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Phlobaphenes (or phlobaphens, CAS No.:71663-19-9) are reddish, alcohol-soluble and water-insoluble phenolic substances. They can be extracted from plants, or be the result from treatment of tannin extracts with (tanner's red).
(1992). 9780306442520, Springer. .
The name phlobaphen come from the Greek roots φλoιὀς ( phloios) meaning bark and βαφή ( baphe) meaning .Römpp CD 2006, Georg Thieme Verlag 2006

No biological activities have currently been reported for phlobaphenes. Phlobaphene on Dr. Duke's Phytochemical and Ethnobotanical Databases Phlobaphenes from fruits ( Fructus Crataegi) may have a specific action on the coronary circulation. They are converted into in soils. A Manual of pharmacology and its applications to therapeutics and toxicology by Torald Sollmann, M. D.


Naturally formed phlobaphenes
Natural phlobaphenes are the common bark, , and seed coat ( testa) . They have not been found in flowers, unless the brown and black pigments in the involucrum of certain compositae are found to be of the phlobaphene type.

In bark, phlobaphenes accumulate in the layer of cork cambium, part of the mixture.

(2000). 9780849336379, CRC Press. .
Par James A. Duke


Occurrences
Many barks contain a particular tannin, cinchotannic acid, which by oxidation rapidly yields a dark-coloured phlobaphene Cinchona Bark (Cortex Cinchonae). Part 3 called red cinchonic, Cinchonaceae on chestofbooks.com cinchono-fulvic acid or cinchona red. Quinine on www.1902encyclopedia.com

They are common in barks like Sequoia sempervirens or in oak barks where the chief constituent, quercitannic acid, a molecule also present in , is an unstable substance, having a tendency to give off water to form anhydrides (phlobaphenes), one of which is called oak-red (C28H22O11).

L., the European dodder, is reported to contain 30,000 ppm in the root.Hager's Handbuch der Pharmazeutischen Praxis, List, P.H. and Horhammer, L., Vols. 2–6, Springer-Verlag, Berlin, 1969–1979
Phlobaphenes can be extracted from the root of the ( Potentilla erecta) as tormentil red.

Phlobaphens can be found in the (where they are called kola red), (called cocoa red) or in the red skins or testa of the peanut. They are also reported in the fruits of the genus ( Fructus Crataegi)or can be extracted from flowers. The Principles Of Hop-Analysis, Cech G. O.

The chief constituent of kino is , of which it contains 70 to 80 per cent. It also contains kino red, a phlobaphene produced from kinotannic acid by oxidation. Kino on www.henriettesherbal.com

Phlobaphenes are not present in the model plant Arabidopsis thaliana but can be studied as the pigment responsible for the red color in some monocot cereals, including , or . Phlobaphene on trophort.com


Biosynthesis
In maize, phlobaphenes are synthesized in the flavonoids synthetic pathway from polymerisation of flavan-4-ols by the expression of maize pericarp color1 (p1) gene which encodes an R2R3 myb-like transcriptional activator Structural And Transcriptional Analysis Of The Complex P1-wr Cluster In Maize. Wolfgang Goettel, Joachim Messing. Plant & Animal Genomes XVI Conference of the A1 gene encoding for the dihydroflavonol 4-reductase (reducing into flavan-4-ols) while another gene (Suppressor of Pericarp Pigmentation 1 or SPP1) acts as a suppressor. The p1 gene encodes an Myb-homologous transcriptional activator of genes required for biosynthesis of red phlobaphene pigments, while the P1-wr allele specifies colorless kernel and red , and unstable factor for orange1 (Ufo1) modifies P1-wr expression to confer pigmentation in kernel pericarp, as well as vegetative tissues, which normally do not accumulate significant amounts of phlobaphene pigments. The maize P gene encodes a Myb homolog that recognizes the sequence CCT/AACC, in sharp contrast with the C/TAACGG bound by vertebrate Myb proteins.

In the sorghum, the corresponding yellow seed 1 gene (y1) also encodes a R2R3 type of Myb domain protein that regulates the expression of chalcone synthase, chalcone isomerase and dihydroflavonol reductase genes required for the biosynthesis of 3-deoxyflavonoids.


Chemically formed phlobaphenes
It is a dark-colored resin-like substance made of water-insoluble, alcohol-soluble polymers. Dihydroquercetin dimers by oxidative coupling reactions. Gonzalez-Laredo, Ruben F., Malan, Johannes C.S., Chen, Jie, Todd, Jim, Karchesy, Joseph J. 2nd International Electronic Conference on Synthetic Organic Chemistry (ECSOC-2), September 1–30, 1998

Phlobaphens can be formed under action of acids or heating of or of the fraction of tannins called phlobatannins. Water containing soda can be used for the conversion of tannins into phlobaphens.Dingler's Polytech. Journ., C. Etti, 1878, p. 354. When heated with hydrochloric acid, tannins in yield a glucose and a phlobaphene.Warden C. J. H., Pharm. Jour., 3, xviii. 985

Ordinary or warm soluble quebracho (also known as insoluble quebracho) is the natural extract obtained directly from the . This type of extract is rich in condensed tannins of natural high molecular weight (phlobaphenes), which are not easily soluble. Its use is therefore limited to small additions during sole leather tannage carried out in hot liquors (temperature above 35 °C) to improve the yield and the water-proofness of the leather. The cold soluble extracts are obtained by subjecting the ordinary extract to a which transforms the phlobaphenes into completely soluble tannins. The cold soluble quebracho extracts are the most universally known and used types. The main properties of these extracts are: a very rapid penetration, a high tannin content and a relatively low percentage of non-tannins. The rather low acid and medium salt content characterise them as mild tanning extracts (low astringency).

Phlobaphenes formation (tannins condensation and precipitation) can be minimized in using strong nucleophiles, such as , m-phenylenediamine and , during pine tannins extraction.

The use of synthetic tannin D can help solubilize phlobaphene in tanning solutions.

(2007). 9781406773019, Read Books. .


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