| Revision as of 15:46, 12 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 418787460 |
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| Watchedfields = changed |
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| verifiedrevid = 428771482 |
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| ImageFile = Sodium stearoyl lactylate.svg |
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| ImageFile = Sodium stearoyl lactylate.svg |
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| ImageSize = 250px |
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| ImageSize = 250px |
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| ImageClass = skin-invert |
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| ImageAlt = |
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| ImageAlt = |
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| IUPACName = Sodium 2-((2-(stearoyloxy)propanoyl)oxy)propanoate |
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| PIN = Sodium 2-<nowiki/>{oxy}propanoate |
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| OtherNames = Sodium stearoyl-2-lactylate; Sodium stelate |
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| OtherNames = octadecanoic acid, 2-(1-carboxyethoxy)-1-methyl-2-oxoethyl ester, sodium salt; sodium 2-<nowiki/>{oxy}propanoate; sodium stearoyl lactylate; sodium stearoyl-2-lactylate; sodium stearyl-2-lactylate; sodium 2-stearoyllactylate; sodium stelate; stearoyl-2-lactylic acid, sodium salt; sodium alpha-(alpha-(stearoyloxy)propionyloxy)propionate; sodium 2-(1-carboxyethoxy)-1-methyl-2-oxoethyloctadecanoate; ], ester with lactate of ], sodium salt; stearic acid ester with lactic acid bimol. ester sodium salt; sodium 2-(1-carboxylatoethoxy)-1-methyl-2-oxoethyl stearate |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 25383-99-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 25383-99-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 23671849 |
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| UNII = IN99IT31LN |
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| SMILES = O=C(C(C)OC(CCCCCCCCCCCCCCCCC)=O)OC(C)C()=O.}} |
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| PubChem = 23671849 |
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| Section2 = {{Chembox Properties |
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| EC_number = 246-929-7 |
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| C=24|H=43|Na=1|O=6 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Appearance = |
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| ChemSpiderID = 8065662 |
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| Density = 1.063 g/cm<sup>3</sup><ref name=sciencelab> at sciencelab.com</ref> |
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| InChI = 1S/C24H44O6.Na/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25) |
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| MeltingPtC = 49 |
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29-21(3)24(28)30-20(2)23(26)27;/h20-21H,4-19H2,1-3H3,(H,26,27);/q;+1/p-1 |
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| Melting_notes = <ref name=sciencelab/> |
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| SMILES = O=C(C(C)OC(CCCCCCCCCCCCCCCCC)=O)OC(C)C()=O.}} |
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| BoilingPt = |
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|Section2={{Chembox Properties |
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| Solubility = }} |
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| C=24 | H=43 | Na=1 | O=6 |
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| Section3 = {{Chembox Hazards |
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| Appearance = a white or cream-colored powder with a caramel odor<ref name = FCC-SSL>{{cite book | title = Food Chemical Codex | edition = 7 | chapter = Sodium Stearoyl Lactylate | pages = 964–965}}</ref><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 | pages= 400, 654, 868, 875–876, 882}}</ref> |
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| MainHazards = |
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| Density = 1.063 g/cm<sup>3</sup><ref name=sciencelab> {{Webarchive|url=https://web.archive.org/web/20080319235253/http://www.sciencelab.com/page/S/PVAR/10426/SLS2431 |date=2008-03-19 }} at sciencelab.com</ref> |
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| FlashPt = |
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| Autoignition = }} |
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| MeltingPtC = 49 |
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| MeltingPt_ref = <ref name=sciencelab/> |
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| BoilingPt = |
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| Solubility = dispersible in warm water<ref name = Ash/>}} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPtC = }} |
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'''Sodium stearoyl-2-lactylate''' (sodium stearoyl lactylate or SSL) is a versatile, ] ] used to improve the mix tolerance and volume of processed foods. It is one type of a commercially available ]. SSL is ],<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 = ] | volume = 48 | issue = 10 | year = 2010 | pages= 2663–2669 | doi=10.1016/j.fct.2010.06.037 | pmid=20600527}}</ref> ],<ref name = Schaefer>{{citation | 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 | year = 2007}}</ref> and typically manufactured using ] ].<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 = B. Hazan, R.R. Fisher, J.J. Kolstad, B.F. Stewart| title = Lactic Acid Production, Separation, and/or Recovery Process | patent-number = 5892109 | country-code = US | issue-date = Apr. 6, 1999}}</ref> Because SSL is a safe and highly effective food additive, it is used in a wide variety of products ranging from ] and ]s to ]s.<ref name = Ash/><ref name = CFR-SSL>{{citation | title = Title 21 Code of Federal Regulations, part 172 | chapter = Sodium stearoyl lactylate | date = January 1, 2010}}</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 | journal = Official Journal of the European Union | date = 1995-03-18 | pages = L61/1–63}}</ref><ref name = AAFCO>{{cite book | last = AAFCO | chapter = Feed Ingredients | title = Feed Inspector's Manual | edition = 2nd | publisher = Association of American Feed Control Officials Inspection and Sampling Committee | place = Oxford, IN | year = 2000 | pages = 13–14}}</ref><ref name = CFR-CSL3>{{citation | title = Title 21 Code of Federal Regulations, part 172 | chapter = Cellophane | date = January 1, 2010}}</ref> |
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'''Sodium stearoyl lactate''' and '''calcium stearoyl lactate''' ('''stearoyl-2-lactylates''') are ]s used as a ]s (] E481) in the ]. |
