Pelretin

Pelretin

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Names
IUPAC name 4-[(1E,3E,5E)-4-Methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5-hexatrien-1-yl]benzoic acid
Identifiers
CAS Number	91587-01-8
ChEMBL	ChEMBL39861 Y
ChemSpider	4940263
Jmol 3D model	Interactive image
KEGG	D05402 Y
PubChem	6435504
UNII	H9MC68UEZ9 Y
InChI InChI=1S/C23H28O2/c1-17(10-15-21-18(2)8-6-16-23(21,3)4)7-5-9-19-11-13-20(14-12-19)22(24)25/h5,7,9-15H,6,8,16H2,1-4H3,(H,24,25)/b9-5+,15-10+,17-7+ Key: YRNAHKPMDMVFMV-GMICYETFSA-N InChI=1/C23H28O2/c1-17(10-15-21-18(2)8-6-16-23(21,3)4)7-5-9-19-11-13-20(14-12-19)22(24)25/h5,7,9-15H,6,8,16H2,1-4H3,(H,24,25)/b9-5+,15-10+,17-7+ Key: YRNAHKPMDMVFMV-GMICYETFBM
SMILES CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/c2ccc(cc2)C(=O)O)/C
Properties
Chemical formula	C23H28O2
Molar mass	336.48 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pelretin is a synthetic retinoid. It was tested in the 1980s on animals in the hopes that it could be used to eliminate wrinkles.

Synthesis

File:Pelretin synthesis.svg

Pelretin synthesis:

The key reaction in the construction of this compound consists in Wittig reaction of the ylide from phosphonate 3 with the extended aldehyde 4 used in the synthesis of tretinoin itself. Reaction of para-bromomethylbenzoate (1) with triethylphosphite probably proceeds by initial displacement of halogen by phosphorus to give a transient intermediate charged species such as 2. Displacement by one of the ethyl groups on phosphorus by bromide ion from the frist displacement followed by bond reorganization leads to phophonate (3), and EtBr as a by-product. Reaction of the ylide from that product with aldehyde 4 affords the extended polyene. Saponification then yields pelretin.