PRODUCTS

SODIUM STEAROYL-2-LACTYLATE

SODIUM STEAROYL LACTYLATE

SSL

CAS Number: 25383-99-7
Chemical formula: C24H43NaO6
Molecular Weight: 450.592

Sodium stearoyl-2-lactylate (sodium stearoyl lactylate or SSL) is a versatile, FDA approved food additive used to improve the mix tolerance and volume of processed foods.
Sodium stearoyl-2-lactylate is one type of a commercially available lactylate.

Sodium stearoyl-2-lactylate is non-toxic, biodegradable, and typically manufactured using biorenewable feedstocks.
Because Sodium stearoyl-2-lactylate is a safe and highly effective food additive, Sodium stearoyl-2-lactylate is used in a wide variety of products ranging from baked goods and desserts to pet foods.

As described by the Food Chemicals Codex 7th edition, Sodium stearoyl-2-lactylate is a cream-colored powder or brittle solid.
Sodium stearoyl-2-lactylate is currently manufactured by the esterification of stearic acid with lactic acid and partially neutralized with either food-grade soda ash (sodium carbonate) or caustic soda (concentrated sodium hydroxide).

Commercial grade Sodium stearoyl-2-lactylate is a mixture of sodium salts of stearoyl lactylic acids and minor proportions of other sodium salts of related acids.
The HLB for Sodium stearoyl-2-lactylate is 10-12.

Sodium stearoyl-2-lactylate is slightly hygroscopic, soluble in ethanol and in hot oil or fat, and dispersible in warm water.
These properties are the reason that Sodium stearoyl-2-lactylate is an excellent emulsifier for fat-in-water emulsions and can also function as a humectant.

Sodium stearoyl-2-lactylate is a white or light yellow powder or a brittle solid with a characteristic smell.
Sodium stearoyl-2-lactylate is a combination of sodium salts of stearoyl lactylic acids and minor proportions of sodium salts of related acids.

Sodium stearoyl-2-lactylate is a plant-derived ingredient.
Sodium stearoyl-2-lactylate is used in hundreds of personal care and cosmetic products, including moisturizer, sunscreen, baby lotion, conditioner, foundation, body wash and other products.
Sodium stearoyl-2-lactylate does not dissolve in water.

In our products, sodium stearoyl lactylate is a moisturizer that helps the skin stay soft and pliable.
However, Sodium stearoyl-2-lactylate is also an effective, food-grade emulsifier, stabilizer and a surfactant.

As a result, Sodium stearoyl-2-lactylate is a common food additive and dough strengthener often found in baked products, puddings, fillings, dips, gravies, liqueurs and other prepared foods.
Sodium stearoyl-2-lactylate also has a sweet taste, which allows food manufacturers to add less sugar.

Sodium stearoyl-2-lactylate is a versatile emulsifier used in bread, buns and other bakery products as a dough strengthener and crumb softener.

Due to Sodium stearoyl-2-lactylate ionic and nonpolar nature, Sodium stearoyl-2-lactylate is able to interact with gluten proteins promoting their aggregation.
Sodium stearoyl-2-lactylate nonpolar portion allows Sodium stearoyl-2-lactylate to interact with the hydrophobic regions of starch to delay the onset of staling.

The linear-shaped chemical structure of Sodium stearoyl-2-lactylate gives Sodium stearoyl-2-lactylate te capacity to access gelatinized amylose inner helix.
Sodium stearoyl-2-lactylate lipophilic moiety binds to the interior of the helix and the hydrophilic side to water, hence retarding retrogradation.

Sodium stearoyl-2-lactylate or Sodium stearoyl-2-lactylate, also known as Sodium stearoyl-2-lactylate (abbreviation), Sodium stearoyl-2-lactylate is the sodium salt of stearic acid with lactic acid dimer.
Sodium stearoyl-2-lactylate is commonly used as an emulsifier and stabilizer in high-fat bakery and with the European food additive number E481.

Together with calcium stearoyl lactylate (E482), they are the second category (lactylates) of popular emulsifier after mono- and diglycerides of fatty acids in food applications.

