[Federal Register Volume 61, Number 133 (Wednesday, July 10, 1996)]
[Rules and Regulations]
[Pages 36287-36290]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 96-17542]


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DEPARTMENT OF HEALTH AND HUMAN SERVICES

Food and Drug Administration

21 CFR Part 184

[Docket No. 88G-0388]


Direct Food Substances Affirmed as Generally Recognized as Safe; 
Cocoa Butter Substitute Derived From High-Oleic Safflower or Sunflower 
Oil

AGENCY: Food and Drug Administration, HHS.

ACTION: Final rule.

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SUMMARY: The Food and Drug Administration (FDA) is amending its 
regulations to affirm that cocoa butter substitute manufactured from 
high-oleic safflower or sunflower oil is generally recognized as safe 
(GRAS). This action is in response to a petition filed by Fuji Oil Co., 
Ltd. (Fuji).

DATES: Effective July 10, 1996.

FOR FURTHER INFORMATION CONTACT: Nega Beru, Center for Food Safety and 
Applied Nutrition (HFS-206), Food and Drug Administration, 200 C St. 
SW.,-Washington, DC 20204, 202-418-3097.

SUPPLEMENTARY INFORMATION:

I. Background-

     In accordance with the procedures described in Sec. 170.35 (21 CFR 
170.35), Fuji Oil Co., Ltd., 6-1, Hachiman-cho, Minami-ku, Osaka 542, 
Japan, submitted a petition (GRASP 8G0348) requesting that 
Sec. 184.1259 (21 CFR 184.1259) be amended to affirm that the use of 
safflower or sunflower oil in the manufacture of cocoa butter 
substitute is GRAS.
     In the Federal Register of January 26, 1989 (54 FR 3853), FDA 
published a notice of filing of Fuji's petition and gave interested 
parties an opportunity to submit comments to the Dockets Management 
Branch (HFA-305), Food and Drug Administration, 12420 Parklawn Dr., rm. 
1-23, Rockville, MD 20857. FDA received three comments in response to 
that notice. These comments are discussed below.
     In the filing notice, the agency gave notice that the petition had 
requested that Sec. 184.1259 be amended to permit the use of safflower 
or sunflower oil in the manufacture of cocoa butter substitute. 
However, the petition requested, and the agency evaluated, the use of 
high-oleic safflower or sunflower oil in the manufacture of cocoa 
butter substitute. Therefore, because the filing notice did not make 
clear that the proposed starting materials for the manufacture of the 
petitioner's cocoa butter substitute are high-oleic rather than the 
typical high-linoleic safflower and sunflower oils, the agency 
published an amended filing notice in the Federal Register of April 28, 
1995 (60 FR 20998), to give interested persons an opportunity to 
comment with respect to the above-mentioned change. No comments were 
received in response to the amended filing notice.

II. Standards for GRAS Affirmation

     Pursuant to Sec. 170.30 (21 CFR 170.30), general recognition of 
safety may be based only on the views of experts qualified by 
scientific training and experience to evaluate the safety of substances 
added to food. The basis of such views may be either: (1) Scientific 
procedures, or (2) in the case of a substance used in food prior to 
January 1, 1958, experience based on common use in food 
(Sec. 170.30(a)). General recognition of safety based upon scientific 
procedures requires the same quantity and quality of scientific 
evidence as is required to obtain approval of a food additive and 
ordinarily is to be based upon published studies, which may be 
corroborated by unpublished studies and other data and information 
(Sec. 170.30(b)). General recognition of safety through experience 
based on common use in food prior to January 1, 1958, may be determined 
without the quantity or quality of scientific procedures required for 
approval of a food additive, and ordinarily is to be based upon 
generally available data and information concerning the pre-1958 
history of use of the substance in food (Sec. 170.30(c)(1)).
     Cocoa butter substitute from high-oleic safflower or sunflower oil 
was not used in food prior to 1958, and therefore cannot qualify for 
GRAS status based on a history of common use in food (Sec. 170.30(c)). 
Accordingly, FDA has evaluated the ingredient on the basis of 
scientific procedures (Sec. 170.30(b)).
     In evaluating this petition, the agency reviewed data and 
information concerning: (1) The chemical composition of the cocoa 
butter substitute; (2) the process used to manufacture it; (3) the 
functional equivalence of the cocoa butter substitute to cocoa butter 
substitute made from palm oil; (4) use of the cocoa butter substitute 
in food; and (5) information regarding the safety of the cocoa butter 
substitute.

