CAS 550-24-3|Embelin
Introduction：Basic information about CAS 550-24-3|Embelin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| 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 | ChineseUSA | Flash Point | 229.1±25.2 °C |
Names
| Name | Embelin |
|---|---|
| Synonym | More Synonyms |
Embelin BiologicalActivity
| 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 | Signaling Pathways >>Apoptosis >>IAPNatural Products >>QuinonesResearch Areas >>Cancer |
| References | [1]. Siegel C, et al. miR-23a regulation of X-linked inhibitor of apoptosis (XIAP) contributes to sex differences in the response to cerebral ischemia. Proc Natl Acad Sci U S A. 2011 Jul 12;108(28):11662-7. [2]. Hu R, et al. Embelin induces apoptosis through down-regulation of XIAP in human leukemia cells. Med Oncol. 2011 Dec;28(4):1584-8. [3]. Siegelin MD, et al. The XIAP inhibitor Embelin enhances TRAIL-mediated apoptosis in malignant glioma cells by down-regulation of the short isoform of FLIP. Neurochem Int. 2009 Nov;55(6):423-30. [4]. Kalyan Kumar G, et al. Embelin reduces cutaneous TNF-α level and ameliorates skin edema in acute and chronic model of skin inflammation in mice. Eur J Pharmacol. 2011 Jul 15;662(1-3):63-9. [5]. Kumar G K, et al. Embelin ameliorates dextran sodium sulfate-induced colitis in mice. Int Immunopharmacol. 2011 Jun;11(6):724-31. [6]. Xue Z, et al. Embelin suppresses dendritic cell functions and limits autoimmune encephalomyelitis through the TGF-β/β-catenin and STAT3 signaling pathways. Mol Neurobiol. 2014 Apr;49(2):1087-101. |
Chemical & Physical Properties
| 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Mammal - species unspecified
- DOSE/DURATION :
- 44 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- IJPPAZ Indian Journal of Physiology and Pharmacology. (All India Institute of Medical Sciences, Dept. of Physiology, Ansari Nagar, New Delhi 110 029, India) V.1- 1957- Volume(issue)/page/year: 21,31,1977 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 5040 mg/kg/6W-I
- TOXIC EFFECTS :
- Liver - multiple effects Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
- REFERENCE :
- PHYREH Phytotherapy Research. (Heyden & Son Ltd., Spectrum House, Hillview Gardens, London, NW4 2JQ, UK) V.1- 1987- Volume(issue)/page/year: 8,257,1994 ** REPRODUCTIVE DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 50 mg/kg
- SEX/DURATION :
- female 1-5 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
- REFERENCE :
- JRIHDC Journal of Research in Indian Medicine Yoga and Homoeopathy. (Banaras Hindu Univ., Varanasi-5, India) V.11- 1976- Volume(issue)/page/year: 11(4),84,1976
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 250 mg/kg
- SEX/DURATION :
- female 1-5 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
- REFERENCE :
- IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 18,1359,1980
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 50 mg/kg
- SEX/DURATION :
- female 1-5 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - other effects
- REFERENCE :
- IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 16,1187,1978
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 300 mg/kg
- SEX/DURATION :
- male 15 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 39,307,1989
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 4 gm/kg
- SEX/DURATION :
- male 14 week(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - testes, epididymis, sperm duct
- REFERENCE :
- ANDRDQ Andrologia. (Grosse Verlag GmbH, Kurfuerstenstr. 112-113, D-1000 Berlin 30, Fed. Rep. Ger.) V.6- 1974- Volume(issue)/page/year: 15,486,1983
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 50 mg/kg
- SEX/DURATION :
- female 5 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - other measures of fertility
- REFERENCE :
- JRIHDC Journal of Research in Indian Medicine Yoga and Homoeopathy. (Banaras Hindu Univ., Varanasi-5, India) V.11- 1976- Volume(issue)/page/year: 11(4),84,1976
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intramuscular
- DOSE :
- 210 mg/kg
- SEX/DURATION :
- male 14 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - other effects on male Endocrine - androgenic
- REFERENCE :
- CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 44,311,1991
Safety Information
| 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 |
Customs
| 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% |
Articles27
More Articles| 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... |
Synonyms
| 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 |
