12-Hydroxystearic acid
CAS Number: 106-14-9
EC / List no.: 203-366-1
Mol. formula: C18H36O3
Molecular Weight: 300.48
Synonyms: 12-Hydroxyoctadecanoic acid, 12-Hydroxystearic acid, 12-HSA
Linear Formula: CH3(CH2)5CH(OH)(CH2)10COOH
While many traditional chemicals are classified as petrochemicals, hydroxystearic acid is categorized as an oleochemical.
The castor oil derivative 12-hydroxystearic acid — also known as 12-hydroxy stearic acid or 12-HSA — can transform into a thickening agent in personal care products and as a chemical intermediate in chemical applications.
From coatings and adhesives to sealants and elastomers, you’ll find an extensive variety of uses for this sustainable product.
Standard-grade 12-HSA is a saturated fatty acid produced by hydrogenating castor oil, which is naturally derived from castor beans.
The oil’s double bonds are saturated as a result of hydrogenation, producing stearic acid.
Manufacturers perform the process at room temperature using pressure and an alcohol solvent.
Standard-grade 12-HSA is incredibly versatile, useful in applications spanning personal consumer products and industrial purposes. Its benefits are best described when the product is broken down into its two main uses — personal care and chemical applications.
12-HSA is a useful component in hot-melt adhesives, inks and polishes, that reacts with acrylic esters to create durable and strong thermosetting polymers. These thermosetting polymers are used as a coating in metal-decorative finishes, industrial appliances and high-quality automotive applications.
Uses
Lubrication: 12-Hydroxy stearic acid (12-HSA) gives better Lithium, Barium and Calcium multi-purpose greases. It provides excellent resistance to water, oils, solvents and crude petroleum, wide temperature range stability and high drop point.
Cosmetics: 12-HSA is used for gelling liquid Paraffin in creams and ointments, which easily liquefy on the skin. Esters of 12-HSA are used in various cosmetic products (lipsticks, deodorant and antiperspirant sticks, shaving creams, etc.).
Coatings: 12-HSA is reacted with acrylic esters to produce hard, durable thermosetting polymers used in the high quality automotive, industrial appliance and metal decorative finishes.
Rubber: functions as an activator and internal lubricant for natural and synthetic rubbers
Others: 12-HSA is an useful component in polishes, inks and hot melt adhesives
Uses
Lithium greases, chemical intermediates.
12-Hydroxystearic Acid is a C18 straight chain fatty acid
12-Hydroxystearic Acid uses and applications include: Emulsifier; major component in lithium greases; chemical intermediate; lubricant for PVC and plastics processing; emulsifier, cleansing agent, surfactant in cosmetics, toiletries; wax blends; polishes; inks; hot-melt adhesives; paints; thickener; defoamer in food-contact paperpaperboard; in lubricants for incidental food-contact use
Definition
ChEBI: A hydroxy fatty acid that is stearic acid bearing a hydroxy substituent at position 12.
12-HYDROXYSTEARIC ACID IN PERSONAL CARE APPLICATIONS
Skin care product manufacturers have long favored 12-HSA for its emollient, surfactant and thickening properties. In fact, cosmetics and personal care are the most common applications of the ingredient. You’ll find hydroxystearic acid in the ingredients list of products such as:
Lotions, gels and creams
Makeup products
Sun lotions and tanning creams
Hair care products like shampoos and conditioners
Deodorants and antiperspirants
Facial cleansers and other body care products
Choosing 12-HSA as an ingredient in your personal care products offers a wide range of benefits. Some of its unique advantages include:
Safety: 12-hydroxy stearic acid is a low-risk substance that won’t irritate skin or harm the body. It also does not come into contact with any common allergens during manufacturing. These qualities make it an excellent choice for consumers and a low-risk option for manufacturers.
Eco-friendliness: 12-Hydroxystearic acid is also an eco-friendly alternative to many traditional makeup products. The ingredient is derived from entirely natural sources and is sourced sustainably.
Versatility: You can use 12-HSA in nearly any personal care product, which means even a single bag of the substance will be well worth the cost.
