Trilobatin

Modify Date: 2024-01-02 16:05:23

Trilobatin Structure
Trilobatin structure
Common Name Trilobatin
CAS Number 4192-90-9 Molecular Weight 436.409
Density 1.6±0.1 g/cm3 Boiling Point 787.9±60.0 °C at 760 mmHg
Molecular Formula C21H24O10 Melting Point 163 °C
MSDS N/A Flash Point 277.1±26.4 °C

 Use of Trilobatin


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].

 Names

Name 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
Synonym More Synonyms

 Trilobatin Biological Activity

Description 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].
Related Catalog
Target

HIV-1

SGLT1/2

In Vitro Trilobatin protects against oxidative injury in neuronal PC12 cells through regulating mitochondrial reactive oxygen species (mtROS) homeostasis in the first time, which is, at least partly, mediated through the AMPK/Nrf2/Sirt3 signaling pathway[1].
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.

[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.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 787.9±60.0 °C at 760 mmHg
Melting Point 163 °C
Molecular Formula C21H24O10
Molecular Weight 436.409
Flash Point 277.1±26.4 °C
Exact Mass 436.136932
PSA 177.14000
LogP 1.43
Vapour Pressure 0.0±2.9 mmHg at 25°C
Index of Refraction 1.686

 Synthetic Route

~49%

Trilobatin Structure

Trilobatin

CAS#:4192-90-9

Literature: Gupte, Amol; Buolamwini, John K. Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 3 p. 917 - 921

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Trilobatin Structure

Trilobatin

CAS#:4192-90-9

Literature: Jorio Annali di Chimica (Rome, Italy), 1959 , vol. 49, p. 1929,1936

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Trilobatin Structure

Trilobatin

CAS#:4192-90-9

Literature: Jorio Annali di Chimica (Rome, Italy), 1959 , vol. 49, p. 1929,1936

~%

Trilobatin Structure

Trilobatin

CAS#:4192-90-9

Literature: Jorio Annali di Chimica (Rome, Italy), 1959 , vol. 49, p. 1929,1936

 Synonyms

UNII:23298I791N
1-Propanone, 1-[4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
3,5-Dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside
p-Phloridzin
phloretin-4-D-glucoside
T6OTJ BOR CQ EQ DV2R DQ&& CQ DQ EQ F1Q &&β-D-Gluco Form
p-Phlorizin
1-Propanone, 1-(4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-
Trilobatin
1-(4-(β-D-Glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone
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