87980-68-5

Basic information

• Product Name: Ingenol-5,20-acetonide-3-O-angelate
• Synonyms: Ingenol-5,20-acetonide-3-O-angelate;Ingenol 5,20-acetonide 3-angelate
• CAS NO: 87980-68-5
• Molecular Formula: C28H38O6
• Molecular Weight: 470.598
• EINECS: -0
• Mol File: 87980-68-5.mol

Chemical Properties

• Boiling Point: 582.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• PKA: 11.38±0.70(Predicted)
• CAS DataBase Reference: Ingenol-5,20-acetonide-3-O-angelate(CAS DataBase Reference)
• NIST Chemistry Reference: Ingenol-5,20-acetonide-3-O-angelate(87980-68-5)
• EPA Substance Registry System: Ingenol-5,20-acetonide-3-O-angelate(87980-68-5)

Safety Data

• Hazardous Substances Data: 87980-68-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ingenol-5,20-acetonide-3-O-angelate is used as a pharmaceutical agent for its anti-tumor activity. It is particularly effective when applied topically for the treatment of actinic keratosis, a precancerous skin condition caused by prolonged exposure to ultraviolet radiation. Ingenol-5,20-acetonide-3-O-angelate's ability to target and eliminate abnormal skin cells makes it a valuable asset in dermatological treatments.
Ingenol-5,20-acetonide-3-O-angelate is also being investigated for its potential applications in cancer therapy, given its anti-tumor properties. Further research is needed to explore its efficacy and safety in treating various types of cancer and to develop suitable drug delivery systems for optimal therapeutic outcomes.

Upstream product

• 67-64-1 acetone 
• 75567-37-2 ingenol mebutate 
• 565-63-9 Angelic acid 
• 77573-43-4 (6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one 
• 30220-46-3 ingenol 
• 94487-74-8 (Z)-2-methyl-2-butenoic anhydride 
• 137601-32-2 (2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride 
• 35660-94-7 (Z)-2-methyl-2-butenoyl chloride 
• 80-59-1 Tiglic acid 

Downstream Products

• 75567-37-2 ingenol mebutate 
• 1356187-27-3 ingenol-3-tigliate 
• 82425-35-2 ingenol 20-acetate-3-angelate 

Relevant articles and documents

Identification, structural modification, and dichotomous effects on human immunodeficiency virus type 1 (HIV-1) replication of ingenane esters from Euphorbia kansui

Euphorbia kansui showed potent anti-HIV-1 activity during screening of a library composed of plant extracts from Euphorbiaceae and Thymelaeaceae families. Bioassay-guided isolation led to identification of ingenane esters as the active compounds. Further chemical modification resulted in 3-(2-naphthoyl)ingenol (23), which exhibited the most potent anti-HIV-1 activity. Compound 23 also acted as an HIV-1-latency-reversing agent on activation of HIV-1 replication in a latently infected U1 cell model and a T cell latent HIV-1 model JLat-A2.

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.

Semisynthesis of ingenol 3-angelate (PEP005): Efficient stereoconservative angeloylation of alcohols

A high-yielding method was developed for the preparation of ingenol 3-angelate (PEP005, ingenol mebutate) via the corresponding 5,20-acetonide without concomitant isomerization of the angelate (Z-form) to the corresponding tiglate (E-form). The general sc

A METHOD OF PRODUCING INGENOL-3-ANGELATE

The present invention relates to methods of producing ingenol-3-angelate (I) from ingenol (II). Formula (I) and (II). Furthermore, the invention relates to intermediates useful for the synthesis of ingenol-3-angelate (I) from ingenol (II) and to methods of producing said intermediates.

INGENOL-3-ACYLATES I

The invention relates to compounds of general formula (I) wherein R is (C1-C7)alkyl, (C2-C7)alkenyl or (C2-C7)alkynyl; wherein R is substituted with R1; and pharmaceutically acceptable salt