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12-HYDROXYSTEARIC ACID

12-HYDROXYSTEARIC ACID
CAS NO: 106-14-9

12-Hydroxyoctadecanoic acid; 12-HSA; 12-Hydroxystearic acid; 12-HYDROXYOCTADECANOIC ACID; Octadecanoic acid, 12-hydroxy-; 12-Hydroxy-octadecanoic acid; 12-Hydroxy-octadecanoate; DL-12-Hydroxystearic acid;

12-hydroxyoctadecanoic acid is a hydroxy fatty acid that is stearic acid bearing a hydroxy substituent at position 12. It has a role as a plant metabolite and a bacterial xenobiotic metabolite. It is a hydroxyoctadecanoic acid and a secondary alcohol. It is a conjugate acid of a 12-hydroxyoctadecanoate.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.
 

SYNONYMS
12 HYDROXY STEARIC ACID (12 HİDROKSİ STEARİK ASİT; CAS NO: 106-14-9; METATAGS:12-Hydroxyoctadecanoic acid [ACD/IUPAC Name]; 12-Hydroxyoctadecansäure [German] [ACD/IUPAC Name]; 12-Hydroxystearic acid; 253-004-1 [EINECS]; Acide 12-hydroxyoctadécanoïque [French] [ACD/IUPAC Name]; DL-12-hydroxy stearic acid; DL-12-hydroxystearic acid; Octadecanoic acid, 12-hydroxy- [ACD/Index Name]; [106-14-9]; [36377-33-0] 106-14-9 [RN]; 12 HYDROXY STEARIC ACID; 12-(R,S)-HYDROXYSTEARIC ACID [9,10-3H]; 12-?hydroxy-Octadecanoic acid; 12-HAS; 12-HSA; 12-hydroxy stearic acid; 12-Hydroxy-octadecanoic acid; 12-Hydroxysteric acid; Barolub FTO; Cerit Fac 3; Ceroxin GL; Harwax A; Hydrofol acid 200; hydroxystearic acid; Jsp000562; KOW; Loxiol G 21; MFCD00004592 [MDL number]; stearic acid, 12-hydroxy-; UNII:933ANU3H2S; WLN: QV10YQ6; 12-hydroxyoctadecanoic acid; C18H36O3; 12-Hydroxystearic acid; 12-HYDROXYOCTADECANOIC 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; DL-12-hydroxy stearic acid; Stearic acid, 12-hydroxy-; 12-hydroxy-octadecanoic acid; NSC 2385; HSDB 5368; 12-hydroxy stearic acid; EINECS 203-366-1; EINECS 253-004-1; 36377-33-0; BRN 1726730; AI3-19730; CHEBI:85208; (R)-12-Hydroxyoctadecanoic acid; (S)-12-Hydroxyoctadecanoic acid; ULQISTXYYBZJSJ-UHFFFAOYSA-N; ; 12-Hydroxystearic acid estolide; 12-Hydroxystearic acid homopolymer; 12-hydroxy-stearic acid, Octadecanoic acid, 12-hydroxy-, homopolymer; 12-HYDROXYSTEARICACID; DL -12-Hydroxyoctadecanoic acid; NSC2385; (?)-12-Hydroxyoctadecanoic acid; 12-HYDROXYSTEARIC ACID, PRACT; Casid® HSA (12-Hydroxystearic Acid); ;LEMOSOL COAGULANT;12-HYDROXYSTEARIC ACID;DL-12-HYDROXYSTEARIC ACID;12-HYDROXYOCTADECANOIC ACID; HİDROKSİ STEARİK ASİT; 12, hydroxy, stearic, acid; 12, hidroksi, stearik, asit;;12-hydroxy stearic acid;12-Hydroxystearic acid;12-HYDROXYOCTADECANOIC ACID;106-14-9;Octadecanoic acid, 12-hydroxy-;Harwax A;Cerit Fac 3;Hydrofol acid 200;DL-12-Hydroxystearic acid;Ceroxin GL;Barolub FTO;Loxiol G 21;Stearic acid, 12-hydroxy-;DL-12-hydroxy stearic acid;12-hydroxy-octadecanoic acid;NSC 2385;HSDB 5368;12-hydroxy stearic acid;12-HSA;12-hydroxy stearic acid;12-Hydroxy-octadecanoic acid;12-Hydroxysteric acid;18417-00-0 [RN];27924-99-8 [RN];36377-33-0 [RN];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;Harwax A;Hydrofol acid 200;hydroxystearic acid;Jsp000562;KOW;Loxiol G 21;MFCD00004592 [MDL number];stearic acid, 12-hydroxy-;WLN: QV10YQ6;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;KOW;12-HSA;harwaxa;d-12HSA;Harwax A;ceritfac3;ceroxingl;loxiolg21;Ceroxin gl;barolubfto;DIHYDROOUABAIN 11,12-DIACETOXY BUTYL STEARATE HYOCHOLIC ACID STEARYL 12-HYDROXYSTEARATE monensin methyl ester Madecassoside DL-12-HYDROXYSTEARIC ACID METHYL ESTER,12-HYDROXYSTEARIC ACID METHYL ESTER METHYL 12-DOXYL-STEARATE 18alpha-Glycyrrhetinic acid 12-DOXYLSTEARIC ACID HYODEOXYCHOLIC ACID METHYL ESTER Enoxolone Hyodeoxycholic acid 3-alpha-Ethoxycarbonyl-12-alpha-hydroxy-7-oxocholan-24-oic acid, methy l ester 12-HYDROXYSTEARIC ACID ETHYL ESTER; 12-hydroxystearic acid, octadecanoic acid, 12-hydroxy, harwax a, cerit fac 3, hydrofol acid 200, dl-12-hydroxystearic acid, ceroxin gl, barolub fto, loxiol g 21, stearic acid, 12-hydroxy