12-HYDROXYSTEARIC ACID IN CHEMICAL APPLICATIONS
Standard-grade 12-HSA is praised for its numerous chemical qualities. Its waxiness makes it ideal for creating long-lasting greases for the automotive industry and industrial applications. Most greases and lubricants available today use some form of the product.
12-hydroxystearic acid is also widely available for CASE applications. When reacted with acrylic esters, it produces strong polymers for a lustrous finish you can use to coat automotive and industrial machinery.
Use: Intermediate, Activator / Accelerator.
12-Hydroxystearic acid is ingredient in Lithium Grease and Lithium Complex Grease.
12-Hydroxystearic acid is also used in Personal Care Products as an Emollient and in Underarm Deodorants.
12-hydroxy stearic acid is one of many castor oil derivatives sold by ATAMAN CHEMICALS.
Also known as 12-hydroxystearic acid and 12-HSA, it is used as a thickener for silicon grease, as a rubber activator/accelerator and in the manufacture of certain personal care products, among other applications.
Use our product as a sustainable alternative to other emollients and thickeners.
Also called 12-hydroxy stearic acid and 12-HSA, hydroxystearic acid is a fatty acid surfactant, emollient and thickener.
Hydroxystearic acid is used widely in a variety of personal care and cosmetics products, including skin care preparations, hair products and deodorizing products.
Structurally similar to stearic acid, hydroxystearic acid is entirely vegetable-based and derived from naturally-occurring fats and oils, most commonly castor oil.
12-HSA is synthesized by oxidizing 2-hexylcyclododecanone with a mixture of permaleic and peracetic acids in methylene chloride.
This forms the lactone of hydroxystearic acid, and alkaline hydrolysis of the lactone produces 12-HSA.
Sold in solid flakes, hydroxystearic acid has a typical shelf life of up to two years past date of manufacture.
To get the longest life out of hydroxystearic acid, store the chemical according to material safety data sheet (MSDS) recommendations.
The most popular use for hydroxystearic acid is in the cosmetics and personal care industry.
Because 12-HSA is effective in a range of functions, it is a versatile and popular ingredient for many different products.
Some of the most popular applications for hydroxystearic acid include the following products:
Lotions
Creams
Gels
Make-up and decorative cosmetics
Hair care, such as shampoos, conditioners and styling products
Skin care, such as facial care and cleansing, body care and baby care products
SPF enhancement
Sun care, such as sun protection, self-tanning and after-tanning products
Underarm deodorants
In any given cosmetics product, hydroxystearic acid is used in three primary functions — as a surfactant, emollient and thickener.
12-Hydroxystearic acid is used as surfactant, emollient and thickener in cosmetic formulations.
As a surfactant, hydroxystearic acid helps water mix with oils and dirt.
When used in cosmetic products, 12-HSA helps clean hair and skin of any grease or debris.
Once loosened, the various oils and dirt are easily rinsed away, resulting in a fresh, clean surface.
As an emollient, hydroxystearic acid improves the feel and workability of cosmetic products.
The emollient effect of 12-HSA is especially useful in skin care products such as facial creams and lotions, although it is also beneficial in hair products and spreadable, cream-based make-up.
Although hydroxystearic acid is more often used as a surfactant or emollient, it also has thickening properties.
Manufacturers include hydroxystearic acid as a thickening agent in products such as lotions or deodorants, and its cleansing and softening effects give a formula additional benefits.
The benefits of hydroxystearic acid extend beyond the cosmetics industry — the surfactant, lubricating and thickening properties of 12-HSA are also beneficial in a wide range of manufacturing applications.
Common manufacturing applications of hydroxystearic acid:
Rubber products: Hydroxystearic acid works as an activator, accelerator and internal lubricant for both synthetic and natural rubber.
This property makes 12-HSA an ideal choice for the rubber production industry.
Lubricants: 12-HSA can be used in calcium and barium, free multifunctional lithium, glycerol and higher-quality lubricants designed for use in cars, airplanes and other types of machinery.
