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W. L. Brown ANNUUM)PERFECTION PIMIENTO (CAPSICUMTHE RED PIGMENT IN THE

CHEMISTRY OF PEPPER PIGMENTS:A CONTRIBUTION TO THEARTICLE:

1935, 110:91-94.J. Biol. Chem.

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A CONTRIBUTION TO THE CHEMISTRY OF PEPPERPIGMENTS*

THE RED PIGMENT IN THE PERFECTION PIMIENTO

CAP~ICUM ANNTJ~M)

BY W. L. BROWN

(From the Department of Chemistry, Georgia Agricultural ExperimentStation, Experiment)

(Received for publication, March 20, 1935)

Zechmeister and von Cholnoky (1) were the first to show thatthe red pigment of the capsicum fruits was not a hydrocarbon.Their analyses indicated the formula C34H4803, which they calledcapsanthin. Later work (2) caused them to revise the formula toC I~oO~. Finally (3), by chromatographing the synthetic esters

of capsanthin on CaCO+ they were able to isolate a purer prepara-tion which, on analysis, indicated a formula of GoH6803, thusplacing capsanthin in the Go series of polyene pigments. They(4) worked on Japanese chillies (Cap cum frutescens jczponicum)also, and isolated a red pigment which corresponded with thecapsanthin isolated from Hungarian paprika.

While both the Perfection pimiento and the pepper used for theproduction of paprika in Hungary are generally considered to be

varieties of Capsicum annuum, the pimiento fruit is quite differentfrom that of the paprika. The pimiento fruit is ox heart and coni-cal in shape, is about 9 cm. long, 8 cm. in maximum diameter, andthe shell is 4 to 8 mm. thick. There is no pungency in any part ofthis variety, as even the placenta and seed are free of capsaicin.

So far as is known, the work of Zechmeister and von Cholnokyon capsanthin has not been confirmed by other investigators. ThePerfection pimiento is a different type of pepper from that used in

their studies. For these reasons, and because of the importance of* Published with the approval of the Director as paper No. 40, Journal

Series.91

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92 Pepper Pigments

the pimiento canning industry in the United States, it was thoughtadvisable to isolate and examine the red pigment of the pimiento.

EXPERIMENTAL

Isolation of Pigment-The cores were removed from the pimi-entos, the shells were ground coarsely, washed, and pressed toremove part of the sugar which causes difficulty in drying. Thepress-cake was dried at 35 and ground. A capsanthin content of

1.5 to 3.0 gm. per kilo has been found in various dried pimientoproducts, depending upon the ripeness and method of preparationand the length of the storage period. Washing and pressing beforedrying give a preparation of lower capsanthin content, but onewhich dries more readily and is not hygroscopic. The dried andground product was stored at a temperature of 4 in bottles filledwith nitrogen.

In general, the more recent procedure given by Zechmeister and

von Cholnoky (4) was used for the extraction, hydrolysis, andseparation of capsanthin. All solvents used for recrystallizationwere redistilled in a current of nitrogen. Concentrations werecarried out in vacua in apparatus having ground-in connections.Preparations were kept in a desiccator by evacuating and allowingnitrogen to ilow in, this being repeat.ed to insure removal of oxygen.The desiccators were stored at 4 in the dark. Nitrogen was pre-ferred to CO2 because of the greater ease with which it may be

freed of oxygen.Purification for Analysis-All crude preparations were recrys-tallized twice from CSZ, filtered at the pump, and washed with ice-cold ether while on the filter to remove tarry matter. Prepara-tions I and II were recrystallized from hot methanol and yieldedfine brick-red crystals which melted at 173-174 (corrected).After washing with ice-cold ether, a preparation was partly dis-solved in hot methanol and filtered, the filtrate yielding on crystal-lization Preparation III, which had the same appearance andmelting point as Preparations I and II. The undissolved residueobtained in preparing the solution for crystallizing Preparation IIIwas dissolved in methanol, filtered, and allowed to crystallize.The beautiful lustrous blue-black crystals which separated oncooling were 1 to 2 mm. long and were clusters of thick, archedrods. This preparation (No. IV) had a melting point of 174-175

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W. L. Brown 93

(corrected) and amounted to about 25 mg. The preparations weredried in vctcuo over PzO6 and paraffin shavings at 70 in an Abder-halden drying pistol before melting points were determined andanalyses carried out.

Crystal forms corresponded to those found by Zechmeister andvon Cholnoky. Precipitating from ether with petroleum ethergave bent needles. Recrystallizing from CS, gave crystals of afir twig pattern.

The crystals of Preparation IV were weighed out for analysiswithout being ground, which probably accounts for the variationin the analyses of this preparaGon.

Preparation Z-Found. C 79.99, H 9.91.

Preparation ZZ-Found. C 79.89, H 9.90.Preparation III-Found. C 80.01, H 10.26.Preparation IV3.608 mg. substan ce: 10.760 mg. CO, and 3.141 mg. Hz0

3.901 : 11.674 3.486 C10H5803. Calculated. C 81.84, H 9.97Found. 81.33, 81.61, 9.74, 9.99

Preparation IV is probably as pure a preparation of capsanthinas can be obtained in this manner. According to Zechmeister andvon Cholnoky (3), the carbon content was 0.5 per cent too low in apreparation with only a trifling heterogeneity. They were ableto improve this only by preparing the dicaprate, chromatographing

its benzine solution, eluting the capsanthin dicaprate zone withbenzine containing a little alcohol, hydrolyzing the dicaprate, andrecovering the purified capsanthin.

Solubility-At room temperature the purified pigment wasfairly soluble in CHC , ethanol, and methanol, less soluble in etherand benzene, difficultly soluble in CS2, and almost insoluble inpetroleum ether. It is much more soluble in the hot solvents.

Absorption Spectrum-A solution of 5 mg. of the pigment perliter of CSS in a 10 mm. cell exhibited absorption bands at 550 to532 and 513 to 493 rnp.

SUMMARY

The characteristic red coloring matter of the Perfection pimientohas been isolated and examined. The red pigment from the pimi-ento was found to be identical with capsanthin isolated from Hun-garian paprika.

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94 Pepper Pigments

BIBLIOGRAPHY

1. Zechmeister, L., and von Cholnoky, L.,Ann. Chem., 464, 54 1927).2. Zechmeister, L., and von Cholnoky, L.,Ann. Chem., 487, 197 1931).3. Zechmeister, L., and von Cholnoky, L.,Ann. Chem., 609, 269 (1934).4. Zechmeister, L., and von Cholnoky, L.,Ann. Chem., 469, 1 1931).

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