. ARCHIVES

FISHF;RIES AND MARINE SERVICE

Translation Series No. 3841

Content of sterols in distillates from the deodorization

of sunflower-seed, soy-bean and corn oils

by A. Popov, Ts. Milkova, and N. Marekov

Original title: S"D"Rzhanie na Steroli v Distilatite ot Desodoratziyata

na SL"Nchogledovo, Soevo i Tsarevichno Maslo

From., Khim. Tekhnol. Topl. Masel 11: 1-9, 1975

Translated by the Translation Bureau(BA)Multilingual Services Division

Department of the Secretary of State of Canada

Department of the EnvironmentFisheries and Marine Service

Halifax LaboratoryHalifax, N.S.

1976

11 pages typescript

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A. Popov, Ts. Milkova and N. Marekov TITLE IN ENGLISH - TITRE ANGLAIS

Content of sterols in distillates from the deodorization

of sunflower-seed, soy-bean and corn oils.

TITLE IN FOREIGN LANGUAGE (TRANSLITERATE FOREIGN CHARACTERS) TITRE EN LANGUE ÉTRANGÉRE (TRANSCRIRE EN CARACTÈRES ROMAINS)

S"D"RZHANIE NA STEROLI V DISTILATITE OT DESODORATZIYATA

NA SL"NCHOGLEDOVO, SOEVO I TSAREVICHNO MASLO. REFERENCE IN FOREIGN LANGUAGE (NAME OF BOOK OR PUBLICATION) IN FULL. TRANSLITERATE FOREIGN CHARACTERS. RÉFÉRENCE EN LANGUE ÉTRANGÉRE (NOM DU LIVRE OU PUBLICATION), AU COMPLET, TRANSCRIRE EN CARACTÈRES ROMAINS.

KHIMIYA I TEKHNOLOGIYA

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KHIMIYA I TECHNOLOGIYA 11, 1, 1975, 1-9

Content of sterols in distillates from the deodorization of sunflower seed, soy-bean and corn oils.

by

A. Popov, Ts. Milkova and N. Marekov.

Crude vegetable oils contain volatile compounds which 1*

give them their characteristic taste and odor. These compounds

are formed during the very process of oil formation in the

seeds. They can also be formed during the storage of seeds

(especially in increased humidity and temperature) as well as

during the extraction of crude oils, their storage and

refinement. •

The odor and taste bearing substances in the oils

include compounds such as: low fatty acids and their glycerides,

aliphatic hydrocarbons, terpenes, aldehydes, ketones, hydroxy-

acids, the byproducts of phosphatide decomposition, carotenoids,

sulfo-nitro compounds and others.

The boiling point of the substances mentioned is

considerably different from the boiling point of glycerides.

*Numbers in the right hand margin indicate the corresponding pages in the original.

SOS-2.00-10-31

uNEDflDTRANStAT ION

r-Qr infz:rtv,;:icm only

TRADUCTION NON REVIZLE informdion sot.3le-=nt

2

This allows the removal of the volatile odorous compounds by

di:>ti_llation. This is the basis of the -process of deodor, i.za.tion

du?°inr; which the oils are subjected to penetration of super--

hea.ted water vapor by vacuum. The quantity of substances

distilled by the water vapor (deodorization distillate,

deo4orization vapor) is small - constituting 0.1-0.5j; of the oil.

According to some reports (1-6), the deodorization

distillate is a complex mixture containing fat hydrocarbons,

mono-, di-, triglycerides, terpene alcohols, free fatty acids,

tocopherols as well as sterols (free and esterified).

So far, the studies on the content of deodorization 2"

foams indicate that there is a considerable concentration of

tocopherols and sterols in them, The concentration of

tocopherols may reach 10-12% of the foam (7), sterols up to

25% (j) while the initial oils contain no more than 0.4^i; sterols

and about 0.1% tocopherols,

The increased concentration of tocoprerols in the

deodorization foams is of interest because of the vitamin

activity and the anti-oxidative action of these compounds.

Also to be noted is the high content of sterQls in the deodor-

i.zation distillate because of the increased search for certain

sterols such as stigmasterol used as raw material for the

synthesis of biologically active steroids.

Under the present conditions of vegetable oil refinement,

the distillates of deodorization are not being separated.

Isolation of considerable amounts of this byproduct is expected

when the new refinery shops are put into action.

3

The subject of the present study is the preparation,

under laboratory conditions, of deodorization distillates

from the most important vegetable oils and the quantitative

determination of sterols in the distillates obtained.

Materials and methods.