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As described by the ] 7th edition, SSL is a cream-colored powder or brittle solid.<ref name = FCC-SSL/> SSL is currently manufactured by the esterification of ] with ] and partially neutralized with either food-grade soda ash (]) or caustic soda (concentrated ]). Commercial grade SSL is a mixture of ] ] of stearoyl lactylic acids and minor proportions of other sodium salts of related acids. The ] for SSL is 10–12. SSL is slightly ], soluble in ] and in hot oil or fat, and dispersible in warm water.<ref name = Ash/> These properties are the reason that SSL is an excellent ] for fat-in-water emulsions<ref name = Narsimhan>{{cite book | last1=Nylander | first1=G. |last2=Wang | first2=Z. | chapter = Guidelines for Processing Emulsion-Based Foods | title = Food Emulsifiers and Their Applications | editor1-last=Hasenhettl | editor1-first=G.L. | editor2-last = Hartel | editor2-first = R.W. | publisher=Springer | place = New York | year = 2010 | edition = 2 | pages = 349–394}}</ref> and can also function as a ].<ref name = Orthoefer>{{cite book | last1=Orthoefer | first1=F. | chapter = Applications of Emulsifiers in Baked Foods | title = Food Emulsifiers and Their Applications | editor1-last=Hasenhettl | editor1-first=G.L. | editor2-last = Hartel | editor2-first = R.W. | publisher=Springer | place = New York | year = 2010 | edition = 2 | pages = 263–284}}</ref> |
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They are produced by first esterifying ] to produce ], performing a second esterification with ], and then reacting the result with ] or ] to make the ] or ] ]. These salts are used as ]s in processed foods. |
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==Food labeling requirements== |
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Replacing the lactic acid with ] gives ], a compound with similar uses. |
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To be labeled as SSL for sale within the United States, the product must conform to the specifications detailed in 21 CFR 172.846<ref name = CFR-SSL/> and the “Food Chemicals Codex,” 3d Ed. (1981), pp. 300-301. In the EU, the product must conform to the specifications detailed in Regulation (EC) No 96/77.<ref name = EU2>{{cite journal | 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> For the 7th edition of the FCC<ref name = FCC-SSL/> and Regulation (EC) No 96/77, these specifications are: |
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{| class="wikitable" |
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The commercially available food additive is not composed of chemically pure stearoyl-2-lactylate. Rather, the lactic acid esterification produces a variety of polylactyls (typically numbering from one to three lactyl groups), while the chain length of the acyl fatty acid may also vary from 14 to 22 carbons, thus including palmitic and arachidic acid. Pure stearoyl-2-lactylates can be produced through an intermediate ] ] derivative.<ref>{{cite journal | last1 = Elliger | first1 = Carl A. | title = A convenient preparation of pure stearoyl-2-lactylic acid | journal = Journal of Agricultural and Food Chemistry | volume = 27 | pages = 527 | year = 1979 | doi = 10.1021/jf60223a037}}</ref> |
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!Specific Test |
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!Acceptance Criterion (FCC) |
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!Acceptance Criterion (EU) |
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|] |
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| 60-80 |
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| 60 - 130 |
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| Ester Value |
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| 150 - 190 |
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| 90 - 190 |
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|- align = "center" |
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| Sodium Content |
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| 3.5% - 5.0% |
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| 2.5% - 5% |
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| Total Recoverable Lactic Acid |
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| 31.0% - 34.0% |
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| 15% - 40% |
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To be labeled as SSL for sale in other regions, the product must conform to the specifications detailed in that region's codex. |
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== Applications == |
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Sodium stearoyl-2-lactylate is an emulsifier with a very high hydrophilic-lipophilic balance (HLB) and is therefore an excellent ] for fat-in-water emulsions. It also functions as a humectant. It finds widespread application in baked goods, liqueurs, cereals, chewing gum, desserts, and powdered beverage mixes. Stearoyl-2-lactylates are found in the majority of manufactured ]s, ]s, wraps and ]s, and many similar bread-based products.{{Citation needed|date=March 2009}} |
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Because of its efficiency as an emulsifier, it is possible to use less of it than other similar additives; for example, it can be used in quantities only a tenth as large as soya-based emulsifiers. |
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== Health and safety == |
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==Food applications and maximum use levels== |
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SSL finds widespread application in ], ]s, ]s, ]s, ], ], ]s, ], ], ]s, ], ], powdered ], ], ]s, ], ], ]s, ], ], ], minced and diced ], ], and ].<ref name = CFR-SSL/><ref name=EU1/><ref name = AAFCO/> Approved uses and maximum use levels in the United States are described in 21 CFR 172.846<ref name = CFR-SSL/> and 21 CFR 177.120.<ref name = CFR-CSL3/> In the European Union, the approved uses and maximum use levels are described in Regulation (EC) No 95/2.<ref name=EU1/> |
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Current applications are generally not restricted for health and safety reasons with regards to traditional uses of this emulsifier. Dietary studies in rats and dogs found no effect when this additive constituted less than 2.5% of the diet. The approximate {{LD50}} was found to be 30 g/kg for rats - which would correspond to an intake of nearly 2 kilograms for an adult man. |
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{| class="wikitable" |
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In the United States, sodium stearoyl-2-lactylate is approved for use in foods as described in FDA 21CFR 172.846. Maximum usage levels of 0.5% based on flour in the U.S. and 0.375% in Canada. |
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!colspan="2" | United States |
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!colspan="4" | European Union |
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!Application |
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!Maximum Use Level |
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!Application |
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!Maximum Use Level |
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!Application |
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!Maximum Use Level |
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| Baked goods, pancakes, waffles |
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| align = "left" | 0.5% of flour |
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| Fine baked goods |