The phase behaviour of Sodium stearoyl-2-lactylate in water varies according to the pH of the system as Sodium stearoyl-2-lactylate contains a considerable amount of free fatty acids.
When Sodium stearoyl-2-lactylate is dispersed in water at a pH below 5, Sodium stearoyl-2-lactylate forms hexagonal II phases above Sodium stearoyl-2-lactylate Krafft point (approx. 45 °C) At a higher pH, the fatty acids are ionised and lamellar phases form at a temperature of 45–85 °C.
Combinations of Sodium stearoyl-2-lactylate and distilled, saturated monoglycerides are used as aqueous dispersions to improve the aeration of bakery products (cakes) or low-fat, non-dairy whipping creams.

Sodium 2-{[2-(octadecanoyloxy)propanoyl]oxy}propanoate belongs to the class of organic compounds known as tricarboxylic acids and derivatives.
These are carboxylic acids containing exactly three carboxyl groups.

Food Additive Definition of Sodium stearoyl-2-lactylate:

EU Food Additive Definition:
A mixture of the sodium salts of stearoyl lactylic acids and Sodium stearoyl-2-lactylate polymers and minor amounts of sodium salts of other related acids, manufactured by the reaction of stearic acid and lactic acid.
Other food fatty acids may also be present, free or esterified, due to their presence in the stearic acid used.

Food labeling requirements:
To be labeled as Sodium stearoyl-2-lactylate for sale within the United States, Sodium stearoyl-2-lactylate must conform to the specifications detailed in 21 CFR 172.846 and the most recent edition of the Food Chemical Codex.
In the EU, the product must conform to the specifications detailed in Regulation (EC) No 96/77.
For the 7th edition of the FCC and Regulation (EC) No 96/77, these specifications are:

Specific Test - Acceptance Criterion (FCC) - Acceptance Criterion (EU)
Acid Value   - 50 - 86   - 60 - 130
Ester Value - 120 - 190   - 90 - 190
Sodium Content - 3.5% - 5.0% -     2.5% - 5%
Total Recoverable Lactic Acid - 23.0% - 34.0%   - 15% - 40%

To be labeled as Sodium stearoyl-2-lactylate for sale in other regions, Sodium stearoyl-2-lactylate must conform to the specifications detailed in that region's codex.

Food applications and maximum use levels:
Sodium stearoyl-2-lactylate finds widespread application in baked goods, pancakes, waffles, cereals, pastas, instant rice, desserts, icings, fillings, puddings, toppings, sugar confectionaries, powdered beverage mixes, creamers, cream liqueurs, dehydrated potatoes, snack dips, sauces, gravies, chewing gum, dietetic foods, minced and diced canned meats, mostarda di frutta, and pet food.
Approved uses and maximum use levels in the United States are described in 21 CFR 172.846 and 21 CFR 177.120.
In the European Union, the approved uses and maximum use levels are described in Regulation (EC) No 95/2.

The largest marketed use of Sodium stearoyl-2-lactylate is in yeast-raised bakery products.
Sodium stearoyl-2-lactylate is used in the majority of manufactured breads, buns, wraps, tortillas, 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 flour used.

Compared to calcium stearoyl-2-lactylate (CSL), Sodium stearoyl-2-lactylate offers some advantages.
First, Sodium stearoyl-2-lactylate disperses and hydrates more readily in water than CSL.

Therefore, Sodium stearoyl-2-lactylate does not require pre-hydration.
Second, Sodium stearoyl-2-lactylate provides better crumb softening than CSL.

Sodium stearoyl-2-lactylate crumb softening effect is noticeable up to 5–7 days after baking.
Third, in rich bread formulations (e.g. pan bread and hamburger buns), Sodium stearoyl-2-lactylate provides better dough strengthening than CSL.

Use of Sodium stearoyl-2-lactylate in these formulations will yield (nearly) perfect symmetry in the finished baked good.
Because of these characteristics, Sodium stearoyl-2-lactylate is currently used in more baking applications than CSL.

Research has explored the possibility of replacing Sodium stearoyl-2-lactylate with the use of enzymes.
Enzyme technologies, by themselves, have not been able to completely replace Sodium stearoyl-2-lactylate.

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 Sodium stearoyl-2-lactylate to maximize the shelf life of bread.
Sodium stearoyl-2-lactylate 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.

