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SML2652

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
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD01742209
Assay:
≥97% (HPLC)
Form:
powder
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assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

OC(=O)\C=C(/C)\C=C\C=C(\CC\C=C(\CCC=C(C)C)/C)/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

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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