cucurbitacin E
alpha-elaterin
 
Notes:
signals for an action; that specific portion of a perceptual field or pattern of stimuli to which a subject has learned to respond.
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      Product(s):
      18444-66-1 cucurbitacin E >98%
      Cucurbitacin E, also known as NSC 106399, extracted from Ecballium elaterium, belongs to the family of Cucurbitacins. Cucurbitacin E is a cytotoxic sterol natural with broad spectrum of potential anti-inflammatory, antitumor andantioxidant effects. Antineoplastic/anti-proliferative
       
       
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CAS Number: 18444-66-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 242-325-2
FDA UNII: V8A45XYI21
Nikkaji Web: J14.209C
Beilstein Number: 2343323
XlogP3-AA: 3.20 (est)
Molecular Weight: 556.69628000
Formula: C32 H44 O8
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
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Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
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PubMed: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 712.60 °C. @ 760.00 mm Hg (est)
Flash Point: 436.00 °F. TCC ( 224.40 °C. ) (est)
logP (o/w): 3.150 (est)
Soluble in:
 water, 0.09289 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Alfa Biotechnology
For experimental / research use only.
Cucurbitacin E 98%
BOC Sciences
For experimental / research use only.
cucurbitacin E >98%
Odor: characteristic
Use: Cucurbitacin E, also known as NSC 106399, extracted from Ecballium elaterium, belongs to the family of Cucurbitacins. Cucurbitacin E is a cytotoxic sterol natural with broad spectrum of potential anti-inflammatory, antitumor andantioxidant effects. Antineoplastic/anti-proliferative
ExtraSynthese
For experimental / research use only.
Cucurbitacin E (HPLC) ≥95%
Sigma-Aldrich: Sigma
For experimental / research use only.
Cucurbitacin E ≥95% (HPLC)
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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:
oral-mouse LD50  340 mg/kg
Chimica Therapeutica. Vol. 5, Pg. 205, 1970.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for cucurbitacin E usage levels up to:
 not for fragrance use.
 
