SYNTHESIS OF FERULIC ACID DERIVATEIVES - …



Suberic acid, nonanedioic acid (and its mono-unsaturated derivative:2-nonenedioic acid), decanoic acid (and its mono-unsaturated derivative:2-decenedioic acid) are present in honey () and are of special interest becausethey have long been recognized as part of the pheromone system of the honeybee (). They are producedin the mandibular glands of the queen and the worker honeybees, they regulatetheir activities in the hive.

It was shown that all these dicarboxylic acids are formed during the dryingprocess of and that thedetermination of these decomposition products may be of value in determining theage of old samples.

The higher weight dicarboxylic acids (n=10 to 21) are found in different plant lipids, particularly in what was named erroneously (triglycerides containing C20, 21, 22 and 23 dicarboxylic acids besides normal fatty acids) from the sumach tree (Rhus sp.). Among them, Thapsic acid (n=14) was isolated from the dried roots of the Mediterranean "deadly carrot", Thapsia garganica (Umbelliferae), but others, as Brassylic acid (n=11), were prepared chemically from different sources.
Brassylic acid can be produced chemically from erucic acid by ozonolysis but also by microorganisms () from . This diacid is produced on a small commercial scale in Japan for the manufacture of fragrances.
A review on the applications and the industrial biotechnology of these moleculeshas been released by Kroha K ().

A large survey of the dicarboxylic acids present in Mediterranean nuts revealed unusual components (). A total of 26 minor acids (from 2 in pecan to 8% in peanut) were determined : 8 species derived from butanedioic acid, likely in relation with photosynthesis, and 18 species with a chain from 5 to 22 carbon atoms.

Higher weight acids (>C20) are found in present at vegetal surfaces (outer bark, root epidermis). C16 to C26

Synthesis, antioxidant and antimicrobial evaluation of simple aromatic esters of ferulic acid

Vitamin C, 100% L-Ascorbic Acid, USP, Ultrafine powder is a water soluble . Vitamin C, a potent, naturally occurring is an important constituent of skin. It plays a pivotal role in the prevention of dry skin and wrinkles, collagen synthesis and skin regeneration. Ascorbate is found in all layers of the skin, but is more concentrated in the epidermis than the dermis. However, it is readily depleted by about two thirds in tissue stores with exposure to UV light. Biochemically, the body relies on ascorbate in the collagen biosynthetic pathway. It functions as a cofactor for two enzymes, lysyl and prolyl hydroxylases. These are dependent on iron and Vitamin C prevents iron oxidation and thus inactivation of these hydroxylases, thereby maintaining their activity.

Vitamin C has been shown to be effective in increasing collagen deposits and also enhancing collagen lattice contractions, implying that Vitamin C application contributes to strengthening the collagen framework and maintaining a healthy dermis. Topical application of Vitamin C has been shown to reduce the appearance of fine lines and wrinkles. Caused by mechanisms supporting collagen production, this leads to improving the appearance of the skin. It has further been proven to reduce the severity of sunburns and age spots.

levels of Vitamin C cannot be achieved well by ingestion, hence topical application is essential for preventing oxidative damage resulting from pollution, smoke and sunlight. Its use has been shown to increase generation of stratum corneum barrier lipids and stabilize lipid profiles, in particular glucosphingolipids and ceramides.

The difficulty for the cosmetic formulator is that L-Ascorbic Acid is very unstable in solutions, as it starts to oxidize immediately, gradually producing color changes (orange/brown shift) and a reduction in activity as it converts to dehydroascorbic acid. For cosmetic use, it is best stabilized in an anhydrous lipid or silicone base, although some have reported increased stability with the use of Ferulic Acid as part of formulations. This product is an ultrafine powder, ready to use in anhydrous formulations without further grinding.


ACE-FERULIC: Photo Aging Defense Serum - Solvaderm

All of the ferulic acid amide derivatives were prepared from ferulic acid 1 according to the synthetic route in Scheme .

Two series of ferulic acid derivatives have been synthesized efficiently. The bioassay showed title compounds not only inhibit the plant viral infection, but also prevented the spread of plant virus by insect vectors. These findings therefore demonstrate that the ferulic acid amides represent a new template for future antiviral studies.


Ferulic Acid Methyl Ester - LKT Labs

14C-Labeled phenylalanine, 4-coumaric acid, 4-hydroxybenzaldehyde, 4-hydroxybenzyl alcohol, ferulic acid, and methionine were applied to disks of green vanilla pods 3 and 6 months after pollination (immature and mature pods), and the conversion of these compounds to vanillin or glucovanillin was investigated. In mature green vanilla pods, radioactivities of 11, 15, 29, and 24% from 14C-labeled phenylalanine, 4-coumaric acid, ferulic acid, and methionine, respectively, were incorporated into glucovanillin within 24 h. In the incorporation processes of methionine and phenylalanine into glucovanillin, some of the 14C labels were also trapped by the unlabeled ferulic acid. However, 14C-labeled 4-hydroxybenzaldehyde and 4-hydroxybenzyl alcohol were not converted to glucovanillin. On the other hand, in immature green vanilla pods radioactivities of the above six compounds were not incorporated into glucovanillin. Although 4-coumaric acid, ferulic acid, 4-hydroxybenzaldehyde, and 4-hydroxybenzyl alcohol were converted to the respective glucose esters or glucosides and vanillin was converted to glucovanillin, their conversions were believed to be from the detoxication of the aglycones. These results suggest that the biosynthetic pathway for vanillin is 4-coumaric acid → → ferulic acid → → vanillin → glucovanillin in mature vanilla pods.

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In conclusion, two series of ferulic acid derivatives have been synthesized efficiently. The bioassay showed title compounds not only inhibit the plant viral infection, but also prevented the spread of plant virus by insect vectors. Compounds 7a, 7b and 7d in particular exhibited good levels of antiviral and insecticidal activity. These findings therefore demonstrate that the ferulic acid amides represent a new template for future antiviral studies.