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Merck
CN

P148

4α-Phorbol 12-myristate 13-acetate

solid, ≥95% (TLC)

Synonym(s):

4α-PMA

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About This Item

Empirical Formula (Hill Notation):
C36H56O8
CAS Number:
63597-44-4
Molecular Weight:
616.83
NACRES:
NA.77
PubChem Substance ID:
24898203
UNSPSC Code:
12352211
MDL number:
MFCD00153860
Assay:
≥95% (TLC)
Form:
solid
Quality level:
100

Key Documents

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Product Name

4α-Phorbol 12-myristate 13-acetate, solid, ≥95% (TLC)

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

SMILES string

CCCCCCCCCCCCCC(=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(C)=O

InChI key

PHEDXBVPIONUQT-LQLWEASQSA-N

assay

≥95% (TLC)

form

solid

color

white

solubility

H2O: ~2 μM
DMSO: soluble
ethanol: soluble

storage temp.

−20°C

Quality Level

100

Biochem/physiol Actions

Negative control for phorbol ester activation of protein kinase C.

Disclaimer

Photosensitive

General description

Though having aqueous solubility, it is recommended that this compound first be dissolved in a water miscible organic solvent before dilution to working concentrations in aqueous media.

Packaging

Sealed glass ampule.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR3206
MKCQ1294
MKCN8591
MKCL0558
MKCG5400

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B L Van Duuren et al.
Cancer research, 39(7 Pt 1), 2644-2646 (1979-07-01)
4a alpha-Phorbol-9,9a-didecanoate, 4a alpha-phorbol-9-myristate-9a-acetate, and phorbol-9-myristate-9a-acetate-3-aldehyde were tested for skin tumor-promoting activity by using 7,12-dimethylbenz(a)anthracene as the initiating agent. There were 30 female ICR/Ha mice/group, and tests were continued for 434 to 461 days. 4a alpha-Phorbol-9,9a-didecanoate and 4a alpha-phorbol-9-myristate-9a-acetate were
Gautam Bhave et al.
Proceedings of the National Academy of Sciences of the United States of America, 100(21), 12480-12485 (2003-10-03)
Protein kinase C (PKC) modulates the function of the capsaicin receptor transient receptor potential vanilloid 1 (TRPV1). This modulation manifests as increased current when the channel is activated by capsaicin. In addition, studies have suggested that phosphorylation by PKC might
Amani Batarseh et al.
Biochemistry, 47(48), 12886-12899 (2008-11-04)
Translocator protein (TSPO) is an 18-kDa cholesterol-binding protein that is expressed at high levels in steroid synthesizing and several cancer cells where it is involved in steroidogenesis and cell proliferation, respectively. The factors regulating Tspo expression are unknown. We analyzed
Izabela Woclawek-Potocka et al.
Prostaglandins & other lipid mediators, 79(3-4), 287-297 (2006-05-02)
Corpus luteum (CL) is a reproductive gland that plays a crucial endocrine role in the regulation of the estrous cycle, fertility, and pregnancy in cattle. The main function of CL is secretion of progesterone (P4), an important hormone for establishment
Feng Xu et al.
British journal of pharmacology, 140(2), 413-421 (2003-09-13)
1. We investigated whether protein kinase C (PKC) activation stimulates Ca2+ entry in HEK 293 cells transfected with human TRPV4 cDNA and loaded with fura-2. 2. Phorbol 12-myristate 13-acetate (PMA), a PKC-activating phorbol ester, increased the intracellular Ca2+ concentration ([Ca2+]i)
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