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P8014

Sigma-Aldrich

4α-Phorbol 12,13-didecanoate

solid

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Synonym(s):
4α-Phorbol 12-13-dicaprinate, 4αPDD
Empirical Formula (Hill Notation):
C40H64O8
CAS Number:
27536-56-7
Molecular Weight:
672.93
Beilstein:
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.

Signal Word

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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)
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
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
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
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