This substance is used in the following products: washing & cleaning products, adhesives and sealants, lubricants and greases, polishes and waxes, fertilisers, coating products and air care products. Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids).Release to the environment of this substance can occur from industrial use: formulation of mixtures. Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use,indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment), outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and outdoor use in long-life materials with high release rate (e.g. tyres, treated wooden products, treated textile and fabric, brake pads in trucks or cars, sanding of buildings (bridges, facades) or vehicles (ships)).This substance can be found in complex articles, with no release intended: vehicles.This substance can be found in products with material based on: rubber (e.g. tyres, shoes, toys), stone, plaster, cement, glass or ceramic (e.g. dishes, pots/pans, food storage containers, construction and isolation material), fabrics, textiles and apparel (e.g. clothing, mattress, curtains or carpets, textile toys) and plastic (e.g. food packaging and storage, toys, mobile phones).This ubstance is intended to be released from scented: clothes.This substance is used in the following products: washing & cleaning products and polishes and waxes.This substance is used in the following areas: formulation of mixtures and/or re-packaging.This substance is used for the manufacture of: chemicals.Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).This substance is used in the following products: washing & cleaning products and polishes and waxes. This substance is used in the following areas: formulation of mixtures and/or re-packaging.This substance is used for the manufacture of: chemicals.Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).Release to the environment of this substance can occur from industrial use: formulation of mixtures and formulation in materials.This substance is used in the following products: polymers, washing & cleaning products, textile treatment products and dyes, metal surface treatment products, pH regulators and water treatment products, leather treatment products and lubricants and greases.This substance is used in the following areas: formulation of mixtures and/or re-packaging.This substance is used for the manufacture of: chemicals, textile, leather or fur and plastic products.Release to the environment of this substance can occur from industrial use: in processing aids at industrial sites, in the production of articles, as processing aid, as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.Release to the environment of this substance can occur from industrial use: manufacturing of the substance, as an intermediate step in further manufacturing of another substance (use of intermediates) and in processing aids at industrial sites.Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).12-Hydroxyoctadecanoic acid was used in the preparation of vegetable oil based organogels and gel's in-situ supramolecular network structure has been investigated by cryo-scanning electron microscopy. Non-isothermal nucleation rate of a self-assembling fibrillar network of 12-hydroxyoctadecanoic acid (12-hydroxystearic acid) in canola oil has been reported It is commonly used as gelling agent for organic solvents Self-assembled monolayers of 12-hydroxyoctadecanoic acid and its 4,4'-bipyridinium salt have been observed on the solution graphite interface using scanning tunnelling microscopy. 12-Hydroxy stearic acid is a saturated hydroxy fatty acid. It's a waxy, odourless, tasteless and cream coloured compound in flakes / powder.12-hydroxy stearic acid is one of many castor oil derivatives sold by Acme-Hardesty. 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.Non-isothermal nucleation rate of a self-assembling fibrillar network of 12-hydroxyoctadecanoic acid (12-hydroxystearic acid) in canola oil has been reported. It is commonly used as gelling agent for organic solvents. Self-assembled monolayers of 12-hydroxyoctadecanoic acid and its 4,4'-bipyridinium salt have been observed on the solution graphite interface using scanning tunnelling microscopy.12-Hydroxyoctadecanoic acid was used in the preparation of vegetable oil based organogels and gel's in-situ supramolecular network structure has been investigated by cryo-scanning electron microscopy.Properties: Vegetable based. Gels hydrocarbons, many esters and certain silicones. Moisturizing via occlusivity and humectancy. Salts made in situ function as primary oil/water emulsifiers. Higher melting point than stearic acid.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 — the exact shelf life will vary based on storage conditions. To get the longest life out of hydroxystearic acid, store the chemical according to material safety data sheet (MSDS) recommendations.While many traditional chemicals are classified as petrochemicals, hydroxystearic acid is categorized as an oleochemical.Petrochemicals are produced from petroleum oil-based products, and they are not known for their environmentally-friendly effects — many critics condemn petrochemicals for damaging the air, soil and water. Petrochemicals also tend to absorb easily into the skin, potentially creating issues in human health.Alternately, oleochemicals are chemicals derived from natural sources, most commonly plant and animal fats. Because they are typically pollution-free, biodegradable and have very low toxicity, oleochemicals are an attractive alternative to traditional petrochemical compounds. Consumers are increasingly concerned about the ingredients of their cosmetic products — if something comes into contact with their skin, they want it to be natural and healthy.Nonflammable, non-reactive and not an explosive hazard, hydroxystearic acid isn’t irritating to skin and doesn’t lead to respiratory distress. This makes hydroxystearic acid an especially attractive alternative to petroleum-based thickeners, emollients and surfactants on the market.

