212832-31-0

Upstream product

• 80-26-2 terpinyl acetate 

Relevant academic research and scientific papers

2,6-cyclolycopene-1,5-diol: Total synthesis of a naturally occurring oxidation product of lycopene

2,6-Cyclolycopene-1,5-diol (3) was synthesized in 9 steps starting from α-terpinyl acetate (11). This represents the first total synthesis of an oxidative metabolite of lycopene (2). The synthesis was performed according to a C15 + C10 + C15 = C40 strategy using the Wittig olefination to couple the end groups to the central building block. An intramolecular aldol addition was used to introduce two new stereocenters with a defined relative stereochemistry.

Process for making metabolites of lycopene

The invention is concerned with a multi-stage process for making an oxidative metabolite of the carotenoid lycopene, 2,6-cyclolycopene-1,5-diol having the formula STR1 In this process α-terpinyl acetate is oxidatively dihydroxylated to a cyclohexanediol (IV), the cyclohexanediol (IV) is oxidatively cleaved to a ketoaldehyde (V), the ketoaldehyde (V) is subjected to an intramolecular aldol condensation to give a cyclopentanol (VI), the cyclopentanol (VI) is silylated to its silylated derivative formylcylopentane (VII), the formylcyclopentane (VII) is subjected to a C3 -chain lengthening with acetone and simultaneously to a saponification for the cleavage of the acetyl group to give a cyclopentylbutenone (VIII), the cyclopentylbutenone (VIII) is reacted with vinyl magnesium bromide to give a pentadienol (IX), the pentadienol (IX) is converted with deprotection of the silylated hydroxy group into a phosphonium salt (X), this salt is subjected to a Wittig reaction with 2,7-dimethyl-2,4,6-octatriene-1,8-dial to give a tridecahexaenal (XII) and the tridecahexaenal (XII) is subjected to a Wittig reaction with a (3,7,11-trimethyl-dodeca-2,4,6,10-tetraenyl)triphenylphosphonium salt to give the desired 2,6-cyclolycopene-1,5-diol (II). A variant of this process, also in accordance with the invention, comprises converting the cyclopentylbutenone (VIII) into the phosphonium salt (X) via two alternative intermediates, namely a pentadienoic acid ester (XIV) and a different pentadienol (XV), into the same phosphonium salt (X). Moreover, the invention is concerned with the novel intermediates (V), (VI), (VII), (VIII), (IX), (X), (XII), (XIV) as well as (XV) and the individual process steps which lead to these novel intermediates. 2,6-cyclolycopene-1,5-diol is useful in the prevention of cancer growth in human cells.

THE STEREOSPECIFIC HYDROXILATION OF ENDOCYCLIC ETHYLENIC LINKAGE IN THE BIOTRANSFORMATION OF α- TERPINYL ACETATE WITH CULTURED SUSPENSION CELLS OF NICOTIANA TABACUM

The biotransformation of (+/-)-8-acetoxy-p-menth-1-ene (α-terpinyl acetate) with the cultured cells of Nicotiana tabacum was found to result in the predominant formation of 8-acetoxy-c-4-p-menthane-r-1, t-2-diol.This experimental result indicates that the hydroxylation of the endocyclic ethylenic linkage with the cultured suspension cells is stereospecific.