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

(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 is an iridoid monoterpenoid with a complex chemical structure, characterized by its unique arrangement of hydroxy, hydroxymethyl, and carboxylic acid groups. This molecule exhibits a range of biological activities, making it a promising candidate for various applications in the pharmaceutical and medical fields.

Uses

Used in Pharmaceutical Applications:
(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 is used as a therapeutic agent for promoting cell viability and migration in bone marrow-derived endothelial progenitor cells (BM-EPCs). It is particularly effective at concentrations ranging from 0.1 to 1,000 μM.
Used in Anti-inflammatory Applications:
In the treatment of inflammatory conditions, this compound is used as an anti-inflammatory agent. It inhibits apoptosis and reduces levels of matrix metalloproteinase-3 (MMP-3) and MMP-13 in chondrocytes, as well as LPS-induced nuclear translocation of NF-κB and the expression of COX-2, inducible nitric oxide synthase (iNOS), TNF-α, and IL-1β mRNA in RAW 264.7 cells.
Used in Gastrointestinal Applications:
(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 is used as a therapeutic agent for reducing 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).
Used in Orthopedic Applications:
In the field of orthopedics, this compound is used to increase bone mineral content, bone mineral density, and improve bone microstructure in ovariectomized mice when administered at doses of 40 or 80 mg/kg.
Used in Pain Management Applications:
(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 is used as an analgesic agent, reducing acetic acid-induced writhing in mice and carrageenan-induced paw edema in rats.
Used in Wound Healing Applications:
In the field of wound care, this compound is used to decrease macrophage infiltration, wound healing time, and increase blood vessel formation in a rat model of wound healing.
Used in Cosmetic Applications:
(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 is used as an active ingredient in cosmetic products for its potential anti-inflammatory, analgesic, and wound healing properties, which can contribute to skin health and appearance.
Used in the Food Industry:
In the food industry, this compound may be used as a natural additive for its potential health benefits, such as anti-inflammatory and analgesic properties, to enhance the nutritional value and appeal of certain products.
Please note

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.