DESCRIPTION
12-Hydroxystearic acid, also known as 12-hydroxy-octadecanoate or DL-12-hydroxy stearate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 12-Hydroxystearic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.A comprehensive review of the features driving self-assembly of 12-hydroxystearic acid (12-HSA), a low-molecular-weight gelator, and its applications in drug delivery and as other soft innovative materials are presented herein. 12-HSA is obtained via hydrogenation of ricinoleic acid naturally found in high concentrations in castor oil. The ability of 12-HSA to self-assemble is associated with the presence, position, and enantiomeric purity of the hydroxy group along the fatty acid chain.The polarity and position of the hydroxyl group facilitates more interaction possibilities leading to its exceptional self-assembly behavior giving rise to fibers, ribbons, and tubes in a variety of solvents. Upon self-assembly, 12-HSA undergoes crystallization resulting in the formation of high aspect ratio fibrillar structures due to noncovalent, intermolecular interactions forming self-spanning, three-dimensional networks (called self-assembled fibrillar networks) in both aqueous and organic solvents. Herein, emphasis is placed on emerging applications of 12-HSA supramolecular assemblies (i.e. responsive aqueous foams, gelled complex fluids, drug delivery systems, hydrogels, organogels, xerogels, and aerogel). 

APPLICATION
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:Hair care, such as shampoos, conditioners and styling products, Skin care, such as facial care and cleansing, body care and baby care products, Sun care, such as sun protection, self-tanning and after-tanning products. In any given cosmetics product, hydroxystearic acid is used in three primary functions — as a surfactant, emollient and thickener.While water loosens dirt and debris, it is repelled by grease and oil — to help water clean effectively, another substance must be added to the water to lower its surface tension. This is why surfactants are essential in cleaning products. Designed to reduce the surface tension of water, surfactants help water molecules interact with grease and oil.Surfactants work by using opposing forces. These cleansing molecules have a hydrophilic head and a hydrophobic tail, and both components are essential for a surfactant to work effectively — the hydrophilic head binds to water molecules, while the hydrophobic tail binds to dirt and oils. The hydrophobic tail also repels water molecules, creating more space and reducing the overall surface tension of the liquid. 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. Emollients are important conditioning compounds in the cosmetics industry. These chemicals are responsible for the softening effect of lotions and creams — emollients improve the texture of the skin and hair, and they impart shine after use.When used in lotions, skin creams and hair products, emollients modify the way formulations feel on the skin. They also increase the spreadability of products and the length of time they remain effective.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.In many spreadable products, consumers look for a thick, luscious consistency — cosmetics that are too thin or watery are more difficult to spread over the skin.Thickening agents help products reach the right texture — they make thin formulas creamier and easier to spread. Thickeners are used to enhance the consistency of a broad range of products, from conditioners to sun tanning lotions.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.

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