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embelin
2,5-dihydroxy-3-undecyl-p-benzoquinone

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Name:2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
CAS Number: 550-24-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-979-8
FDA UNII: SHC6U8F5ER
Nikkaji Web:J6.710E
Beilstein Number:1885786
MDL:MFCD00016369
XlogP3-AA:5.40 (est)
Molecular Weight:294.39102000
Formula:C17 H26 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 142.50 °C. @ 760.00 mm Hg
Boiling Point: 431.89 °C. @ 760.00 mm Hg (est)
Flash Point: 444.00 °F. TCC ( 229.10 °C. ) (est)
logP (o/w): 5.024 (est)
Soluble in:
 water, 2.599 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Embelin 97%
BOC Sciences
For experimental / research use only.
Embelin >98%
Odor: characteristic
Use: Embelin, a quinone isolated from the Japanese Ardisia herb, is an inhibitor of X-linked inhibitor of apoptosis (XIAP) with IC50 of 4.1 uM.
ExtraSynthese
For experimental / research use only.
Embelin
Penta International
EMBELIN
Santa Cruz Biotechnology
For experimental / research use only.
Embelin
Sigma-Aldrich: Sigma
For experimental / research use only.
Embelin ≥98% (HPLC), powder
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mammal (species unspecified) LD50 44 mg/kg
Indian Journal of Physiology and Pharmacology. Vol. 21, Pg. 31, 1977.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for embelin usage levels up to:
 not for fragrance use.
 
Recommendation for embelin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3218
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
Chemidplus:0000550243
 
References:
 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):3218
Pubchem (sid):135024675
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10342
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 embelia fruit
Search PMC Picture
 
Synonyms:
2,5-cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-undecyl-
2,5-dihydroxy-3-undecyl-[1,4]benzoquinone
2,5-dihydroxy-3-undecyl-1,4-benzoquinone
2,5-dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione
2,5-dihydroxy-3-undecyl-p-benzoquinone
2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
 

Articles:

