ISODECYL OLEATE Isodecyl Oleate What Is Isodecyl Oleate? Decyl Oleate and Isodecyl Oleate are made from decyl alcohol and oleic acid. Decyl Oleate is made from straight chained decyl alcohol, while Isodecyl Oleate is made from branched chain decyl alcohol. Decyl Oleate and Isodecyl Oleate are used in a variety of cosmetics and personal care products, including makeup, and skin and hair care products. Why is Isodecyl Oleate used in cosmetics and personal care products? Decyl Oleate and Isodecyl Oleate act as lubricants on the skin surface, which gives the skin a soft and smooth appearance. These ingredients also form a thin film on the skin that is neither greasy nor tacky. The unique properties of Decyl Oleate and Isodecyl Oleate facilitate the application and removal of makeup. Scientific Facts: Decyl Oleate and Isodecyl Oleate are made from a naturally occurring fatty acid, oleic acid. Decyl Oleate and Isodecyl Oleate have good lubrication properties and possess low viscosity. Molecular Weight 422.7 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) XLogP3-AA 11.8 Computed by XLogP3 3.0 (PubChem release 2019.06.18) Hydrogen Bond Donor Count 0 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Hydrogen Bond Acceptor Count 2 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Rotatable Bond Count 24 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Exact Mass 422.412381 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) Monoisotopic Mass 422.412381 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) Topological Polar Surface Area 26.3 Ų Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Heavy Atom Count 30 Computed by PubChem Formal Charge 0 Computed by PubChem Complexity 373 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Isotope Atom Count 0 Computed by PubChem Defined Atom Stereocenter Count 0 Computed by PubChem Undefined Atom Stereocenter Count 0 Computed by PubChem Defined Bond Stereocenter Count 1 Computed by PubChem Undefined Bond Stereocenter Count 0 Computed by PubChem Covalently-Bonded Unit Count 1 Computed by PubChem Compound Is Canonicalized Yes CAS Number 3687-46-5 EINECS/ELINCS No: 222-981-6 COSING REF No: 75506 Chem/IUPAC Name: Decyl oleate What Is Decyl Oleate ? Decyl Oleate and Isodecyl Oleate are made from decyl alcohol and oleic acid. Decyl Oleate is made from straight chained decyl alcohol, while Isodecyl Oleate is made from branched chain decyl alcohol. Decyl Oleate and Isodecyl Oleate are used in a variety of cosmetics and personal care products, including makeup, and skin and hair care products. Why is Decyl Oleate used in cosmetics and personal care products? Decyl Oleate and Isodecyl Oleate act as lubricants on the skin surface, which gives the skin a soft and smooth appearance. These ingredients also form a thin film on the skin that is neither greasy nor tacky. The unique properties of Decyl Oleate and Isodecyl Oleate facilitate the application and removal of makeup.Decyl oleate * Made from the naturally occurring fatty acid, oleic acid. Primarily used as a lubricant.Emollient, Skin conditioning It creates a thin, non-greasy film that gives the skin a smooth and soft appearance. It's frequently used used in products geared at removing makeup. You can find this ingredient in cosmetics such as facial moisturizer/lotion, anti-aging treatment, sunscreen, eye shadow, hand & foot cream, conditioner, aftershave and eye cream.Functions: Primarily used as a lubricant. It creates a thin, non-greasy film that gives the skin a smooth and soft appearance. It's frequently used used in products geared at removing makeup. You can find this ingredient in cosmetics such as facial moisturizer/lotion, anti-aging treatment, sunscreen, eye shadow, hand & foot cream, conditioner, aftershave and eye cream. Safety Measures/Side Effects: The Cosmetic Ingredient Review (CIR) Expert Panel has assessed this ingredient as non-toxic and non-irritating, thus determining it as safe to use in cosmetic products. It has been shown to be comedogenic (clog the pores), and should be avoided by those with oily and acne prone skin types.Decyl Oleate and lsodecyl Oleate are esters of oleic acid. Decyl Oleate is used in cosmetic products at concentrations ranging from I 0.1 to > 50%. Isodecyl Oleate is used at concentrations of > 0.1-25%. Animal studies