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| align = "left" | 5 g/kg |
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| Bread |
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| align = "left" | 3 g/kg |
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|- align = "center" |
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| Icings, fillings, puddings, toppings |
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| align = "left" | 0.2% |
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| Fat Emulsions |
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| align = "left" | 10 g/kg |
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| Desserts |
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| align = "left" | 5 g/kg |
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| Beverage creamers |
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| align = "left" | 0.3% |
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| Beverage whiteners |
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| align = "left" | 3 g/kg |
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| Hot powder beverage mixes |
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| align = "left" | 2 g/L |
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|- align = "center" |
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| Dehydrated potatoes |
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| align = "left" | 0.5% |
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| Quick cook rice |
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| align = "left" | 4 g/kg |
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| Breakfast cereals |
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| align = "left" | 5 g/kg |
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|- align = "center" |
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| Snack dips |
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| align = "left" | 0.2% |
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| Cereal-based snacks |
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| align = "left" | 2 g/kg |
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| Cereal- and potato-based snacks |
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| align = "left" | 5 g/kg |
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|- align = "center" |
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| Sauces and gravies |
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| align = "left" | 0.25% |
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| Minced and diced canned meats |
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| align = "left" | 4 g/kg |
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|''Mostarda di frutta'' |
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| align = "left" | 2 g/kg |
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|- align = "center" |
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| Prepared mixes of above |
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| align = "left" | As indicated above |
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| Chewing gum |
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| align = "left" | 2 g/kg |
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| Sugar confectionery |
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| align = "left" | 5 g/kg |
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|- align = "center" |
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| Cream liqueurs |
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| align = "left" | 0.5% |
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| Emulsified Liqueur |
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| align = "left" | 8 g/L |
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| Spirits <15% alcohol |
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| align = "left" | 8 g/L |
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|- align = "center" |
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|] |
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| align = "left" | 0.5% weight of cellophane |
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| Dietetic foods |
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| align = "left" | 2 g/L |
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The largest marketed use of SSL is in ]-raised bakery products. SSL is used in the majority of manufactured ]s, ]s, ]s, ]s, and similar bread-based products to ensure consistent product quality. Use levels for baked goods will vary between 0.25 - 0.5% based on flour. The typical application level is 0.375% and will be adjusted depending on the type and quality of ] used.<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 | url=https://archive.org/details/emulsifiersfoodt00whit | url-access=limited | editor-last = Whitehurst | editor-first=R.J | publisher = Blackwell Publishing | place = Oxford | year=2004 | pages=–225| isbn=9781405118026 }}</ref> |
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] |
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Compared to ] (CSL), SSL offers some advantages. First, SSL disperses and hydrates more readily in water than CSL. Therefore, SSL does not require pre-hydration. Second, SSL provides better crumb softening than CSL. SSL's crumb softening effect is noticeable up to 5–7 days after baking. Third, in rich bread formulations (e.g. pan bread and hamburger buns), SSL provides better dough strengthening than CSL. Use of SSL in these formulations will yield (nearly) perfect symmetry in the finished baked good. Because of these characteristics, SSL is currently used in more baking applications than CSL.<ref name = Boutte/> |
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Research has explored the possibility of replacing SSL with the use of ]. Enzyme technologies, by themselves, have not been able to completely replace SSL. A major limitation of enzymes is the production of gummy bread of unpredictable quality. Also, enzymes often do not augment dough strength, which is necessary to prevent loaf collapse during baking. Currently, enzymes are being used in conjunction with SSL to maximize the shelf life of bread. SSL is very good at increasing softness of bread during the first week after baking. Enzyme technology works best after the first five days of shelf life. Therefore, bread with optimal softness throughout the desired shelf life is obtained by using a combination of these technologies.<ref name = Boutte/> |
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== Health and safety == |
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], including SSL, have been subjected to extensive safety evaluations prior to being ] for use as a food additive.<ref name = Lamb/> The oral ] of SSL for rats was established by Schuler and Thornton in 1952 as being over 25 g/kg body weight.<ref name = JECFA/> In 2010, Lamb established the ] of SSL at 5% of the total diet and recommended an ] of 22.1 mg/kg bw/day for human consumption.<ref name = Lamb/> |
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==References== |
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==References== |
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