PubMed:Protective Effects of Embelin on Myocardial Ischemia-Reperfusion Injury Following Cardiac Arrest in a Rabbit Model.
PubMed:XIAP inhibitors induce differentiation and impair clonogenic capacity of acute myeloid leukemia stem cells.
PubMed:Exploiting natural products to build metalla-assemblies: the anticancer activity of embelin-derived Rh(III) and Ir(III) metalla-rectangles.
PubMed:Cardioprotective effect of embelin on isoproterenol-induced myocardial injury in rats: possible involvement of mitochondrial dysfunction and apoptosis.
PubMed:Design, synthesis, and SAR of embelin analogues as the inhibitors of PAI-1 (plasminogen activator inhibitor-1).
PubMed:Embelin suppresses growth of human pancreatic cancer xenografts, and pancreatic cancer cells isolated from KrasG12D mice by inhibiting Akt and Sonic hedgehog pathways.
PubMed:Embelin reduces colitis-associated tumorigenesis through limiting IL-6/STAT3 signaling.
PubMed:Embelin inhibits endothelial mitochondrial respiration and impairs neoangiogenesis during tumor growth and wound healing.
PubMed:Discovery of novel second mitochondria-derived activator of caspase mimetics as selective inhibitor of apoptosis protein inhibitors.
PubMed:XIAP antagonist embelin inhibited proliferation of cholangiocarcinoma cells.
PubMed:Thermosensitive injectable hydrogel enhances the antitumor effect of embelin in mouse hepatocellular carcinoma.
PubMed:Activation of p38/JNK pathway is responsible for embelin induced apoptosis in lung cancer cells: transitional role of reactive oxygen species.
PubMed:Embelin - a drug of antiquity: shifting the paradigm towards modern medicine.
PubMed:XIAP inhibitor and antiestrogen embelin abrogates metastasis and augments apoptosis in estrogen receptor positive human breast adenocarcinoma cell line MCF-7.
PubMed:Embelin suppresses pancreatic cancer growth by modulating tumor immune microenvironment.
PubMed:Effect of Embelin on TRAIL receptor 2 mAb-induced apoptosis of TRAIL-resistant A549 non-small cell lung cancer cells.
PubMed:Embelin suppresses dendritic cell functions and limits autoimmune encephalomyelitis through the TGF-β/β-catenin and STAT3 signaling pathways.
PubMed:Anti-tumor activity of the X-linked inhibitor of apoptosis (XIAP) inhibitor embelin in gastric cancer cells.
PubMed:Ellagic acid and embelin affect key cellular components of pancreatic adenocarcinoma, cancer, and stellate cells.
PubMed:Stress degradation studies on embelin.
PubMed:Elevated cell proliferation and VEGF production by high-glucose conditions in Müller cells involve XIAP.
PubMed:Multicomponent synthesis of antibacterial dihydropyridin and dihydropyran embelin derivatives.
PubMed:Potent inhibition of human 5-lipoxygenase and microsomal prostaglandin E₂ synthase-1 by the anti-carcinogenic and anti-inflammatory agent embelin.
PubMed:Anti-diabetic activity of embelin: involvement of cellular inflammatory mediators, oxidative stress and other biomarkers.
PubMed:Probing p300/CBP associated factor (PCAF)-dependent pathways with a small molecule inhibitor.
PubMed:Embelin-induced brain glioma cell apoptosis and cell cycle arrest via the mitochondrial pathway.
PubMed:Embelin induces apoptosis in human glioma cells through inactivating NF-κB.
PubMed:Structural insight into inactivation of plasminogen activator inhibitor-1 by a small-molecule antagonist.
PubMed:Embelin-induced MCF-7 breast cancer cell apoptosis and blockade of MCF-7 cells in the G2/M phase via the mitochondrial pathway.
PubMed:Hemisynthesis of selected embelin analogs and investigation of their proapoptotic activity against cancer cells.
PubMed:Embelin accelerates cutaneous wound healing in diabetic rats.
PubMed:PEG-derivatized embelin as a nanomicellar carrier for delivery of paclitaxel to breast and prostate cancers.
PubMed:In-vivo and In-vitro Activities of Medicinal Plants on Ecto, Endo and Haemoparasitic Infections: A review.
PubMed:Embelin-induced apoptosis of HepG2 human hepatocellular carcinoma cells and blockade of HepG2 cells in the G2/M phase via the mitochondrial pathway.
PubMed:Insulin sensitization via partial agonism of PPARγ and glucose uptake through translocation and activation of GLUT4 in PI3K/p-Akt signaling pathway by embelin in type 2 diabetic rats.
PubMed:Embelin inhibits growth and induces apoptosis through the suppression of Akt/mTOR/S6K1 signaling cascades.
PubMed:PEG-derivatized embelin as a dual functional carrier for the delivery of paclitaxel.
PubMed:Inhibition of UVB-induced oxidative damage and apoptotic biochemical changes in human lymphocytes by 2,5-dihydroxy-3-undecyl-1,4-benzoquinone (embelin).
PubMed:The flavonolignan silibinin potentiates TRAIL-induced apoptosis in human colon adenocarcinoma and in derived TRAIL-resistant metastatic cells.
PubMed:XIAP inhibition and generation of reactive oxygen species enhances TRAIL sensitivity in inflammatory breast cancer cells.
PubMed:Combination therapy of antiandrogen and XIAP inhibitor for treating advanced prostate cancer.
PubMed:Preventive effect of embelin from embelia ribes on lipid metabolism and oxidative stress in high-fat diet-induced obesity in rats.
