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Flal/ANO/VE GLYCOS/DE PLANT MATER/AL 5 LOQWER Ph OF

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Flal/ANO/VE GLYCOS/DE PLANT MATER/AL 5 LOQWER Ph OF May 2-7, 1947. R, H, H|GBY_ 2,421,061 METHODS FOR RECOVERY OF FLAVANONE GLYCOSIDES Filed March 11. 1944 / FLAl/ANO/VE GLYCOS/DE PLANT MATER/AL $00205 MA Z'ER/AL _ A6 c/mus PULP 2 FIRM 0R HARD/5N ~45 W/TH LIME a ALKALINE EXTRA CT/ON — AS WITH Na 0/)’ 0/? All/4 0/,’ 4 L/QUOR REMOVAL —A6 BY PRL'SS/NG 5 LOQWER pH OF LIQUOR - A6 W/Th' 5c‘! 6 CEYSTALL/ZAT/O/V ‘ 7 SEPARATION 0/‘ CRYSTALS 8 REC‘EYSTALL/ZAT/ON — //" DES/RED //V l/ENTOR> RALPH H. H/GBY I ‘i. a A T TOENE Y Patented May 27, 1947 2,421,061 UNITED STATES PATENT OFFICE 2,421,061 METHODS FOR RECOVERY OF FLAVANONE GLYCOSIDES Ralph H. Higby, Ontario, Calif., assignor to Cali fornia Fruit Growers Exchange, Los Angeles, Calif., a corporation of California Application March 11, 1944, Serial No. 526,087 4 Claims. (Cl. 260-210) _ This invention relates to a new and useful which the mass is handled through various types process for the recovery of ?avanone glycosides of equipment. from plant source material. This produces a representative source material, An object of this invention is the recovery of indicated at l on the drawing. The pulp is then flavanone glycosides from their source materials, mixed with a su?icient amount of calcium hy e. g., citrus fruits. It involves alkaline extraction droxide to cause a hardening, indicated at 2. of the ?avanone glycosides from their source Since a portion of the calcium hydroxide will be materials. ' neutralized by any acid present, the particular These and further objects and advantages will amounts of calcium hydroxide to be added will appear more fully to those skilled in the art from 10 vary, depending upon the acidity of the mass be a consideration of the invention as set forth in ing treated. Where the preliminary process has the following description and in the appended been such as to include in this pulp a fair amount claims. of the natural acid of the fruit, as in a bulk or The drawing is a ?ow sheet containing an mechanical juicing operation, and particularly illustrative showing of my preferred process. in those cases in which there is a moderately large Convenient sources of certain of the commer proportion of natural acid in the fruit, as in the cially useful ?avanone glycosides are the wastes case of grapefruit or some of the more acidic accumulating in those establishments which are oranges, I ?nd that the amount of lime added engaged in assembling and processing citrus at this point may suitably run as high as ?fteen fruits to recover other valuables, such as essen 20. pounds per ton in order to alkalinize the pulp tial oil, pectin, citric acid, and many of the su?iciently to give the best v‘hardening. Where numerous types of juice products. The two most the peel has been separated with little or no commonly identi?ed ?avanone glycosides occur admixture of juice, and in those cases where in citrus. They are hesperidin and naringin. the fruit is naturally very low in acid, amounts Eriodictin (also referred to in the literature as 25 as low as ?ve or six pounds per ton will produce eriodictyol glycoside or “glucoside”) has also been suitable hardening. Intimate mixing of the lime reported as occurring in citrus. A number of with the peel will promote more rapid harden other ?avanone glycosides have been identi?ed, me’. among which may be mentioned sakuranin, liq In carrying out step 2 of the process. I have uiritin, citronin, and neohesperidin. 30 found it desirable to use a tank of suitable capac My process will be illustrated as applied to ity, as for example 500 gallons and one equipped the extraction of ?avanone glycosides from cit with an agitator. In this tank are placed ap rus, and particularly from the fruit portion proximately 200 gallons of water to which I add thereof. about 10 pounds of slaked lime. This is suffi The fruits are ?rst preferably treated to re 35 cient water to suspend approximately one ton move the juice therefrom, or the juice portion of the chopped pulp, which is agitated therein of the fruit may be removed or separated from for approximately 15 minutes, after which there the peel in its entirety. The juice may be re is added, as indicated at 3, a 25% caustic soda moved by reaming from the fruit or passing the 40 solution until the pH value of the liquor, when whole fruit through a pulping machine or a suit in equilibrium with the peel, remains de?nitely able press. In some commercial processes for the alkaline. The preferred extraction range will canning of grapefruit