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30220-46-3,MFCD27980538
Catalog No.:AA00I5LG

30220-46-3 | Ingenol

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1mg
99+%
in stock  
$6.00   $4.00
- +
5mg
99+%
in stock  
$12.00   $8.00
- +
10mg
99+%
in stock  
$16.00   $11.00
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25mg
99+%
in stock  
$26.00   $18.00
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50mg
99+%
in stock  
$44.00   $31.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00I5LG
Chemical Name:
Ingenol
CAS Number:
30220-46-3
Molecular Formula:
C20H28O5
Molecular Weight:
348.4333
MDL Number:
MFCD27980538
SMILES:
OCC1=C[C@H]2[C@H]3[C@H](C3(C)C)C[C@H]([C@]3([C@@]([C@@H]1O)(O)[C@@H](O)C(=C3)C)C2=O)C
Properties
Computed Properties
 
Complexity:
707  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
1  
XLogP3:
0.2  

Downstream Synthesis Route

[1]TetrahedronLetters,1973,p.881-884

[1]TetrahedronLetters,1973,p.881-884

[1]ZeitschriftfurNaturforschung,TeilB:AnorganischeChemie,OrganischeChemie,1981,vol.36,p.878-887

[1]ZeitschriftfurNaturforschung,TeilB:AnorganischeChemie,OrganischeChemie,1981,vol.36,p.878-887

[2]AgriculturalandBiologicalChemistry,1980,vol.44,p.1351-1356

[1]TetrahedronLetters,2017,vol.58,p.1421-1424

[2]ZeitschriftfurNaturforschung,TeilB:AnorganischeChemie,OrganischeChemie,1981,vol.36,p.878-887

[3]EuropeanJournalofOrganicChemistry,1999,p.3413-3420

Literature

Title: Dual role of novel ingenol derivatives from Euphorbia tirucalli in HIV replication: inhibition of de novo infection and activation of viral LTR.

Journal: PloS one 20140101

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Bioactivity-guided isolation of antiproliferative diterpenoids from Euphorbia kansui.

Journal: Phytotherapy research : PTR 20120601

Title: Ingol and ingenol diterpenes from the aerial parts of Euphorbia royleana and their antiangiogenic activities.

Journal: Journal of natural products 20090601

Title: The regulation of glycine transporter GLYT1 is mainly mediated by protein kinase Calpha in C6 glioma cells.

Journal: Neurochemistry international 20081201

Title: Modern synthetic efforts toward biologically active terpenes.

Journal: Nature chemical biology 20070701

Title: HIV type 1 inhibition by protein kinase C modulatory compounds.

Journal: AIDS research and human retroviruses 20060901

Title: A comparison of the roles of protein kinase C in long-term potentiation in rat hippocampal areas CA1 and CA3.

Journal: Cellular and molecular neurobiology 20050601

Title: Total synthesis of ingenol.

Journal: Journal of the American Chemical Society 20041222

Title: Selective 1,5-alkylidenecarbene insertion reactions on [3.2.1] oxabicyclic ethers: a new approach toward the AB ring system of ingenol.

Journal: Organic letters 20040819

Title: Characterization of the interaction of ingenol 3-angelate with protein kinase C.

Journal: Cancer research 20040501

Title: The effects of protein kinase C activity on synaptic transmission in two areas of rat hippocampus.

Journal: Brain research 20031114

Title: Total synthesis of ingenol.

Journal: Journal of the American Chemical Society 20030212

Title: The first total synthesis of (+/-)-ingenol.

Journal: Journal of the American Chemical Society 20020821

Title: Synthetic studies on the ingenane diterpenes. An improved entry into a trans-intrabridgehead system.

Journal: Organic letters 20020307

Title: Protein kinase C epsilon mediates the induction of P-glycoprotein in LNCaP prostate carcinoma cells.

Journal: Cellular signalling 20020101

Title: Upregulation of HIV-1 replication in chronically infected cells by ingenol derivatives.

Journal: Archives of virology 19980101

Title: Hasler CM, et al. Specific binding to protein kinase C by ingenol and its induction of biological responses. Cancer Res. 1992 Jan 1;52(1):202-8.

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