III. Identity, Specifications, and Manufacturing Process

     The common or usual name of the petitioned substance is ``cocoa 
butter substitute primarily from high-oleic safflower or sunflower 
oil.'' Its chemical name is 1,3-distearoyl-2-olein (CAS Reg. No. 2846-
04-0). The petitioner provided evidence to demonstrate that the 
specifications for cocoa butter substitute primarily from high-oleic 
safflower or sunflower oil conform to those for cocoa butter substitute 
primarily from palm oil, 1-palmitoyl-2-oleoyl-3-stearin, which are set 
forth in Sec. 184.1259(b)(1) through (b)(9).
     Traditional safflower and sunflower oils typically contain high 
levels of linoleic acid and low levels of oleic acid. However, in the 
manufacture of its cocoa butter substitute, Fuji uses high-oleic acid-
containing safflower or sunflower oil. The high-oleic acid varieties of 
safflower and sunflower were obtained through common breeding 
techniques and are the subjects of several published articles (Refs. 1 
through 7).
     According to Fuji, its cocoa butter substitute is manufactured by 
reacting ethyl stearate (obtained from food-grade stearic acid) with 
high-oleic safflower oil or sunflower oil under nitrogen gas in the 
presence of a catalyst (lipase enzyme preparation adsorbed onto 
granular celite (diatomaceous earth)) at 37 to 47  deg.C for 48 hours. 
After completion of the reaction, the catalyst

[[Page 36288]]

is removed by filtration. The remaining free fatty acids and ethyl 
esters of fatty acids are distilled off at high temperature under 
vacuum. The reaction product is fractionated with hexane to remove 
high- and low-melting point fractions and refined by the ordinary 
refining process for edible fats and oils (deacidification, bleaching, 
deodorization).

IV. Functional Equivalence to Cocoa Butter Substitute Primarily 
from Palm Oil

     Cocoa butter substitutes have been described as nonhydrogenated 
vegetable oils that contain a monounsaturated fatty acid at the 2 
position and saturated fatty acids at the 1 and 3 positions (Ref. 8).
     Cocoa butter substitute derived from palm oil is a mixture of 
triglycerides containing oleic acid at the 2 position and saturated 
fatty acids (mostly palmitic and stearic acids) at the 1 and 3 
positions. Cocoa butter substitute from high-oleic safflower or 
sunflower oil is a mixture of triglycerides containing oleic acid at 
the 2 position and mostly stearic acid at the 1 and 3 positions.
     Although the fatty acid composition of cocoa butter substitute 
from high-oleic safflower or sunflower oil is different from that of 
cocoa butter substitute derived from palm oil (higher in stearic acid 
and lower in palmitic acid content), this difference in composition 
does not affect the function of this cocoa butter substitute in food 
(Ref. 9). The petitioner provided a published study by Feuge, et al. 
(Ref. 10), who tested three mixtures (one consisting essentially of 
oleopalmitostearin, another consisting essentially of oleostearin, and 
a third consisting mostly of oleopalmitin) for their ability to 
function as cocoa butter substitutes. The results showed that all three 
products, when mixed with cocoa butter, had melting properties closely 
resembling those of cocoa butter and therefore could be satisfactory 
cocoa butter substitutes. Further, the petitioner stated that although 
cocoa butter substitute from high-oleic safflower or sunflower oil by 
itself can be used to make chocolate, it can also be blended with other 
approved triglycerides to produce a cocoa butter substitute that is 
similar in chemical composition to natural cocoa butter and to cocoa 
butter substitute primarily from palm oil.

