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Safety Information

P148

Sigma-Aldrich

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
MDL number:
MFCD00153860
UNSPSC Code:
12352211
PubChem Substance ID:
24898203
NACRES:
NA.77

Quality Level

100

Assay

≥95% (TLC)

form

solid

color

white

solubility

H2O: ~2 μM
DMSO: soluble
ethanol: soluble

storage temp.

−20°C

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

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

InChI key

PHEDXBVPIONUQT-LQLWEASQSA-N

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.

Biochem/physiol Actions

Negative control for phorbol ester activation of protein kinase C.

Packaging

Sealed glass ampule.

Caution

Photosensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

P148-5MG:
P148-1MG-PW:
P148-BULK:
P148-VAR:
P148-1MG:

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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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
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
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
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
R A Nichols et al.
Journal of neurochemistry, 48(2), 615-621 (1987-02-01)
Neurotransmitter release from rat brain synaptosomes was measured following pretreatment with various phorbol esters. Ca2+-dependent, evoked neurotransmitter release was increased by phorbol esters that were active in stimulating protein kinase C. Protein kinase C activation was demonstrated by increased incorporation
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