cucurbitacin D

19-nor-9-beta,10-alpha-lanosta-5,23-diene-3,11,22-trione, 9-methyl-2-beta,16-alpha,20,25-tetrahydroxy-

CAS: 3877-86-9 C30 H44 O7 MW: 516.67508000

Identification

Namecucurbitacin D
IUPAC(2S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
CAS Number3877-86-9
FDA UNII5I62H4ORC7
Molecular FormulaC30 H44 O7
Molecular Weight516.67508000
MDL NumberMFCD01711333
Nikkaji NumberJ8.271F

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 684.00 °C. @ 760.00 mm Hg (est)
Flash Point 719.00 °F. TCC ( 381.40 °C. ) (est)
logP (o/w) 1.480 (est)
Soluble in water, 5.08 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintravenous-cat LD50 900 ug/kg
Dermal Toxicitysubcutaneous-mouse LD50 4600 ug/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorypharmaceuticals / chemical synthisis
Recommendation for cucurbitacin D usage levels up tonot for fragrance use.
Recommendation for cucurbitacin D flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

cucumber sprout gourd calabash gourd fruit

Synonyms

cucurbitacine (D) (2S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6- dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione elatericin A elatericine A 19-nor lanosta-5,23-diene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2beta,9beta,10alpha,16alpha,23E)- (9CI) 19-nor-9-beta,10-alpha- lanosta-5,23-diene-3,11,22-trione, 9-methyl-2-beta,16-alpha,20,25-tetrahydroxy- PubMed: Cucurbitacin-D-induced CDK1 mRNA up-regulation causes proliferation arrest of a non-small cell lung carcinoma cell line (NSCLC-N6). PubMed: Morphological and physicochemical characterization of liposomes loading cucurbitacin E, an anti-proliferative natural tetracyclic triterpene. PubMed: Trichosanthes kirilowii Ethanol Extract and Cucurbitacin D Inhibit Cell Growth and Induce Apoptosis through Inhibition of STAT3 Activity in Breast Cancer Cells. PubMed: Cucurbitacin D is a new inflammasome activator in macrophages. PubMed: Natural compounds as potential treatments of NF2-deficient schwannoma and meningioma: cucurbitacin D and goyazensolide. 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: Cucurbitacin D induces growth inhibition, cell cycle arrest, and apoptosis in human endometrial and ovarian cancer cells. PubMed: [Studies on chemical constituents in roots of Helicteres angustifolia]. PubMed: Apoptosis induction through proteasome inhibitory activity of cucurbitacin D in human T-cell leukemia. PubMed: Cucurbitacin D induces fetal hemoglobin synthesis in K562 cells and human hematopoietic progenitors through activation of p38 pathway and stabilization of the γ-globin mRNA. PubMed: Studies toward the total syntheses of cucurbitacins B and D. PubMed: New cucurbitane-type triterpenoids from Bryonia aspera. PubMed: Interaction of cucurbitacins with human serum albumin: Thermodynamic characteristics and influence on the binding of site specific ligands. PubMed: Cucurbitacin D isolated from Trichosanthes kirilowii induces apoptosis in human hepatocellular carcinoma cells in vitro. PubMed: Cogniauxia podolaena: bioassay-guided fractionation of defoliated stems, isolation of active compounds, antiplasmodial activity and cytotoxicity. PubMed: Phytochemical and biological investigation of Begonia heracleifolia. PubMed: Cucurbitane triterpenes from the fruiting bodies and cultivated mycelia of Leucopaxillus gentianeus. PubMed: Effect of cucurbitacins on bilirubin-albumin binding in human plasma. PubMed: Pregnane, coumarin and lupane derivatives and cytotoxic constituents from Helicteres angustifolia. PubMed: [Relationships of Aulacophora beetles feeding behavior with cucurbitacin types in host crops]. PubMed: A new cucurbitacin D related 16,23-epoxy derivative and its isomerization products. PubMed: Inhibition of nitric oxide generation by 23,24-dihydrocucurbitacin D in mouse peritoneal macrophages. PubMed: Cytotoxic cucurbitacin constituents from Sloanea zuliaensis. PubMed: Cucurbitacins from Trichosanthes kirilowii as the inhibitory components on tyrosinase activity and melanin synthesis of B16/F10 melanoma cells. PubMed: Ellagic acid derivatives and cytotoxic cucurbitacins from Elaeocarpus mastersii. PubMed: Cucurbitacins are insect steroid hormone antagonists acting at the ecdysteroid receptor. PubMed: Cytotoxic constituents ofSorbaria sorbifolia var.stellipila. PubMed: Effect of cucurbitacin D on in vitro growth of Xenorhabdus and Photorhabdus spp., symbiotic bacteria of entomopathogenic nematodes. PubMed: [Studies on the constituents of "Trichosanthes root". IV. Constituents of roots of Trichosanthes multiloba Miq., Trichosanthes miyagii Hay. and Chinese crude drug "karo-kon"]. PubMed: [Studies on the constituents of trichosanthes root. III. Constituents of roots of Trichosanthes bracteata Voigt]. PubMed: [Studies on the constituents of trichosanthes root. I. Constituents of roots of Trichosanthes kirilowii Maxim. var. japonicum Kitam]. PubMed: Cucurbitacins : Plant-derived defense compounds for diabroticites (Coleoptera: Chrysomelidae). PubMed: [Poisoning with a kind of Bitter Edible Gourd]. PubMed: Pharmaco-dynamic activity of elatericin (cucurbitacin D).