V. Use in Food

     The petitioned use of the ingredient is in the following food 
categories: confections and frostings as defined in Sec. 170.3(n)(9) 
(21 CFR 170.3(n)(9)); in coatings of soft candy as defined in 
Sec. 170.3(n)(38); and in sweet sauces and toppings as defined in 
Sec. 170.3(n)(43). The petition proposes that use of the ingredient in 
food be limited to levels consistent with current good manufacturing 
practice (CGMP).

VI. Safety Information

     The petition relies in part on the data developed to establish the 
safety of cocoa butter substitute derived from palm oil. Section 
184.1259 provides for the interesterification of partially saturated 
1,2,3-triglycerides (derived from palm oil) with ethyl stearate in the 
presence of a suitable lipase enzyme preparation. This is also used in 
the manufacture of the cocoa butter substitute derived from high-oleic 
safflower or sunflower oil.
     Cocoa butter substitute made from high-oleic safflower or 
sunflower oil consists predominantly of the triglyceride 1,3-
distearoyl-2-oleine. The components of this cocoa butter substitute are 
glycerol and oleic and stearic acids. These components are naturally 
found as part of glycerides, lipids, lipoproteins, and membranes of 
both plants and animals. Moreover, they are the same fatty acids and 
glycerol components as are found in a broad range of edible fats and 
oils that are GRAS. The synthesis and metabolism of these substances 
are well understood and are documented in biochemistry textbooks (for 
example, Ref. 11).
     The only difference between cocoa butter substitute derived from 
high-oleic safflower or sunflower oil, on the one hand, and cocoa 
butter substitute derived from palm oil, on the other hand, is a 
difference in fatty acid composition, specifically, the ratio of 
stearic acid to palmitic acid. The agency finds that this difference 
does not pose a safety concern. Both of these fatty acids have been 
safely consumed as common, naturally-occurring compounds in foods (Ref. 
12), and the proposed use will not change dietary consumption 
significantly. Therefore, the agency concludes that cocoa butter 
substitute prepared from high-oleic safflower or sunflower oil is 
equivalent to cocoa butter substitute prepared from palm oil with 
respect to safety, provided it meets the specifications for the similar 
palm oil-derived product.
     Further, the petitioner submitted three published studies to 
support its contention that cocoa butter substitute made from high-
oleic safflower or sunflower oil is safe (Refs. 13 through 15). The 
studies included an acute oral toxicity study in rats, a subchronic 
(90-day) oral toxicity study in rats, and a study to assess 
mutagenicity in bacteria. The bacterial study showed that cocoa butter 
substitute derived from high-oleic safflower or sunflower oil is not 
mutagenic; no significant effects from consumption of the cocoa butter 
substitute were found in the acute and subchronic toxicity studies.

VII. Response to Comments

     FDA received three comments in response to the notice announcing 
the filing of the petition. All of the comments supported the proposed 
GRAS affirmation of cocoa butter substitute derived from high-oleic 
safflower or sunflower oil.
     Two comments stated that the GRAS affirmation regulation should 
provide for the use of food-grade stearic acid as an alternative to 
ethyl stearate as a starting material in manufacturing the petitioned 
cocoa butter substitute. The comments asserted that it was common 
industry practice to use both ethyl stearate and stearic acid in 
interesterification reactions. In addition, the comments pointed out 
that not only is stearic acid a natural metabolite, but food-grade 
stearic acid is affirmed as GRAS (21 CFR 184.1090), and FDA permits the 
use of stearic acid as a raw material to produce various substances 
approved as food additives, including polysorbate 60, polysorbate 65, 
sorbitan monostearate, and calcium stearoyl-2-lactylate (21 CFR 
172.836, 172.838, 172.842, and 172.844, respectively). Moreover, the 
comments asserted that stearic acid is a more desirable starting 
material than ethyl stearate because an end product cocoa butter 
substitute devoid of residual fatty acid ethyl esters can be produced.
     The agency finds that, although the petitioner stated that ethyl 
stearate would be used as a starting material in the 
interesterification reaction during the manufacturing of its cocoa 
butter substitute, it is also common industry practice to use stearic 
acid in the manufacturing process (Ref. 16). Further, the agency notes 
that ethyl stearate is itself made from the GRAS substance stearic 
acid. In essence, direct use of stearic acid in the interesterification 
reaction bypasses the intermediate step of first converting stearic 
acid to ethyl stearate. The resulting cocoa butter substitute is the 
same regardless of whether ethyl stearate or stearic acid is used in 
the manufacturing process. Therefore, the agency agrees that the direct 
use of stearic acid as a starting material, without first converting it 
to ethyl stearate, does not affect the GRAS status of the petitioned 
cocoa butter substitute. Moreover, the agency concludes that an 
opportunity for public comment on the

