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CAS NUMBEER: 141-22-0
MOLECULAR FORMULA: C18H34O3
MOLECULAR WEIGHT: 298.5
Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid.
Ricinoleic acid is an unsaturated omega-9 fatty acid and a hydroxy acid.
Ricinoleic acid is a major component of the seed oil obtained from mature castor plant seeds or in sclerotium of ergot .
About 90% of the fatty acid content in Ricinoleic acid is the triglyceride formed from ricinoleic acid.
Ricinoleic acid is a (9Z)-12-hydroxyoctadec-9-enoic acid in which the 12-hydroxy group has R-configuration.
Ricinoleic acid is a conjugate acid of a ricinoleate.
Ricinoleic acid is the primary constituent of Ricinoleic acid, which comes from the seeds of the castor bean plant.
Ricinoleic acid should be noted that with such a high percentage of ricinoleic acid in Ricinoleic acid, essentially it is a technical grade product—something that rarely happens in nature with plant oils.
Ricinoleic acid has a unique molecular structure attributed to the hydroxyl group located in the middle of the unsaturated chain.
In the triglycerol form, hydrogen bonding occurs with the hydroxyl groups resulting in greater viscosity than in other oils.
For this reason, Ricinoleic acid is a superior lubricant as compared to other vegetable.
In addition, the hydroxyl group only separated from the double bond by a methylene group—imparts increased oxidative stability, thereby providing Ricinoleic acid a longer shelf-life.
Furthermore, this structural feature also affects the solvation properties and miscibility of ricinoleic acid.
Unlike most fatty acids, ricinoleic acid is soluble in more polar solvents.
Ricinoleic acid has about 90% ricinoleic acid of the total fatty acids that is a uniquely hydroxylated, monounsaturated, 18 carbon aliphatic monobasic acids having a terminal carboxyl group, and a branch out hydroxyl group whose twelfth carbon is asymmetrical.
Ricinoleic acid is a vegetable oil obtained from the seeds of the Ricinus communis plant.
A number of ingredients made from Ricinoleic acid may also be used in cosmetic products.
These ingredients include Cetyl Rinoleate, Ethyl Ricinoleate, Glyceryl Ricinoleate, Glyceryl Ricinoleate SE (SE stands for self-emulsifying, which means it contains a small amount of sodium or potassium stearate), Glycol Ricinoleate, Hydrogenated Ricinoleic acid, Isopropyl Ricinoleate, Methyl Ricinoleate, Octyldodecyl Ricinoleate, Potassium Ricinoleate, Ricinoleic Acid, Sodium Ricinoleate and Zinc Ricinoleate.
In cosmetics and personal care products, Ricinoleic acid and related ingredients are used in the formulation of many different cosmetic and personal care products including lipstick, skin-care products, and bath soaps.
Ricinoleic acid is an unsaturated omega-9 fatty acid and is an important component of the seed oil
obtained from mature castor plants seeds. The compound is produced for industries by fractional distillation or saponification of hydrolysed Ricinoleic acid.
Ricinoleic acid is normally used in manufacturing personal care products such as deodorants.
Much of ricinoleic acid characteristics and effects can be associated with Ricinoleic acid.
USES OF RICINOLEIC ACID:
Sebacic acid ((CH2)8(CO2H)2), which is used in preparing certain nylons, is produced by cleavage of ricinoleic acid. The coproduct is 2-octanol.
Ricinoleic acid is used in personal care products such as deodorants.
In cosmetics, Ricinoleic acid is found in variety of products including hair preparations, soaps, and skin ointments. In addition, one of the largest applications of Ricinoleic acid in personal care is in lipstick preparations.
In fact it has been quoted: “Ricinoleic acid is one of the stalwarts of lipstick formulation since it creates the highest gloss of all natural oils when applied to the skin.
Ricinoleic acid is occlusive, water-repellant, tacky, and very protective to the skin.”
Ricinoleic acid is found in high concentrations in lipsticks.
There are also a number of ricinoleic acid derivatives used in a variety of personal care formulations including cetyl ricinoleate, ethyl ricinoleate, glyceryl ricinoleate, and zinc ricinoleate as well as polyethoxylated esters of ricinoleic acid.
Overall, these materials are deemed safe for use in cosmetics.
More than likely, the broad use of Ricinoleic acid in cosmetics comes from the compatibility of ricinoleic acid with polar and nonpolar ingredients.
Ricinoleic acid is used in many diverse areas including cosmetics, coatings, detergents, food, medicine, and plasticizer technology.
Ricinoleic acids traditional use as a household remedy has been known for many years to treat constipation, condition hair and skin, and alleve arthritis and muscle pain.
During the middle and early twentieth century In the United States, many parents used Ricinoleic acid to deter their children from misbehaving.
Ricinoleic acid was common to threaten, “If you don’t behave, you are going to have to take your Ricinoleic acid.”
This was even famously portrayed in the cartoon series Tom and Jerry in a 1953 episode.
