Ingenol
Grundinformationen
- CAS
30220-46-3- Standard-SMILES
CC1=C[C@]23C(=O)[C@@H](C=C(CO)[C@@H](O)[C@]2(O)[C@H]1O)[C@H]1[C@@H](C[C@H]3C)C1(C)C- InChIKey
VEBVPUXQAPLADL-POYOOMFHSA-N- Summenformel
- C20H28O5
- Durchschnittliche Molmasse
- 348,4 g/mol
Überblick
Ingenol is a tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by methyl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastereomer). It is a cyclic terpene ketone and a tetracyclic diterpenoid.
Namen und Bezeichner
- Bevorzugter Name
- Ingenol
- IUPAC
- (1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
- Englischer Name
- Ingenol
- Summenformel
- C20H28O5
- Molmasse
- 348.43
Namen und Synonyme
ingenol30220-46-3IC77UZI9G8(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-oneCHEBI:5922(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one1H-2,8A-METHANOCYCLOPENTA(A)CYCLOPROPA(E)CYCLODECEN-11-ONE, 1A,2,5,5A,6,9,10,10A-OCTAHYDRO-5,5A,6-TRIHYDROXY-4-(HYDROXYMETHYL)-1,1,7,9-TETRAMETHYL-, (1AR,2S,5R,5AR,6S,8AS,9R,10AR)-(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta(a)cyclopropa(e)(10)annulen-11-one(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo(7.5.1.01,5.010,12)pentadeca-2,7-dien-15-oneRefChem:1482871a alpha,2 alpha,5 beta,5a beta,6 beta,beta,9 alpha, 10,10a alpha-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a alpha-methano cyclopenta(a)cyclopropa(e)cyclodecen-11-one636-889-2
Weitere Namen anzeigen
IngenoInglenookIngenol, BRIngenol >99%Ingenol baseIngenol USP/EP/BPINGENOL,HIGHPURITYIngenol 30220-46-3
(+)-IngenolUNII-IC77UZI9G8INGENOL [MI](-)-Ingenol1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one,1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-, (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-SCHEMBL17691258MFCD27980538INGENOL [WHO-DD]
Datenbank-Bezeichner
- CAS
30220-46-3- PubChem CID
- 442042
- ChEMBL
CHEMBL2165402- ChEBI
CHEBI:5922- UNII
- IC77UZI9G8
- EC Number
- 636-889-2
- Nikkaji
- J315.813F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,2
- Polarare Oberfläche (TPSA)
- 98 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 25
- Formalladung
- 0
- Komplexität
- 707
Physikochemische Eigenschaften
- Schmelzpunkt
- 153 °C · 153 °C
- Siedepunkt
- 523.8 · 523.8±50.0 °C(Predicted)
- Dichte
- 1.33 · 1.33±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- DMSO: soluble
- Aggregatzustand
- film
- pka
- 12.06 · 12.06±0.70(Predicted)
- Farbe
- colorless
- InChIKey
- VEBVPUXQAPLADL-POYOOMFHSA-N
- SMILES
- [C@@]12(O)[C@@H](O)C(C)=C[C@@]31C(=O)[C@@]([H])(C=C(CO)[C@H]2O)[C@]1([H])C(C)(C)[C@]1([H])C[C@H]3C
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, and P362+P364 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2914409000
- risk_code
- 38-41
- hazard_code
- Xi
- safety_code
- 26-36
Chemie und Industrie
Anwendungen
BeschreibungIngenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus. It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro. Most ingenol esters are tumor-promoting. However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.
VerwendenIngenol, is the analogue of Ingenol 3-Angelate (I655800), which has anti-tumor activity when used topically for the treatment of actinic keratosis.
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Ergänzende Hinweise
DefinitionChEBI: A tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by met yl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastere mer).
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