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

• ChemBase ID: 155156
• Molecular Formular: C36H56O8
• Molecular Mass: 616.82504
• Monoisotopic Mass: 616.39751875
• SMILES: CCCCCCCCCCCCCC(=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)C)O)C
• Canonical SMILES: CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)C)C3(C)C)C=C(C[C@]1([C@H]2C=C(C1=O)C)O)CO
• InChI: InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30?,32-,34-,35-,36-/m1/s1
• InChIKey: PHEDXBVPIONUQT-CMMOZPOHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6R,10S,11R,13S,14R,15R)-13-(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-14-yl tetradecanoate
• IUPAC Traditional name: phorbol ester
• Synonyms: 12-O-Tetradecanoylphorbol 13-acetate; 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate; PMA; TPA; Phorbol 12-myristate 13-acetate

Database IDs

• CAS Number: 16561-29-8
• MDL Number: MFCD00036736
• Beilstein Number: 2407201
• PubChem SID: 24887446; 24898219; 162249294; 24278653
• PubChem CID: 27924

CALCULATED PROPERTIES

• Acid pKa: 12.570371
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 5.692159
• LogD (pH = 7.4): 5.6921563
• Log P: 5.692159
• Molar Refractivity: 169.3183 cm^3
• Polarizability: 67.11437 Å^3
• Polar Surface Area: 130.36 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: chloroform: soluble10 mg/mL, clear, colorless to light yellow; DMSO: soluble (Dissolve in water-miscible organic solvent prior to preparing aqueous solutions. DMSO solutions can be stored dark at -20 °C for at least six months.); DMSO: soluble (DMSO solutions can be stored dark at -20 °C for at least six months.); ethanol: soluble; ethanol: soluble (Dissolve in water-miscible organic solvent prior to preparing aqueous solutions.)
• Apperance: film or powder

Safety Information

• RTECS: QH4377000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 38
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC); ≥99% (TLC)
• Grade: for molecular biology
• Quality: synthetic
• Empirical Formula (Hill Notation): C36H56O8

DETAILS

Sigma Aldrich - P1585

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Analysis Note
Tested for stimulation of interleukin production in Jurkat cells.
Biochem/physiol Actions
Potent tumor promoter; activates protein kinase C in vivo and in vitro.
Caution
Photosensitive

Sigma Aldrich - 79346

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Potent tumor promoter; activates protein kinase C in vivo and in vitro.
Other Notes
Activates protein kinase C in vivo and in vitro at nanomolar concentrations1; Highly potent tumor promotor and mitogen: active principle of croton oil. Review2

Sigma Aldrich - P8139

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Potent tumor promoter; activates protein kinase C in vivo and in vitro.
Caution
Photosensitive