208647-48-7

Basic information

• Product Name: 1-NAPHTHYL-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: ALPHA-NAPHTHYL-ALPHA-D-GLUCOSIDE;ALPHA-NAP-ALPHA-D-GLC;1-NAPHTHYL-ALPHA-D-GLUCOPYRANOSIDE;1-Naphthyla-D-glucopyranoside;1-naphthyl-α-D-glucopyranoside*crystalline
• CAS NO: 208647-48-7
• Molecular Formula: C16H18O6
• Molecular Weight: 306.31
• EINECS: 1533716-785-6
• Mol File: 208647-48-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 568℃
• Flash Point: 297℃
• Appearance: /
• Density: 1.454
• CAS DataBase Reference: 1-NAPHTHYL-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-NAPHTHYL-ALPHA-D-GLUCOPYRANOSIDE(208647-48-7)
• EPA Substance Registry System: 1-NAPHTHYL-ALPHA-D-GLUCOPYRANOSIDE(208647-48-7)

Safety Data

• Hazardous Substances Data: 208647-48-7(Hazardous Substances Data)

Usage

General Description

1-Naphthyl-α-D-glucopyranoside is a chemical compound that belongs to the family of naphthalene derivatives and is a glycoside formed from naphthalene and glucose. It is commonly used as a substrate for the detection of α-glucosidase activity in biochemical research. 1-NAPHTHYL-ALPHA-D-GLUCOPYRANOSIDE is colorless and soluble in water, and it has a characteristic sweet taste. It is also used in pharmacological and medical research for its potential application in the treatment of various diseases, including diabetes and cancer. Additionally, 1-Naphthyl-α-D-glucopyranoside is used in the food industry as a flavoring and sweetening agent. Overall, this compound has versatile applications in various fields due to its unique chemical and biological properties.

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Relevant articles and documents

UDP-glycosyltransferase 3A metabolism of polycyclic aromatic hydrocarbons: Potential importance in aerodigestive tract tissues

Polycyclic aromatic hydrocarbons (PAHs) are potent carcinogens and are a primary risk factor for the development of lung and other aerodigestive tract cancers in smokers. The detoxification of PAHs by glucuronidation is well-characterized for the UDP-glycosyltransferase (UGT) 1A, 2A, and 2B subfamilies; however, the role of the UGT3A subfamily in PAH metabolism remains poorly understood. UGT3A enzymes are functionally distinct from other UGT subfamilies (which use UDP-glucuronic acid as a cosubstrate) due to their utilization of alternative cosubstrates (UDP-Nacetylglucosamine for UGT3A1, and UDP-glucose and UDP-xylose for UGT3A2). The goal of the present study was to characterize UGT3A glycosylation activity against PAHs and examine their expression in human aerodigestive tract tissues. In vitro metabolism assays using UGT3A2-overexpressing cell microsomes indicated that UGT3A2 exhibits glycosylation activity against all of the simple and complex PAHs tested. The Vmax/Km ratios for UGT3A2 activity with UDP-xylose versus UDP-glucose as the cosubstrate ranged from 0.65 to 4.4 for all PAHs tested, demonstrating that PAH glycosylation may be occurring at rates up to 4.4-fold higher with UDP-xylose than with UDP-glucose. Limited glycosylation activity was observed against PAHs with UGT3A1-overexpressing cell microsomes. While UGT3A2 exhibited low levels of hepatic expression, it was shown by western blot analysis to be widely expressed in aerodigestive tract tissues. Conversely, UGT3A1 exhibited the highest expression in liver with lower expression in aerodigestive tract tissues. These data suggest that UGT3A2 plays an important role in the detoxification of PAHs in aerodigestive tract tissues, and that there may be cosubstrate-dependent differences in the detoxification of PAHs by UGT3A2. SIGNIFICANCE STATEMENT UGT3A2 is highly active against PAHs with either UDP-glucose or UDP-xylose as a cosubstrate. UGT3A1 exhibited low levels of activity against PAHs. UGT3A1 is highly expressed in liver while UGT3A2 is well expressed in extrahepatic tissues. UGT3A2 may be an important detoxifier of PAHs in humans.