have shown both Decyl Oleate and lsodecyl Oleate to possess low acute oral toxicities in rats with LD50s of > 40 ml/kg, Single application dermal and eye studies with rabbits have shown these materials at 100% concentrations produce little or no irritation. Daily applications of 159b or 100% concentrations for 60 days to the skin of rabbits produced a moderate degree of irritation with both Decyl and lsodecyl Oleate. Neither of the ingredients was found to be a sensitizer when tested in guinea pigs at concentrations of 15%. Repeated insult patch tests containing 1-5'1'0 Decyl Oleate showed no signs of sensitization. Testing with formulations containing 5.5% Decyl Oleate produced a low number of reactions in 402 human subjects in the SchwartzPeck Prophetic Patch Test and 204 subjects with undiluted lsodecyl Oleate on nine subjects showed a total irritation score of 1 .O out of a maximum of 756. It is concluded that, because of both the chemical similarity of these compounds and the similarity of the available animal and human data, Decyl and lsodecyl Oleates warrant a conclusion of safe in the concentrations of present practices and use in cosmetics. ecyl Oleate and lsodecyl Oleate are esters of oleic acid. Formed by ester- D ification of oleic acid with decyl or isodecyl alcohol, they have the following structural formulas: Decyl Oleate- lsodecyl Oleate- CH3 (CH CH=CH(CH2) 7COOCH2 (CH2) 6CH (CH3) 27 Methyl Oleate is a compound chemically related to Decyl Oleate and lsodecyl Oleate. Its structural formula is as follows: CH3 (CH2) 7CH=CH (CH2) 7COOCH 3 The safety of methyl oleate is not under review in this report. Information and data pertaining to this compound are included to permit a more complete appraisal of the safety of Decyl Oleate and lsodecyl Oleate.Some of the chemical and physical properties of these esters are given in Reactivity Unsaturated fatty acids and their esters readily undergo aut~xidation.'~) Methyl oleate can serve as a model for autoxidation reactions which all the oleic acid esters exhibited. This compound undergoes autoxidation to give primarily trans-hydro peroxide^,'^) which are highly unstable and readily decompose to keto and hydroxy keto acids.(6) Some hydroperoxides have been found to possess carcinogenic potential.") Methyl oleate undergoes photochemical decomposition in direct sunlight and in the presence of oxygen to form the ozonide of methyl oleic acid.(*) The most important secondary products of autoxidation include alpha, beta-u nsatu rated carbonyl com pou nds.(5) Hemati n com pou nds, (') metals, (lo) and chlorinated hydrocarbon i nsecticides' ") accelerate the autoxidation reaction by shortening the induction period. Analytical Methods Methyl oleate can be generated in purities of 98% or better by repeated distillation with urea at a low temperature.('2) Analysis of this and related compounds is done by gas-liquid or thin-layer chromatography. The position of the double bond can be determined by von Rudolph's oxidation procedure. Infrared spectroscopy can be used to delineate cis-trans i~omers.('~-~~) Although gas-liquid chromatography remains the preferred routine analytical method for fatty acid ester mixtures, utilization of high performance liquid chromatography (HPLC) is increasing; for the latter has the advantage of identifying polymerized and oxidized esters which the former does not dete. PURPOSE AND FREQUENCY OF USE IN COSMETICS Decyl and lsodecyl Oleates have been widely used in cosmetic products. When applied to the skin alone, they deposit a thin oily film that is neither greasy nor tacky. They have good lubrication properties and possess low viscosity.(") Both materials are used as dispersants and lubricants in cosmetic formulations, and these are particularly important in makeup and makeup removers, in which they are used as wetting agents for iron oxide pigments; particles of such pigment are dispersed and easily suspended. The use of these ingredients facilities the application and removal of a suspension. By virtue of its branched chain structure, lsodecyl Oleate possesses several distinct properties. It has the ability to lower the freezing point of the emulsion phase of products, as well as to control product viscosity. In dispersible bath oils, it forms a white emulsion, giving the tub water a rich and milky appearance. It also has the ability to suspend aluminum chlorohydrate, which makes it valuable for dry antiperspirant formulations. Lipstick formulations have employed lsodecyl Oleate because its coupling properties increase the hardness and strength of the product without reducing its flow characteristics. Table 2 indicates categories of product use and concentrations of use for Decyl and lsodecyl Oleate.