[[Page 36289]]

direct use of stearic acid as a starting material is not necessary 
because the two substances are so closely related. Therefore, in 
amending Sec. 184.1259, the agency is including stearic acid as an 
alternative raw material in the manufacture of cocoa butter substitute 
from high-oleic safflower or sunflower oil.
     One of the comments also stated that acetone should be allowed as 
a solvent in the fractional crystallization of the petitioned cocoa 
butter substitute during the manufacturing process and suggested a 
residual acetone specification of not more than 5 parts per million. 
The comment stated that acetone is a well-recognized solvent in the 
edible oils industry and cited a number of FDA regulations that permit 
its use as a solvent. Indeed, acetone is approved as an extractant for 
annatto extract (21 CFR 73.30(a)(1)(ii)), as a diluent for color 
additive mixtures made with D&C Red No. 39 (21 CFR 74.1339(a)(2)), as 
an optional bleaching ingredient with flour (21 CFR 137.105(a)(6)), as 
a processing solvent in the manufacture of the food additive N-acetyl-
L-methionine (21 CFR 172.372(a)(4)) and in the extraction of spice (21 
CFR 173.210). The agency notes that the safety of the use of acetone as 
a solvent is well recognized in the food oil industry. However, the 
agency has no basis to set a specification for residual acetone because 
it did not evaluate the use of acetone as a solvent in manufacturing 
cocoa butter substitute. The agency also notes that, as always, any 
residual solvent that becomes or may reasonably be expected to become a 
functional component of food must be an approved food additive or GRAS 
for use in that food.
     The third comment consisted of a report by a panel of scientific 
experts who evaluated evening primrose oil as a dietary supplement and 
concluded that it was safe. The comment stated that the report on the 
safety of evening primrose oil should aid FDA in determining the GRAS 
status of Fuji's product because evening primrose oil is chemically 
related to both safflower and sunflower oils in that the primary 
constituent of all these oils is the GRAS substance linoleic acid. The 
comment stated that it was submitted because FDA must consider 
chemically and pharmacologically related substances in the diet when 
considering the GRAS status of any substance (Sec. 170.3(i)(2)).
     The safflower and sunflower oils the petitioner proposed to use as 
raw material for the production of cocoa butter substitute are derived 
from high-oleic variant seeds containing approximately 75 percent oleic 
acid in their triglycerides instead of linoleic acid, which is the 
major fatty acid in evening primrose oil and in oils derived from 
traditional safflower and sunflower. Thus, the assertion that evening 
primrose oil is similar to high-oleic safflower and sunflower oils 
based on fatty acid content is erroneous.
     More importantly, the petition does not seek to affirm the GRAS 
status of safflower oil and sunflower oil, both of which are common 
food items, but rather cocoa butter substitute derived by chemical 
processes from high-oleic safflower or sunflower oil. For these 
reasons, the agency finds this comment not relevant to the question of 
whether cocoa butter substitute derived from high-oleic safflower or 
sunflower oil is GRAS.

VIII. Conclusions

     Based on the published literature about the petitioned cocoa 
butter substitute and the data supporting the safety of cocoa butter 
substitute from palm oil, corroborated by widely available information 
about the safe consumption of glycerol and of oleic and stearic acids, 
the agency concludes that cocoa butter substitute from high-oleic 
safflower or sunflower oil is GRAS when used in accordance with CGMP 
(21 CFR 184.1(b)(1)).

