RICINOLEIC ACID

RICINOLEIC ACID
(Ricinolate = Castor oil acid)

IUPAC name: (9Z,12R)-12-hydroxyoctadec-9-enoic acid
CAS Number: 141-22-0
EC Number: 205-470-2
UNII: I2D0F69854
INCI name: Ricinus communis (castor) seed oil
Molecular Formula: C18H34O3
Beilstein/REAXYS Number: 1727813
SMILES string: CCCCCC[C@@H](O)CC=C/CCCCCCCC(O)=O
InChI: 1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1

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 (Ricinus communis L., Euphorbiaceae) seeds or in sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). 
About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.
Ricinoleic Acid is A 12-hydroxy fatty acid that can be a used as a substrate for conjugated linoleic acid synthesis.
Ricinoleic acid is a colorless to yellow, viscous, liquid, water-insoluble, unsaturated hydroxyl acid, C18H34O3, occurring in castor oil in the form of the glyceride: used chiefly in soaps and textile finishing.
ricinoleic acid is a monounsaturated fatty acid.

Ricinoleic acid is an oily unsaturated hydroxy fatty acid C18H34O3 that occurs in castor oil as a glyceride and yields esters important as plasticizers.
Ricinoleic acid is the main fatty acid constituent of castor oil which has antimicrobial activity.
Ricinoleic acid is a high-value hydroxy fatty acid with broad industrial applications.
Ricinoleic acid is a naturally occurring 12-hydroxy fatty acid.
Ricinoleic acid has impressive anti-inflammatory properties.
Ricinoleic acid, cis-12-hydroxy-9-octadecenoic acid, has an unusual polarity due to position of hydroxyl group.
Castor oil is the only commercially available vegetable oil containing hydroxy functionality of a fatty acid present abundantly (70–90%) because of ricinoleic acid.

Ricinoleic acid (12-hydroxy-9-cis-octadecenoic acid) is an unsaturated omega-9 fatty acid that naturally occurs in mature Castor plant (Ricinus communis L., Euphorbiaceae) seeds or in sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae).
Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid.
Ricinoleic acid, an unsaturated hydroxy acid (i.e., one containing an ―OH group), occurs in castor oil. 
When ricinoleic acid is pyrolyzed (heated in the absence of air), it breaks down to give undecylenic acid and n-heptaldehyde.
Ricinoleic acid is a poly-unsaturated fatty acid and its high concentration in castor seeds might be responsible for castor oil’s remarkable properties.

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. ricinoleic acid 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.
Ricinoleic acid is a long-chain fatty acid, hydroxy fatty acid, unsaturated fatty acid, secondary alcohol, monocarboxylic acid or derivatives, carboxylic acid, carboxylic acid derivative, organic oxygen compound, organic oxide, hydrocarbon derivative, organooxygen compound, carbonyl group and an aliphatic acyclic compound.
Ricinoleic acid has a unique molecular structure attributed to the hydroxyl group located in the middle of the unsaturated chain.

In the triglycerol form of ricinoleic acid, hydrogen bonding occurs with the hydroxyl groups resulting in greater viscosity than in other oils.
castor which includes ricinoleic acid is a superior lubricant as compared to other vegetable oils.
The hydroxyl group—only separated from the double bond by a methylene group— of ricinoleic acid imparts increased oxidative stability, 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 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.

Uses and Applications

Ricinoleic acid is used in cosmetics, coatings, detergents, food, medicine, and plasticizer technology.
Ricinoleic acid’s 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.
Ricinoleic acid is used in hair preparations, soaps, and skin ointments. In addition, one of the largest applications of castor oil in personal care is in lipstick preparations.
Ricinoleic acid can undergo a wide range of reactions enabling formation of several derivatives like ricinoleyl alcohol, methyl ricinoleate, azelaic acid, and ricinenic acid are used as plasticizer and emulsifier.
Ricinoleic acid derivatives are used in pigment, printing ink, and textile finishing. 
Ricinoleic acid of castor oil is unique among all other vegetable oils, making it attractive for a wide spectrum of applications.

Ricinoleic acid can serve as a substrate for the synthesis of conjugated linoleic acids.
About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.
Ricinoleic acid is considered safe and non-toxic as a food constituent in humans
Ricinoleic acid are thought to increase absorption in the skin and are sometimes used in the treatment of various skin conditions, including dermatosis, psoriasis, and acne.
The presence of ester linkage, a double bond and the hydroxyl group in ricinoleic acid favours the oil as a suitable renewable resource for many chemical reactions, modifications and transformations.

