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P0077

Sigma-Aldrich

Prostratin

≥98% (HPLC)

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Synonym(s):
12-Deoxyphorbol-13-acetate, CCRIS 6292, NSC 623310
Empirical Formula (Hill Notation):
C22H30O6
CAS Number:
60857-08-1
Molecular Weight:
390.47
MDL number:
MFCD00674138
PubChem Substance ID:
329820006
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

C[C@@H]1C[C@]2(OC(C)=O)[C@H]([C@@H]3C=C(CO)C[C@@]4(O)[C@@H](C=C(C)C4=O)[C@@]13O)C2(C)C

InChI

1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1

InChI key

BOJKFRKNLSCGHY-HXGSDTCMSA-N

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This Item
SML1897P8014O9890
Prostratin ≥98% (HPLC)

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P0077

Prostratin

NSC73306 ≥98% (HPLC)

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SML1897

NSC73306

4α-Phorbol 12,13-didecanoate solid

Sigma-Aldrich

P8014

4α-Phorbol 12,13-didecanoate

5Z-7-Oxozeaenol ≥98% (HPLC)

Sigma-Aldrich

O9890

5Z-7-Oxozeaenol

form

powder

form

powder

form

solid

form

powder

color

white

color

, yellow to light brown

color

white

color

white to off-white

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: soluble, ethanol: soluble, methanol: soluble

solubility

DMSO: >10 mg/mL

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

Application

Prostratin has been used to reverse the latency of human immunodeficiency virus-1 (HIV-1) and to quantify the transcriptional activation of the long terminal repeat (LTR) in latently HIV-1-infected Jurkat (J-Lat) cell lines.

Biochem/physiol Actions

Prostratin, an unusual non-tumorigenic phorbol ester, is an activator of protein kinase C (PKC) and also an activator of nuclear factor KB (NF-KB) mediated through activation of the IKKs (IKB kinases). Prostratin exhibits potent in vitro activity by inducing HIV expression in latently infected cell lines and primary cells, thus antagonizing HIV latency. Activation of PKC and NF-kB has been proposed as the mechanism of action. Prostratin also inhibits HIV entry into target cells by down-regulating CD4 and CXCR4 receptors.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

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L Yu et al.
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Protein Kinase C (PKC)

Protein kinase C (PKC) is an AGC kinase that phosphorylates serine and threonine residues in many target proteins.

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