The surfactant capability of hydroxystearic acid helps prevent particles from sticking to engine parts, allowing the various components to move easily and keeping the motor in good condition.
Silicon and lithium grease: Hydroxystearic acid is often used as a thickening agent in silicon and lithium-based grease.
Paint production: When introduced to paint, hydroxystearic acid reacts with acrylic esters, producing stable thermosetting polymers. These polymers are often used to create high-quality industrial and automotive equipment, along with producing decorative metal coatings.
Manufacturing of plastic products: Hydroxystearic acid is often used as an additive in the manufacturing of PVC products, including plastic siding, sheets, films, wall panels and window profiles.
Other products: 12-HSA is also used in inks, hot melt adhesives and polishing products. Hydroxystearic acid can be found in drilling fluid additives, food packaging and as an intermediate for pharmaceuticals.
Resistant to oil, solvents and water, hydroxystearic acid can maintain its integrity in a variety of environments. 12-HSA can also withstand a wide range of temperatures, making it an appealing choice for many manufacturing processes.
1. Benefits for Consumers
Hydroxystearic acid provides two key benefits for the consumers and end users of cosmetics — 12-HSA is a natural and relatively safe product, in stark contrast to its petrochemical competition.
Natural: Derived from plant-sourced oils, 12-HSA is entirely vegetable-based, and it isn’t tested on animals during any stage of manufacturing.
Hydroxystearic acid is a vegan compound, which appeals to consumers who are looking for natural, environmentally-friendly products.
Safe: Hydroxystearic acid is classified as a low-risk compound, meaning that it doesn’t carry the same risk associated with other leading petrochemicals.
Hydroxystearic acid won’t cause skin irritation or respiratory distress unless inhaled in excessive amounts, and during manufacturing, 12-HSA doesn’t come into contact with common allergens such as eggs, fish, gluten, grains, wheat or dairy.
Hydroxystearic acid is a natural and low-risk cosmetics ingredient, and besides creating high-quality products, it provides many benefits for consumers.
2. Benefits for Manufacturers
The same benefits that make hydroxystearic acid a perfect choice for consumers also make it advantageous for manufacturers.
Eco-friendly: Many of the traditional cosmetics ingredients are harmful to the environment or human health.
For manufacturers searching for eco-friendly alternatives, hydroxystearic acid is an ideal option.
A vegetable-based oleochemical, hydroxystearic acid is a natural and sustainable resource.
Unlike petrochemicals, 12-HSA is derived from a renewable resource, making hydroxystearic acid an eco-friendly choice for the cosmetics industry.
Low-risk: Hydroxystearic acid is safe for consumers, and it is also a low-risk option for manufacturers.
Nonflammable, non-reactive and not an explosive hazard, hydroxystearic acid is a relatively safe compound for cosmetics companies.
However, as true when handling any chemical compound, make sure you take all standard safety precautions when handling hydroxystearic acid, such as wearing protective clothing, working in a well-ventilated space and administering first aid if it is ingested.
12-Hydroxy Stearic Acid (12-HSA) is a waxy, castor-derived fatty acid that finds use in lithium complex grease and other high performance greases with automotive and industrial applications.
12-HAS is an efficient viscosity builder and gelling agent, and will gel hydrocarbons as well as many esters and some silicones.
Salts made from 12-HSA can function as oil/water emulsifiers.
12-HSA can be used as an emollient in underarm deodorant sticks, gel lipsticks, hair styling products, creams and lotions.
Product Properties
12-hydroxy stearic acid is sold in flakes and packaged in #50 bags and supersacks.
It is available for purchase in our online store, or by contacting our office directly.
Store our 12-hydroxystearic at ambient temperatures for up to two years without worrying about degradation.
12-hydroxy stearic acid is entirely vegetable-based, and not tested on animals at any part of the manufacturing process.
Its GMO-free, and contains no peanuts, tree nuts, wheat, grains, dairy, eggs, fish or gluten.
Precautions
12-hydroxystearic acid is nonreactive, nonflammable and not an explosive hazard.
In flake form, 12-hydroxystearic acid is not irritating to skin and won’t cause respiratory distress.
