33606-81-4

Basic information

• Product Name: myricanol
• Synonyms: (+/-)-MYRCANOL;(9R)-16,17-Dimethoxytricyclo[12.3.1.12,6]nonadeca-1(18),2,4,6(19),14,16-hexaene-3,9,15-triol;(R)-16,17-Dimethoxytricyclo[12.3.1.12,6]nonadeca-1(18),2,4,6(19),14,16-hexaene-3,9,15-triol;Myrical
• CAS NO: 33606-81-4
• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 436.7968
• Product Categories: Aromatic Phenols
• Mol File: 33606-81-4.mol

Chemical Properties

• Boiling Point: 583.5°Cat760mmHg
• Flash Point: 306.7°C
• Appearance: /
• Density: 1.208g/cm³
• Vapor Pressure: 1.86E-14mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: myricanol(CAS DataBase Reference)
• NIST Chemistry Reference: myricanol(33606-81-4)
• EPA Substance Registry System: myricanol(33606-81-4)

Safety Data

• Hazardous Substances Data: 33606-81-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Myricanol is used as a potential therapeutic agent for its antioxidant, anti-inflammatory, and anti-cancer characteristics. It is being researched for its ability to inhibit cancer cell growth, although more studies are needed to validate these findings in human trials.
Used in Cancer Research:
Myricanol is used as a subject of investigation in cancer research for its potential efficacy in inhibiting the growth of cancer cells. It is currently in the preliminary stages of research, and further studies are necessary to establish its role in cancer treatment.
Used in Antioxidant Applications:
Myricanol is used as a natural antioxidant, which may help in protecting cells from damage caused by free radicals. Its antioxidant properties are being studied for potential health benefits and applications in various industries.
Used in Anti-Inflammatory Applications:
Myricanol is used as an anti-inflammatory agent, which may help in reducing inflammation and related symptoms. Its anti-inflammatory effects are being explored for potential use in the treatment of various inflammatory conditions.

InChI:InChI=1/C21H26O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,15,22-24H,3-7,9H2,1-2H3/t15-/m1/s1

Upstream product

• 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

• 74994-68-6 (-)-dibenzylmyricanol 

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.

Inhibitors of nitric oxide production from the bark of Myrica rubra: Structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene

Three new biphenyl type diarylheptanoid glycosides, myricanol 11-O-β-D-glucopyranoside, myricanone 5-O-β-D-glucopyranoside, and neomyricanone 5-O-β-D-glucopyranoside, and a new taraxerane type triterpene, myricetrione, were isolated from the bark of Chinese Myrica rubra. Their structures were elucidated on the basis of chemical and physicochemical evidence. Biphenyl type diarylheptanoids, triterpene, and their polyphenols showed potent inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages. Furthermore, diarylheptanoids, myricanol and myricanone, were found to inhibit induction of inducible nitric oxide synthase.

Diarylheptanoids from Myrica arborea

Investigations of the stem and root bark of Myrica arborea (Myricaceae) have yielded two novel diarylheptanoids, myricarborin and 11-O-β-D-xylopyranosylmyricanol along with the known myricanol and 5-O-β-D-glucopyranosylmyricanol. The structures of the nov

Constituents of Myrica rubra. III. Structures of Two Glycosides of Myricanol

Two new diarylheptanoid glycosides (1 and 2) were isolated together with vanillic acid and six known triterpenoids, maslinic acid, alphitolic acid, arjulonic acid, myricolal, oleanolic acid and oleanolic acid acetate, from the stem bark of Myrica rubra SIEB. et ZUCC. (Myricaceae).On the basis of spectral and chemical evidence, the structures of 1 and 2 were established as myricanol 5-O-β-D-(6'-O-galloyl)-glucopyranoside and myricanol 5-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside, respectively.Keywords-Myrica rubra; Myricaceae; diarylheptanoid glycoside; myricanol galloyglucoside; myricanol gentiobioside; maslinic acid; alphitolic acid; arjulonic acid; myricolal; vanillic acid