39015-85-5

Basic information

• Product Name: terpineol-O-glucopyranoside
• Synonyms: terpineol-O-glucopyranoside
• CAS NO: 39015-85-5
• Molecular Formula: C₁₆H₂₈O₆
• Molecular Weight: 316.38992
• Mol File: 39015-85-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 480.2°C at 760 mmHg
• Flash Point: 244.2°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 3.09E-11mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: terpineol-O-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: terpineol-O-glucopyranoside(39015-85-5)
• EPA Substance Registry System: terpineol-O-glucopyranoside(39015-85-5)

Safety Data

• Hazardous Substances Data: 39015-85-5(Hazardous Substances Data)

Usage

General Description

Terpineol-O-glucopyranoside is a natural chemical compound found in various plants, especially in essential oils and resins. It is a glycoside, which means it consists of a sugar molecule attached to a terpineol molecule. Terpineol is a monoterpene alcohol with a pleasant floral odor, and when it is glycosidically bound to a sugar molecule, it forms terpineol-O-glucopyranoside. terpineol-O-glucopyranoside has been studied for its potential antimicrobial, antioxidant, and anti-inflammatory properties, making it a subject of interest in the fields of pharmaceuticals, cosmetics, and natural medicine. Terpineol-O-glucopyranoside has shown promising effects in various biological systems and has the potential for use in developing new natural products for health and wellness.

InChI:InChI=1/C16H28O6/c1-9-4-6-10(7-5-9)16(2,3)22-15-14(20)13(19)12(18)11(8-17)21-15/h4,10-15,17-20H,5-8H2,1-3H3/t10?,11-,12-,13+,14-,15+/m1/s1

Upstream product

• 98-55-5 terpineol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 50-99-7 D-glucose 
• 84582-23-0 (+/-)-α-terpineol-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Relevant articles and documents

Cholagogic action and characteristics of (+)-α-terpineol-β-D-O-glucopyranoside, a new monoterpenoid glucoside

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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.