Note: Descriptions are shown in the official language in which they were submitted.
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OBTENIION OF CURCUMINE SOLID DERIVAT~VES
DESCR~ ON
s l~U~ OSE C~F l~lE INV~N IlON
This invention refers to a procedure to obtain yellow, water ~oluble alld ~tablecolorunng, both ~n aqueous solution ~nd powder, which can be used ~n hllmun
and animal food. The procedure involves the use of a natur~l product, as
curcl~n ine resin, together with another natural water ~oluble product with
abundant hydrox~l groups, such as polyethylcne glycol -chain of ~ce~ e units-
or starch. lhe pJocedure consists of ~g;tatlng curcun~ resin for a period of
between five and nine~ miml~es in a liquid m~ m at a te~ erature below
100~C, in the presence of the other rlatural cQ~ .~ln~l The colouring is obta~ned
from the ~01~1tio n cooled at room temperature. Stability can be adjusted durlngpreparation, in order to adapt the colouring to spe~;fi~ app!ic~tinnst in which the
main characteristic i5 the colou~ing stability or its ~ u~atic intenSity.
BACKGROUND TO THE INVEN IION
At pre~ent, ~li~rcllt procedures are know~ to l..e~a~e curcumine wate~ sol~ble
compounds which, in general, originate from a first s~age in which a Cura~min~-
oleoresin is solubiU~ed in an a~ ine meclium, after which the re~lting ~lkflllne2s salts are made to react with a high molec~ r weight and water sol~l~le organic
substrate. These stages end by ~ ti~ the reaction m.~ m and, a~ a result,
the organ~c ~ o~ acquire the acid stTuctu~e confer~ing the yellow
colouring. The re~ti~n product is buffered with an organic acid irl order to
m~qint~in a pH below 7. The product dries by means of ~to~nic~tio~l Having
ca~ried out these ~teps, the colouring may be applied in dry n.ialures or in
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r~e products.
Thcr~for~, these procedures are made up of a series of 6tages requi~ing spe~iflcpeno~lC of t~me, and to obtain a colour~ng ~akes ~ignifi~ant time. RPc;de~ to forrn
s the curcllminoifl substrate compleJc, a ~o1~1ti~ n with the co~r~cl)u~ ~ orga~ic
substrate mu~t be prepared, adding a basic re~ct~nt w~ich allows di~solving at
least part of the cu~ oleoresin, which means ~n added cost as dif~erent
products are u ed. The main disadvantage is the quick ~lecoTnpo~Cition (20~o in
weig~t per hour) of cur~vminoi~1c in an ~ R1;n~ me~ m at the nececc~ly
temperature for re~t~ot- This ~1eco,~ osiLion, apart from c~vsin~ the loss of
costly r~w mflteriPI, produce~ a brown colouring material which ta~nt~ the des~red
yellow colour aud provides organ~c products of an unknown structure which are,
thcrefore, not rccQ~ nrled for food applic~ff~-n.c.
DESCRIPTION OF THE INVENl~ON
The obtention of the colou~ng follo Iving the procedure involved in this invention
is bssed on a curcl~miT~e resin which is made oil-~ee by means of any of tlle
procedures described in the bibliogi~l~, wch as cIy6t~llic~tion in organic
~olvent or, preferably, pmifi(~pti9n IIl s~ll,er~i.iLical fluid (PCr/ES97/00015).
Starting ~om a Curc~ e resin punfied ~n supercritical fluid - without previously~ub---i~ g it to an ~ ine puri~ication sta~e ~ c~ tly ~ncreases ~he globsl
performance of the proce~s and preseIves the edible and chromatic qualib of the
fimal product, guar~tees the ~senre of solvent, even in trace q~l~ntitie~, and
al~o guarantees that the aromatic components of the oleoresi~ are practically
~liminp~t~ th minim.lm inte"ference in the aroma of the final product. These
q~ itie~ confcr spe~l ad~J~nt~e~ ~ fou~l ~rpll~t~
The vehicle, in the ~r~t varisnt of the methn~, lS a polyethylene ~glycol with am-~le~ r weight p.~,fel~bly between 4,000 and 6,000, and with a melting point
below 85~C. Cur~min~ resin dissolves cQ~rletely in the melted polyethy}ene
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glycoL being the weight ratio bc~.. eell the cur~mir~e resin and the acth~e orgaD~c
o~gens of the polyethylene glycol below 1:20, preferably around 1:600. The
solution i8 ~t~te~l for a few minute~, ~oint~inin~ the temperature between 70~C
and 80~C.
After agitation, the solution is cooled in an anhydrous ~tn~-sph~re and the
resulti~g material is exposed to certain cQnl1itin~l~ to allow the solid to be
industrially han~lle~l, in granule, flake or powder form, u~ing the cul-4;~o~
m~cllin~qs .;u.lel ~ ava~ e~ Ouc~ as grinding mp~hine~ to obtain po..del~.
The resulting solid product i8~0111ble in water, does not gG~ ate turbidity, doe~
not lose any of the basic raw m~terial, whlch is ~llr~ n~ resin, is not
cQrlt~nin~e~ by any ~l~cQn~position by-product and has a strong, clear, yellow
colour.
The vehicle, in the ~econd variant of the metbod, is a starch. C~.r~u.,.;.~- resin
is dissolved in an ~ ine aqueous sollltio n, v~ith a pH of 11-14, which is
previou~ly heated to 30-40~C. Another solution, compo~ed of 10~o to 20~ of
starch in water, is added to the previou~ sollltio~l- ~e weight ratio of ~ ne
zu resin and starch ~s between 1:1 and 1:50.
The sollltinn is agitated at the requ~red temperature for S to 90 ~[lulc6, afterwhich it i6 ~ lified until a pH of bel~eell 8 and ~ ~ re~heA The acid u~ed caD
be an edible quality, inorganic acid, such as phosphoric, hydrochloric or sulphuric
~5 acid, or an organic acid, such a~ citric or acetic acid.
l~e res~llting preririt~te is filtered and dried in an o~en at 40~C. Once is dry, it
is ~ound until the desired particle size f~r the required application is obtained.
ThiS proces6 e6tablishes the characteristics of the final solid~ in order to adapt
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it to the physical and ~ emi~l conditions of a large ~umber of matrice~ which
ine~ e ~ erc.,l foods, drinks, pharmaceutical products, etc. Depending on tbe
r~a~tion times, tenl~elal~Jres and pH, products w~th a high chromatic stability to
ter~l~,elature and light can be acbieved, n~o~ing them particularly good for
s ~ti~erie and cater~ or u~th a high colou~ng ~ , particularly good for
soft drinks and pickle~.
'I'be colour~ng obtained by me~ns of the ~lesenl variant has a greater colou~g
,capacity, greater stability to light and greater storage stability than colourings
o obtained by metho~l~ described in the bibliography. h~e-~o~lres are c~rried out
~Eollo~ methodl~ described ~ usual bibllouapby. I;~ he~n~ore, qua~ c
~performance ~ncrea~e~.
s ]~UN EX~MPLE8 ~F THE INVENTION
~Example 1. 0.518 gr. of curc~lminP resin, obtained follow~ng the procedure ~n
]PCr/~S07/00015, a~e dissolved in 21 gr. of polyethylene glycol with a lnolec~
weight of 6,000, previously melted at 78nC. The ~ ture is ~ nt~in~ at this
l:emp¢rature under ~t~tion for 8 minl~te~ After the agitation time, the paste isleft to solidiiy in aDhydrous ~tn o~rhere. 21.5 gr of a water soluble solid
colouring are obtained.
I~ample 2. 3.0007 U- Of water ~oluble starch are di~solved in 18.8 ml. of water
2S at 40~C. 0.G ml. of sodium hydrox~de at 40% (p/v) are added, the ~klur~
bomogenire~l and then 1.0005 gr. of curcum;nP resin, obtained follou~ng the
procedure ~Il PCI'/ES07/00015, are added. The ~L re is Pgitated for 60
snin~ c, m~int~ini~l~ the pH between 12 alld 12.5 and the ~ml,cr~ture be~veen
4 0~C and 45~C.
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After thi~, the solllt)on L neut~alised with p!lo~11~ric add 1 n~rm~l until
pH=7.1. After neutralisatiorl, the ~nl~ n i~ left for 3 m;nlltos One m~ itre Of
the resulting pa~te, diluted ~n 370 ml. of water, pr~entC an absorbance of 1,009,
providing a chromatic capacity 15~o above commercially marketed kuL~ e.
s
Th~s so~ m~ aftcr keeping it exposed to white light for 2 hours under ~t~tion
and at 60~C, pr~s~..te~1 an absorbance of 1,004.
The re~ ting paste is left to cool in t~e oven at 40~C for 48 to 72 llours,
obt~ 3.4 gr. of water soluble solid yellow product.
The dricd product wa~ m~int~ine~l in the oven, under controlled ~tmosphere~ at
60~C and ~ moisture of 90~ for 30 natural days. As a result of thi~ ~,rocess, the
product lost 28.6% of its chromatic ac~ivity and partially lost its water solubility
~pocity~ ~ ~l ppm sQlntio~c have perm~nA~t turbidiy even after h~?~tir~a at 40
SO~C.
Example 3. 3.0007 gr. of water s~luble starch are dissolved ~n 18.8 rnl. of water
at 40~C 0.6 ml. of so~ m hydro~nde at 40% (p/v) are added, the mixt~e ~
ao homo~e~iced aDd therl 1.0002 gr. of cur~lmine re~in, obtained follow~ng the
procedure in P~ S07/OOOlS, are added. The ~ lurC iS agitated for 60
minute6, ms~int~ining the pH between 12 and 12.5 and tbe t~ml,crature bcn~een
40~C alld 45~C.
2~ Afte~ this, the sol~ nn is neu~alised with phosphoric acid 1 normal until,pH=7.2. After neutr~lis~ti~n ,the solution ~s left for 3 ~ tcs. One m~ tre of
the reslllting paste, diluted ~ 400 ml. of water, pil:sel~tC a~ll absorballce of 1,204,
provlding an eqwvalent chromatic capaci~ 79% above commercially~m~ t~d
l:artraz~ne.
... . .. ..... , .. . _ .. ..... . ... . .. ,,, _ .. ....... ..... ...... . .. ...
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oll~t;~ n, after keep~ng it e~tpo~e~l to wbite light for 2 hours under ~git~t;~
and at 60~C, presPnted aIl absorbance of 0.926.
The resulting paste is left to cool down in the oven at 40~C for 48 to 72 hours,s obtaining 4.4 ~r. of water ~oluble solid ycllow product.
The drled product wa~ m~int~inecl ~n the overl, under controlled ~tmo~here, at
60~C and a ~o~ e of 90~o for 30 natural days. As a result of this process, the
;product lost 28.6% of its cl~ro~ lic ~ctivity and parually lost its water sol~bility
o ~capacity, a~ 221 ppm solutions have perln~n~nt turbidity even after h~tiT~ at 40-
SO~C.
