141206-20-4

Basic information

• Product Name: perilloside A
• Synonyms: perilloside A
• CAS NO: 141206-20-4
• Molecular Formula: C₁₆H₂₆O₆
• Molecular Weight: 314.37404
• Mol File: 141206-20-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 494.8°Cat760mmHg
• Flash Point: 253°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 7.28E-12mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: perilloside A(CAS DataBase Reference)
• NIST Chemistry Reference: perilloside A(141206-20-4)
• EPA Substance Registry System: perilloside A(141206-20-4)

Safety Data

• Hazardous Substances Data: 141206-20-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H26O6/c1-9(2)11-5-3-10(4-6-11)8-21-16-15(20)14(19)13(18)12(7-17)22-16/h3,11-20H,1,4-8H2,2H3/t11-,12-,13-,14+,15-,16-/m1/s1

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 50-99-7 D-glucose 
• 536-59-4 (-)-perillyl alcohol 
• 13265-84-4 D-glucal 
• 163982-16-9 (1S,3R,4R,5S,6R)-3-((pivaloyloxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane-4,5-diyl bis(2,2-dimethylpropanoate) 
• 149198-97-0 3,4,6-tri-O-pivaloyl-D-glucal 
• 200501-84-4 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-5-hydroxy-6-((S)-4-isopropenyl-cyclohex-1-enylmethoxy)-tetrahydro-pyran-4-yl ester 
• 141206-21-5 (-)-perillyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Relevant articles and documents

Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds

The synthesis of terpenoid glycosides typically uses a chemical strategy since few biocatalysts have been identified that recognise these scaffolds. In this study, a platform of 107 recombinant glycosyltransferases (GTs), comprising the multigene family of small molecule GTs of Arabidopsis thaliana have been screened against a range of model terpenoid acceptors to identify those enzymes with high activity. Twenty-seven GTs are shown to glycosylate a diversity of mono-, sesquiand diterpenes, such as geraniol, perillyl alcohol, artemisinic acid and retinoic acid. Certain enzymes showing substantial sequence similarity recognise terpenoids containing a primary alcohol, irrespective of the linear or cyclical structure of the scaffold; other GTs glycosylate scaffolds containing secondary and tertiary alcohols; the carboxyl group of other terpenoids also represents a feature that is recognized by GTs previously known to form glucose esters with many different compounds. These data underpin the rapid prediction of potential biocatalysts from GT sequence information. To explore the potential of GTs as biocatalysts, their use for the production of terpenoid glycosides was investigated by using a microbial-based whole-cell biotransformation system capable of regenerating the cofactor, UDP-glucose. A high cell density fermentation system was shown to produce several hundred milligrams of a model terpenoid, geranyl-glucoside. The activities of the GTs are discussed in relation to their substrate recognition and their utility in biotransformations as a complement or alternative to chemical synthesis.

Inhibitory effects of perillosides A and C, and related monoterpene glucosides on aldose reductase and their structure-activity relationships.

Monoterpene glucosides, perillosides A and C, obtained from the leaves of Perilla frutescens, were found to be inhibitors of aldose reductase (EC 1.1.1.21) which is considered to be a key enzyme in diabetic complications such as cataract. The apparent typ