Calcium stearoyl-2-lactylate: Difference between revisions - Wikipedia
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{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 450799296
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| ImageFile = Calcium stearoyl-2-lactylate.svg
| ImageSize = 250px
| IUPACNamePIN = calciumCalcium bis(2-(<nowiki/>{[2-octadecanoyloxypropanoyloxy(octadecanoyloxy)propanoyl]oxy}propanoate)
| OtherNames = {{Bulleted list
| OtherNames = octadecanoic acid, 2-(1-carboxyethoxy)-1-methyl-2-oxoethyl ester, calcium salt; calcium bis(2-{[2-(stearoyloxy)propanoyl]oxy}propanoate); calcium verate; calcium stearoyl lactylate; calcium stearoyl-2-lactylate; calcium stearyl-2-lactylate; calcium stelate; stearoyl-2-lactylic acid, calcium salt; calcium alpha-(alpha-(stearoyloxy)propionyloxy)propionate; calcium 2-(1-carboxyethoxy)-1-methyl-2-oxoethyloctadecanoate; stearic acid, ester with lactate of lactic acid, calcium salt; stearic acid ester with lactic acid bimol. ester calcium salt; calcium bis(2-(1-carboxylatoethoxy)-1-methyl-2-oxoethyl) distearate
| E482
| Section1 = {{Chembox Identifiers▼
| octadecanoic acid, 2-(1-carboxyethoxy)-1-methyl-2-oxoethyl ester, calcium salt
| CASNo = 5793-94-2▼
| calcium bis(2-<nowiki/>{[2-(stearoyloxy)propanoyl]oxy}propanoate)
| CASNo_Ref = {{cascite|correct|??}}▼
| calcium verate
| PubChem = 22037▼
| calcium stearoyl lactylate
| EINECS = 227-335-7▼
| calcium stearoyl-2-lactylate
| EC-number = E482
| calcium stearyl-2-lactylate
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}▼
| calcium stelate
| stearoyl-2-lactylic acid, calcium salt
| calcium alpha-(alpha-(stearoyloxy)propionyloxy)propionate
| calcium 2-(1-carboxyethoxy)-1-methyl-2-oxoethyloctadecanoate
| stearic acid, ester with lactate of lactic acid, calcium salt
| stearic acid ester with lactic acid bimol. ester calcium salt
| calcium bis(2-(1-carboxylatoethoxy)-1-methyl-2-oxoethyl) distearate
}}
▲| Section1 = {{Chembox Identifiers
▲| CASNo = 5793-94-2
▲| CASNo_Ref = {{cascite|correct|??}}
▲| PubChem = 22037
▲| EINECS = 227-335-7
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 30MXH4012A
▲| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 20709
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/2C24H44O6.Ca/c2*1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)29-21(3)24(28)30-20(2)23(26)27;/h2*20-21H,4-19H2,1-3H3,(H,26,27);/q;;+2/p-2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OEUVSBXAMBLPES-UHFFFAOYSA-L
| SMILES = O=C(C(C)OC(CCCCCCCCCCCCCCCCC)=O)OC(C)C([O-])=O.O=C(C(C)OC(CCCCCCCCCCCCCCCCC)=O)OC(C)C([O-])=O.[Ca2Ca+2]}}
| Section2 = {{Chembox Properties
| C=48 | H=86 | Ca=1 | O=12
| Appearance = a cream-colored nonhygroscopic powder with a caramel odor<ref name = FCC-CSL/><ref name="Ash"/>
| MeltingPtC = 45
| MeltingPt = 45 °C<ref name="Ash"/>
| SolubilityMeltingPt_ref = sparingly soluble<ref name="Ash"/>}}
| Solubility = sparingly soluble<ref name="Ash"/>}}
}}
