| Name: | [(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 |
| CAS Number: | 18444-66-1 |  3D/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, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
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
|
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.
|
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 :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 |
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 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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-nor | lanosta-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 |
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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