In order to obtain comparable data from the studies,

the following industrial crude oils were used as starting

samples:

- Press produced sunflower seed oil (from the Chemical plants

"G. Dimitrov" at r,r, station Kostinbrod):

- Extracted corn oil (from Chem. plants "G. Dimitrov" at

r.r. station Kostinbrod);

- Extracted soybean oil (from FZ tilurgash" r.r. station-Yana).

The crude oils were hydrated in the laboratory by mixing 3 *

with 5-6% water during one hour at 50-600. After separation

of the hydration sediments and the drying of the hydrate0 oils,

the latter were defined by the refraction coefficient, acid

number, saponification number, iodine number and by the

content of unsaponified compounds and sterols. These indices

are presented in table 1.

The first four indices were determined by the testing

methods of I3DS 1552-68, while the unsaponified materials were

determined according to T.UPA0 method D -53, The content of

free sterols was determined by their precipitation using

digitonin in chloroform solution accordin to the method of

Copius Peereboom and Roos (8). The total quantity of free

LN

and esterified sterols was determined by precip:itating the

unsaponified ^^aterials using digitonin in alcohol solution

according to the method of Schramme (9). Thereafter, the sun-

flower seed, soybean and corn oils were processed in the

laboratory applying the technology for the production of natural

deodorized sunflower seed oil. Diagram 1 illustrates the

apparatus used for the deodorization of the oils. Superheated

water vapor, produced in steam generator 2 by the heat of an

infrared lamp 3, is introduced through the oil placed in flask

1. The lowered pressure in the system (4-5mm Hg) is obtained

by the action of an oil pump ?. When the oil is heated to

1E0-1?0C the volatile compounds contained in it are distilled

with the.water vapor. Any oil drops are stopped in the drop

trap 4, while the vapors condense in the condensers 5, The

distilled odorous substances are deposited on the condensers

walls. The low temperature in the latter is maintained by a

cooling mixture (ice with salt). Oil is deodorized for a period

of three hours. The water separated in the condensers is

removed and the deodorization distillate is extracted with V

a2S0Yethyl ether. After drying of the distillate with N the

solvent evaporates.

The deodorization distillates were examined by thin

layer chromatography usin- siplica gel G. The chromatogr«m was

obtained in a systetr, of petroleum ether ; ethyl ether (?0:5).

The spots became visible after sprayin{, with 50;^ sulphuric acid

and }1e .ttl.n^; at 1^^0C .

0,30 0,25

0,08 • • 0,42

0,38 • 0,67

0,21

0,07

.5

The quantitative content of free sLerols in the

deodorized oils and in the deodorized distil:lutes of the sane

oils were determined by precipitation with a digitonin in

chloroform solution.

Table 1

Ta(5:f.tyLg. a 1 •

fiân0NA3IŒE.11 •e craHumegoBo oe.30 DmeDmquo mac.uo =zo

■■••••■

•1.HoegxeHT Ha liperlynDaHe •

2.KmceilmEao

3. 0CagyHMTe1140 WeIC .71.0

limmo

5.1leocanymemm

6.C.Teposim %

,e."..i.)cDoCiorTam . •

7icl.ecTep4ml.mp2lui

o 0). 0 • •

1,4745 1 ,4712 1,4745

1,20 . 0,85 2,55

1204 • . 188,6 189,9 -

130,6 126,8 131,5

1,20 • •i 1;65 0,90

Table 1. 1. Refraction coefficient, 2, Acid number. 3. .3apon-ification number, 4. Iodine number. 5. UnsaPoniriab]e • 6. Sterols .1), 7. Free, 8. Esterified, 9. Total. 10. Index. 11. Sunflower seed oil. 12. Soy-bean oil. 13. Corn oil.

6

Diagram 1

14esogopaTop •

2 JfapoPeHepaTop -

3 Wpa.. -v-epe-da xamna.

4 :1-Canu oysiop ET au

5.H.G.74eusaTopx

60 Mauomeri.-Lp

7. Maueira. nonia

1. Deodorization flask. 2. Steam generator. 3. Infrared lamp . 4. Drop trap. 5. Condensers , 6. U.anometer. 7. 011 pump.

7

?-esults and discussion

The thin layer chromatography of the deodorization

distillates from the three oils indicates •hat they also

contain hydrocarbons, glycerides, free fatty acids as well as

free sterols. The latter form a spot of considerable surface

on the chromatogram with Re value 0.10. For Rll three oils

there is absence of a spot with an Rf value corresponding to

sterol ester (0,90). Evidently, during the deodorization of

the oils, only the free sterols are removed in the distillate.

The results obtained by the quantitative determination

of sterol content in the oils before and after deodorization

and in the resulting deodorization distillates are shown in

table 2.