('*) The cosmetic product formulation computer printout which is made available by the Food and Drug Administration (FDA) is compiled through voluntary filing of such data in accordance with Title 21 Part 720.4 of the Code of Federal Regulations (1979). Ingredients are listed in prescribed concentration ranges under specific product type categories. Since certain cosmetic ingredients are supplied by the manufacturer at less that 100% concentration, the value reported by the cosmetic formulator may not necessarily reflect the true, effective concentration found in the finished product; the effective concentration in such a case would be a fraction of that reported to the FDA. The fact that data are only submitted within the framework of preset concentration ranges also provides the opportunity for overestimation of the actual concentration of an ingredient in a particular product. An entry at the lowest end of a concentration range is considered the same as one entered at the highest end of that range, thus introducing the possibility of a two- to ten-fold error in the assumed ingredient concentration. The compounds are employed in a variety of cosmetics, including makeup preparations, skin care preparations, and eye-shadow. Concentrations of use range from 50.1 to > for Decyl Oleate and > 0.1-25% for I sod ec y I 0 leate. Products containing these two materials are applied with varying frequency to all areas of the skin. In such formulations as blushers and moisturizing creams, exposure may occur several times a day, while in other cases there may be daily (deodorants) or less frequent (rinses, hair conditioners) applications. This occasional or daily use may extend over a period of years. Animal Toxicology Decyl Oleate: This ingredient was administered to Wistar rats by intragastric intubation at dose levels of 2.5, 5.0, 10.0, 20.0, and 40.0 mllkg COSMETIC INGREDIENT REVIEW two female rats per dose The animals were fasted for 24 hours prior to dosing. All animals were observed daily for 14 days following administration and no deaths were recorded. The acute LD50 of undiluted Decyl Oleate was greater than 40.0 mllkg of body weight. Wistar-derived rats (groups of five male, five female) were dosed by gavage with either 5.0 glkg of undiluted Decyl Oleate or 5.0 glkg of 20 percent Decyl Oleate, 80% mineral The rats were fasted for 18 hours prior to dosing. The animals were observed for signs of pharmacologic activity and drug toxicity at 1, 3, 6, and 24 hours post-dosing, after which daily observations were made for a total of 14 days. One death was recorded for male animals in the diluted sample group, and one female died following treatment with the undiluted sample. No treatment-related effects were noted in any of the surviving animals. Examination of tissues of nons,urvivors and survivors at gross autopsy revealed no abnormalities. lsodecyl Oleate: This ingredient was administered to Wistar rats by intragastric intubation at dose levels of 2.5, 5.0, 10.0, 20.0, and 40.0 mllkg (two female and three male rats per dose The animals were fasted for 24 hours prior to dosing. One death was recorded at the highest dose level. The acute LD50 of undiluted Isodecyl Oleate was reported to be greater than 40.0 ml/kg of body weight. Dermal irritation Decyl Oleate: Drai~e'~~) and Federal Hazardous Substances Labeling Act(22) (FHSA) methods were used to conduct primary skin irritation studies. Test samples of Decyl Oleate (undiluted, 10 percent in corn oil and 20% in mineral oil) were applied (0.5 ml) to clipped areas of intact and abraded albino rabbits skin (six animals in each group). The abrasions were longitudinal, epidermal incisions sufficiently deep to penetrate the stratum corneum, but not so deep as to disturb the dermis. Following application of the test material, the exposed area was covered with a patch and the entire experimental area was sealed with impervious