However, standard precautions should be taken when handling this product – work in a well-ventilated area, wear protective clothing and administer first aid if flakes are accidentally ingested.
12-hydroxyoctadecanoic acid is a hydroxy fatty acid that is stearic acid bearing a hydroxy substituent at position 12.
12-hydroxyoctadecanoic acid has a role as a plant metabolite and a bacterial xenobiotic metabolite.
12-hydroxyoctadecanoic acid is a hydroxyoctadecanoic acid and a secondary alcohol.
12-hydroxyoctadecanoic acid is a conjugate acid of a 12-hydroxyoctadecanoate.
Other names: Octadecanoic acid, 12-hydroxy-; Cerit Fac 3; Harwax A; Hydrofol Acid 200; Stearic acid, 12-hydroxy-; 12-Hydroxyoctadecanoic acid; Barolub FTO; Ceroxin GL; KOW; Loxiol G 21; DL-12-Hydroxystearic acid; NSC 2385
12-HYDROXYOCTADECANOIC ACID
12-Hydroxystearic acid
106-14-9
Octadecanoic acid, 12-hydroxy-
Harwax A
DL-12-Hydroxystearic acid
Cerit Fac 3
Hydrofol acid 200
Ceroxin GL
Barolub FTO
Loxiol G 21
Stearic acid, 12-hydroxy-
12-hydroxy-octadecanoic acid
NSC 2385
DL-12-hydroxy stearic acid
36377-33-0
(R)-12-Hydroxyoctadecanoic acid
12-hydroxy stearic acid
MFCD00004592
CHEBI:85208
27924-99-8
KOW
DSSTox_CID_6725
DSSTox_RID_78200
DSSTox_GSID_26725
CAS-106-14-9
HSDB 5368
12-Hydroxystearic acid homopolymer
EINECS 203-366-1
EINECS 253-004-1
UNII-YXH47AOU0F
BRN 1726730
AI3-19730
12-Hydroxystearic acid estolide
Octadecanoic acid, 12-hydroxy-, homopolymer
Polyhydroxystearic acid (2300 MW)
ACMC-1ACPY
12-hydroxy-stearic acid
YXH47AOU0F
EC 203-366-1
SCHEMBL17773
WLN: QV10YQ6
4-03-00-00942 (Beilstein Handbook Reference)
POLYHYDROXYSTEARIC ACID
12-HSA
CHEMBL292352
12 HYDROXY STEARIC ACID
DTXSID8026725
NSC2385
(?)-12-Hydroxyoctadecanoic acid
12-Hydroxyoctadecanoic acid, 99%
NSC-2385
EINECS 227-283-5
EINECS 242-295-0
Tox21_201492
Tox21_303035
ANW-15316
LMFA02000130
AKOS016010128
MCULE-9965131742
NCGC00164350-01
NCGC00164350-02
NCGC00257021-01
NCGC00259043-01
8039-23-4
FT-0607234
H0308
ST51039859
V0108
W-108773
W-110875
Q27158401
12-Hydroxystearic acid, United States Pharmacopeia (USP) Reference Standard
Benzyl(2S,3aS,7aS)-octahydro-1H-indole-2-carboxylate4-methylbenezenesulfonate
78642-86-1
106-14-9 [RN]
12-HSA
12-Hydroxyoctadecanoic acid [ACD/IUPAC Name]
12-Hydroxyoctadecansäure [German] [ACD/IUPAC Name]
12-Hydroxystearic acid
253-004-1 [EINECS]
36377-33-0 [RN]
Acide 12-hydroxyoctadécanoïque [French] [ACD/IUPAC Name]
DL-12-hydroxy stearic acid
DL-12-hydroxystearic acid
MFCD00004592 [MDL number]
Octadecanoic acid, 12-hydroxy- [ACD/Index Name]
WI3850000
[106-14-9]
[36377-33-0]
12 HYDROXY STEARIC ACID
12-(R,S)-HYDROXYSTEARIC ACID [9,10-3H]
12-?hydroxy-Octadecanoic acid
12-HAS