Function of Sodium stearoyl-2-lactylate:
Sodium stearoyl-2-lactylate provides the following functionality in baked goods:

Improves the textural shelf-life of bread and buns
Produces softer and more pliable tortillas

Boosts ovenspring by enhancing gas retention capacity of dough
Imparts greater sidewall strength to loaves (prevention of keyholing)
Gives bread a desirable resilient crumb

Application of Sodium stearoyl-2-lactylate:
SLA, the primitive form of Sodium stearoyl-2-lactylate, is a waxy solid that is difficult to disperse in bread doughs and cake batters.
As for Sodium stearoyl-2-lactylate, Sodium stearoyl-2-lactylate is a brittle solid that is readily soluble in water.

Also, Sodium stearoyl-2-lactylate can be converted to a fine powder.
The powder form can be conveniently added to the mixing bowl along with other dough ingredients.

Sodium stearoyl-2-lactylate is also soluble in hot shortening.
Sodium stearoyl-2-lactylate can be pre-melted into the fat as an alternate method of incorporation.

In bread and bun formulations, Sodium stearoyl-2-lactylate levels range from 0.3 to 0.5% (baker’s %).
Adding Sodium stearoyl-2-lactylate into flour brews (liquid sponges) is beneficial for minimizing foaming in fermentation and holding tanks.

In “composite flours,” Sodium stearoyl-2-lactylate has traditionally permitted the use of a considerable proportion of non-wheat flours (e.g. corn flour, rye flour, whole grains) to make high quality bread using no-time or straight dough systems.

Application Area of Sodium stearoyl-2-lactylate:
Sodium stearoyl-2-lactylate is primarily used for Sodium stearoyl-2-lactylate emulsifying and stabilizing properties in food and cosmetics.
In food, Sodium stearoyl-2-lactylate mixes water and oil together and mostly used as a dough strengthener and crumb softener in bakery; in cosmetics, Sodium stearoyl-2-lactylate is a viscosity enhancer and conditioner.

Food:
Sodium stearoyl-2-lactylate is mainly used in high fat & yeast-leavened bread as a dough conditioner/emulsifier for the purposes of:

dough strengthening: increase volume and obtain a better crumb structure
crumb softening: interacts with flour to form gluten proteins/starch/lactylate complex which produce a soft and elastic bread and prevents bread retrogradation (aging)
If without Sodium stearoyl-2-lactylate, the loaf will become hardened.

Sodium stearoyl-2-lactylate is also used in cookies, crackers, pastries, noodles, and the like to improve the texture, mouthfeel and prolong the freshness or shelf time.
In cookie and cracker, Sodium stearoyl-2-lactylate is used to distribute shortening uniformly in the dough.

Sodium stearoyl-2-lactylate can be directly added to flour or dispersed in warm water and then blended with flour for use.

Other food may contain with Sodium stearoyl-2-lactylate:
Whipped toppings and desserts (an aerating agent)
Non-dairy coffee creamers (a complexing agent stable the emulsion)
Whitening powder ( a fat replacer)
Spreads
Cosmetics
Sodium stearoyl-2-lactylate is used as an emulsifying agent (3) to stabilize oil-in-water formulations of cosmetics and personal care products.

Sodium stearoyl-2-lactylate may be found in the following cosmetics:

Skin care products:
Shampoo
Lotion

Intendet Usage of Sodium stearoyl-2-lactylate:
Sodium stearoyl-2-lactylate enhances dough standard and the volume capacity of leavened products.
Sodium stearoyl-2-lactylate ensures thin bread crust formed

Sodium stearoyl-2-lactylate retards staling
Sodium stearoyl-2-lactylate ensures quality products are produced with frozen leavened products

Little pore structure of pastry and cakes ( sponge cakes) ensures long term freshness.
Albumin enhances shaking quality

Uses of Sodium stearoyl-2-lactylate:
Personal care - eye care and contacts - eye cream
Personal care - general moisturizing - hand/body lotion
Antibacterial
Biocide
Emulsifying

Approved uses of Sodium stearoyl-2-lactylate:
Sodium stearoyl-2-lactylate application is listed together with calcium stearoyl lactylate (E482) with the maximum permitted levels (MPLs) from 1000 to 10000 mg/kg in foods.