sheeting. The animals were immobilized for a 24-hour period. The mean scores for 24- and 72-hour gradings were averaged to determine final irritation values. The primary irritation index (PII) for undiluted Decyl Oleate was calculated to be 0.28.L25) Itwas also determined that Decyl Oleate had primary irritation indices of 0.08 as a 10 percent solution in corn oil(22) and 0.05 as a 20% solution in mineral A modified Draize method was used to conduct primary dermal irritation studies with undiluted and 15% Decyl Oleate diluted in polyoxyethylene sorbitan stearate (3%), a perservative (2%)) and water; the material was found to be nonirritating (Table 3).("j) ISODECYL OLEATE ISODECYL OLEATE is classified as : Emollient Skin conditioning CAS Number 59231-34-4 EINECS/ELINCS No: 261-673-6 COSING REF No: 34643 Chem/IUPAC Name: Isodecyl oleate Isodecyl Oleate Definition Isodecyl Oleate is a moisturizer that can also be found in cosmetics. As a moisturizer in our products, decyl oleate helps prevent a product or surface, like leather, from drying out by helping it retain moisture. This makes it softer and more pliable. Clinical Assessment of Safety Decyl Oleate: A human repeated insult patch test was conducted on 103 subjects with a skin conditioner containing 1-5% Decyl Oleate. Patches containing approximately 0.2 ml of undiluted sample were applied on Monday, Wednesday, and Friday for three consecutive weeks. Fourteen days after the final insult patch, challenge patches containing the undiluted skin conditioner were applied, and results were graded 48 and 96 hours later. No evidence of sensitization was found; no information on irritation potential was Four formulations of a foundation containing Decyl Oleate (5.5%) were tested in the Schwartz-Peck Prophetic Patch Test and the Draize-Shelanski Repeated Insult Patch Test. "Virtually zero reactions occurred in 402 subjects in the Schwartz-Peck Test and 204 subjects in the Draize-Shelanski Test."(23) lsodecyl Oleate: A single insult (24-hour) occlusive patch test was conducted on 19 human subjects with undiluted lsodecyl Oleate. The test material did not elicit any erythematous reactions. A summary report of the study concluded that Isodecyl Oleate exhibits an acceptably low incidence of primary skin irritation under occlusive patch test According to an industry raw material evaluation, a procedure was undertaken with lsodecyl Oleate under the conditions of a Maibach-type Cumulative lrritancy Assay. When lsodecyl Oleate was applied undiluted under patch conditions to the skin of nine subjects for 21 consecutive days, it was found to have a total irritation score of 1 .O out of a maximum possible 756.(30) SUMMARY Decyl Oleate and lsodecyl Oleate are esters of oleic acid. Decyl Oleate is used in cosmetic products at concentrations ranging from 10.1 to >50°/o. lsodecyl Oleate is used at concentrations of > 0.1 -25%. Animal studies have shown Decyl Oleate and lsodecyl Oleate to possess low acute oral toxicities in rats; both have LD50s of > 40 mllkg. Single application dermal and eye studies with rabbits have shown that these materials in concentrations up to 100% produce little or no irritation. When 15% or 100°/o concentrations were applied to the skin of rabbits daily for 60 days, both Decyl Oleate and lsodecyl Oleate produced moderate degrees of irritation. Neither ingredient was found to be a sensitizer when it was tested in guinea pigs at concentrations of 15%. Repeated human insult patch tests on 103 subjects with a skin conditioner containing 1-5% Decyl Oleate showed no signs of sensitization. Industrial testing with formulations containing 5.5% Decyl Oleate produced a low number of reactions in 402 human subjects in the Schwartz-Peck Prophetic Patch Test and in 204 subjects in the Draize-Shelanski Patch Test. Repeated insult patch tests with undiluted Isodecyl Oleate on an unspecified number of human subjects showed a total irritation score of 1 .O out of a possible maximum of 756. A single insult occlusive patch test on 19 human subjects with undiluted lsodecyl Oleate produced a low level of primary skin irritation. No chronic, oral subchronic, carcinogenicity, mutagenicity, or teratogenicity animal testing data were available to the Panel. Nor were there any phototoxicity or photosensitization studies in humans.