PubMed:Co-expression of XIAP and cyclin D1 complex correlates with a poor prognosis in patients with hepatocellular carcinoma.
PubMed:Estimation of Embelin in Embelia tsjeriam-cottam Fruits by HPLC to Standardize Harvesting Time.
PubMed:Antioxidant activity and protection of pancreatic β-cells by embelin in streptozotocin-induced diabetes.
PubMed:Redox and non-redox mechanism of in vitro cyclooxygenase inhibition by natural quinones.
PubMed:Inhibition of X-linked inhibitor of apoptosis with embelin differentially affects male versus female behavioral outcome following neonatal hypoxia-ischemia in rats.
PubMed:Bioinformatics in crosslinking chemistry of collagen with selective cross linkers.
PubMed:Natural IAP inhibitor Embelin enhances therapeutic efficacy of ionizing radiation in prostate cancer.
PubMed:Synthesis and evaluation of analgesic and anti-inflammatory activities of most active free radical scavenging derivatives of embelin-A structure-activity relationship.
PubMed:Protective effect of embelin from Embelia ribes Burm. against transient global ischemia-induced brain damage in rats.
PubMed:miR-23a regulation of X-linked inhibitor of apoptosis (XIAP) contributes to sex differences in the response to cerebral ischemia.
PubMed:Embelin suppresses STAT3 signaling, proliferation, and survival of multiple myeloma via the protein tyrosine phosphatase PTEN.
PubMed:Embelin reduces cutaneous TNF-α level and ameliorates skin edema in acute and chronic model of skin inflammation in mice.
PubMed:Embelin ameliorates dextran sodium sulfate-induced colitis in mice.
PubMed:Protective effect of embelin against acetic acid induced ulcerative colitis in rats.
PubMed:Chemopreventive and hepatoprotective effects of embelin on N-nitrosodiethylamine and carbon tetrachloride induced preneoplasia and toxicity in rat liver.
PubMed:[Effect of Embelin on proliferation, differentiation and aopotosis of HL-60 cells.]
PubMed:Chemical speciation of binary complexes of embelin with some biologically important metal ions.
PubMed:WITHDRAWN: Evaluation of antidiabetic effect of embelin from Embelia ribes in alloxan induced diabetes in rats.
PubMed:Embelin suppresses osteoclastogenesis induced by receptor activator of NF-κB ligand and tumor cells in vitro through inhibition of the NF-κB cell signaling pathway.
PubMed:Synthesis and characterization of amphiphilic lipopolymers for micellar drug delivery.
PubMed:RP-HPLC-DAD method for the estimation of embelin as marker in Embelia ribes and its polyherbal formulations.
PubMed:XIAP gene expression protects β-cells and human islets from apoptotic cell death.
PubMed:Prognostic significance of XIAP expression in DLBCL and effect of its inhibition on AKT signalling.
PubMed:Embelin induces apoptosis through down-regulation of XIAP in human leukemia cells.
PubMed:Anticonvulsant activity of embelin isolated from Embelia ribes.
PubMed:Comparative in vitro bioactivities of tea extracts from six species of Ardisia and their effect on growth inhibition of HepG2 cells.
PubMed:X-linked inhibitor of apoptosis protein inhibits apoptosis in inflammatory breast cancer cells with acquired resistance to an ErbB1/2 tyrosine kinase inhibitor.
PubMed:Activation of endothelial nitric oxide synthase by the pro-apoptotic drug embelin: Striking discrepancy between nitric oxide-mediated cyclic GMP accumulation and L-citrulline formation.
PubMed:Lysosomal destabilization and cathepsin B contributes for cytochrome c release and caspase activation in embelin-induced apoptosis.
PubMed:XIAP-mediated protection of H460 lung cancer cells against cisplatin.
PubMed:Effects of embelin on lipid peroxidation and free radical scavenging activity against liver damage in rats.
PubMed:Peroxisome proliferator-activated receptor-gamma contributes to the inhibitory effects of Embelin on colon carcinogenesis.
PubMed:Micellar delivery of bicalutamide and embelin for treating prostate cancer.
PubMed:The XIAP inhibitor Embelin enhances TRAIL-mediated apoptosis in malignant glioma cells by down-regulation of the short isoform of FLIP.
PubMed:Cell-penetrating peptide-conjugated XIAP-inhibitory cyclic hexapeptides enter into Jurkat cells and inhibit cell proliferation.
PubMed:Protein-protein recognition as a first step towards the inhibition of XIAP and Survivin anti-apoptotic proteins.
PubMed:Trastuzumab signaling in ErbB2-overexpressing inflammatory breast cancer correlates with X-linked inhibitor of apoptosis protein expression.
PubMed:Effect of the XIAP inhibitor Embelin on TRAIL-induced apoptosis of pancreatic cancer cells.
PubMed:Free radical scavenging reactions and antioxidant activity of embelin: biochemical and pulse radiolytic studies.
PubMed:Microwave-assisted extraction of embelin from Embelia ribes.
PubMed:Wound healing activity of embelin isolated from the ethanol extract of leaves of Embelia ribes Burm.
PubMed:Embelin, an inhibitor of X chromosome-linked inhibitor-of-apoptosis protein, blocks nuclear factor-kappaB (NF-kappaB) signaling pathway leading to suppression of NF-kappaB-regulated antiapoptotic and metastatic gene products.
