(1S,2S,6R,10S,11R,13S,14R,15R)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-13-yl acetate

• ChemBase ID: 134198
• Molecular Formular: C24H32O8
• Molecular Mass: 448.50608
• Monoisotopic Mass: 448.20971798
• SMILES: C[C@@H]1[C@H]([C@@]2([C@@H](C2(C)C)[C@H]2[C@]1([C@@H]1C=C(C(=O)[C@]1(CC(=C2)CO)O)C)O)OC(=O)C)OC(=O)C
• Canonical SMILES: OCC1=C[C@H]2[C@H]3[C@@](C3(C)C)(OC(=O)C)[C@@H]([C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)OC(=O)C
• InChI: InChI=1S/C24H32O8/c1-11-7-17-22(29,19(11)28)9-15(10-25)8-16-18-21(5,6)24(18,32-14(4)27)20(31-13(3)26)12(2)23(16,17)30/h7-8,12,16-18,20,25,29-30H,9-10H2,1-6H3/t12-,16+,17-,18?,20-,22-,23-,24-/m1/s1
• InChIKey: OMHXSAMFEJVCPT-ALSUQTPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6R,10S,11R,13S,14R,15R)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-13-yl acetate
• IUPAC Traditional name: (1S,2S,6R,10S,11R,13S,14R,15R)-14-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-13-yl acetate
• Synonyms: PDA; Phorbol 12,13-diacetate

Database IDs

• CAS Number: 24928-15-2
• MDL Number: MFCD00036735
• Beilstein Number: 2317312
• PubChem SID: 162228475; 24899011
• PubChem CID: 72293

CALCULATED PROPERTIES

• Acid pKa: 12.570371
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.10136804
• LogD (pH = 7.4): 0.10136515
• Log P: 0.10136808
• Molar Refractivity: 114.0804 cm^3
• Polarizability: 45.10134 Å^3
• Polar Surface Area: 130.36 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: white powder

Safety Information

• RTECS: GZ0651000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 26/27/28-36/37/38
• Safety Statements: 26-27-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H315-H319-H330-H335
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - P9143

Biochem/physiol Actions
Activates protein kinase C.
Caution
Photosensitive.
General description
Phorbol ester with enhanced hydrophilicity.
Other Notes
Less potent but more water soluble than phorbol 12,13-dibutyrate.
Reconstitution
Although having aqueous solubility, it is recommended that this compound first be dissolved in a water miscible organic solvent before dilution to working concentrations in aqueous media.