16203-27-3

Basic information

• Product Name: (-)-menthyl β-D-glucopyranoside
• Synonyms: (-)-menthyl β-D-glucopyranoside
• CAS NO: 16203-27-3
• Molecular Weight: 318.411
• Mol File: 16203-27-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (-)-menthyl β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-menthyl β-D-glucopyranoside(16203-27-3)
• EPA Substance Registry System: (-)-menthyl β-D-glucopyranoside(16203-27-3)

Safety Data

• Hazardous Substances Data: 16203-27-3(Hazardous Substances Data)

Upstream product

• 56650-22-7 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 133-89-1 UDP-glucose 
• 2216-51-5 (-)-menthol 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 15356-70-4 menthol 

Downstream Products

• 67462-22-0 (-)-menthol α-D-glucoside 
• 2216-51-5 (-)-menthol 
• 79466-08-3 (-)-Menthol glucuronide 

Relevant articles and documents

Improvement of the pharmacological activity of menthol via enzymatic β-anomer-selective glycosylation

Menthol has a considerable cooling effect, but the use range of menthol is limited because of its extremely low solubility in water and inherent flavor. (?)-Menthol β-glucoside was determined to be more soluble in water (>27 times) than (?)-menthol α-glucoside; hence, β-anomer-selective glucosylation of menthol is necessary. The in vitro glycosylation of (?)-menthol by uridine diphosphate glycosyltransferase (BLC) from Bacillus licheniformis generated (?)-menthol β-glucoside and new (?)-menthol β-galactoside and (?)-menthol N-acetylglucosamine. The maximum conversion rate of menthol to (?)-menthol β-d-glucoside by BLC was found to be 58.9%. Importantly, (?)-menthol β-d-glucoside had a higher cooling effect and no flavor compared with menthol. In addition, (?)-menthol β-d-glucoside was determined to be a non-sensitizer in a skin allergy test in the human cell line activation test, whereas menthol was a sensitizer.

Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C. roseus enantioselectively glucosylated (±)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols.