Chemical and physical properties of pyrodextrins

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I1ICAL A m H tS S X & L M@ m I f l l S

OF PHtGDSXfRXHS

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j j i|f»»i*iM f>A g jp tiiilM it.'l

I Thesis Subm itted to tfe * t e t i i » i # R e a lt y f o r th e io § rs # o f

m m m of i i » 0 « ! . flftjo r ® » b |# # tf F lo a t Chemistry

A p p ro v e d ?

jQ

Iowa S ta te C ollege

1942

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UMI Number: DP12597

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A# Barly B l e f e O f y * * * * * , * * , * , 3 B* O rig in o f th e Term , P y ro d e x trin r and I t s L a te r O o n n o t a t i o n s . . . 0# Reversion of Oluoeae to Higher S accharides. • D. Attem pts a t F o llo w in g th e Course o f D e x trin le & t io n , 1892-191® « * • * • * . . « * • • * * - , * B. A lk a li l a b i l i t y a© a T ool In D e x trln lz a tio n

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F* M icroscopic O bservations on D e x trin iz e d S r& a s fle a *.....a *,,.,,.*,**,,,.,.* t * Recent S tu d ies on B e x tr ln lx a tte a * 1933-1942. B. Work of 1* la y e r on S tarch s tr u c tu r e . ....... I I I * SXPERIHBHTAL

11 14

A* Comparison o f th e Changes O ccurring d u rin g Conversion o f Pour Types o f P y ro d e x trin s * 1* Methods of c h a ra c te rlz ln g . . . . . . . . . . . . . . .

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1 * Cbeatlaal and P h ys ic al P ro p e rtie s o f a Water-Soluble D e x trin Fraction in Rela­ t io n to its Mole sola? St m o to r® * * # * # » * • * * 1 , F r a c tio n a tio n ... . . . . . . . . . . . . . . . . . . . . . . . . 2 * A eld h y d r o ly s is # * * * * # * * * * * .,# * * * * ,. . # . * • » 3# P e rio d ic a c id o x i d a t i o n . . . . . . . . . . . . . . . . .

4. Preparation of aonoformate. 5 * D ig e s t ib ilit y by Sohardingsr e n zy m e **.** ©» D ig e s t ib ilit y by a-amylase.##**.**.•**** *t* Digestibility by p-anylas#,***.*,,»*«*,* 8 , A bsorption c o e ffic ie n t o f d e x tr in io d id e c a ;v ip le x ...... . . . . . . . . . . . . . . . . . 9 . P o te n tto m e trie t i t r a t i o n w ith io d in e * * ., 10* f isc o s tiles o f d e x tr in * i t s a e s ta te and m ethylated d e r iv a tiv e . . . . . . . . . . * * 11* M e th y la tio n and end-groap a s s a y * * . . . , * . , /1 2 * Proposed m o lecular s tru c tu re fo r # fr a c tio n 3 0 - 7 0 .,.......... ftft

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Pyro& extrins s rs d tg n d s tlM t proflsieis o f star©to ©to-

tfttaod b y ro o s tin g * © t t f t tr aion© os la tb© pr®s@ne© o f sm all •v o w *** o f o s ta ty ti® ag ents*

Wy

l a lb© tlra® and

iMpM t ai i of roasting «&&' tbo oaiiiiyst «##€* Inm&rods of dlfforosb tadirtdMil prodnofco* all olas.tif.iod as d e x trin ® , ■^*sr ]|J3?OCy^lf*8sscl> JTC^3P ay^Cl.^t'S t » r f « r f t Im «ps# th o u .a®tiii?aM.s®i o tito 801 and roo®ir«y®a ..by s **« !p & b fttl«R w iite 9 0 w tilsaao l*

Mm mi f i n a l

yeofedkr- » § f * **

m€Lmrtm* — A 2$ s o lu tio n o f S o s trf® 6 was auto**

©Jawed a t 18 lb * * ihpm m rv* (1 8 0 *3 *) fa® 4 'h o w s * was tafc#» for d ig e s tio n *

A® a l f f it o t

8*dtt«Sqg m lm m ts e ro a s o d im m if

t o 250 -Mmims tfc l» ttis e * • * g»a e t 1 oaat i ©a♦— fh eae fy a « iie ® § wmm d es erib ed os page 5 4 , Table X I.

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d . ^ c e tT la tlo n a rt. a a p o n if 1 ca t lo n »— fe n p i* o f F ra c tio n 3 0 -f© «as d is s o lv e d a t mmm

'Is 100 » 1 . d ry p y r l*

d i r t , TO m l* »e®%i@ anhydride was r t d r t a r t th© m ixtu re allow ed i # s t a r t f o r f e e * days*

Xfe w et t ie s poured inft®. two

l i f t * * * o f too w a te r* f i lt e r e d a r t d r ie d to. © It on m porous p lo t© *

Sine® an alyst© «a**e*p en A ei o n ly to two a c e ty l co n test

of

th© a e e ty liitio n was. rep eated a t b efo re except th a t a

ie a p e ra te r# o f 4®®f* was «*#£«

ft© a e e ty l cost e a t o f th e

f i n a l p r o to n was 44«0£ CSsC&i © a ir t* f » C % % % .3G % 00>n • 4 i» f &

d e x trin tr ia c e t a t e

& a m ****® attem pts a t a © s ty le *

ti© B we la g 'd if f e r e n t m m m M o f reagents and d if f e r e n t temp­ e ra tu re s , th e a o e iy l oostoo* a f t e r th e f i r s t a c e ty la tio n to rle d from f® t o SS^f two m th re e o e o ty la tlo w were always necessary to reach th e tb o o ro tio ftl amount« ¥h® ra is e s wor# d o te ra iiw d b y o ilo r ig g 0 *6 g «* a o o te i# to s t a r t o ve rn ig h t la if- m l. o f 0*g *» OVf Jf 1»©S in S0-80$ «§«#©«» methanol a r t to M k * tlt* » tln g w ith g tiU

Wh® as© -of aqueous t e t l f a l l r t t o

sa p o n ify thee® p rrtite i© e© 8tpl«tely* S m p l® *** a te th rt | f i | mm used f o r reco very o f th e d e x trin fr o » th e ««*% *% •*

Tmm ,®»* o f tr ia c e t a t e was su e-

p e rte d l a 4© a l*. ab s o lu te a e th a a o l « © r t*ja |a g 1© * 1 * Of 0«'l H CEgOla a r t

to s t a r t M hoars a t m m tem perature

w ith ffegm m d sh akin g .

fh e sixhw re was c e n trifu g e d a rt. th®

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aaalyat* atMMftd that iJa# mm§M hat m% bees e#iapi#i@ly s a p o n ifie d { < % & * 4 * -t# )f Q «a**«M ttfcXy

mm NfMiift at 4#b;G» .five eat

above gpweetava

ffaw of aaataia*

ffo © 4 * x t * i& « « • a&fcalnad f le a * 6 0 )*

fh # m m *!** o f th # *b *? t aapurM afea (aaam rlaM t la f&tol# I f ) #h@ir«A th a t i t * liafeaga efcleh fclaft«**6 p-atBjlas© digestloa.wm® .apparently q a lt# stab le a ftt « « re ta in e d tbrought #»% a v a rie ty o f g b y e ie tl t if t ataaadaal' eligyages*

fable W B ffa a i o f fa rlo w a tre atm en ts on th # D ig e s t ib ilit y o f © e x trin C % 0*Aagrleee

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4 number mi ®bt»«f* fnoiasfe* wmm asst tweot ignboi. Im order to find i t they oaitatbiied * stall** vsslstsas* to enoyme notion* fable V g%mm the properties of these produois sat their digestibility miMh p -amylase after beating sa a boiling water bath. SO ataatoMt -ppoitott# to addition of the SSISyBlO*

These result* are o®afi»»ito» that the tssrssss in digestibility to brought about by the toariattaftsstleft process Itself*

It eyidsnity to sot d«« to the proa©see of m m

foreign ^wabeteso* wMeti inhibits ths easy#®, atso© ft to un­ likely that this sshstsass would be present la products fr®» ao Tarled a sears** The t«pi#i»# m$®# and oatastsrefti pyrodextrine (#9* l#t sad 11# "labl# f| firaa so* company were a# acre- digestible than the protfoaoly dssarSbed esfastsrsh' -- asotrsl dextrine from * difforest company, or the dextrin prepared la this l«b®**b«fy by even-drying'f#M I* The sug­ gest lorn that branching might be present to considerable extent in the loos easily converted pfredsxtrias to strengthesod % the high sswosrtfbiltojr «f' ttoa aaiyledexiyis (#16), shish to considered to. be a strsl^btt-dksla titm M m *.

further experi-

asats os onxyaati® degradation as rototot to molecular etombare are reported la fort' C of this seeiien* frefaraitoa ©f &£nl% Stadurtftt SO gras, of Fraction 30*70 la 100 al. of water buffered with phosphate solution woo

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was reached (th e o r* w 45*4^ 00% fg§* ( OglfO2 *3 €h$0}&}{ i M # t o lx * ©a® not. increased by m e tb y la tla g ©gate under th e aame e o n d itio n a .

Although Mf*r 1441 believe* that toi* treatisest ««*«•» ■partial togrx&atlett #f *tortot it to '»or© free from c r itic is m then any -Of the-ether commonly used B©toyi»ii@» tec h n iq u es , fleeesity data t® act- l a t t e to degradablea la tola mm@ (T ab le « »

p . 5 1 )*

to # s o lv e n t ©SEtraeilea nebbed o f t o l l (5 ) a p p lie d to s ta rc h by Is w s td «xA © « e f t l ) was used f o r xxpexxfttoB o f th e m ethyl gtotoeto tototoMI O f h y d ro ly s is 'of th e m ethylated to s to to *

fhree separate totoaatetlaaa

wmrm m r rted out «a two

d iffe r e n t batches o f t r ia e t h y l d re to te *

S ix g n u * of- sample

wo* placet is .0 vacuum teeteeater for «a© hoar with St tal*

glacial a c e tic a c id .

Thorn ©0 si* o f g$ I d

wo* added and

to# a « M S * a faftete «& * b o ilin g water bath for. to hours •

Tfe© cooled s o lu tio n was allow ed to stand

mmm

night with t

gut* merit©* The fiXtorwAj, m ostly d e c o lo rize d selwblea was part-ly a m t e * * * x t with 11 gp» ta©tgt after which the water' and aeeti©- « * tft were renewed by. 'Veewn# distillation, apt dry*

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* ms «*

tu g in--m o tto a t ■90* fo r ® s m ra l o jn tra e t# # 'Is a M

th e d ry s o lid was

i l fo r Sft M F s - s ltti d ry benzene*

Up­

on o m p o rtttio is o f th o b#w «a## th e c r y s t a llin e re s id u e o f

t r t * a n t,to tra ia o ih fl gloom ## « * • o b ta in e d in f 0 (4*8 g s * l* a f iM

y ie M

mrnm tii# oeaspoiiiisi# o f t h is ' r s ir iiii# w#r# so p -

b y « fe io ro f« ra i^ & t» r e x tr a c tio n * th e th re e d if f e r e n t

O jc p o rtw its y l# M # # ,f r e s p e c tiv e ly , # * 5 1 f# © *S ? tf and 0*485 gm* o f a p p ftta lila * to ira is o tlty l g l * « m *

M eth exyl c o n te n t:

found* 4 f * # * 4S *$£ 0 0 ^1) «#14U. f o r % % % .4 i% © * §2*§St 00%

.*

fit# tr ts a e tliy l g tu o o a ** «& *» i s « F y » t* U lM i fe rn ,: was n o t s u b je c te d t o metboxy1 fta *3 y » l» s i s * m u l l mwmmtw o f is tp tn lfio s would s e t h# n m * ! * # t y t h is M M w t a a t lo a * fh ® y a a ifta * fm m e x b ra o iio n w ith benzene wms d r ie d «nft w ith e t h y l

lp «

m y o v ftt& o tt o f bit® s o l­

v en t , d im e th y l gMmmm rentalned a# a. e y n tp * 0 *2 5 0 , 0 *1 4 0 , and 0 * t f t g p *#

tt& tM x y l eenfrt&fcl

fo u n d , 2 9 .1 $

ftO fef e a le d * f o r C6E1004 *2CK3 0 * 99*90 © 0 % . S e f « # mm%®g t l i i r -iftt# to-

th e number o f a a a *

re d u c in g on# group# p er m e le e # !# * '« ***# £ » weaknesses i s th e

settled t e i i fee- p o in t# # oats, . | a | © n ly ab o u t 190 o f th e t* i« * x M t# tr & n e th y l glucoses p re d ic te d fe e s th e w e ig h t s f s t a r t in g m a te r ia l was rec o v e re d a f t e r benzene e x tr a c tio n o f ft»# h y d ro ly s s t# * ' la s a id and lo r #

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{51} 1 * t h e ir vevlt m. mmm s i avife o b tain ed m similar y ie ld . :l t t» mot known w hether th e le s s M t n m d ©atirely la the

triaethyl glucose fr a c tio n ©r whether i t was proportioned © f« a lly between t h e tw o .

atnsMMl .valid be ©xpeeied t© e x ­

t r a c t te b ra iie ilJ .fi g l t a e e a e mere © f f t e ie a t ly t h a n t r l r a e t h y l . fit© qmafc&m * * a * im i w hether t e

©ad g r o u p s frost

th e p *#p © rit© » © f t e t r a r a e t h y l t © t r ia e t it y l glace#© a c ia a lly 'i*o 2 a t*d .:e r t v th e th e o r e tic a l eacKKit © f ir ts is tb y l glueo®© v h itd aheuld have been o b tain ed *

fti© l e t t e r v a l u e h a s b e a n

© set w ith the- « a i-« *ta a ftia g t t e t th e t s n l t i re p re s e n t a a te S a m WMfcer ©f end groups#

■|b| the- recovery of dimethyl g hzm m 1® the three &©tvndffitiiMKV

varlabl# end mpieresbiy SjMMvpletv, although

the aetltoxyl ©oat©at was ©lea.© be the- theeretieal*

A rell- .

able .method ter ©eiiatatles of the tiwethyl glwmm® as an indication of ■brandling Is badly needed* the number of branches' per iBQieeal© is aor© accurately calculated from the rvdaelais value and the asMfit of ivftnowtfeyl glue©#© pro­ duced.

'

If any straight chains were present* these calcula­

tions weald again shew a w i n g m number of branch®® for the branched seleetiiee*

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