Recommendation for cucurbitacin E flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5281319
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 [(E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
Chemidplus: 0018444661
RTECS: RC6305500 for cas# 18444-66-1
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References:
 [(E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5281319
Pubchem (sid): 135044767
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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): C08797
HMDB (The Human Metabolome Database): Search
FooDB: FDB014623
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cantaloupe fruit
Search Trop  Picture
 cucumber fruit
Search Trop  Picture
 watermelon fruit
Search Trop  Picture
 watermelon leaf
Search Trop  Picture
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Synonyms:
25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione (9beta,10alpha,16alpha,23E)-
25-(acetyloxy)-2b,16a,20-trihydroxy-9b-methyl-19-nor-10a-lanosta-1,5,23E-triene-3,11,22-trione
 cucurbitacine-E
[(E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
A-elaterin
alpha-elaterin
 elaterin, alpha
alpha-elaterine
19-nor-9beta,10alpha-lanosta-1,5,23-triene-3,11,22-trione, 2,16alpha,20,25-tetrahydroxy-9-methyl-, 25-acetate (8CI)
19-norlanosta-1,5,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9beta,10alpha,16alpha,23E)-
2,16alpha,20,25-tetrahydroxy-9beta-methyl-10alpha,-19-norlanosta-1,5,23(E)-triene-3,11,22-trione 25-acetate
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Articles:
PubMed: Infection of Porcine Circovirus 2 (PCV2) in Intestinal Porcine Epithelial Cell Line (IPEC-J2) and Interaction between PCV2 and IPEC-J2 Microfilaments.
PubMed: Effects of Cucurbitacin E, a Tetracyclic Triterpene Compound from Cucurbitaceae, on the Pharmacokinetics and Pharmacodynamics of Warfarin in Rats.
PubMed: GADD45γ induces G2/M arrest in human pharynx and nasopharyngeal carcinoma cells by cucurbitacin E.
PubMed: Cucurbitacin E induces cell cycle G2/M phase arrest and apoptosis in triple negative breast cancer.
PubMed: Identification of cucurbitacins and assembly of a draft genome for Aquilaria agallocha.
PubMed: Cucurbitacin-E inhibits multiple cancer cells proliferation through attenuation of Wnt/β-catenin signaling.
PubMed: Therapeutic ROS targeting of GADD45γ in the induction of G2/M arrest in primary human colorectal cancer cell lines by cucurbitacin E.
PubMed: Inducement of mitosis delay by cucurbitacin E, a novel tetracyclic triterpene from climbing stem of Cucumis melo L., through GADD45γ in human brain malignant glioma (GBM) 8401 cells.
PubMed: Morphological and physicochemical characterization of liposomes loading cucurbitacin E, an anti-proliferative natural tetracyclic triterpene.
PubMed: Growth inhibitory effect of Cucurbitacin E on breast cancer cells.
PubMed: Cucurbitacin E as inducer of cell death and apoptosis in human oral squamous cell carcinoma cell line SAS.
PubMed: Antimycobacterial activity of Citrullus colocynthis (L.) Schrad. against drug sensitive and drug resistant Mycobacterium tuberculosis and MOTT clinical isolates.
PubMed: Preparation and characterization of liposomes incorporating cucurbitacin E, a natural cytotoxic triterpene.
PubMed: Cucurbitacin E exhibits anti-inflammatory effect in RAW 264.7 cells via suppression of NF-κB nuclear translocation.
PubMed: ATP mediates NADPH oxidase/ROS generation and COX-2/PGE2 expression in A549 cells: role of P2 receptor-dependent STAT3 activation.
PubMed: The cucurbitacins E, D and I: investigation of their cytotoxicity toward human chondrosarcoma SW 1353 cell line and their biotransformation in man liver.
PubMed: [Search for biofunctional constituents from medicinal foods-elucidation of constituents with anti-proliferation effects and the target molecule from Citrullus colocynthis].
PubMed: Cucurbitacin E inhibits breast tumor metastasis by suppressing cell migration and invasion.
PubMed: The natural product cucurbitacin E inhibits depolymerization of actin filaments.
PubMed: Cucurbitacin E Induces G(2)/M Phase Arrest through STAT3/p53/p21 Signaling and Provokes Apoptosis via Fas/CD95 and Mitochondria-Dependent Pathways in Human Bladder Cancer T24 Cells.
PubMed: In vitro and in vivo study of cucurbitacins-type triterpene glucoside from Citrullus colocynthis growing in Saudi Arabia against hepatocellular carcinoma.
PubMed: Cucurbitane glucosides from the root of Machilus yaoshansis.
PubMed: Anti-inflammatory activities of cucurbitacin E isolated from Citrullus lanatus var. citroides: role of reactive nitrogen species and cyclooxygenase enzyme inhibition.
PubMed: Cucurbitacin E, a tetracyclic triterpenes compound from Chinese medicine, inhibits tumor angiogenesis through VEGFR2-mediated Jak2-STAT3 signaling pathway.
PubMed: Cucurbitacin E as a new inhibitor of cofilin phosphorylation in human leukemia U937 cells.
PubMed: The induction of G2/M cell-cycle arrest and apoptosis by cucurbitacin E is associated with increased phosphorylation of eIF2alpha in leukemia cells.
PubMed: [Inhibitory effect of cucurbitacin E on the proliferation of ovarian cancer cells and its mechanism].
PubMed: Inhibitory effect of cucurbitacin E on pancreatic cancer cells growth via STAT3 signaling.
PubMed: Enhancement of doxorubicin concentration in the M5076 ovarian sarcoma cells by cucurbitacin E co-treatment.
PubMed: Stability of cucurbitacin E in human plasma: chemical hydrolysis and role of plasma esterases.
PubMed: Interaction of cucurbitacins with human serum albumin: Thermodynamic characteristics and influence on the binding of site specific ligands.
PubMed: Quantitative determination of cucurbitacin E and cucurbitacin I in homoeopathic mother tincture of Gratiola officinalis L. by HPLC.
PubMed: Direct interaction of Cucurbitacin E isolated from Alsomitra macrocarpa to actin filament.
PubMed: Screening of biochemical modulator by tumor cell permeability of doxorubicin.
PubMed: Cucurbitacin glucosides: antioxidant and free-radical scavenging activities.
PubMed: [Determination of the cucurbitacins from Cucubita pepo cv dayangua by HPLC].
PubMed: A new cucurbitacin from Bolbostemma paniculatum Franguent.
PubMed: Cucurbitacins from Bacopa monnieri.
PubMed: Bioactive saponins and glycosides. XXVII. Structures of new cucurbitane-type triterpene glycosides and antiallergic constituents from Citrullus colocynthis.
PubMed: Effect of cucurbitacins on bilirubin-albumin binding in human plasma.
PubMed: Immunomodulatory activity of cucurbitacin E isolated from Ecballium elaterium.
PubMed: 1H and 13C NMR signal assignment of cucurbitacin derivatives from Citrullus colocynthis (L.) Schrader and Ecballium elaterium L. (Cucurbitaceae).
PubMed: [Studies on chemical constituents in bulbs of Bolbostemma paniculatum].
PubMed: Stabilization of cucurbitacin E-glycoside, a feeding stimulant for diabroticite beetles, extracted from bitter Hawkesbury watermelon.
PubMed: Inhibition of seed germination by extracts of bitter Hawkesbury watermelon containing cucurbitacin, a feeding stimulant for corn rootworm (Coleoptera: Chrysomelidae).
PubMed: Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis.
PubMed: Chemical stimulants of leaf-trenching by cabbage loopers: natural products, neurotransmitters, insecticides, and drugs.
PubMed: Morierinin: a new cytotoxic cucurbitacin from the leaves of Morierina montana Vieill.
PubMed: Effect of a phloxine B-cucurbitacin bait on diabroticite beetles (Coleoptera: Chrysomelidae).
PubMed: Ecballium elaterium: an in vitro source of cucurbitacins.
PubMed: Rapid high-performance liquid chromatography method to quantitate elaterinide in juice and reconstituted residues from a bitter mutant of hawkesbury watermelon.
PubMed: Cucurbitacin E targets proliferating endothelia.
PubMed: Cucurbitacin E-induced disruption of the actin and vimentin cytoskeleton in prostate carcinoma cells.
PubMed: Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides.
PubMed: Oviposition stimulants and deterrents regulating differential acceptance ofIberis amara byPieris rapae andP. napi oleracea.
PubMed: A new cucurbitacin profile forCucurbita andreana: A candidate for cucurbitacin tissue culture.
PubMed: Biosynthesis of cucurbitacins in Bryonia dioica seedlings.
PubMed: The functional groupings of cucurbitacin E (alpha-elaterin).
PubMed: The functional groupings of alpha-elaterin (cucurbitacin E).
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