Ingenol 3-mebutate

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Names

[ Name ]:
Ingenol 3-mebutate

[Synonym ]:
Indoxyl |A-D-galactopyranoside
3-O-angeloylingenol
2-Butenoic acid, 2-methyl-, (1aR,2R,5R,5aS,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-6-yl ester, (2Z)-
Ingenol 3-angelate
3-Indolyl-b-D-galactopyranoside
(1S,4S,5S,6R,9R,10R,12R,14R)-5,6-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0<sup>1,5</sup>.0<sup>10,12</sup>]pentadeca-2,7-dien-4-yl (2Z)-2-methyl-2-butenoate
indican (glucoside)
Picato
Ingenol mebutate
(1S,4S,5S,6R,9R,10R,12R,14R)-5,6-Dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0.0]pentadeca-2,7-dien-4-yl (2Z)-2-methyl-2-butenoate
Ingenol-3-angelate
3-Ingenyl angelate
3-Angeloylingenol

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
576.9±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₅H₃₄O₆

[ Molecular Weight ]:
430.534

[ Flash Point ]:
191.4±23.6 °C

[ Exact Mass ]:
430.235535

[ PSA ]:
104.06000

[ LogP ]:
5.18

[ Appearance of Characters ]:
white to beige

[ Vapour Pressure ]:
0.0±3.6 mmHg at 25°C

[ Index of Refraction ]:
1.594

[ Storage condition ]:
?20°C

[ Water Solubility ]:
DMSO: soluble15mg/mL, clear | Soluble in 100% ethanol, DMSO, dichloromethane, and methanol. Insoluble in water.

MSDS

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Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

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Precursor & DownStream

Precursor

ingenol-20-(tert-butyldimethylsilyl)-ether-3-angelate
ingenol-5,20-(di(tert-butyl)silylene) ether 3-angelate
Angelic acid
Ingenol-5,20-acetonide
Ingenol
(2Z)-2-Methyl-2-butenoic anhydride
ingenol-5,20-(di(tert-butyl)silylene) ether

DownStream

Articles

RasGRPs are targets of the anti-cancer agent ingenol-3-angelate.

PLoS ONE 8 , e72331, (2013)

Ingenol-3-angelate (I3A) is a non-tumor promoting phorbol ester-like compound identified in the sap of Euphoria peplus. Similar to tumor promoting phorbol esters, I3A is a diacylglycerol (DAG) analogu...