IX. Environmental Effects

     The agency has carefully considered the potential environmental 
effects of this action. FDA has concluded that the action will not have 
a significant impact on the human environment, and that an 
environmental impact statement is not required. The agency's finding of 
no significant impact and the evidence supporting that finding, 
contained in an environmental assessment, may be seen in the Dockets 
Management Branch (address above) between 9 a.m. and 4 p.m., Monday 
through Friday.

X. Analysis of Impacts

     FDA has examined the impacts of this final rule under Executive 
Order 12866 and the Regulatory Flexibility Act (Pub. L. 96-354). 
Executive Order 12866 directs agencies to assess all costs and benefits 
of available regulatory alternatives and, when regulation is necessary, 
to select regulatory approaches that maximize net benefits (including 
potential economic, environmental, public health and safety, and other 
advantages; distributive impacts; and equity). According to Executive 
Order 12866, a regulatory action is significant if it meets any one of 
a number of specific conditions, including having an annual effect on 
the economy of $100 million; adversely affecting in a material way a 
sector of the economy, competition, or jobs; or raising novel legal or 
policy issues. The Regulatory Flexibility Act requires agencies to 
minimize the economic impact of their regulations on small businesses.
     FDA finds that this final rule is not a significant regulatory 
action as defined by Executive Order 12866. The rule does not raise 
novel legal or policy issues. The compliance cost to firms currently in 
the industry is zero because the rule prohibits no current activity. 
Potential benefits of the rule include the wider use of this cocoa 
butter substitute because of reduced uncertainty concerning its 
regulatory status, and any resources saved by eliminating the need to 
prepare further petitions to affirm the GRAS status of the use of this 
cocoa butter substitute.
     Finally, in compliance with the Regulatory Flexibility Act, FDA 
certifies that the final rule will not have a significant economic 
impact on a substantial number of small businesses. Therefore, under 
the Regulatory Flexibility Act, no further analysis is required.

XI. Effective Date

     As this rule recognizes an exemption from the food additive 
definition in the Federal Food, Drug, and Cosmetic Act, and from the 
approval requirements applicable to food additives, no delay in 
effective date is required by the Administrative Procedure Act (5 U.S.C 
553(d)). The rule will therefore be effective immediately (5 U.S.C. 
553(d)(1)).

XII. References

     The following references have been placed on display in the 
Dockets Management Branch (address above) and may be seen by interested 
persons between 9 a.m. and 4 p.m., Monday through Friday.

    1. Winter, G., ``A New Safflower Oil with a Low Iodine Value,'' 
Nature, 179:582-583, 1957.
    2. Knowles, P. F., A. B. Hill, and J. E. Ruckman, ``High Oleic 
Acid Content in New Safflower, UC-1,'' California Agriculture, p. 
15, 1965.
    3. Fick, G. N., ``Genetics and Breeding of Sunflower,'' Journal 
of the American Oil Chemists' Society, 60:1252-1253, 1983.
    4. Purdy, R. H., ``Oxidative Stability of High Oleic Sunflower 
and Safflower Oils,'' Journal of the American Oil Chemists' Society, 
62:523-525, 1985.-
    5. Smith, J. R., ``Safflower: Due for a Rebound,'' Journal of 
the American Oil Chemists' Society, 62:1286-1291, 1985.
    6. Purdy, R. H., ``High Oleic Sunflower: Physical and Chemical 
Characteristics,'' Journal of the American Oil Chemists' Society, 
63:1062-1066, 1986.

