Embelin

Modify Date: 2024-01-03 12:51:43

Embelin Structure
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 Embelin


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].

 Names

Name Embelin
Synonym More Synonyms

 Embelin Biological Activity

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.

 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

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

 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

 Synthetic Route

dilauroyl peroxide structure

dilauroyl peroxide

CAS#:105-74-8

~%

Embelin Structure

Embelin

CAS#:550-24-3

Literature: Journal of the American Chemical Society, , vol. 70, p. 74
Dodecanoyl chloride structure

Dodecanoyl chloride

CAS#:112-16-3

~%

Embelin Structure

Embelin

CAS#:550-24-3

Literature: Journal of the American Chemical Society, , vol. 70, p. 74
2,5-bis-methylamino-3-undecyl-[1,4]benzoquinone structure

2,5-bis-methyla...

CAS#:775350-90-8

~%

Embelin Structure

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
3-undecyl-benzene-1,2,4,5-tetraol structure

3-undecyl-benze...

CAS#:850878-20-5

~%

Embelin Structure

Embelin

CAS#:550-24-3

Literature: Archiv der Pharmazie (Weinheim, Germany), , vol. 238, p. 22
2-phenylamino-5-hydroxy-6-undecyl-1,4-naphthoquinone structure

2-phenylamino-5...

CAS#:56923-51-4

~%

Embelin Structure

Embelin

CAS#:550-24-3

structure

CAS#:74497-02-2

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

 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
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Related Compounds: More...
6-iodo-embelin
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6-bromo-embelin
88792-40-9
Embelin-monoanil
56923-51-4
6-chloro-embelin
88792-39-6
Embelin-dibenzoat
5796-41-8
5-O-Methylembelin
56005-10-8
embelin disemicarbazone
5796-42-9
6-chloro-embelin diacetate
88792-42-1
2,5-Diisobutylamino embelin
60198-38-1
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1158522-08-7
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
940364-43-2
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134104-43-1
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
131615-57-1
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6906-52-1
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
930439-75-1
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
1018584-77-4
tert-Butyl-DL-alanine
1375289-11-4
4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide
849349-65-1
N-[3-(Aminooxy)propyl]-N-butyl-1-butanamine
127437-46-1
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