Key Documents

View All Documentation

SML1318

Ingenol-3-angelate

Name: Ingenol-3-angelate
Brand: SIGMA

From semisynthetic, ≥95% (HPLC), protein kinase C activator, powder

Synonym(s):

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-Dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclpropa[e][10]annulen-6-yl (2Z)-2-methylbut-2-enoate, 3-Angeloylingenol, 3-Ingenyl angelate, I3A, Ingenol mebutate, PEP005

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₂₅H₃₄O₆

CAS Number:

75567-37-2

Molecular Weight:

430.53

UNSPSC Code:

12352200

PubChem Substance ID:

329825782

NACRES:

NA.77

Assay:

≥95% (HPLC)

Form:

powder

Quality level:

100

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Product Name

Ingenol-3-angelate, ≥95% (HPLC)

biological source

semisynthetic

Quality Level

100

assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C1[C@@]2(C=C(C)[C@@H]3OC(/C(C)=C\C)=O)[C@]3(O)[C@H](O)C(CO)=C[C@@]1([H])[C@@](C4(C)C)([H])[C@@]4([H])C[C@H]2C

InChI

1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1

InChI key

VDJHFHXMUKFKET-WDUFCVPESA-N

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Biochem/physiol Actions

Ingenol-3-angelate, is a phorbol ester-like compound or a diacylglycerol analog that is used in the treatment of several disorders like skin cancer. It is also known as PEP005. Ingenol-3-angelate stimulates the initiation of the enzyme by providing PKCs (protein kinase C) to cellular membranes.

Ingenol 3-Angelate is a diterpenoid ester isolated from Euphorbia peplus that induces rapid cell death with keratinocytes and some cancer cell lines. Ingenol 3-Angelate is a protein kinase C activator that displays potent antileukemic activity. Ingenol 3-Angelate (ingenol mebutate) is used for treatment of actinic keratosis.

Ingenol 3-Angelate is a protein kinase C activator.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ferulic acid ameliorates nonalcoholic fatty liver disease and modulates the gut microbiota composition in high-fat diet fed ApoE-/- mice.

Yunci Ma et al.

Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 113, 108753-108753 (2019-03-12)

The objective of this study was to investigate the effects of ferulic acid (FA) on nonalcoholic fatty liver disease (NAFLD) and gut microbiota, and its regulation mechanism in ApoE-/- mice fed on a high-fat diet (HFD). Liver morphology, blood lipids

Ingenol-3-Angelate Suppresses Growth of Melanoma Cells and Skin Tumor Development by Downregulation of NF-kappaB-Cox2 Signaling

Wang D and Liu P

Medical Science Monitor : International Medical Journal of Experimental and Clinical Research, 24, 486-486 (2018)

Dopamine receptor antagonists as potential therapeutic agents for ADPKD.

Parama Paul et al.

PloS one, 14(5), e0216220-e0216220 (2019-05-07)

Autosomal dominant polycystic kidney disease (ADPKD) is caused mostly by mutations in polycystin-1 or polycystin-2. Fluid flow leads to polycystin-dependent calcium influx and nuclear export of histone deacetylase 5 (HDAC5), which facilitates the maintenance of renal epithelial architecture by de-repression

Compounds producing an effective combinatorial regimen for disruption of HIV-1 latency.

Pargol Hashemi et al.

EMBO molecular medicine, 10(2), 160-174 (2017-12-17)

Highly active antiretroviral therapy (HAART) has improved the outlook for the HIV epidemic, but does not provide a cure. The proposed "shock-and-kill" strategy is directed at inducing latent HIV reservoirs, which may then be purged via boosted immune response or

Latency reversal agents affect differently the latent reservoir present in distinct CD4+ T subpopulations.

Judith Grau-Expósito et al.

PLoS pathogens, 15(8), e1007991-e1007991 (2019-08-20)

Latency reversal agents (LRAs) have proven to induce HIV-1 transcription in vivo but are ineffective at decreasing the size of the latent reservoir in antiretroviral treated patients. The capacity of the LRAs to perturb the viral reservoir present in distinct

View All Related Papers

Global Trade Item Number

SKU	GTIN
SML1318-1MG	04061826132937

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service