Ricinoleic acid has been used in several applications, such as the production of biodiesels, biomass, antioxidants and drugs.
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.
The zinc salt of ricinoleic acid is used in personal care products such as deodorants.
Ricinoleic acid exerts analgesic and anti-inflammatory effects.
Ricinoleic acid acts as a specific algicide for the control of cyanobacteria (formerly called blue-green algae).
Using the Fe3O4 nanoparticles modified by ricinoleic acid, the final polymeric material had an increase in the reaction rate, exhibiting good thermal stability and behaving as superparamagnetic material.
The production of polyester from ricinoleic acid with and without in situ insertion of magnetic Fe3O4 nanoparticles with their surface modified by ricinoleic acid has been obtained
Ricinoleic acid is used In cosmetics and personal care products, Castor Oil 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 and ricinoleic acid’s derivatives are used in: 
Anticaking agent - Zinc Ricinoleate
Deodorant agent - Zinc Ricinoleate
Emulsion stabilizer - Glycol Ricinoleate
Opacifying agent - Zinc Ricinoleate
Skin conditioning agent - emollient - Ethyl Ricinoleate, Glyceryl Ricinoleate, Glyceryl Ricinoleate SE, Glycol Ricinoleate, Isopropyl Ricinoleate, Methyl Ricinoleate
Skin conditioning agent - occlusive - Ricinus Communis (Castor) Seed Oil; Cetyl Ricinoleate, Hydrogenated Castor Oil, Octyldodecyl Ricinoleate
Surfactant - cleansing agent - Potassium Ricinoleate, Sodium Ricinoleate, Ricinoleic Acid
Surfactant - emulsifying agent - Glyceryl Ricinoleate, Glyceryl Ricinoleate SE, Potassium Ricinoleate, Sodium Ricinoleate
Viscosity increasing agent - nonaqueous - Hydrogenated Castor Oil

Aside from getting rid of acne, ricinoleic acid also helps detoxify the skin.
Ricinoleic acid helps break up the oils that clog glands and pores on the face.
Ricinoleic acid released from the oil in the intestine, is responsible for the analgesic and anti-inflammatory effects.
Ricinoleic acid increases scalp blood flow, which can promote healthier hair and growth while also cutting down on inflammation.
Ricinoleic acid can be used as surfactant, emulsifier, and can be used in pharmaceutical industry as energy storage, energy source and membrane stabilizer.

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil. 
The zinc salt of ricinoleic acid is used in personal care products, such as deodorants
Ricinoleic acid (12-hydroxy-cis-9-octadecaenoic acid) was an effective substrate for conjugated linoleic acid (CLA) production by washed cells of Lactobacillus plantarum AKU 1009a.
Ricinoleic acid as a green capping agent in the synthesis of nanomaterials.
Polymerization of the ricinoleic acid lactones with catalysts commonly used for ring-opening polymerization of lactones, under specific reaction conditions, resulted in oligomers.
Ricinoleic acid, a hydroxy fatty acid, is an attractive feedstock for the production of high-performance lubricants, cosmetics, polymers, surfactants, and coatings.

The inclusion of 2 g/day of ricinoleic acid (RA) in diets of dairy cows improved the performance, without any risk to health and welfare of animals, being a promising additive in ruminant nutrition.
Ricinoleic acid, the main constituent of castor oil, aids the stability of the formed emulsion 
The ricinoleic acid derivatives that are widely used are in the form of esters which can function primarily as skin conditioning agents, emulsion stabilizers, cosmetic surfactants, and can act as antimicrobial agents. 
Ricinoleic acid is used in metalworking fluids and construction chemicals.
Readily undergoes multi-directional chemical and biochemical transformations to produce derivatives with the retained carbon skeleton or with its degradation.
The carboxyl and hydroxy groups in the dimeric ricinoleic acid may further undergo esterification, providing the oligomeric ricinoleic acid with different oligomerization degree.
 

More than 90% of castor oil’s fatty acid content is ricinoleic acid. 
Ricinoleic acid’s omega-9 has pain relief and anti-inflammatory effects., when applied to the skin may help relieve issues like joint pain and menstrual cramps.
Ricinoleic acid (1, RA), from castor oil, is an important commodity in the chemical and pharmaceutical industry due to an unusual chemical structure, which has an additional hydroxyl group compared with other oleic acids.
Ricinoleic acid—a type of fatty acid found to fight inflammation. 
When ricinoleic acid is applied to the scalp, it’s purported to enhance the health of the hair follicles and, in turn, promote hair growth (as well as protect against hair loss).
Ricinoleic acid is used as intermediate for detergents, soaps, resins, lubricants; lubricant, rustproofing in cutting oils; in textile finishing, resin plasticizers, inks, coatings, cosmetics; modifier for coatings and adhesive polymers; sometimes added to Turkey red oil, dry-cleaning soap; ingred. in vaginal jellies to maintain/restore normal vaginal acidity
Due to the presence of the hydroxyl group in homoallylic position and asymmetrically substituted carbon atom, ricinoleic acid may undergo a number of chemical and biochemical transformations resulting in the products with some specific bioactivities.
Ricinoleic acid is mainly used in pigments, printing inks, and textile finishing.
Ricinoleic acid is used to generate different oleochemicals as chemical intermediates.

