680617-50-9

Basic information

• Product Name: MegastigM-7-ene-3,5,6,9-tetraol
• Synonyms: (3S,5R,6R,7E,9R)-3,5,6,9-Tetrahydroxymegastigman-7-ene
• CAS NO: 680617-50-9
• Molecular Formula: C13H24O4
• Molecular Weight: 244.32726
• Mol File: 680617-50-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 344.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.203±0.06 g/cm3(Predicted)
• PKA: 13.77±0.70(Predicted)
• CAS DataBase Reference: MegastigM-7-ene-3,5,6,9-tetraol(CAS DataBase Reference)
• NIST Chemistry Reference: MegastigM-7-ene-3,5,6,9-tetraol(680617-50-9)
• EPA Substance Registry System: MegastigM-7-ene-3,5,6,9-tetraol(680617-50-9)

Safety Data

• Hazardous Substances Data: 680617-50-9(Hazardous Substances Data)

Usage

General Description

Megastigm-7-ene-3,5,6,9-tetraol is a naturally occurring chemical compound found in various plants and fruits. It belongs to the class of terpenes, which are organic compounds composed of isoprene units. This specific tetraol compound has been identified in several plants, including cinnamon and saffron, and is known for its potential health benefits. Research suggests that megastigm-7-ene-3,5,6,9-tetraol may have antioxidant and anti-inflammatory properties, making it potentially valuable in the treatment of various conditions. Additionally, its pleasant aroma has led to its use as a flavoring and fragrance ingredient in the food and perfume industries.

Upstream product

• 39763-31-0 (±)-(3E)-4-[1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one 
• 14398-35-7 (3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one 
• 79-77-6 (E)-β-ionone 
• 1363802-85-0 (3R,5S,6S,7E,9R)-megastigman-7-ene-3,5,6,9-tetraol 3-O-β-D-glucopyranoside 
• 1033434-17-1 (3R,5S,6S,7E,9S)-megastigman-7-ene-3,5,6,9-tetraol 9-O-β-D-glucopyranoside 

Relevant articles and documents

Megastigmanes from the aerial part of Euphorbia heterophylla

Three unprecedented megastigmanes together with twelve known compounds were isolated from the aerial part of Euphorbia heterophylla. The structural elucidation was based on extensive uses of spectroscopic data. The absolute configuration assignment of 1 was based on NOESY correlations and comparison of the experimental and calculated ECD spectra. Selected isolates obtained in sufficient quantity were evaluated for their cytotoxic activity.

Inhibitory constituents from the aerial parts of Polygala tenuifolia on LPS-induced NO production in BV2 microglia cells in commemoration of Professor Xin-Sheng Yao's 80th Birthday

Five new phenolic glycosides, tenuisides A-E (1-5), and a new megastigmane glycoside, tenuiside F (6), along with seventeen known compounds (7-23) were isolated from the aerial parts of Polygala tenuifolia Willd. Their structures were established by detailed analysis of NMR and HRESIMS spectroscopic data, and the absolute configurations of compounds 5 and 6 were determined by CD spectra and in-NMR-tube Mosher's method. The inhibitory effects of these compounds were evaluated on NO production in LPS-activated BV-2 microglia cells. Compound 17 showed the strongest activity, with an IC50 value of 7.4 μM, while compounds 1, 8, 14, and 18 showed the moderate activities, with IC50 values of 16.2-38.5 μM. And their primary structure-activity relationships (SARs) of NO inhibitory effects were also briefly discussed.

Euodionosides A-G: Megastigmane glucosides from leaves of Euodia meliaefolia

From a 1-BuOH-soluble fraction of the MeOH extract of leaves of Euodia meliaefolia, collected in Okinawa, seven megastigmane glucosides, named euodionosides A-G, were isolated together with three known megastgmane glucosides, and two aliphatic and three phenolic compounds. Their structures were elucidated through a combination of spectroscopic analyses and application of the modified Mosher's method.