standard.html
Purity
90.000000
Smiles
O=C1C=C(C)C2=CC3=C(OC(C)=C3)C(C)=C2O1
Molecular Formula
C14H12O3
Molecular Weight
228.24
References & Citations
[1]M T Chuan, et al. Effectiveness of psoralen photochemotherapy for vitiligo. J Formos Med Assoc. 1999 May;98 (5) :335-40.|[2]A Marco van Coevorden, et al. Comparison of oral psoralen-UV-A with a portable tanning unit at home vs hospital-administered bath psoralen-UV-A in patients with chronic hand eczema: an open-label randomized controlled trial of efficacy. Arch Dermatol. 2004 Dec;140 (12) :1463-6.|[3]A Kuusilehto, et al. The effect of PUVA on langerhans cells in rat oral epithelium photosensitized with systemic methoxsalen or topical trioxsalen. Photodermatol Photoimmunol Photomed. 2000 Jun;16 (3) :129-33.|[4]L F Cohen, et al. Interstrand DNA crosslinking by 4,5'8-trimethylpsoralen plus monochromatic ultraviolet light. Studies by alkaline elution in mouse L1210 leukemia cells. Biochim Biophys Acta. 1980 Nov 14;610 (1) :56-63.|[5]H Sánchez Ruderisch, et al. Trioxsalen in the presence of UVA is able to induce nuclear factor kappa B binding activity in HaCaT keratinocytes. Skin Pharmacol Appl Skin Physiol. Sep-Oct 2002;15 (5) :335-41.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference Standards

Chemical Information

Trimethylpsoralen

Trioxsalen is 7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis. It has a role as a photosensitizing agent and a dermatologic drug.

CAS Number3902-71-4
PubChem CID5585
IUPAC Name2,5,9-trimethylfuro[3,2-g]chromen-7-one
Molecular FormulaC14H12O3
Molecular Weight228.24
XLogP3
Topological Polar Surface Area39.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Heavy Atom Count17
Formal Charge0
Complexity374
SMILES
CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C
InChI
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
InChIKey
FMHHVULEAZTJMA-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Trimethylpsoralen
CAS: 3902-71-4
CID: 5585
Formula: C14H12O3
MW: 228.24
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight228.24
XLogP33
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass228.078644241
Monoisotopic Mass228.078644241
Topological Polar Surface Area39.4 Ų
Heavy Atom Count17
Formal Charge0
Complexity374
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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