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil.
Ricinoleic acid exerts analgesic and anti-inflammatory effects. 
Ricinoleic acid can be hydrolyzed to various long chain alcohols.
Ricinoleic acid, from castor (Ricinus communis) seed oil, is a high-value hydroxy fatty acid with broad industrial applications. 
Ricinoleic acid is an attractive feedstock for the production of high-performance lubricants, cosmetics, polymers, surfactants, and coatings.
Ricinoleic acid is used as cleaning Agent since ricinoleic acid helps keeping a clean surface.
Ricinoleic acid is used as emollient since ricinoleic acid softens the skin. Ricinoleic acid is used as emulsifying agent since ricinoleic acid promotes the formation of intimate mixtures between immiscible liquids by modifying the interfacial tension (water and oil).
Ricinoleic acid is used as surfactant since ricinoleic acid reduces the surface tension of cosmetics and contributes to the uniform distribution of the product during its use.
 
 

 
 
Physical and Chemical Properties

Appearance: Yellowish, Clear Viscous liquid
Molecular Weight: 298.5
XLogP3-AA: 5.7
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 15
Exact Mass: 298.25079494
Monoisotopic Mass: 298.25079494
Topological Polar Surface Area: 57.5 Ų
Heavy Atom Count: 21
Formal Charge: 0
Complexity: 261
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 1
Acid Value: 175 - 186 mg KOH/gm
Iodine Value: 84 - 95 Wijs g 12/100g
Saponification Value: 180 - 186 mg KOH/gm
Hydroxyl Value: 155 Min mg KOH/gm
Specific Gravity: 0.935 - 0.945 gm/ml @ 25C

Refractive Index: 1.4695 - 1.4720 @ 25C
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Boiling Point: 245 °C at 10 mm Hg
Melting Point: 245 °C at 10 mm Hg
Flash point: 248°C
Optical activity: α]/D 6.5±1.5°, c = 2 in acetone
Solubility: 3460 mg/L (at 25 °C), Soluble in alcohol, acetone, ether, chloroform, In water, 3.46X10+3 mg/L at 25 °C
Density: 0.940 at 27.4 °C/4 °C
Vapor pressure: 10 mm Hg at 226 °C, 4.49X10-3 mm Hg at 25 °C (est)

log Kow = 6.19 (est)
logS: -5.1
Henry's Law constant = 3.7X10-10 atm-cu m/mol at 25 °C (est)
Viscosity: 400 cSt at 25 °C
Refractive Index Specific optical rotation: +6.67 deg at 22 °C/D; +7.15 deg at 26 °C/D (C = 5 in acetone); index of refraction: 1.4716 at 20 °C/D
pKa = 4.74 (est)
Neutralization value: 187.98
Iodine value: 85.05
Pour point: -23 °C
Acid value: 180
Saponification value: 186

Hydroxyl radical reaction rate constant = 8.45X10-11 cu cm/molec-sec at 25 °C 
Ozone reaction rate constant = 1.30X10-16 cu cm/molec-sec at 25 °C 
Thermal conductivity: 4.727 W/m°C3
IR Spectra, IR: 21992
Dextrorotary
Formula: C18H34O3
Molecular weight: 298.46
Physical state: Viscous yellow liquid
Melting point: 5.5°C
Boiling point: 246°C
Specific gravity: 0.94
Density: 0.940 kg/mm3
Vapor pressure: 4.49 × 10− 3 mmHg
Viscosity: 400 cSt (25°C)
Solubility: in Alcohol, acetone, ether, chloroform

Storage temperature: −20°C
Mass Composition: C 72.44%; H 11.48%; O 16.08%
Optical Rotation: [a]26D +7.15 (c, 5 in Me2CO)
pKa (Strongest Acidic): 4.99
pKa (Strongest Basic): -1.3
Storage: In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)

Production

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil.
Ricinoleic acid can be easily made by saponification of castor oil. For better purification, fractional distillation can be employed; due to ricinoleic acid’s  high boiling point, vacuum distillation is often employed.
The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.
Industrially, ricinoleic acid is manufactured by saponification or fractional distillation of hydrolyzed castor oil
Ricinoleic acid can be produced by hydrolysis of castor oil.
biological source: natural (organic)
Ninety percent of the fatty acids in Castor Oil are ricinoleic acid which is a monounsaturated, 18-carbon fatty acid