'''Calcium stearoyl-2-lactylate''' (calcium stearoyl lactylate or CSL) or '''E482''' is a versatile, [[Regulation of food and dietary supplements by the U.S. Food and Drug Administration#Food additives|FDA approved]] [[food additive]]. It is one type of a commercially available [[lactylate]]. CSL is [[Toxicity|non-toxic]],<ref name="JECFA">{{cite book | editor = JECFA | year = 1974 | chapter = Toxicological Evaluation of Some Food Additives Including Anticaking Agents, Antimicrobials, Antioxidants, Emulsifiers and Thickening Agents 539. Stearoyl Lactic Acid, Calcium and Sodium Salts | title = Seventeenth Report of the Joint FAO/WHO Expert Committee on Food Additives, Who Food Additive Series 5}}</ref><ref name="Lamb">{{cite journal | last1 = Lamb | first1 = J. | last2 = Hentz | first2 = K. | last3 = Schmitt | first3 = D. | last4 = Tran | first4 = N. | first5 = D. | last5 = Jonker | first6 = K. | last6 = Junker, | title = A one-year oral toxicity study of sodium stearoyl lactylate (SSL) in rats | journal = [[Food and Chemical Toxicology]] | volume = 48 | issue = 10 | year = 2010 | pages = 2663–2669 | doi = 10.1016/j.fct.2010.06.037 | pmid = 20600527}}</ref> [[Biodegradation|biodegradable]],<ref name="Schaefer">{{Cite document | last1 = Schaefer | first1 = E.C | last2 = Matthews | first2 = M.E | title = Fatty Acids, C16-18 and C18-Unsaturated, Reaction Products with Lactic Acid and Monosodium Lactate (CAS# 847904-46-5): Ready Biodegradability by the Carbon Dioxide Evolution Test Method, Project No. 645E-101 for Caravan Ingredients | publisher = Wildlife International, Ltd. | place = Easton, Maryland | date = 2007. | postscript = {{inconsistent citations}}}}</ref> and typically manufactured using [[Renewable resource|biorenewable]] [[Raw material|feedstocks]].<ref name="Markley">{{cite book | last = Markley | first = K.S. | chapter = Historical and General | editor-last = Markley | editor-first = K.S. | title = Fatty Acids Their Chemistry, Properties, Production, and Uses Part 1 | publisher = Interscience Publishers, Inc. | place = New York | year = 1960 | pages = 16–21}}</ref><ref name="Baniel">{{Cite patent | inventor1-last = Baniel | inventor1-first = A.M. | inventor2-last = Eval | inventor2-first = A.M. | inventor3-last = Mizrahi | inventor3-first = J. | inventor4-last = Hazan | inventor4-first = B. | inventor5-last = Fisher | inventor5-first =Hazan, R.R. | inventor6-last = Kolstad | inventor6-first =Fisher, J.J. | inventor7-last = Stewart | inventor7-first =Kolstad, B.F. Stewart | title = Lactic Acid Production, Separation, and/or Recovery Process | patent-number = 5892109 | country-code = US | issue-date = Apr. 6, 1999 | postscript = {{inconsistent citations}}}}</ref> Because CSL is a safe and highly effective food additive, it is used in a wide variety of products from [[Baking|baked goods]] and [[dessert]]s to [[packaging]].<ref name="Ash">{{cite book | title = Handbook of Green Chemicals | edition = 2 | last1 = Ash | first1 = M. | last2 = Ash | first2 = I. | publisher = Synapse Information Resources | year = 2004 | place = Endicott, NY | page = 400 | unused_data = 654, 868, 875-876, 882}}</ref><ref name="CFR-CSL">{{Cite book | title = Title 21 Code of Federal Regulations, part 172 | chapter = Calcium stearoyl-2-lactylate | date = January 1, 2010 | postscript = {{inconsistent citations}}}}</ref><ref name="EU1">{{cite journal | title = Regulation (EC) No 95/2 of the European Parliament and of the Council of 20 February 1995 on Food Additives Other Than Colours and Sweeteners |url=https://www.fsai.ie/uploadedFiles/European_Parliament_and_Council_Directive_No_95_2_EC.pdf| journal = Official Journal of the European Union | date = 1995-03-18 | pages = L61/1–63}}</ref><ref name="CFR-CSL3">{{Cite book | title = Title 21 Code of Federal Regulations, part 172 | chapter = Cellophane | date = January 1, 2010 | postscript = {{inconsistent citations}}}}</ref>
