| Identification | Back Directory | [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 | [CAS]
5945-50-6 | [Synonyms]
Monotropein
Monotropeine
Morinda officinalis How
Monotropein >=98% (HPLC)
Monotropein, 98%, from Monotropa uniflora L.
1α-(β-D-Glucopyranosyloxy)-1,4aα,7,7aα-tetrahydro-7β-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid
Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, (1S,4aS,7R,7aS)-
(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 USP/EP/BP
(1S,4aS,7R,7aS)-7-Hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid | [Molecular Formula]
C16H22O11 | [MDL Number]
MFCD00238650 | [MOL File]
5945-50-6.mol | [Molecular Weight]
390.34 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [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 |
| Hazard Information | Back Directory | [Description]
Monotropein is an iridoid glycoside originally isolated from M. officinalis roots and has diverse biological activities.1,2,3,4,5 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.1 Monotropein inhibits apoptosis and reduces levels of matrix metalloproteinase-3 (MMP-3) and MMP-13 in chondrocytes.2 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.3 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; Item No. 23250). 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.4 Monotropein (20 and 30 mg/kg) reduces acetic acid-induced writhing in mice and carrageenan-induced paw edema in rats.5 It also decreases macrophage infiltration and wound healing time and increases blood vessel formation in a rat model of wound healing.1 | [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 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
(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)1HNMR
(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)IR1
(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)IR2
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