hearts or sections, the peel vary somewhat from member to member of the is removed by hand from the juice ball. group. One well-known member of the group If the peel is separated in large pieces from 45 namely, naringin, will be extracted to some ex the juice portion, the peel should now preferably tent at the very low alkalinity of pH 7.5, and be disintegrated to such an extent as to be of exhibits a preferred extraction range under com uniformly small particle size so as to permit con mercial operating conditions of about pH 8.4 to venient access by the reagent. I have found that about pH 9.1; while another member of the group, if the peel is passed through a press of the food 50 which from its structural formula appears to be chopper variety in which the face plate has open very much like naringin, namely, hesperidin, can ings of about % inch in diameter, the peel par be extracted satisfactorily at the very much higher ticles will be satisfactory for my purpose. It alkalinity of pH 11.5, and seems to exhibit a pre should be understood that as much of the rag and ferred extraction range under commercial oper interior pulp as may be desired may be included 55 ating conditions of about pH 10.8 to about pH 11.4. with the peel in my ?avanone glycoside recovery This suspension or slurry is preferably agitated process. The particular manner in which the for a further period of time, usually about 30 peel and pulp is comminuted is of signi?cant minutes, in order to give the best extraction and importance only insofar as it may affect the is then subjected to a pressing operation, indi access of reagents to the pulp and the ease with 60 cated at 4, for the purpose of separating the 2,421,081 3 4 liquor containing the ?avanone glycoside from has reported naringin as appearing in Indian the pulp. shaddock, which is apparently a clearly distin The liquor should be adjusted to within a range guished variety of Citrus maxima (Webster’s New of about pH 4 to about pH 5, which I find gives International Dictionary, second edition). good crystallization or precipitation with the Eriodictin (also referred to as eriodictyol gly members of the group generally. Some variation coside) , which is so far only reported as occurring among the members with respect to crystalliza in lemon peel, appears not to have been de?nitely tion is also found. Referring again speci?cally to identi?ed as to structure but may be presumed to hesperidin and naringin, hesperidin will be found have the empirical formula C27Ha201s and the to begin to crystallize slowly when pH 9 is reached 10 structural formula: and to crystallize at a commercially satisfactory rate at pH 6, while naringin will begin to crystal lize at about pH '7 and increases to a moderately Sugar residue-O satisfactory rate at about pH 6. This acidi?ca tion is conveniently and economically effected 15 with hydrochloric acid, and is indicated at 5. After adjustment of the pH, the flavanone HO O glycoside is allowed to crystallize from the liquor. Eriodictin according to this View, is theoretically The crystallization step is indicated generally at capable of being formed by the demethylation of 8. The ?avanone glycoside separation step may 20 hesperidin. be carried out in any desired and known manner, Sakuranin, having the empirical formula and is indicated on the flow sheet at ‘I. If it is CHI-124010, and the probable structural formula: desired to improve the purity of this product, puri?cation may be effected by subsequent re 0 H crystallization steps, which are all well known, 25 H300 —-- OH and are indicated at 8. Hesperidin has the empirical formula C28H34015 H: and can now with little or no doubt be assigned the following structural formula: Gluco (I) on 30 has been isolated from the bark of the Prunus o H 'Jedoensis Matsumura. Sugar residue-0 0 CH: Liquiritin, with the empirical formula C21H22O9, and the apparent structural formula: H: 35 0 H H t H0 #00 Gluco In this formula the sugar residue contains one Hi molecule of rhamnose and one molecule of glu ll cose. Hesperidin is a natural glycoside appar 0 ently occurring in most citrus fruits. While per 40 haps the most proli?c source of hesperidin is the is obtained from the root of the licorice, Glycyr albedo of the citrus fruit, some has been found rhz'za glabra L. var. glandulifera. in the juice portion of the fruit, and traces have Citronin, with the empirical formula C2aHa4O14, also been found in the leaves, twigs, and bark of and the probable structural formula: citrus trees. This flavanone glycoside has been OCH: reported as occurring rather widely in nature.
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