As described by the [[United States Pharmacopeia|Food ChemicalChemicals Codex]] 7th edition, CSL is a cream-colored powder.<ref name="FCC-CSL">{{cite book | title = Food Chemical Codex | edition = 7 | chapter = Calcium Stearoyl Lactylate | pages = 157–159}}</ref> CSL is currently manufactured by the esterification of [[stearic acid]] and [[lactic acid]] with partial neutralization using food-grade hydrated lime ([[calcium hydroxide]]). Commercial grade CSL is a mixture of calcium salts of stearoyl lactic acid, with minor proportions of other salts of related acids. The [[Hydrophilic-lipophilic balance|HLB]] for CSL is 5.1. It is slightly soluble in hot water. The [[pH]] of a 2% aqueous suspension is approximately 4.7.<ref name="Ash" />
==Food labeling requirements==
To be labeled as CSL for sale within the United States, the product must conform to the specifications detailed in 21 CFR 172.844.<ref name = CFR-CSL/> In the EU, the product must conform to the specifications detailed in Regulation (EC) No 96/77.<ref name="EU2">{{cite journal |url=http://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX%3A32001L0030| title = Regulation (EC) No 96/77 of the European Parliament and of the Council of 2 December 1996 on Laying Down Specific Purity Criteria on Food Additives Other Than Colours and Sweeteners | journal = Official Journal of the European Union | date = 1996-12-30 | pages = L339/1–171}}</ref> Tests for these specifications can be found in the Food Chemical Codex,.<ref name = FCC-CSL/> Acceptance criteria for these two regions are as follows:
{| class="wikitable"
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|- style="text-align:center;"
| [[Acid value|Acid Value]]
| 50 - 86
| 50 - 130
|- style="text-align:center;"
| Calcium Content
| 4.2% - 5.2%
| 1% - 5.2%
|- style="text-align:center;"
| Ester Value
| 125 - 164
| 125 - 190
|- style="text-align:center;"
| Total Recoverable Lactic Acid
| 32.0% - 38.0%
| 15% - 40%
|}
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==Food applications and maximum use levels==
CSL finds widespread application in [[Baking|baked goods]], [[cereal]]s, [[pastas]], [[instant rice]], [[dessert]]s, [[Icing (food)|icings]], [[Buttercream|fillings]], [[pudding]]s, [[Cake#Cake decorating|toppings]], [[Confectionery|sugar confectionaries]], powdered [[Drink#Hot beverages|beverage mixes]], [[Non-dairy creamer|creamers]], [[cream liqueur]]s, [[Instant mashed potatoes|dehydrated potatoes]], [[Dip (food)|snack dips]], [[sauce]]s, [[Gravy|gravies]], [[chewing gum]], [[Diet food|dietetic foods]], minced and diced [[Potted meat|canned meats]], and [[Mostarda|''mostarda di frutta'']].<ref name="EU1" /><ref name="CFR-SSL">{{Cite book | title = Title 21 Code of Federal Regulations, part 172 | chapter = Sodium stearoyl lactylate | date = January 1, 2010 | postscript = {{inconsistent citations}}}}</ref> In the United States, approved uses and use levels are described in 21 CFR 172.844,<ref name = CFR-CSL/> 21 CFR 176.170<ref name="CFR-CSL2">{{Cite book | title = Title 21 Code of Federal Regulations, part 172 | chapter = Components of paper and paperboard in contact with aqueous and fatty foods. | date = January 1, 2010 | postscript = {{inconsistent citations}}}}</ref> and 21 CFR 177.120.<ref name = CFR-CSL3/> while the corresponding regulations in the EU are listed in Regulation (EC) No 95/2.<ref name="EU1"/>
