| Identification | Back Directory | [Name]
PRUNINDIHYDROCHALCONE | [CAS]
4192-90-9 | [Synonyms]
Trilobatin
p-Phlorizin
p-Phloridzin
TRILOBATIN(SH)
PRUNINDIHYDROCHALCONE
Phloretin 4'-glucoside
Trilobatin, 98%, from leaf of strigose hydrangea
1-[4-(β-D-Glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
1-Propanone, 1-[4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one | [Molecular Formula]
C21H24O10 | [MDL Number]
MFCD21333313 | [MOL File]
4192-90-9.mol | [Molecular Weight]
436.41 |
| Chemical Properties | Back Directory | [Melting point ]
170-173 °C | [Boiling point ]
787.9±60.0 °C(Predicted) | [density ]
1.555±0.06 g/cm3(Predicted) | [FEMA ]
4674 | TRILOBATIN | [storage temp. ]
4°C, protect from light | [solubility ]
DMF: 20 mg/ml; DMSO: 25 mg/ml; Ethanol: 20 mg/ml; PBS (pH 7.2): 0.1 mg/ml | [form ]
A crystalline solid | [pka]
6.85±0.40(Predicted) | [color ]
White to off-white | [JECFA Number]
2171 | [InChIKey]
GSTCPEBQYSOEHV-LKLLPNDVNA-N | [SMILES]
C(C1C(=CC(O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=1O)O)(=O)CCC1C=CC(O)=CC=1 |&1:6,7,8,10,12,r| | [LogP]
1.36 |
| Safety Data | Back Directory | [WGK Germany ]
WGK 3 | [HS Code ]
29329990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Soluble in organic solvents such as methanol, ethanol, and DMSO. | [Uses]
Trilobatin, a natural sweetener derived from?Lithocarpus polystachyus?Rehd[1], Trilobatin?is an HIV-1 entry inhibitor targeting the HIV-1 Gp41 envelope[2]. Neuroprotective effects[1]. Trilobatin is also a SGLT1/2 inhibitor that selectively induces the proliferation of human hepatoblastoma cells[3]. | [Definition]
ChEBI: Trilobatin is an aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage. It is isolated from the leaves of the Chinese sweet tea Lithocarpus polystachyus and exhibits significant anti-hyperglycemic, anti-oxidative and anti-inflammatory properties. It has a role as an anti-inflammatory agent, a sweetening agent, an antioxidant and a plant metabolite. It is an aryl beta-D-glucoside, a member of dihydrochalcones and a monosaccharide derivative. It is functionally related to a phloretin. | [IC 50]
HIV-1; SGLT1; SGLT2 | [References]
[1] Gao J, et al. Trilobatin?Protects Against Oxidative Injury in Neuronal PC12 Cells Through Regulating Mitochondrial ROS Homeostasis Mediated by AMPK/Nrf2/Sirt3 Signaling Pathway. Front Mol Neurosci.?2018 Jul 30;11:267. DOI:10.3389/fnmol.2018.00267
[2] Yin S,?et al. Trilobatin?as an HIV-1 entry inhibitor targeting the HIV-1 Gp41 envelope. FEBS Lett.?2018 Jul;592(13):2361-2377. DOI:10.1002/1873-3468.13113 |
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