- Soaps:
Ricinoleic acid can be reacted with various bases (caustic, ammonia, ethanolamines, etc.) to produce soaps having the desired characteristics (solubility, physical characteristics, polarity, etc.) depending on the final application.
Some of them are: cutting oils, industrial lubricants, emulsifiers and metal working fluids.
Transparent bar soaps & high solids liquids soaps are made possible by using Ricinoleic acid.
The same for industrial germicides, disinfectants and heavy duty detergents (solubilization of phenolic and cresylic bodies).
-Surface Coating:
Ricinoleic acid is used as an efficient pigment/dye dispersants in inks, coatings, plastics, cosmetics, etc.
-Textiles:
Ricinoleic acid provides polarity, surface wetting and lubricity.
-Rubber:
The sodium/potassium soaps of Ricinoleic acid are emulsifiers and foam stabilizers.
-Vinyl polymers:
Ricinoleic acid's sodium soap is useful as emulsifier, stabilizer and defoamer for emulsion polymerization of resins such as PVC & PVAc
-Food Additives:
Ricinoleic acid's used in the production of PGPR (polyglycerol polyricinoleate) for use in chocolate.
APPLICATION OF RICINOLEIC ACID:
Primary uses include coatings, plastics, inks and cosmetics.
Poly(anhydrides) are hydrolytically degradable polymers used as vehicles for the controlled delivery of drugs.
A new class of biodegradable polyanhydride based on ricinoleic acid has been synthesized Ricinoleic acid is effective in preventing the growth of viruses, bacteria, yeasts and molds.
The bleach is successful as a topical treatment for keratoses, dermatitis, abrasions, fungal infected finger and toenails, acne, and chronic pruritus (itching).
Usually, for these conditions, the affected area is wrapped with a Ricinoleic acid-soaked cloth every night.
Ricinoleic acid is also used as a bactericide.
For this reason, Ricinoleic acid is sometimes recommended to wash wounds with ricinoleic acid at prescribed dilution levels.
Ricinoleic acid acts as a blood coagulant Macrolactones and polyesters can be derived from ricinoleic acid
Ricinoleic acid has been used in contraceptive jellies.
Esters, industrial lubricants, emulsifiers, metalworking compounds are used in soaps, amine compounds, cutting oils.
Ricinoleic acid soaps are patented as algaecides for aquaculture systems.
Ricinoleic acid is used in dispersions of pigments and dyes.
Ricinoleic acid is used in resins, thermosetting acrylics and non-drying plasticizer esters.
Ricinoleic acids based on ricinoleates and hydroxy stearate are used for cosmetic skin and hair care, personal products, germicides and textile treatment agents.
-Anticaking agent
-Deodorant agent
-Emulsion stabilizer
-Skin conditioning agent - emollient inoleate, Isopropyl Ricinoleate, Methyl Ricinoleate
-Skin conditioning agent - occlusive
-Surfactant - cleansing agent
-Surfactant - emulsifying agent
-Viscosity increasing agent - nonaqueous
PROPERTIES OF RICINOLEIC ACID:
-Viscosity: 889 cS3
-Density: 0.959 g/mL3
-Thermal conductivity: 4.727 W/m°C3
-Boiling point: 245 °C7
-Melting point: -2 to -5 °C3
-LogP: log Kow = 6.19 (est)8
-Refractive index: 1.4803
-Solubility: alcohol, acetone, ether, chloroform7
CHEMICAL PROPERTIES OF RICINOLEIC ACID:
-Ricinoleic acid (synonym Ricinoleic acid fatty acid) is an unsaturated fatty acid prepared from Ricinoleic acid.
-When Ricinoleic acid is pyrolyzed (heated in the absence of air), it breaks down in undecylenic acid and n-heptaldehyde.
-Colorless to yellow, viscous liquid.
-Soluble in most organic solvents; insoluble in water. Combustible.
-appearance: yellowish, clear, viscous liquid
-specific gravity: (at 25°C) 0.938 - 0.944
-refractive index: (at 25°C) 1.4695 - 1.4700
-acid value mg KOH/g: min.175
-iodine value: 82 - 90
-saponification value mg: KOH/g 180 - 190
-hydroxyl value: 150 - 160
-unsaponifiable matter: max. 1
-colour Gardner: max. 7
PRODUCTION METHOD OF RICINOLEIC ACID:
Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed Ricinoleic acid.
The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.
SYNONYM:
Ricinolic acid
(R,Z)-12-Hydroxyoctadec-9-enoic acid
Ricinic acid
Ricinoleic acid acid
12-Hydroxy-cis-9-octadecenoic acid
Kyselina ricinolova
(9Z,12R)-12-hydroxyoctadec-9-enoic acid
D-12-Hydroxyoleic acid
Oleic acid, 12-hydroxy-
12-hydroxyoleic acid
Nouracid CS 80
9-Octadecenoic acid, 12-hydroxy-, [R-(Z)]-
UNII-I2D0F69854
Kyselina 12-hydroxy-9-oktadecenova
l'acide ricinoleique
NSC 281242