{| class="wikitable"
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|- style="text-align:center;"
!Application
!Maximum Useuse Levellevel
!Application
!Maximum Useuse Levellevel
!Application
!Maximum Useuse Levellevel
!Application
!Maximum Useuse Levellevel
|- style="text-align:center;"
|Yeast Yeast-leavened bakery products
| style ="text-align:left;"| 0.5% of flour
| Fine baked goods
| style ="text-align:left;"| 5 g/kg
| Bread
| style ="text-align:left;"| 3 g/kg
| Breakfast cereals
| style ="text-align:left;"| 5 g/kg
|- style="text-align:center;"
| Liquid and frozen egg whites
| style ="text-align:left;"| 0.05%
| Fat Emulsionsemulsions
| style ="text-align:left;"| 10 g/kg
| Desserts
| style ="text-align:left;"| 5 g/kg
| Sugar confectionaryconfectionery
| style ="text-align:left;"| 5 g/kg
|- style="text-align:center;"
| Dried egg whites
| style ="text-align:left;"| 0.5%
| Beverage whiteners
| style ="text-align:left;"| 3 g/kg
| Hot powder beverage mixes
| style ="text-align:left;"| 2 g/Ll
| Dietetic foods
| style ="text-align:left;"| 2 g/Ll
|- style="text-align:center;"
| Whipped vegetable oil topping
| style ="text-align:left;"| 0.3%
|Quick Quick-cook rice
| style ="text-align:left;"| 4 g/kg
| Minced and diced canned meats
| style ="text-align:left;"| 4 g/kg
| ''Mostarda di frutta''
| style ="text-align:left;"| 2 g/kg
|- style="text-align:center;"
| Dehydrated potatoes
| style ="text-align:left;"| 0.5%
| Cereal-based snacks
| style ="text-align:left;"| 2 g/kg
| Cereal- and potato-based snacks
| style ="text-align:left;"| 5 g/kg
| Chewing gum
| style ="text-align:left;"| 2 g/kg
|- style="text-align:center;"
| [[Paper]] and [[paperboard]] [[packaging]] component
| style ="text-align:left;"| Not Limitedlimited
| Emulsified Liqueurliqueur
| style ="text-align:left;"| 8 g/Ll
| Spirits <15% alcohol
| style ="text-align:left;"| 8 g/Ll
| colspan ="2" |
|- style="text-align:center;"
| [[Cellophane]]
| style ="text-align:left;"| 0.5% weight of cellophane
| colspan ="4" |
|}
The largest application of CSL is in yeast leavened bakery products. Although CSL was introduced to the market first, most applications utilizeuse [[Lactylate#Sodium_stearoylSodium stearoyl-2-lactylate|SSL]]. The main reason for the preference of SSL over CSL is that CSL has less crumb softening effects than SSL. However, CSL is still preferred in some applications, such as lean hearth bread -type formulations. In these applications, CSL is preferred because CSL performs better than SSL as a dough strengthener, while the finished product does not require a soft crumb or a perfectly symmetrical loaf shape.<ref name="Boutte">{{cite book | last1=Boutte | first1=T. | last2 = Skogerson | first2=L. | chapter = Stearoyl-2-lactylates and oleoyl lactylates | title = Emulsifiers in Food Technology | editor-last = Whitehurst | editor-first=R.J | publisher = Blackwell Publishing | place = Oxford | year=2004 | pages=207–225|doi=10.1002/9780470995747.ch9|isbn=9780470995747}}</ref>
==References==
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[[Category:Food additives]]
[[Category:LactatesSalts of carboxylic acids]]
[[Category:Calcium compounds]]
[[Category:E-number numbersadditives]]
[[de:Calciumstearoyl-2-lactylat]]
[[hu:Kalcium-sztearoil-2-laktilát]]