Your document download will begin shortly. 29(3): 283-330, 1999. For use herein, the encapsulation forms a protective system to prohibit or inhibit the oxidation of the retinoid. Other adverse effects Hydroquinone is used as a topical application in skin whitening to reduce the color of skin. Hydroquinone undergoes oxidation under mild conditions to give benzoquinone, process which is reversible. 77, No. It is found in wheat, rye, and barley.It is a precursor to diverse industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners. At 40C, 4% hydroquinone compositions are more likely to excessively discolor and magnesium ascorbyl phosphate helps to stabilize the color, by preventing the brownish black discoloration and maintaining an amber color. Appearance: Free-flowing white crystalsOdor: OdorlessMolecular weight: 110.11Empirical formula: C6H6O2Assay (Anhydrous basis): 99.0-100.5 %Melting point: 172-174CWater: 0.5 wt % max.Residue on ignition: 0.5 % maxSolubility: Moderately soluble in water, glycerin, propylene glycol, and highly soluble in ethanol, Can work in conjunction with glycolic acid to help reduce pigment in melasma Non-GMOExtremely low vapor pressureUSP GradeEuropean Pharma GradeDrug master file available upon request. ChemPoint will not under any circumstances release personal user information to individuals or companies. Then take the water and put the measurement into the microwave until boiled. 12.4. This is a prescription-only ingredient in some countries, including the member states of the European Union under Directives 76/768/EEC:1976. So, does anybody know of another solvent I could use that has a higher solubility and is relatively non-toxic. Color stability improvement is evident at all levels. This range of pH has been preferred for hydroquinone compositions, because it has been believed that the hydroquinone is less likely to excessively discolor under acid conditions. The solubilities in binary and ternary systems of hydroquinone (1,4-dihydroxybenzene) and p-quinone (1,4-benzoquinone) in supercritical carbon dioxide were measured in the pressure range 10.0 to 35.0 MPa at temperatures of 333, 348 and 363 K.In binary systems, the solubility of hydroquinone was three orders of magnitude lower than that of p-quinone. Solubility of Hydroquinone. You take the cream, put it in a container, take the powder measurement and add it. Classical photo shops also sell hydroquinone. Diamines, useful in the rubber industry as antiozone agents, are similarly produced from aniline: Hydroquinone has a variety of uses principally associated with its action as a reducing agent that is soluble in water. HYPERPIGMENTARY STAIN ELIMINATING CREAM FOR FACE SKIN AND ITS USE. While the hydroquinone is effective for the pigmentation disorder treatment, retinoid is used for its skin treatment benefits. Also in this embodiment is a cationic salt of acidic ascorbyl esters, which further helps to maintain the acceptable color desired in the hydroquinone composition. Chem. The solubilities of benzoic acid, salicylic acid, resorcinol and hydroquinone in water and in 1-octanol were measured by the dynamic method which is also called the synthetic method from 297.25K to 334.45K. Using differential scanning calorimetry (DSC Q2000 and SDT Q600), the melting temperature and the enthalpy of fusion of these solutes were determined. 0 7 r @ &. [21][25][23] NTP evaluation showed some evidence of long-term carcinogenic and genotoxic effects[26], While hydroquinone remains widely prescribed for treatment of hyperpigmentation, questions raised about its safety profile by regulatory agencies in the EU, Japan, and USA encourage the search for other agents with comparable efficacy. If you have any specific questions, please include them in the comments section. I understand the concentrations are high but I have used them before, its just too expensive to keep buying from a compounding pharmacy. The Molecular Weight is 110.11 g/mol. This compound is gathered from the beaver's castor sacs.