The following food may contain Sodium stearoyl-2-lactylate:
Flavoured fermented milk products
Beverage whiteners
Fat and oil emulsions
Mostarda difrutta
Sugar confectionery
Chewing gum
Desserts, decorations, coatings and fillings
Breakfast cereals
Quick-cook rice
Bread and rolls
Fine bakery wares
Minced and diced canned meat products

Industry Uses of Sodium stearoyl-2-lactylate:
Food industry

Consumer Uses of Sodium stearoyl-2-lactylate:
Food industry

Manufacturing of Sodium stearoyl-2-lactylate:
Sodium stearoyl-2-lactylate is manufactured by the reaction of lactic acid and stearic acid and conversion to sodium salts.
Typically, lactic acid — a naturally occurring substance — is neutralized with sodium or calcium hydroxide, and the excess water is distilled out.

Stearic acid — also a naturally occurring substance found in animal and vegetable fats — is then added and esterification occurs.
Water is again removed via distillation.
Some manufacturers bleach the final product with hydrogen peroxide (the product is then heated to destroy excess peroxide).

Sodium stearoyl-2-lactylate is synthesized from food-grade stearic acid (mostly from palm oil), lactic acid (from the fermentation of sugar beet or chemical synthesis) and sodium hydroxide.
There are two manufacturing processes of producing Sodium stearoyl-2-lactylate based on the reaction sequence.

The FDA mentioned that Sodium stearoyl-2-lactylate can be produced by the esterification of stearic acid and lactic acid to form stearoyl lactylic acid and then neutralized into the sodium salt with sodium hydroxide. (1)

The information from the EFSA is the neutralization first and then the esterification (2).
The brief manufacturing process as follows:

Mixture: mix aqueous stearic acid (control the temperature above Sodium stearoyl-2-lactylate solidification point) with aqueous lactic acid
Neutralization: add sodium hydroxide to the mixture and the neutralization reaction will take place between sodium hydroxide and lactic acid
Esterification

Sodium stearoyl-2-lactylate is hygroscopic and will become sticky in moist air.
So sometimes Sodium stearoyl-2-lactylate powder is blended with an anti-caking agent (e.g. calcium carbonate) to make Sodium stearoyl-2-lactylate not sticky and free-flowing.

General Manufacturing Information of Sodium stearoyl-2-lactylate:

Industry Processing Sectors:
Food chemical additive

FDA regulation of Sodium stearoyl-2-lactylate:
According to CFR §172.846 Sodium stearoyl-2-lactylate can be used in bakery formulations at levels up to 0.5%, based on flour weight.
If used as stabilizer in icings, fillings, puddings, and toppings, Sodium stearoyl-2-lactylate can be added to the formulation at a level up to 0.2% (based on the weight of the finished food).

Origin of Sodium stearoyl-2-lactylate:
Sodium stearoyl-2-lactylate is a natural food-grade emulsifier derived from the sodium salt of lactic acid and stearic acid.
Sodium stearoyl-2-lactylate is produced through food-grade chemical reactions.
Lactic and stearic acid are used in the presence of a base (alkali).

Lactic acid is found in milk.
Also, Sodium stearoyl-2-lactylate can be produced by lactic acid bacteria in large-scale fermentations.
Stearic acid is found in animal fat or as the product of the hydrogenation of unsaturated vegetable oils.

Commercial production of Sodium stearoyl-2-lactylate:
Sodium stearoyl-2-lactylate is manufactured by reacting two organic acids: lactic and stearic.
The reaction product is stearoyl lactylic acid (SLA) which can be readily converted by neutralization with sodium hydroxide to sodium stearoyl lactylate (SSL).

Health and safety of Sodium stearoyl-2-lactylate:
Lactylates, including Sodium stearoyl-2-lactylate, have been subjected to extensive safety evaluations prior to being FDA approved for use as a food additive.
The oral LD50 of Sodium stearoyl-2-lactylate for rats was established by Schuler and Thornton in 1952 as being over 25 g/kg body weight.
In 2010, Lamb established the no-observed-adverse-effect level of Sodium stearoyl-2-lactylate at 5% of the total diet and recommended an acceptable daily intake of 22.1 mg/kg bw/day for human consumption.