12-hydroxy stearic acid
12-Hydroxy-octadecanoic acid
12-hydroxystearic acid tech. grade
12-hydroxystearic acid, 95%
12-hydroxystearic acid, tech. 85%
12-Hydroxysteric acid
18417-00-0 [RN]
27924-99-8 [RN]
4-[(1R)-1-Hydroxyethyl]phenol [ACD/IUPAC Name]
4-03-00-00942 [Beilstein]
5762-36-7 [RN]
654637-88-4 [RN]
78642-86-1 [RN]
8039-23-4 [RN]
860114-96-1 [RN]
Barolub FTO
Cerit Fac 3
Ceroxin GL
DL-12-HYDROXY STEARIC ACID|12-HYDROXYOCTADECANOIC ACID
Harwax A
http:////www.amadischem.com/proen/608207/
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:85208
Hydrofol acid 200
hydroxystearic acid
Jsp000562
KOW
lemosol coagulant
Loxiol G 21
stearic acid, 12-hydroxy-
tech., 85%
WLN: QV10YQ6
12-hydroxystearic acid
Barolub FTO
Cerit Fac 3
Ceroxin GL
DL-12-Hydroxystearic acid
Harwax A
Hydrofol acid 200
Hydroxystearic acid
KOW
Loxiol G 21
Octadecanoic acid, 12-hydroxy-
Stearic acid, 12-hydroxy-
CAS names
Octadecanoic acid, 12-hydroxy-
IUPAC names
12 HSA
12-HSA
12-Hydroxy octadecanoic acid
12-Hydroxy stearic acid
12-Hydroxyoctadecanoic acid
12-HYDROXYSTEARIC ACID
12-Hydroxystearic Acid
12-hydroxystearic acid (12-HSA)
12-Hydroxystearinsäure
12-hydroxysteraic acid
Octadecanoic acid, 12-hydroxy-
• 12-hydroxy-octadecanoicaci
• 12-hydroxystearic
• 12-hydroxy-stearicaci
• 12-Hydroxysteric acid
• 12 hydroxy calcium stearate
• 12-Hydroxystearic acid Factory
• 12-Hydroxystearic acid COA TDS MSDS
• Twelve hydroxy acid
• 12-Hydroxystearic acid, technical, 85%
• Barolub fto
• barolubfto
• Cerit Fac 3
• ceritfac3
• Ceroxin gl
• ceroxingl
• Harwax A
• harwaxa
• Hydrofol Acid 200
• hydrofolacid200
• KOW
• Loxiol G 21
• 12-Hydroxyoctadecanoic acid,12-Hydroxystearic acid
• 12-Hydroxystearic Acid (200 mg)
• 12-HSA
• 12-Hydroxyoctadecanoic Acid 12-
• 12-Hydroxystearic acid MSDS Free sample
• loxiolg21
• Octadecanoic acid, 12-hydroxy-
• Hydroxystearicacid
• LEMOSOL COAGULANT
• DL-12-HYDROXYOCTADECANOIC ACID
• DL-12-HYDROXYSTEARIC ACID
• (+/-)-12-HYDROXYOCTADECANOIC ACID
• 12-HYDROXYOCTADECANOIC ACID
• 12-HYDROXYSTEARIC ACID
• 12-HYDROXYSTEARIC ACID, TECH.
• DL-12-Hydroxystearic acid, tech., 90%
• hydroxy stearic acid 12
• (±)-12-Hydroxyoctadecanoic acid, Technical Grade
• d-12HSA
• 16-Hydroxyoctadecanoic acid
• 16-Hydroxystearic acid
• Polyethylene Glycol Monooleate(2E.O.)
• DL-12-Hydroxystearic acid,99+%
• DL-12-Hydroxystearic acid,90%,tech.
• 12-HydroxystearicAcid>
• 106-14-9
• 1123-81-4
• CH3CH25CHOHCH210COOH
• CH3CH25CHOHCH210CO2H
• C18H36O3
• Organic Building Blocks
• Building Blocks
• C13 to C42+
• Carboxylic Acids
• Carbonyl Compounds
• Biochemicals and Reagents
• Building Blocks
Lithium 12-hydroxystearate (C18H35LiO3) is a chemical compound classified as a lithium soap.