[35]. 0000053439 00000 n Eastman Hydroquinone, USP, meets or exceeds the requirements of the United States Pharmacopoeia and is produced under conditions of current good manufacturing practices (cGMP). However, these hydroquinone-containing compositions were in the acidic pH range and did not contain cationic salts of acidic ascorbyl esters, such as magnesium ascorbyl phosphate. At 40C, 4% hydroquinone compositions have the same color stability with slightly more sodium metabisulfite, at least about 0.01% at about 3.5 to about 4.0 pH; at least about 0.05% sodium metabisulfite at about 4.5 to about 6.0 pH; and at pH; at least about 0.05% sodium metabisulfite at about 4.5 to about 6.0 pH; and at least about 0.10% sodium metabisulfite at about 6.5 to about 7.0 pH. Remove contact lenses, if present and easy to do. Retinoids are included from about 0.01% to about 5%, preferably from about 0.025% to about 2%, more preferably 0.05% to about 1.0%, and most preferably from about 0.025% to about 0.5%. Variations in pH have proven to result in excessive discoloration ranging from brownish to black. This is a preview of subscription content, access via your institution. In hydroquinone and sodium metabisulfite compositions, it is believed that the sodium metabisulfite oxidizes first and delays the start of any oxidation of the hydroquinone, so that excessive discoloration is delayed or totally avoided. Glycerol and citric acid, non-toxic and renewable reagents, were crosslinked by a melt polymerization reaction at temperatures from 90-150C. Using a laser-monitoring observation technique, the solubility of hydroquinone in water, methanol, ethanol, 2-propanol, ethyl acetate, butyl acetate, and acetic acid were measured at temperatures ranging from 276.65 K to 345.10 K under the atmospheric pressure. Exceptional antioxidant qualities are seen at 0.10% (all percentages in the application are weight percent) and above, preferably from about 0.05% to about 0.5% for sodium metabisulfite. Hydroquinone is soluble in alcohol solvents such as ethanol and methanol [17]. Human exposure to hydroquinone can occur by dietary, occupational, and environmental sources. This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions. Water Solubility 73000 mg/L at 25C 2.6B pH pKa 4.0 - 4.7 pK1 = 9.9 2.12 Oxidation:Reduction Potential +286 mV at 25C and pH 7 ENVIRONMENTAL FATE/BIODEGRADATION x- [ 0}y)7ta>jT7@t`q2&6ZL?_yxg)zLU*uSkSeO4?c. R -25 S>Vd`rn~Y&+`;A4 A9 =-tl`;~p Gp| [`L` "AYA+Cb(R, *T2B- 552591, Z. Esina, M. Korchuganova, Theor. HYdroquinone can be found in various skin care products. 2005 Wiley-VCH, Weinheim. Other solubilities: soluble in alcohol and ether,slightly soluble in benzene,readily soluble in ethanol,acetone and methanol, Needle-like Crystals or Crystalline Powder. The process of making a stable hydroquinone composition having a pH of about 5.5 to about 8.0 comprising: combining the following ingredients, in a carbon dioxide atmosphere: first, magnesium ascorbyl phosphate and sodium metabisulfite, then, third, magnesium ascorbyl phosphate, then, Application filed by Medicis Pharmaceutical Corp, [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O*, OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C, 3-aminopropyl [(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-5-oxo-2H-furan-4-yl] hydrogen phosphate, NCCCOP(O)(=O)OC1=C(O)[C@@H]([C@@H](O)CO)OC1=O, OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C, OC(=O)/C=C(\C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C, trisodium;[(5R)-5-[(1S)-1,2-dihydroxyethyl]-2-oxido-4-oxofuran-3-yl] phosphate, [Na+].[Na+]. G(DC:!c?5w [QDP, f\01j&8ea]Ke~z d _5H^j0M.|Y^bYb[Rm~-[ImSv. ;4kNNw?r yn^EOwCDyd>_?TU^vyss*|g9A1 avr 2o~molpb|CZTu(70 CKRu)(5O_^6|Qta', uG70]'vt|n3Xh[vMTc.