I3381

Sigma-Aldrich

Ingenol

film

Synonym(s):
(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-Octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one
Empirical Formula (Hill Notation):
C20H28O5
CAS Number:
Molecular Weight:
348.43
PubChem Substance ID:

form

film

color

colorless

solubility

DMSO: soluble
hexane: soluble

storage temp.

−20°C

SMILES string

CC1CC2C(C3C=C(CO)C(O)C4(O)C(O)C(C)=CC14C3=O)C2(C)C

InChI

1S/C20H26O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(16(19)23)6-11(8-21)17-20(19,15(9)22)25-24-17/h6-7,10,12-15,17,21-22H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,17-,19+,20-/m1/s1

InChI key

VDVYIMWLGLOPHL-CRAGLPIHSA-N

Biochem/physiol Actions

Activates PKC (protein kinase C), especially δ and ε; diterpene related to phorbol.

Packaging

Product supplied in a sealed glass ampule.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Noemi Kedei et al.
Cancer research, 64(9), 3243-3255 (2004-05-06)
Ingenol 3-angelate (I3A) is one of the active ingredients in Euphorbia peplus, which has been used in traditional medicine. Here, we report the initial characterization of I3A as a protein kinase C (PKC) ligand. I3A bound to PKC-alpha in the...
M H E Jansen et al.
The British journal of dermatology, 183(4), 738-744 (2020-01-22)
Actinic keratosis (AK) is a common premalignant skin condition that might have the ability to progress into squamous cell carcinoma. Due to the high incidence of AK, treatment of this disease significantly impacts healthcare spending. To determine which commonly prescribed field-directed...
Eliezer Flescher et al.
Cellular signalling, 14(1), 37-43 (2001-12-19)
P-glycoprotein (P-gp) mediates drug resistance. Protein kinase C (PKC) expression correlates with drug resistance in several types of cancer. We determined whether PKC signals the induction of P-gp in LNCaP human prostate cancer cells, and identified a specific isozyme involved...
Takayuki Ohyoshi et al.
Angewandte Chemie (International ed. in English), 51(20), 4972-4975 (2012-04-11)
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...
M Blanco-Molina et al.
Chemistry & biology, 8(8), 767-778 (2001-08-22)
Ingenol derivatives have received constant and multidisciplinary attention on account of their pleiotropic pattern of biological activity. This includes activation of protein kinase C (PKC), tumour-promotion, anticancer, and anti-HIV properties, and the possibility of dissecting co-cancerogenic and clinically useful activities...

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

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.