181228-75-1

Basic information

• Product Name: (+/-)-MYRICANOL
• Synonyms: (+/-)-MYRICANOL
• CAS NO: 181228-75-1
• Molecular Formula: C21H26O5
• Molecular Weight: 358.43
• Mol File: 181228-75-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 205-206°C
• Appearance: /
• CAS DataBase Reference: (+/-)-MYRICANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-MYRICANOL(181228-75-1)
• EPA Substance Registry System: (+/-)-MYRICANOL(181228-75-1)

Safety Data

• Hazardous Substances Data: 181228-75-1(Hazardous Substances Data)

Usage

General Description

(+/-)-MYRICANOL is a natural product derived from the bark of the bayberry tree, Myrica cerifera. It is a member of the triterpenoid family and has shown promising potential in various biological activities including anti-cancer, anti-inflammatory, and anti-viral properties. Its chemical structure consists of a pentacyclic triterpenoid backbone with multiple hydroxyl groups. Studies have shown that (+/-)-MYRICANOL exhibits cytotoxic effects on cancer cells by inducing apoptosis and inhibiting the proliferation of cancer cells. Additionally, it has also demonstrated anti-inflammatory effects by inhibiting the production of pro-inflammatory mediators. Its antiviral activity has been studied in the context of HIV and herpes simplex virus, showing potential for further development as a therapeutic agent in infectious diseases. Overall, (+/-)-MYRICANOL is a compound of significant interest due to its potential pharmacological properties and may play a role in the development of novel pharmaceuticals for various diseases.

Upstream product

• 90052-02-1 (+)-S-myricanol 5-O-β-D-glucopyranoside 
• 74432-58-9 4-(4-(benzyloxy)phenyl)butan-2-one 
• 1335227-07-0 2-(benzyloxy)-1-bromo-3,4-dimethoxybenzene 
• 68510-47-4 (+/-)-myricanol 

Downstream Products

• 32492-74-3 myricanone 

Relevant articles and documents

Synthesis, stereochemical analysis, and derivatization of myricanol provide new probes that promote autophagic Tau clearance

We previously discovered that one specific scalemic preparation of myricanol (1), a constituent of Myrica cerifera (bayberry/southern wax myrtle) root bark, could lower the levels of the microtubule-associated protein tau (MAPT). The significance is that tau accumulates in a number of neurodegenerative diseases, the most common being Alzheimers disease (AD). Herein, a new synthetic route to prepare myricanol using a suitable boronic acid pinacol ester intermediate is reported. An X-ray crystal structure of the isolated myricanol (1) was obtained and showed a co-crystal consisting of (+)-aR,11S-myricanol (2) and (-)-aS,11R-myricanol (3) coformers. Surprisingly, 3, obtained from chiral separation from 1, reduced tau levels in both cultured cells and ex vivo brain slices from a mouse model of tauopathy at reasonable mid-to-low micromolar potency, whereas 2 did not. SILAC proteomics and cell assays revealed that 3 promoted tau degradation through an autophagic mechanism, which was in contrast to that of other tau-lowering compounds previously identified by our group. During the course of structure-activity relationship (SAR) development, we prepared compound 13 by acid-catalyzed dehydration of 1. 13 had undergone an unexpected structural rearrangement through the isomyricanol substitution pattern (e.g., 16), as verified by X-ray structural analysis. Compound 13 displayed robust tau-lowering activity, and, importantly, its enantiomers reduced tau levels similarly. Therefore, the semisynthetic analogue 13 provides a foundation for further development as a tau-lowering agent without its SAR being based on chirality.