ChemicalBook Product Catalog Biochemical Engineering Chinese Herbs (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

(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

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
CAS5945-50-6
MFC16H22O11
MW390.34
EINECS
MOL File5945-50-6.mol

Chemical Properties

Melting point	170-173 °C
Boiling point	717.6±60.0 °C(Predicted)
Density	1.73±0.1 g/cm3(Predicted)
storage temp.	Sealed in dry,Store in freezer, under -20°C
solubility	Soluble in methanol and water
form	powder
pka	4.31±0.60(Predicted)
color	White
Major Application	metabolomics vitamins, nutraceuticals, and natural products
InChI	1S/C16H22O10/c17-3-7-5-24-14(10-8(7)1-2-16(10,23)6-19)26-15-13(22)12(21)11(20)9(4-18)25-15/h1-3,5,8-15,18-23H,4,6H2/t8-,9-,10-,11-,12+,13-,14+,15+,16+/m1/s1
InChIKey	CYYIGLDAAXXQAI-PSWNKMJPSA-N
SMILES	O[C@H]1[C@H](O)[C@@H](O)[C@@](O[C@H]2[C@@]([C@](CO)(O)C=C3)([H])[C@@]3([H])C(C(O)=O)=CO2)([H])O[C@@H]1CO

Safety Information

Safety Statements	24/25
WGK Germany	WGK 3
HS Code	29389090
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

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.

Chemical Properties

White crystalline powder, soluble in water and methanol, derived from Deer tongue grass and Morinda officinalis.

Uses

Monotropein is an iridoid glycoside isolated Morinda officinalis. Monotropein inhibits the expression of inflammatory mediators in dextran sulfate sodium (DSS)-induced colitis mouse model[1].

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).

References

[1] Wang F, et al.Monotropein exerts protective effects against IL-1β-induced apoptosis and catabolic responses on osteoarthritis chondrocytes.Int Immunopharmacol. 2014 Dec;23(2):575-80. DOI:10.1016/j.intimp.2014.10.007

(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 Supplier

(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 manufacturers

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