Identifiers of Sodium stearoyl-2-lactylate:
CAS Number: 25383-99-7
ChemSpider: 8065662
ECHA InfoCard: 100.042.648
EC Number: 246-929-7
E number: E481 (thickeners, ...)
PubChem CID: 23671849
UNII: IN99IT31LN
CompTox Dashboard (EPA): DTXSID8027872
InChI: InChI=1S/C24H44O6.Na/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25) 29-21(3)24(28)30-20(2)23(26)27;/h20-21H,4-19H2,1-3H3,(H,26,27);/q;+1/p-1
SMILES: O=C(C(C)OC(CCCCCCCCCCCCCCCCC)=O)OC(C)C([O-])=O.[Na+]

Properties of Sodium stearoyl-2-lactylate:
Chemical formula: C24H43NaO6
Molar mass: 450.592 g·mol−1
Appearance: a white or cream-colored powder with a caramel odor
Density: 1.063 g/cm3
Melting point: 49 °C (120 °F; 322 K)
Solubility in water: dispersible in warm water

Molecular Weight: 450.6
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 6
Rotatable Bond Count: 22
Exact Mass: 450.29573337
Monoisotopic Mass: 450.29573337
Topological Polar Surface Area: 92.7 Å²
Heavy Atom Count: 31
Complexity: 469
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 2
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 2
Compound Is Canonicalized: Yes

Specification of Sodium stearoyl-2-lactylate:
Other Names:
Sodium stearoyl lactate
Sodium di-2-stearoyl lactate
CAS Number: 25383-99-7
Chemical formula: C24H43NaO6
Molecular Weight: 450.592
Melting Point: 49 °C (120 °F; 322 K)

Appearance of Sodium stearoyl-2-lactylate:
A waxy white or slightly yellowish powder or brittle solid (flake) with a slightly acidic smell.

Structure of Sodium stearoyl-2-lactylate:
Lipophilic group: the long-chain stearoyl group
Hydrophilic group: the carbonium ion of lactic acid

HLB:
10-12, gives oil-in-water emulsions, O/W, Sodium stearoyl-2-lactylate also functions as a humectant.

Solubility In water:
Insoluble in water, disperse in hot water.
With a poor water solubility at low temperature although Sodium stearoyl-2-lactylate is a hydrophilic emulsifier, and therefore heat treatment of water is needed before the use of Sodium stearoyl-2-lactylate.

Solubility In organic solvents:
Soluble in ethanol, hot edible oils and fats.

Names of Sodium stearoyl-2-lactylate:

Preferred IUPAC name of Sodium stearoyl-2-lactylate:
Sodium 2-{[2-(octadecanoyloxy)propanoyl]oxy}propanoate

Other names of Sodium stearoyl-2-lactylate:
octadecanoic acid, 2-(1-carboxyethoxy)-1-methyl-2-oxoethyl ester, sodium salt
sodium 2-{[2-(stearoyloxy)propanoyl]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
stearic acid, ester with lactate of lactic acid, sodium salt
stearic acid ester with lactic acid bimol. ester sodium salt
sodium 2-(1-carboxylatoethoxy)-1-methyl-2-oxoethyl stearate

Synonyms of Sodium stearoyl-2-lactylate:
25383-99-7
Sodium stearoyl-2-lactylate
Sodium stearoyl lactylate
Sodium 2-((2-(stearoyloxy)propanoyl)oxy)propanoate
UNII-IN99IT31LN
IN99IT31LN
Octadecanoic acid, 2-(1-carboxyethoxy)-1-methyl-2-oxoethyl ester, sodium salt
sodium;2-(2-octadecanoyloxypropanoyloxy)propanoate
sodium 2-{[2-(stearoyloxy)propanoyl]oxy}propanoate
Octadecanoic acid,2-(1-carboxyethoxy)-1-methyl-2-oxoethyl ester, sodium salt (1:1)
EINECS 246-929-7
Sodium stearyl-2-lactylate
Sodium stearoyl 2-lactylate
Lactic acid, bimol. ester, stearate, sodium salt
SCHEMBL156076
DTXSID8027872
Sodium 2-(1-carboxyethoxy)-1-methyl-2-oxoethyl octadecanoate
Stearic acid, ester with lactic acid bimol. ester, sodium salt
MFCD29919680
AS-81732
CS-0152206
A911956
Q416058
Octadecanoic acid, 2-(1-carboxyethoxy)-1-methyl-2-oxoethyl ester, sodium salt (1:1)