7437-55-0

Basic information

• Product Name: XANTHOTOXOL GERANYL ETHER
• Synonyms: (E)-9-((3,7-Dimethyl-2,6-octadienyl)oxy)-7H-furo(3,2-G)(1)benzopyran-7-one;7H-Furo(3,2-G)(1)benzopyran-7-one, 9-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-;GERANYLOXYPSORALEN, 8- (P);8-Geranopsoralen;9-((3,7-Dimethylocta-2,6-dien-1-yl)-oxy)-7H-furo[3,2-g]chromen-7-one;9-[[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy]-7H-furo[3,2-g][1]benzopyran-7-one;XANTHOTOXOL GERANYL ETHER
• CAS NO: 7437-55-0
• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.4
• Mol File: 7437-55-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 53-54 °C
• Boiling Point: 503.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.153±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• BRN: 313632
• CAS DataBase Reference: XANTHOTOXOL GERANYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: XANTHOTOXOL GERANYL ETHER(7437-55-0)
• EPA Substance Registry System: XANTHOTOXOL GERANYL ETHER(7437-55-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36-37
• WGK Germany: 3
• Hazardous Substances Data: 7437-55-0(Hazardous Substances Data)

Usage

Uses

8-Geranyloxypsoralen is an anti-bacterial substances that were active against oral bacteria that causes dental caries and periodontitis such as Streptococcus mutans, Prevotella intermedia, and Porphyromonas gingivalis. Also, it is an β-secretase inhibitor.

Upstream product

• 6138-90-5 trans-geranyl bromide 
• 2009-24-7 8-hydroxypsoralen 
• 298-81-7 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one 

Downstream Products

• 68123-30-8 Dihydro-8-hydroxypsoralen 
• 2009-24-7 8-hydroxypsoralen 
• 143390-87-8 6',7'-Epoxy-8-geranyloxypsoralen 

Relevant articles and documents

Natural oxyprenylated coumarins are modulators of melanogenesis

Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor β and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses.

Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4

Furanocoumarins have been shown to inhibit CYP3A4 in vitro with varying degrees of potency [Pharmacogenetics 1997, 7, 391-396; Chem. Res. Toxicol. 1998, 11, 252-259; Drug Metab. Dispos. 1997, 25, 1228-1233; Br. J. Pharmacol. 2000, 130, 1369-1377]. In this study, we report the effects of a series of novel furanocoumarins based on the naturally occurring derivative 8-geranylepoxypsoralen which has been shown to be a more potent inhibitor of CYP3A4 than its 5-position-substituted counterpart bergamottin [Drug Metab. Dispos. 2000, 28, 766-771; Jpn. J. Pharmacol. 2000, 82, 122-129]. Compounds were designed, synthesised and tested for their ability to inhibit CYP3A4 activity in human liver microsomes using testosterone as the marker substrate. Both the saturated and unsaturated phenolic furanocoumarin derivatives were found to be inactive. However, the 8-alkyloxy-furanocoumarin analogues were shown to inhibit CYP3A4 activity in a dose dependent manner, with IC50 values ranging from 0.78 ± 0.11 to 3.93 ± 0.53 μM. The reduced furan derivative dihydro-8-geranyloxypsoralen showed a 4-fold decrease in inhibitory potency, suggesting that the furan moiety plays a role in the interaction between these compounds and CYP3A4.