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Merck
CN

P8014

4α-Phorbol 12,13-didecanoate

transient receptor potential vanilloid 4 agonist, 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
NACRES:
NA.77
PubChem Substance ID:
24898900
UNSPSC Code:
12352211
MDL number:
MFCD00036737
Beilstein/REAXYS Number:
2514324
Form:
solid
Quality level:
100

Key Documents

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Product Name

4α-Phorbol 12,13-didecanoate, solid

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

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 key

DGOSGFYDFDYMCW-OEFRVDPMSA-N

form

solid

color

white

solubility

DMSO: soluble, ethanol: soluble, methanol: soluble

storage temp.

−20°C

Quality Level

100

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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.

Disclaimer

Photosensitive

Preparation Note

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS9465
MKCR5246
MKCS0315
MKCP9077
MKCM2401

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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)
Yasuhito Motojima et al.
Neuroscience letters, 678, 76-82 (2018-05-08)
Pain management remains a major concern regarding the treatment of postoperative patients. Transient receptor potential (TRP) channels are considered to be new therapeutic targets for pain control. We investigated whether the genes Trpv1 and Trpv4 are involved in hind paw
Y Fukushima et al.
The Biochemical journal, 320 ( Pt 1), 27-32 (1996-11-15)
The histamine H2 receptor is a member of the family of G-protein-coupled receptors and is linked to the activation of adenylate cyclase phospholipase C (PLC). In this study we examined the effects of protein kinase C (PKC) activation in Chinese
M C LaPointe et al.
Molecular endocrinology (Baltimore, Md.), 7(10), 1284-1296 (1993-10-01)
During left ventricular hypertrophy, brain natriuretic peptide (BNP) and atrial natriuretic factor (ANF) mRNA levels increase, possibly due to stretch-induced activation of protein kinase C. Phorbol ester treatment of primary cultures of neonatal rat ventricular cardiocytes represents an in vitro
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
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