Castor Oil maintains its fluidity at both extremely high and low temperatures. 
Ricinoleic acid occurs in castor oil and other oils e.g. grape and ergot (Claviceps purpurea) 
Ricinoleic acid is found in corn. 
Ricinoleic acid occurs in castor oil and other oils e.g. grape and ergot.
Rreparative isolation of ricinoleic acid (RA) from Castor oil (CO) for use as building blocks in biopharmaceutical synthesis.
Ricinoleic acid present in the seeds of Ricinus spp, Euphorbiaceae and in the fatty acids of castor and ergot oil

Synonyms
RICINOLEIC ACID
141-22-0
Ricinolic acid
(R,Z)-12-Hydroxyoctadec-9-enoic acid
Ricinic acid
Castor oil 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
9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)-
CHEBI:28592
12-Hydroxyoctadeca-9-enoic acid
12R-hydroxy-9Z-octadecenoic acid
MFCD00084840
12-D-Hydroxy-9-cis-octadecenoic acid
I2D0F69854
12-Hydroxy-9-octadecenoic acid
(R)-12-Hydroxy-cis-9-octadecenoic acid
9-Octadecenoic acid, 12-hydroxy-, (R-(Z))-
DSSTox_CID_21567
DSSTox_RID_79777
DSSTox_GSID_41567
Riconoleic acid
Ricinusoleic acid
Acide ricinoleique
[r]-12-hydroxy-cis-9-octadecenoic acid
CAS-141-22-0
NCGC00161336-02
(cis,R)-12-hydroxyoctadec-9-enoic acid
Acide ricinoleique [French]
Kyselina ricinolova [Czech]
Ricinolsaeure
ricinoleic-acid
9-Octadecenoic acid, 12-hydroxy-
l'Acide ricinoleique [French]
HSDB 5634
9-Octadecenoic acid,12-hydroxy-,(Z)-
NCGC00181322-01
EINECS 205-470-2
VESPULA PENSYLVANICA B708568K062
(9Z,12R)-12-Hydroxy-9-octadecensaeure
(R-(Z))-12-Hydroxy-9-octadecenoic acid
9-Octadecenoic acid, 12-hydroxy-, (Z)-
AI3-17956
9-Octadecenoic acid, 12-hydroxy-, (cis)-
Kyselina 12-hydroxy-9-oktadecenova [Czech]
Ricinoleic acid, >=99%
SCHEMBL18144
Flexricin 100 (Salt/Mix)
BML2-F10
9-Octadecenoicacid,12-hydroxy-
CHEMBL3186422
DTXSID0041567
HY-N6070
12-Hydroxy-9(Z)-octadecenoic acid
Ricinoleic acid, analytical standard
Tox21_113406
Tox21_301098
LMFA02000184
ZINC12954494
12R-Hydroxy-9-cis-octadecenoic Acid
AKOS016005826
(9Z)-(12R)-Hydroxyoctadecenoic acid
DB02955
(Z,R)-12-hydroxyoctadec-9-enoic acid
12-OH 9c-18:1
NCGC00161336-01
NCGC00161336-03
NCGC00181089-01
NCGC00254998-01
(9Z)-12-Hydroxy-9-octadecenoic acid #
AS-65782
CS-0032307
R0027
C08365
Ricinoleic acid, Vetec(TM) reagent grade, 80%
Q424484
9-Octadecenoic acid, 12-hydroxy-, (theta-(Z))-
W-108189
9-Octadecenoic acid, 12-hydroxy-, (R-(Z))- (9CI)
(9Z,12R)-12-HYDROXY-9-OCTADECENOIC ACID
D-12-HYDROXYOLEIC ACID
RICINOLEATE
(R)-12-Hydroxy-cis-9-octadecenoic acid
12-hydroxyoleic acid
ricinelaidic acid
12-Hydroxyoleic acid
12-Hydroxyoleate
Ricinoleate
(9Z)-(12S)-Hydroxyoctadecenoic acid
(9Z)-12-Hydroxy-9-octadecenoic acid
(9Z)-12-Hydroxyoctadec-9-enoic acid
12-Hydroxy-oleic acid
Flexricin 100
Ricinelaidic acid
Ricinic acid
Ricinusoleic acid
Riconoleic acid
CS 80
H 1657
Cenwax C
P -10 acid
NSC 281242
ricinicacid
RICOLEICACID
Edenor Ri 90
castoroilacid