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Key Documents

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

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About This Item

Empirical Formula (Hill Notation):
C20H28O5
CAS Number:
30220-46-3
Molecular Weight:
348.43
UNSPSC Code:
12352200
PubChem Substance ID:
24896033

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
GHS05

signalword

Danger

hcodes

H315,H318

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLBF5335V
088K1270
018K1413
097K1313
034K1278

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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
James H Rigby et al.
Organic letters, 4(5), 799-801 (2002-03-01)
[reaction: see text] The efficient construction of an ingenol intermediate exhibiting "insideminus signoutside" intrabridgehead stereochemistry is reported. The sequence features the net conversion of a cis-intrabridgehead compound into a highly strained trans-species via palladium-mediated isomerization of an allylic epoxide followed
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
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
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