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Usage

Uses

Used in Pharmaceutical Industry:
Dodecanoic acid ingenol ester is used as a pharmaceutical agent for its antinematodal and anti-tumor properties. It is particularly effective in treating actinic keratosis when applied topically, providing a targeted approach to addressing this skin condition.
Used in Antinematodal Applications:
Dodecanoic acid ingenol ester is employed as an antinematodal agent, helping to combat and control nematode infections. Its effectiveness in this area makes it a valuable asset in the development of treatments for various parasitic diseases.
Used in Anticancer Applications:
Dodecanoic acid ingenol ester is used as an anticancer agent, particularly for the topical treatment of actinic keratosis. Its anti-tumor activity allows it to inhibit the growth and progression of cancerous cells, providing a potential therapeutic option for patients with this condition.

Upstream product

• 76663-53-1 3-O-(2.3-dimethylbutyryl)-13-O-n-dodecanoyl-13-hydroxyingenol 
• 184221-52-1 13-O-dodecanoylingenol 3,4,5,20-diacetonide 
• 1380204-62-5 C₂₆H₃₆O₆ 
• 1380204-61-4 C₃₂H₅₆O₆Si₂ 
• 1380204-67-0 C₃₈H₆₀O₆SeSi₂ 

Relevant academic research and scientific papers

Anti-inflammatory Ingenane Diterpenoids from the Roots of Euphorbia kansui

Bioassay-guided fractionation of the ethanolic extract of the roots of Euphorbia kansui led to the isolation of two new ingenane diterpenoids, euphorkans A ( 1 ) and B ( 2 ), together with 16 known analogues ( 3 – 18 ). Their structures were determined by combined spectral and chemical methods. All the isolates were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophage cells. Compounds 1 – 6 and 10 – 13 exhibited pronounced inhibitory activity with IC 50 values in the range of 2.78 – 10.6 μM, and were more potent than the positive control, quercetin (IC 50 = 15.8 μM). Compounds 1 and 5 were selected for further assays toward the key inflammation mediators TNF- α and IL-6, and showed a significant inhibition in a dose-dependent manner. The preliminary mechanistic study revealed that 1 and 5 inhibited NF- κ B activity, which may exert a role in their anti-inflammatory activity.

INGENOL COMPOUNDS AND USE THEREOF IN ANTI-HIV LATENCY TREATMENT

Provided in the present invention are ingenol compounds and a use thereof in preparing an anti-HIV latency drug. In particular, provided in the present invention is a use of ingenol compounds and pharmaceutically acceptable salts thereof for preparing a drug for: (a) intervening with HIV viral latency; (b) activating an HIV virus that has been integrated into mammalian genomes; and/or (c) inducing the expression of the dormant HIV provirus in infected cells. The compounds of the present invention may also be used in combination with antiretroviral drugs to accelerate the removal of latent viral reservoirs.

Total synthesis of natural derivatives and artificial analogs of 13-oxyingenol and their biological evaluation

We have established an efficient synthetic methodology for the 13-oxyingenol natural derivative (13-oxyingenol-13-dodecanoate-20-hexanoate), featuring a ring-closing olefin metathesis reaction for the “direct” construction of a highly strained inside-outside framework and a Mislow-Evans-type [2,3]-sigmatropic rearrangement for the stereoselective introduction of the hydroxy group at C5. We also synthesized artificial analogs of 13-oxyingenol and ingenol by using our synthetic strategy. In vitro activation assays of protein kinase C (PKC) α and δ revealed that the dodecanoyl group at O13 on 13-oxyingenol analogs had a significant role in PKCδ activation. The PKCα- or PKCδ-activating 13-oxyingenol and ingenol analogs induced both distinct morphological changes and increases of CD11b expression in HL-60 cells, which would be typical signs of HL-60 cell differentiation to macrophage-like cells, as expected by previous reports. Intriguingly, however, similar differentiation phenotypes were observed with the use of 13-oxyingenol natural derivatives and 13-oxyingenol-13-dodecanoate showing a remarkably less potent PKCα or PKCδ activation ability, which the PKC inhibitor G?6983 diminished. This indicated the involvement of other PKC isozymes or related kinase activities. 13-Oxyingenol analogs, which induced HL-60 cell differentiation, also induced HL-60 cell death, similar to the action of a phorbol ester, a strong PKC activator.

Total synthesis of (-)-13-oxyingenol and its natural derivative

Ring functionalization: The total synthesis of a natural derivative of (-)-13-oxyingenol, a potent anti-HIV diterpenoid, is reported. The key steps in this synthesis include a ring-closing olefin metathesis and a Mislow-Evans-type [2,3]-sigmatropic rearrangement. This synthesis provides access to (-)-13-oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co-workers. Copyright