Embelin structure
|
Common Name | Embelin | ||
---|---|---|---|---|
CAS Number | 550-24-3 | Molecular Weight | 294.386 | |
Density | 1.131 | Boiling Point | 431.9±45.0 °C at 760 mmHg | |
Molecular Formula | C17H26O4 | Melting Point | 145-146 ºC | |
MSDS | Chinese USA | Flash Point | 229.1±25.2 °C |
Use of EmbelinEmbelin is a cell-permeable benzoquinone compound that exhibits antitumor properties. Specifically antagonizes XIAP-mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 (IC50 = 4.1 uM in a competitive binding assay with Smac peptide).IC50 value: 4.1 uM [1]Target: XIAPin vitro: Embelin induced activation of caspase-9 and embelin-induced apoptosis was prevented by caspase inhibitors [2]. Treatment with subtoxic doses of Embelin broadly sensitized malignant glioma cells to TRAIL-mediated apoptosis. Notably, human astrocytes were not significantly affected by the combined treatment consisting of Embelin and TRAIL. Combined treatment with Embelin and TRAIL augmented the activation of initiator caspases-8/-9 and effector caspases-3/-7, respectively [3]. in vivo: Embelin inhibited topical edema in the mouse ear, leading to substantial reductions in skin thickness and tissue weight, inflammatory cytokine production, neutrophil-mediated myeloperoxidase activity, and various histopathological indicators. Furthermore, embelin was effective at reducing inflammatory damage induced by chronic TPA exposure [4]. Embelin (10, 30 or 50mg/kg body weight) was administrated daily per oral route for 7days. Embelin significantly attenuated DSS-induced DAI scores and tissue MPO accumulation, which implied that it suppressed weight loss, diarrhea, gross bleeding, and the infiltrations of immune cells. Embelin administration also effectively and dose-dependently prevented shortening of colon length and enlargement of spleen size [5]. |
Name | Embelin |
---|---|
Synonym | More Synonyms |
Description | Embelin is a cell-permeable benzoquinone compound that exhibits antitumor properties. Specifically antagonizes XIAP-mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 (IC50 = 4.1 uM in a competitive binding assay with Smac peptide).IC50 value: 4.1 uM [1]Target: XIAPin vitro: Embelin induced activation of caspase-9 and embelin-induced apoptosis was prevented by caspase inhibitors [2]. Treatment with subtoxic doses of Embelin broadly sensitized malignant glioma cells to TRAIL-mediated apoptosis. Notably, human astrocytes were not significantly affected by the combined treatment consisting of Embelin and TRAIL. Combined treatment with Embelin and TRAIL augmented the activation of initiator caspases-8/-9 and effector caspases-3/-7, respectively [3]. in vivo: Embelin inhibited topical edema in the mouse ear, leading to substantial reductions in skin thickness and tissue weight, inflammatory cytokine production, neutrophil-mediated myeloperoxidase activity, and various histopathological indicators. Furthermore, embelin was effective at reducing inflammatory damage induced by chronic TPA exposure [4]. Embelin (10, 30 or 50mg/kg body weight) was administrated daily per oral route for 7days. Embelin significantly attenuated DSS-induced DAI scores and tissue MPO accumulation, which implied that it suppressed weight loss, diarrhea, gross bleeding, and the infiltrations of immune cells. Embelin administration also effectively and dose-dependently prevented shortening of colon length and enlargement of spleen size [5]. |
---|---|
Related Catalog | |
References |
Density | 1.131 |
---|---|
Boiling Point | 431.9±45.0 °C at 760 mmHg |
Melting Point | 145-146 ºC |
Molecular Formula | C17H26O4 |
Molecular Weight | 294.386 |
Flash Point | 229.1±25.2 °C |
Exact Mass | 294.183105 |
PSA | 74.60000 |
LogP | 5.70 |
Appearance of Characters | solid |
Vapour Pressure | 0.0±2.3 mmHg at 25°C |
Index of Refraction | 1.538 |
Storage condition | Store at +4°C |
Water Solubility | DMSO: >10 mg/mL |
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
|
Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
---|---|
RIDADR | NONH for all modes of transport |
WGK Germany | 3 |
RTECS | DK4230000 |
HS Code | 2914690090 |
~% Embelin CAS#:550-24-3 |
Literature: Journal of the American Chemical Society, , vol. 70, p. 74 |
~% Embelin CAS#:550-24-3 |
Literature: Journal of the American Chemical Society, , vol. 70, p. 74 |
~% Embelin CAS#:550-24-3 |
Literature: Yakugaku Zasshi, , vol. 60, p. 105,113; dtsch. Ref. S. 34, 37 Chem.Abstr., , p. 5070 Yakugaku Zasshi, , vol. 60, p. 650,658 Yakugaku Zasshi, , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., , p. 83 |
~% Embelin CAS#:550-24-3 |
Literature: Archiv der Pharmazie (Weinheim, Germany), , vol. 238, p. 22 |
~% Embelin CAS#:550-24-3 |
Literature: Archiv der Pharmazie (Weinheim, Germany), , vol. 238, p. 22 |
Precursor 5 | |
---|---|
DownStream 10 | |
HS Code | 2914690090 |
---|---|
Summary | 2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0% |
Preventive effect of embelin from embelia ribes on lipid metabolism and oxidative stress in high-fat diet-induced obesity in rats.
Planta Med. 78(7) , 651-7, (2012) A high-fat diet (HFD) results in hyperlipidemia and an increase in oxidative stress. The purpose of this study was to investigate the preventive effect of embelin against hyperlipidemia and oxidative ... |
|
Embelin ameliorates dextran sodium sulfate-induced colitis in mice
Int. Immunopharmacol. 11(6) , 724-31, (2011) Embelin has been used to treat fever, inflammatory diseases, and a variety of gastrointestinal ailments for thousands of years. Although reports indicate that embelin has anti-inflammatory and anti-tu... |
|
Inhibition of UVB-induced oxidative damage and apoptotic biochemical changes in human lymphocytes by 2,5-dihydroxy-3-undecyl-1,4-benzoquinone (embelin).
Int. J. Radiat. Biol. 88(8) , 575-82, (2012) The present study investigates the inhibition of Ultraviolet B (UVB, 290-320 nm) radiation-induced oxidative damage in peripheral blood human lymphocytes by embelin extracted from Embelia ribes.Embeli... |
2,5-Dihydroxy-3-undecyl-1,4-benzoquinone |
Embelin |
2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione |
2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-undecyl- |
EINECS 208-979-8 |