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SML2652

Sigma-Aldrich

Peretinoin

≥97% (HPLC)

Synonym(s):

3,7,11,15-Tetramethyl-2,4,6,10,14-hexadecapentaenoic acid, (2E,4E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,4,6,10,14-pentaenoic acid, 4,5-Didehydrogeranyl geranoic acid, ACR, Acyclic retinoid, E 5166, E-5166, E5166, K 333, K-333, K333, NIK 333, NIK-333, NIK333, Polyprenoic acid, all-trans-3,7,11,15-Tetramethyl-2,4,6,10,14-hexadecapentaenoic acid

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About This Item

Empirical Formula (Hill Notation):
C20H30O2
CAS Number:
81485-25-8
Molecular Weight:
302.45
MDL number:
MFCD01742209
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C20H30O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h8-9,11,13-15H,6-7,10,12H2,1-5H3,(H,21,22)/b14-8+,17-11+,18-13+,19-15+

InChI key

UUBHZHZSIKRVIV-KCXSXWJSSA-N

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Biochem/physiol Actions

Peretinoin is an orally active synthetic acyclic retinoid (ACR) whose in vivo anti-hepatocellular carcinoma (HCC) efficacy is attributed to its upregulatory activity toward retinoid nuclear receptors (RARbeta & RXRalpha), as well as negative regulation against sphingosine kinase 1 (SPHK1) expression and, thereby, sphingosine metabolic pathway. Peretinoin inhibits the replication of hepatitis B & C viruses in cultures (HBV & HCV EC50 = 9-25 μM) and shows in vivo efficacy in rodent models of hepatocarcinogenesis among rats (10, 40, or 80 mg/kg/day p.o.) and mice (0.03% or 0.06% in diet) subjected to chronic inflammation induction by diethylnitrosamine (DEN).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Xian-Yang Qin et al.
Proceedings of the National Academy of Sciences of the United States of America, 115(19), 4969-4974 (2018-04-25)
Hepatocellular carcinoma (HCC) is a highly lethal cancer that has a high rate of recurrence, in part because of cancer stem cell (CSC)-dependent field cancerization. Acyclic retinoid (ACR) is a synthetic vitamin A-like compound capable of preventing the recurrence of
Masaya Funaki et al.
Scientific reports, 7(1), 16978-16978 (2017-12-07)
Sphingosine-1-phospate is a potent bioactive lipid metabolite that regulates cancer progression. Because sphingosine kinase 1 and sphingosine kinase 2 (SPHK 1/2) are both essential for sphingosine-1-phospate production, they could be a therapeutic target in various cancers. Peretinoin, an acyclic retinoid
Tetsuro Shimakami et al.
Scientific reports, 4, 4688-4688 (2014-04-16)
Clinical studies suggest that the oral acyclic retinoid Peretinoin may reduce the recurrence of hepatocellular carcinoma (HCC) following surgical ablation of primary tumours. Since hepatitis C virus (HCV) infection is a major cause of HCC, we assessed whether Peretinoin and
Masataka Kagawa et al.
Carcinogenesis, 25(6), 979-985 (2004-01-27)
The present study was designed to determine the effects of NIK-333, a synthetic acyclic retinoid, on N-diethylnitrosamine (DEN)-induced hepatocarcinogenesis in male F344 rats. Animals were given DEN dissolved in drinking water at a concentration of 40 p.p.m. for 5 weeks
Y Muto et al.
The New England journal of medicine, 334(24), 1561-1567 (1996-06-13)
In patients with hepatocellular carcinoma (hepatoma), the rate of recurrent and second primary hepatomas is high despite surgical resection and percutaneous ethanol-injection therapy. We developed an acyclic retinoid, polyprenoic acid, that inhibits hepatocarcinogenesis in the laboratory and induces differentiation and
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