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P8014

Sigma-Aldrich

4α-Phorbol 12,13-didecanoate

solid

Synonym(s):

4α-Phorbol 12-13-dicaprinate, 4αPDD

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About This Item

Empirical Formula (Hill Notation):
C40H64O8
CAS Number:
27536-56-7
Molecular Weight:
672.93
Beilstein/REAXYS Number:
2514324
MDL number:
MFCD00036737
UNSPSC Code:
12352211
PubChem Substance ID:
24898900
NACRES:
NA.77

form

solid

Quality Level

100

color

white

solubility

DMSO: soluble
ethanol: soluble
methanol: soluble

storage temp.

−20°C

SMILES string

CCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)C(C=C(CO)C[C@]3(O)C2C=C(C)C3=O)C4C(C)(C)[C@]14OC(=O)CCCCCCCCC

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

InChI key

DGOSGFYDFDYMCW-OEFRVDPMSA-N

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Application

4α-Phorbol 12,13-didecanoate has been used as a transient receptor potential vanilloid 4 (TRPV4) agonist:
  • to study its effects on Madin-Darby canine kidney (MDCK) cells
  • to study its effects on Ca2+ influx in mice fallopian tubal cells
  • to study its effects on hind paw swelling in mice

Biochem/physiol Actions

4α-Phorbol 12,13-didecanoate is a transient receptor potential vanilloid 4 (TRPV4) agonist. It promotes extracellular calcium influx into the cells.

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.

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Carc. 2 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T A Rose-Hellekant et al.
Molecular reproduction and development, 44(2), 250-255 (1996-06-01)
The purpose of this investigation was to determine if precocious oocyte maturation could be induced by modulating ovarian cAMP-dependent protein kinase (PKA) or protein kinase C (PKC) signal transduction pathways in the intact hamster. The following inhibitors and stimulators were
Tumor-promoting activity of phorbol and four diesters of phorbol in mouse skin.
W M Baird et al.
Cancer research, 31(8), 1074-1079 (1971-08-01)
Jennifer K Lee et al.
Journal of biomechanics, 47(15), 3712-3718 (2014-12-03)
Osteoarthritis, a degenerative disease of the load-bearing joints, greatly reduces quality of life for millions of Americans and places a tremendous cost on the American healthcare system. Due to limitations of current treatments, tissue engineering of articular cartilage may provide
Noriyuki Hatano et al.
Life sciences, 85(23-26), 808-814 (2009-11-03)
Vanilloid type transient receptor potential channel (TRPV) could be a potential environmental sensor to multiple stimuli in many types of cells. In this study, we provide the first evidence of functional vanilloid type 4 transient receptor potential channel (TRPV4) in
Lei Chen et al.
Neuroscience letters, 452(1), 79-83 (2009-05-16)
The present study explored the effect of anisotonicity on action potential (AP) in cultured trigeminal ganglion (TG) neurons. We demonstrate that the number of evoked APs was increased by both hypo- and hypertonic treatment. Transient Receptor Potential Vanilloid 4 receptor
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