5945-50-6

Basic information

• Product Name: (1S,2S,6S,9R)-9-hydroxy-9-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,7-diene-5-carboxylic acid
• Synonyms: (1S,2S,6S,9R)-9-hydroxy-9-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,7-diene-5-carboxylic acid;1α-(β-D-Glucopyranosyloxy)-1,4aα,7,7aα-tetrahydro-7β-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid;Monotropein;Morinda officinalis How;Monotropein, 98%, from Monotropa uniflora L.
• CAS NO: 5945-50-6
• Molecular Formula: C16H22O11
• Molecular Weight: 390.34
• Product Categories: Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 5945-50-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 170-173 °C
• Boiling Point: 717.6 °C at 760 mmHg
• Flash Point: 262 °C
• Appearance: /
• Density: 1.73 g/cm³
• Vapor Pressure: 8.68E-24mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 4.31±0.60(Predicted)
• CAS DataBase Reference: (1S,2S,6S,9R)-9-hydroxy-9-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,7-diene-5-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,6S,9R)-9-hydroxy-9-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,7-diene-5-carboxylic acid(5945-50-6)
• EPA Substance Registry System: (1S,2S,6S,9R)-9-hydroxy-9-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,7-diene-5-carboxylic acid(5945-50-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 5945-50-6(Hazardous Substances Data)

Usage

Description

Monotropein is an iridoid glycoside originally isolated from M. officinalis roots and has diverse biological activities. It increases cell viability and migration of bone marrow-derived endothelial progenitor cells (BM-EPCs) when used at concentrations ranging from 0.1 to 1,000 μM. Monotropein inhibits apoptosis and reduces levels of matrix metalloproteinase-3 (MMP-3) and MMP-13 in chondrocytes. It inhibits LPS-induced nuclear translocation of NF-κB and reduces COX-2, inducible nitric oxide synthase (iNOS), TNF-α, and IL-1β mRNA expression in RAW 264.7 cells. Monotropein (100 and 200 mg/kg) reduces colonic myeloperoxidase (MPO) activity, COX-2 and iNOS mRNA expression, and disease severity in a mouse model of ulcerative colitis induced by dextran sulfate sodium (DSS; ). It increases bone mineral content, bone mineral density, and improves bone microstructure in ovariectomized mice when administered at doses of 40 or 80 mg/kg. Monotropein (20 and 30 mg/kg) reduces acetic acid-induced writhing in mice and carrageenan-induced paw edema in rats. It also decreases macrophage infiltration and wound healing time and increases blood vessel formation in a rat model of wound healing.

Definition

ChEBI: An iridoid monoterpenoid that is 1,4a,7,7a-tetrahydrocyclopenta[c]pyran substituted by a beta-D-glucopyranosyloxy group at position 1, a carboxylic acid group at position 4, and at position 7 by a hydroxy and ydroxymethyl groups respectively (the 1S,4aS,7R,7aS diastereomer).

InChI:InChI=1/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23)/t6-,8?,9-,10?,11?,12?,14+,15?,16+/m1/s1

Upstream product

• 36138-58-6 Andromedoside 

Relevant articles and documents

Andromedoside, a New Iridoide Glycoside from Andromeda polifolia L.

From Andromeda polifolia L. (Ericaceae) two further iridoide glycosides 4 and 6 were isolated and their structures determined.Both compounds are isomeric esters of monotropein (1) with p-hydroxycinnamic acid.Compound 6 was found to be vaccinoside; while the new iridoide andromedoside (4) represents a C-10-monotropein ester of cis-p-hydroxycinnamic acid.