Table 2.

Ta6mr,r_rta 2

C(3, n CBC"ogam CBoogiu;

CTOPOJIM B cTepoimH XliAp.M•% B geam.

• -maeAo m •

, CV ,gesogopau; gecTmaT % cnp -Imo m.

-

'

■•••■•CVICereee••■■

1.e1Hq0DIMB0

2.00t_ISO

3.1WBMgH0

0,21

0,30

0;25

0,20 0,10

0,27 % 044

0,22 0,71

16,0

15,8

3,Y

....eee.■•••••■■■-•-e•••••,••••

1. Sunflower seed. 2. soy bean. 3. Corn. 4. oil. 5. Free sterols in hydrated oil %, 6. Free sterols in the deodorized oil 2. 7 . Deodorization distillate compared to oil. sterols in deodorization distillate

8

The data in the table indicate that, in comnarison

w ith the oils, the deodorization frôths are considerably

enriched with sterols. The distillates of soy bean and

sunflower seed oils contain about 16,X) sterols.

The sterol content in the corn oil distillate is low

-- '7;^. But, the froth quantity obtained during deodorization

of the corn oil is about 7 times greater in comparison with

the froth of sunflower seed o? l. For this reason, the total

content of sterols in the corn oil distillate is of the same

order, as well as in the distillates of the other oils when

the quantity of starting oil is identical.

The results of these laboratory studies confirm the

already existing reports on the high content of sterols in

deodorization'froths and indicate that the byproducts from

the deodorization of our basic vegetable oil. could be used

as a cheap and available source for production of sterols.

It is essential to examine also the distillates of the '

industrial deodorization (after the activation of the new

refinery plants at °tEZ) of the vegetable oils in order to

determine their contents of sterols and tocopherols and to

develop a method for the appropriate exploitation of these two

precious products.

^ •^

I

9

:^eferences n.4

• ^ L:orot T anda G. Coste. 'eV • fr^^ca.1Se des corps1 udet :_. , , • ^

,gras, 1r, 259.

2. "taudet, M., Racotovao, M., and G. Cecchâ.. Rev. francaise des

corps pras, 20, 1973, 27 •

3.=oaÎr^ann, R.-L., Lvans, C.:., and J.C. Cowan. J. Am. Oil Chem..

soc. 41, 1964, 1'6.

4. -FedPi i, ^^., Cortesi, IN., and G. Jacini. Riv. Ital. --ost.

Grasse, Wn-, 1971 ► 536.

5. U.S.P. 2843610.

6. ,{o7 in, IN.,Kastorni, 1,11. , and Peshkova. Isvestia of the i

Institut e for Higher studies, Food Technology, No. 1, 1965, 89.

7,, ti.s.p. 3153055; U.S.P. 3108120.

n. CoT)ius Peereboom, J. W., and Tr. Roos. Fefte-Seifen--

Anstrichmitte1, 62, 1960, 91.

9. Schramme, A., Fette und âiefen, 46, 1939, 4436•

1-0

.lZ M T F. 15 A.x Y PA

1 a.Naud.et M., Moxo i F. A Costue G.', Rev. fxan^alse des corns

2. Naude-b M. e Paco co-vao. r2o Q Cecch3, G, 'Rev:-fxan.Caise des

co7^ps xas, 20y 1973, 2-7.o

3p hoff.^.r^. RaZo Ève-lis 0 6D. p Cowan JoCp, JaAm..Oil Chea„SoG.,

,̂w..1 s.•1^61;•, 11.6n

4. ,Fede7 i, E. ^ Coa^esi Np 9 J'aci.ni G. ? Riv.. Ital. Grasse. . . . .. ,. . r . _48, ^97`t s 536.

5e UoS o.C s 2e36l0.

6. HoaXIlie , ltacTopn,t T,^p, SSezr^tio.sa JI@,

Imponorzas 1965, 89. .

7. U.S.P. 3153055, U.S-P. 3108120.

8e 'Cop:tus Peexebo'otn J.W, a^;OOS Zxe Fè t=^e-^e^.fe^ Axis üxicr. ^^ ^ûe1g

,629 I960? 91.

9.. -Schram,r.e A. 9 Fet-L-e und Seifen, 46, 1939a 41-36-

11

Content of sterols in distillates from the deodorization of sunflower seed, soy bean and corn oils,

by

A. Popov, Ts. nlkova and N. 1::arekov.

Deodorization of sunflower seed, soy bean and corn oils

was conducted under laboratory conditions and the content of

sterols in the resulting distillate was determined.

. • . - . •

• .

• :•• •

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