In chemistry, "soap" refers to salts of fatty acids. Lithium 12-hydroxystearate is a white solid.
Lithium soaps are key component of many lubricating greases.
Use
Lithium 12-hydroxystearate exhibits high oxidation stability and a dropping point up to around 200 °C.
Most greases used today in motor vehicles, aircraft, and heavy machinery contain lithium stearates, mainly lithium 12-hydroxystearate.
Greases can be made with the addition of several different metallic soaps.
Some greases are prepared from sodium, barium, lithium, and calcium soaps.
Lithium soap greases are preferred for their water resistance, and their oxidative and mechanical stability.
Depending on the grease, they also have good performance at high or low temperatures, but not both.
Production
To produce lithium 12-hydroxystearate, lithium hydroxide and the fatty acid are combined in an aqueous medium. With vigorous stirring, dilute monohydrate lithium hydroxide is gradually added to a dispersion of the fatty acid in water heated to slightly below boiling.
Since these lithium soaps are difficult to filter, they are collected by spray drying.
For applications, lithium 12-hydroxystearate is usually dispersed in synthetic oils such as silicone oil and ester oil.
The synthetic oils are preferred for their greater stability and ability to perform at extreme temperatures.
The 12-hydroxystearic acid is prepared by the hydrogenation of castor oil.
After primary reaction of the saturation of most of the double bonds, dehydration and reduction of the hydroxyl group leads to the stearic acid.
Hydrogenated castor oil results in a mixture of 12-hydroxystearic acid and stearic acid.
Lithium 12-hydroxystearic acid has widely been considered a preferred fatty acid in the manufacturing of lithium-based grease thickeners. This fatty acid has had its application in calcium-based grease thickeners as well. Greases formulated with this acid will often be smooth with a buttery texture.
They also tend to have a higher thickener content by weight of about 10-15 percent. The smooth texture and many of the other advantages derived from these thickeners is due to their webbed fibrous pattern, which is only visible on a microscopic scale.
Calcium 12-hydroxystearate grease is one of the most common types of anhydrous calcium-based greases. It has a dropping point of around 275 to 300 degrees F, with a maximum usable temperature of approximately 230 degrees F and average characteristics at low temperatures.
When well-formulated, the grease normally has good oxidation and water resistance, but other additives may be necessary to protect against rust. Calcium 12-hydroxystearate is also generally compatible with many other greases as well.
The vast majority of lithium-based greases are formulated with 12-hydroxystearate soap for versatility. The dropping point for these greases is higher, around 350-400 degrees F.
They also have good resistance to water, although the grease may soften and run when large quantities of water are present. The maximum usable temperature is around 250 degrees F, which is better or equal to most other grease types. Unlike calcium 12-hydroxystearate, lithium 12-hydroxystearate is less compatible with other greases.
When trying to decide which grease is best for your application, evaluate the top performance properties that will impact the application. Some of these properties have been mentioned already, including the dropping point, maximum usable temperature, water resistance and oxidation resistance. The usable temperature range is especially critical when the application will experience temperature extremes.
The grease's consistency will be important to consider in every application. It is determined by the base oil viscosity and the thickener concentration and type. Lithium-based greases remain very common in the industry (as much as 70 percent or more) for their overall performance. Other types of thickeners, like calcium 12-hydroxystearate, will be limited to specific purposes, such as for certain types of seals, chains and roller bearings.
It should also be noted that some greases have thickeners that are mixtures of both lithium and calcium. Other greases may even be manufactured with 12-hydroxystearate as the fatty acid. Much like any specialty grease formulation, these lubricants likely are not intended for multi-purpose applications.
12-Hydroxy Stearic Acid is a castor oil derivative used in a variety of applications. It is used as an ingredient in lithium grease and lithium complex grease. The lithium soaps are free of corrosive properties, which makes them suitable for use in lubricants.
