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550-24-3

550-24-3 structure
550-24-3 structure
  • Name: Embelin
  • Chemical Name: Embelin
  • CAS Number: 550-24-3
  • Molecular Formula: C17H26O4
  • Molecular Weight: 294.386
  • Catalog: Biochemical Plant extracts
  • Create Date: 2018-04-13 08:00:00
  • Modify Date: 2024-01-03 12:51:43
  • 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].
Name Embelin
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
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

[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.
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 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

RTECS NUMBER :
DK4230000
CHEMICAL NAME :
p-Benzoquinone, 2,5-dihydroxy-3-undecyl-
CAS REGISTRY NUMBER :
550-24-3
BEILSTEIN REFERENCE NO. :
1885786
LAST UPDATED :
199612
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C17-H26-O4
MOLECULAR WEIGHT :
294.43
WISWESSER LINE NOTATION :
L6V DVJ BQ C11 EQ

HEALTH HAZARD DATA

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
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
105-74-8 structure

105-74-8

~%

550-24-3 structure

550-24-3

Literature: Journal of the American Chemical Society, , vol. 70, p. 74
112-16-3 structure

112-16-3

~%

550-24-3 structure

550-24-3

Literature: Journal of the American Chemical Society, , vol. 70, p. 74
775350-90-8 structure

775350-90-8

~%

550-24-3 structure

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
850878-20-5 structure

850878-20-5

~%

550-24-3 structure

550-24-3

Literature: Archiv der Pharmazie (Weinheim, Germany), , vol. 238, p. 22
56923-51-4 structure

56923-51-4

~%

550-24-3 structure

550-24-3

74497-02-2 structure

74497-02-2

Literature: Archiv der Pharmazie (Weinheim, Germany), , vol. 238, p. 22
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%

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