PubMed:Design, synthesis, and characterization of new embelin derivatives as potent inhibitors of X-linked inhibitor of apoptosis protein.
PubMed:Effects of administration of Embelin and Curcumin on lipid peroxidation, hepatic glutathione antioxidant defense and hematopoietic system during N-nitrosodiethylamine/Phenobarbital-induced hepatocarcinogenesis in Wistar rats.
PubMed:Cell death in pancreatitis: caspases protect from necrotizing pancreatitis.
PubMed:Embelin derivatives and their anticancer activity through microtubule disassembly.
PubMed:Chemopreventive effects of embelin and curcumin against N-nitrosodiethylamine/phenobarbital-induced hepatocarcinogenesis in Wistar rats.
PubMed:Cytotoxic activity of embelin from Lysimachia punctata.
PubMed:Anti-fertility effects of embelin in female Sprague-Dawley rats may be due to suppression of ovarian function.
PubMed:New compounds from the seeds of Embelia ribes Burm.
PubMed:Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database.
PubMed:Evaluation of anthelmintic properties of extracts from some plants used as livestock dewormers by pastoralist and smallholder farmers in Kenya against Heligmosomoides polygyrus infections in mice.
PubMed:Bioactive alkyl phenols and embelin from Oxalis erythrorhiza.
PubMed:Antibacterial activity of embelin.
PubMed:Ardisiphenols and other antioxidant principles from the fruits of Ardisia colorata.
PubMed:Electrochemically synthesized polymer of the plant substance embelin (2,5-dihydroxy-3-undecyl-1,4-benzoquinone).
PubMed:Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease.
PubMed:A TLC Identification and Spectrophotometric Estimation of Embelin in Embelia ribes.
PubMed:Anthelmintic usage of extracts of Embelia schimperi from Tanzania.
PubMed:[3H]-thymidine uptake and lipid peroxidation by tumor cells on embelin treatment: an in vitro study.
PubMed:Antitumor, anti-inflammatory and analgesic property of embelin, a plant product.
PubMed:Determination of estrogenic/antiestrogenic potential of antifertility substances using rat uterine peroxidase assay.
PubMed:Changes in the concentrations of testosterone, luteinising hormone and progesterone associated with administration of embelin.
PubMed:Effects of embelin, a male antifertility agent, on absorptive and digestive functions of rat intestine.
PubMed:Binding of potassium [3H]embelate to rat brain synaptosomes.
PubMed:Interaction of benzoquinones with mitochondria interferes with oxidative phosphorylation characteristics.
PubMed:Changes in glucose/amino acid/calcium uptake and brush-border membrane-associated enzymes in rat small intestine after the administration of embelin (plant benzoquinone), an antifertility agent.
PubMed:Toxicity studies with potassium embelate, a new analgesic compound.
PubMed:Kinetic fate of potassium embelate, a non-narcotic centrally acting analgesic after oral and intravenous administration.
PubMed:[Studies on the chemical composition of Lysimachia fortunei Maxim].
PubMed:Changes in brain calcium content and CA(++)-ATPase activity in potassium embelate treated rats.
PubMed:Possible interaction of potassium embelate, a putative analgesic agent, with opiate receptors.
PubMed:Antispermatogenic effect of embelin, a plant benzoquinone, on male albino rats in vivo and in vitro.
PubMed:Energy reserves of the brain during potassium embelate-induced antinociception in rat.
PubMed:Antifertility effects of embelin in male rats.
PubMed:Visual deficits and retinotoxicity caused by the naturally occurring anthelmintics, Embelia ribes and Hagenia abyssinica.
PubMed:Non-narcotic orally effective, centrally acting analgesic from an Ayurvedic drug.
PubMed:Reversible contraception like activity of embelin in male dogs (Canis indicus Linn).
PubMed:Antifertility investigations on embelin -- an oral contraceptive of plant origin. Part I -- Biological properties.
PubMed:Antifertility properties of Embelia ribes : (embelin).
PubMed:Antifertility properties of Embelia ribes.
PubMed:Biochemical changes in the uterus & cervix of ovariectomized rats treated with Embelin.
PubMed:Phosphatase activity in testis and prostate of rats treated with embelin and Vinca rosea extract.
PubMed:Biochemical changes in the uterus & uterine fluid of mated rats treated with Embelin--a non-steroidal oral contraceptive.
PubMed:Some pharmacological investigations of embelin and its semisynthetic derivatives.
PubMed:In vitro anthelmintic activity of disalts of embelin.
PubMed:Antifertility activity of embelin in albino rats.
PubMed:[Derivatives of methylenedioxybenzene. 35. A novel synthesis of 3,6 dihydroxy-2-ethyl-1,4-benzoquinone, embelin, vilangin, rapanone, dihydromaesaquinone, bhogatin, spinulosin and oosporein].
PubMed:[STUDY OF VERMIFUGES. I. ISOLATION OF EMBELIN FROM THE FRUIT OF MUGUA-WHA (EMBELIA OBLONGIFOLIA HEMSL.)].
PubMed:Synthesis of embelin, rapoanne and related quinones by peroxide alkylation.
 
Notes:
from embelia fruit (myrsinaceae).
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