[[Page 36290]]

    7. Anonymous, ``U. S. Sun Crop: Potential Still not Realized,'' 
Journal of the American Oil Chemists' Society, 63:1218-1224, 1986.
    8. Faulkner, R. W., ``Cocoa Butter Equivalents are Truly 
Specialty Vegetable Fats,'' The Manufacturing Confectioner, pp. 56-
61, 1981.
    9. Memorandum from M. DiNovi, FDA to L. Lin, FDA, November 2, 
1988.
    10. Feuge, R. O. et al., ``Cocoa Butter-Like Fats from Domestic 
Oils,'' Journal of the American Oil Chemists' Society, 35:194-199, 
1958.
    11. Lehninger, A. L., Principles of Biochemistry, Worth 
Publishers, Inc., New York, NY, 1982.
    12. Memorandum from J. C. Griffiths, FDA to L. Lin, FDA, July 
14, 1989.
    13. Shimoda, T. et al., ``Safety Studies of a Transesterified 
Fat Produced by an Immobilized Lipase: I. Acute Oral Toxicity Study 
in Rats,'' Journal of the American College of Toxicology, 13 (Suppl. 
1):10-18, 1994.
    14. Shimoda, T. et al., ``Safety Studies of a Transesterified 
Fat Produced by an Immobilized Lipase: II. Subchronic Oral Toxicity 
and Recovery Studies in Rats,'' Journal of the American College of 
Toxicology, 13 (Suppl. 1):19-37, 1994.
    15. Shimoda, T. et al., ``Safety Studies of a Transesterified 
Fat Produced by an Immobilized Lipase: III. Bacterial Reversion 
Test,'' Journal of the American College of Toxicology, 13 (Suppl. 
1):38-45, 1994.
    16. MacRae, A. R., ``Lipase-Catalysed Interesterification of 
Oils and Fats,'' Journal of the American Oil Chemists' Society, 
60:291-294, 1983.

List of Subjects in 21 CFR Part 184

    Food ingredients.

    Therefore, under the Federal Food, Drug, and Cosmetic Act and under 
authority delegated to the Commissioner of Food and Drugs and 
redelegated to the Director, Center for Food Safety and Applied 
Nutrition, 21 CFR part 184 is amended as follows:

PART 184--DIRECT FOOD SUBSTANCES AFFIRMED AS GENERALLY RECOGNIZED 
AS SAFE

    1. The authority citation for 21 CFR part 184 continues to read as 
follows:

    Authority: Secs. 201, 402, 409, 701 of the Federal Food, Drug, 
and Cosmetic Act (21 U.S.C. 321, 342, 348, 371).

    2. Section 184.1259 is amended by revising the section heading and 
paragraph (a) to read as follows:


Sec. 184.1259  Cocoa butter substitute.

    (a) The common or usual name for the triglyceride 1-palmitoyl-2-
oleoyl-3-stearin is ``cocoa butter substitute primarily from palm 
oil.'' The common or usual name for the triglyceride 1-3-distearoyl-2-
olein is ``cocoa butter substitute primarily from high-oleic safflower 
or sunflower oil.''
    (1) The ingredient 1-palmitoyl-2-oleoyl-3-stearin is manufactured 
by:
    (i) Directed esterification of fully saturated 1,3-diglycerides 
(derived from palm oil) with the anhydride of food-grade oleic acid in 
the presence of the catalyst trifluoromethane sulfonic acid 
(Sec. 173.395 of this chapter), or
    (ii) By interesterification of partially saturated 1,2,3-
triglycerides (derived from palm oil) with ethyl stearate in the 
presence of a suitable lipase enzyme preparation that is either 
generally recognized as safe (GRAS) or has food additive approval for 
such use.
    (2) The ingredient 1-3-distearoyl-2-olein is manufactured by 
interesterification of partially unsaturated 1,2,3-triglycerides 
(derived from high-oleic safflower or sunflower oil) with ethyl 
stearate or stearic acid in the presence of a suitable lipase enzyme 
preparation that is either GRAS or has food additive approval for such 
use.
* * * * *

    Dated: June 13, 1996.
L. Robert Lake,
Director, Office of Policy, Planning and Strategic Initiatives, Center 
for Food Safety and Applied Nutrition.
[FR Doc. 96-17542 Filed 7-9-96; 8:45 am]
BILLING CODE 4160-01-F