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Ingenol-3-angelate

SIGMA/SML1318 - ≥95% (HPLC)

Synonym: (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

CAS Number: 75567-37-2
Empirical Formula (Hill Notation): C25H34O6
Molecular Weight: 430.53
Linear Formula: C25H34O6
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SML1318-1MG 1 mg
 $191.00
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assay ≥95% (HPLC)
biological source semisynthetic
color white to beige
form powder
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
Quality Level 100 
SMILES string O=C1[C@@]2(C=C(C)[C@@H]3OC(/C(C)=CC)=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
solubility DMSO: 15 mg/mL, clear
storage temp. −20°C
Biochem/physiol Actions: 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.
Biochem/physiol Actions: Ingenol 3-Angelate is a protein kinase C activator.
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.
Packaging: 1 mg in glass bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥95% (HPLC)
Storage Temp. −20°C
UNSPSC 12352200

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