(1S,2S,6S,10S,11R,13S,14R,15R)-14-(decanoyloxy)-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 decanoate

• ChemBase ID: 134152
• Molecular Formular: C40H64O8
• Molecular Mass: 672.93136
• Monoisotopic Mass: 672.46011901
• SMILES: CCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@@]3([C@H]2C=C(C3=O)C)O)CO)[C@@H]2[C@@]1(C2(C)C)OC(=O)CCCCCCCCC)O)C
• Canonical SMILES: CCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@@H]3[C@]1(OC(=O)CCCCCCCCC)C3(C)C)C=C(C[C@@]1([C@H]2C=C(C1=O)C)O)CO
• InChI: InChI=1S/C40H64O8/c1-7-9-11-13-15-17-19-21-32(42)47-36-28(4)39(46)30(24-29(26-41)25-38(45)31(39)23-27(3)35(38)44)34-37(5,6)40(34,36)48-33(43)22-20-18-16-14-12-10-8-2/h23-24,28,30-31,34,36,41,45-46H,7-22,25-26H2,1-6H3/t28-,30+,31-,34?,36-,38+,39-,40-/m1/s1
• InChIKey: DGOSGFYDFDYMCW-XRCYHQPHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6S,10S,11R,13S,14R,15R)-14-(decanoyloxy)-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 decanoate
• IUPAC Traditional name: (1S,2S,6S,10S,11R,13S,14R,15R)-14-(decanoyloxy)-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 decanoate
• Synonyms: 4α-Phorbol 12-13-dicaprinate; 4αPDD; 4α-Phorbol 12,13-didecanoate

Database IDs

• CAS Number: 27536-56-7
• MDL Number: MFCD00036737
• Beilstein Number: 2514324
• PubChem SID: 162228429; 24898900
• PubChem CID: 71308764

CALCULATED PROPERTIES

• Acid pKa: 12.570371
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 7.726401
• LogD (pH = 7.4): 7.726398
• Log P: 7.726401
• Molar Refractivity: 187.7482 cm^3
• Polarizability: 74.46961 Å^3
• Polar Surface Area: 130.36 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform: soluble10 mg/mL, clear, colorless; DMSO: soluble; ethanol: soluble; methanol: soluble
• Apperance: white solid

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28-40-43
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300 +H310 + H330-H334-H351; H300-H310-H330-H334-H351
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C40H64O8

DETAILS

Sigma Aldrich - P8014

Application
Phorbol that is not biologically active, can be used as a negative control.
Biochem/physiol Actions
Skin tumor promoter in experimental animal model.1
Caution
Photosensitive
Reconstitution
Stock solution cannot be made in aqueous media; dissolve in a water-miscible organic solvent before dilution to working concentrations in aqueous media.