14348-23-3

Basic information

• Product Name: 5,8-DIHYDROXYPSORALEN
• Synonyms: 5,8-DIHYDROXYPSORALEN;4,9-Dihydroxy-7H-furo[3,2-g][1]benzopyran-7-one
• CAS NO: 14348-23-3
• Molecular Formula: C11H6O5
• Molecular Weight: 218.16234
• Mol File: 14348-23-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 344.4°C at 760 mmHg
• Flash Point: 162.1°C
• Appearance: /
• Density: 1.667
• Vapor Pressure: 3.31E-05mmHg at 25°C
• Refractive Index: 1.756
• CAS DataBase Reference: 5,8-DIHYDROXYPSORALEN(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-DIHYDROXYPSORALEN(14348-23-3)
• EPA Substance Registry System: 5,8-DIHYDROXYPSORALEN(14348-23-3)

Safety Data

• Hazardous Substances Data: 14348-23-3(Hazardous Substances Data)

Usage

Description

5,8-Dihydroxypsoralen, also known as 5,8-DHP, is a naturally occurring compound derived from the O-demethylation and oxidative cleavage of xanthotoxin, a furanocoumarin photosensitizer. It is characterized by its unique chemical structure and properties, which make it a versatile molecule with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
5,8-Dihydroxypsoralen is used as a therapeutic agent for the treatment of various skin conditions, particularly vitiligo and psoriasis. It works by increasing the sensitivity of the skin to ultraviolet (UV) light, which helps in the repigmentation process in vitiligo and reduces the inflammation and scaling in psoriasis.
Used in Cosmetic Industry:
In the cosmetic industry, 5,8-dihydroxypsoralen is used as an active ingredient in skin lightening and whitening products. Its ability to inhibit the production of melanin, the pigment responsible for skin color, makes it an effective component in formulations aimed at reducing hyperpigmentation and promoting an even skin tone.
Used in Research and Development:
5,8-Dihydroxypsoralen is also utilized in research and development for its potential applications in photochemotherapy and photodynamic therapy. Its photosensitizing properties allow it to be studied for its ability to target and destroy cancer cells when exposed to light, making it a promising candidate for the development of novel cancer treatments.
Used in Agriculture:
In agriculture, 5,8-dihydroxypsoralen can be used as a natural pesticide or repellent due to its phototoxic properties. When exposed to sunlight, it can cause damage to the cells of certain pests, making it a potential alternative to synthetic chemical pesticides.
Used in Analytical Chemistry:
5,8-Dihydroxypsoralen can be employed as a chemical marker or analytical tool in the study of plant metabolomics and the identification of specific plant species. Its unique chemical structure allows for its detection and quantification in various biological samples, providing valuable information about the plant's metabolic processes and potential applications.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 41, p. 4542, 1998 DOI: 10.1021/jm981032o

InChI:InChI=1/C11H6O5/c12-7-2-1-5-8(13)6-3-4-15-10(6)9(14)11(5)16-7/h1-4,13-14H

Upstream product

• 2543-94-4 phellopterin 
• 298-81-7 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one 
• 2009-24-7 8-hydroxypsoralen 
• 483-36-3 furo<3,2-g><1>benzopyran-4,7,9-trione 

Downstream Products

• 15905-39-2 5-geranyloxy-8-methoxypsoralen 
• 14348-22-2 cnidilin 
• 2543-94-4 phellopterin 
• 14348-21-1 cnidicin 
• 49739-62-0 isoimperatorin 
• 1603-47-0 5-methoxy-8-hydroxy psoralen 
• 482-27-9 isopimpinellin 

Related news

The role of 5,8-DIHYDROXYPSORALEN (cas 14348-23-3) in the biosynthesis of isopimpinellin08/02/2019

[3H]5,8-Dihydroxypsoralen was effectively and selectively converted into 5,8-dimethoxypsoralen by roots of Ruta graveolens whereas [3H]8-methoxypsoralen and [3H]5-methoxypsoralen included for comparison were converted to a much lesser extent. These results indicate that 5,8-dihydroxypsoralen is ...detailed

Relevant articles and documents

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Alkoxypsoralens, novel nonpeptide blockers of Shaker-type K+ channels: Synthesis and photoreactivity

A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8- Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.

FUNCTIONALIZED PHENOLIC COMPOUNDS AND POLYMERS THEREFROM

The present invention relates to compounds of formula I, which are functionalized phenolic compounds, and polymers formed from the same. Ar—[O—(X)p—R′]q??I Polymers formed from the functionalized phenolics are expected to have controllable degradation profiles, enabling them to release an active component over a desired time range. The polymers are also expected to be useful in a variety of medical applications.