{o0Y#(O5\/mGfI+L0~1E1~hi:ZY_W6n*EaSn*R+I)Pw|y\^/te;yO. uuid:a150f3fd-7f22-4439-aa26-6f445f4017e5 However, hydroquinone discolors at the pH range of 7.0 to 8.5. The reservoir opens through a muscle-controlled valve onto a thick-walled reaction chamber. One of these, 4-butylresorcinol, has been proven to be more effective at treating melanin-related skin disorders by a wide margin, as well as safe enough to be made available over the counter. Eng. 4]DYR@'c Hydroquinone is a white, odorless, crystalline solid with an extremely low vapor pressure. - 65.21.225.73. 0000008514 00000 n Such carriers are widely known in the art and deliver the composition's ingredients to the skin without excessive degradation, inactivation or other unwanted interaction. Hydroquinone (C 6 H 4 (OH) 2), also known as benzene-1,4-diol or quinol, is an aromatic organic compound, with a variety of uses in chemistry. Substituted derivatives of this parent compound are also referred to as hydroquinones. Correspondence to Boucif Belhachemi. Eng. Continue rinsing.IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.Avoid release to the environment.WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. Production of Hydroquinone Industrial production of hydroquinone usually happens in two ways. Discoloration of hydroquinone compositions may be accelerated by repeated exposure to oxygen or exposing the compositions to high temperatures, which may be found inside a car or delivery vehicle on a hot sunny day. Hydroquinone is combustible when preheated. Solubility: Moderately soluble in water, glycerin, propylene glycol, and highly soluble in ethanol Features & Benefits Can work in conjunction with glycolic acid to help reduce pigment in melasma Non-GMO Extremely low vapor pressure USP Grade European Pharma Grade Drug master file available upon request Applications The drug is freely soluble in water and in alcohol. ADS sulfur acids, imidic, hydrazonic, hydroximic acids, Carboxylic acids, e.g. M1 and M2 microemulsions contain ethanol as co-surfactant. We apologize! 38, 565571 (2006), K. Carlsson, B. Karlberg, Anal. Conversion factors (at 25C and normal atmospheric pressure) 1 ppm = 4.5 mg/m 3 1 mg/m 3 = 0.222 ppm Table 1. AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR, Kind code of ref document: Fill out the form below, and we will send you the document as soon as we can! endstream endobj 276 0 obj <>stream Some documentation and label information may refer to the legacy brand. Eng. When the contents of the reservoir are forced into the reaction chamber, the catalases and peroxidases rapidly break down the hydrogen peroxide and catalyze the oxidation of the hydroquinones into p-quinones. We have discovered that a hydroquinone composition (with about 1 to about 12% hydroquinone, preferably with about 2% to about 10%, more preferably with about 2% to about 8%, more preferably with about 2% to about 4%, most preferably with about 3% to about 4% hydroquinone) with preferably a pH of from about 5.5 to about 8.0, more preferably a pH of from about 5.5 to about 7.5, and most preferably at a pH of from about 6.0 to about 7.5, can include cationic salts of acidic ascorbyl esters, preferably sodium ascorbyl phosphate, more preferably aminopropyl ascorbyl phosphate, most preferably magnesium ascorbyl phosphate as an antioxidant and the color destabilization problems are appreciably less as compared to hydroquinone compositions without such a cationic salt of acidic ascorbyl esters in the neutral pH range: preferably a pH of from about 5.5 to about 8.0, more preferably a pH of from about 5.5 to about 7.5, and most preferably at a pH of from about 6.0 to about 7.5. Skin Contact Wash off immediately with plenty of water for at least 15 minutes. 0000002585 00000 n Found. ORIGINAL CODE: 0009012, Free format text: It is moderately soluble in water and highly soluble in alcohol. [23] This conclusion was reached based on the extent of absorption in humans and the incidence of neoplasms in rats in several studies where adult rats were found to have increased rates of tumours, including thyroid follicular cell hyperplasias, anisokaryosis (variation in nuclei sizes), mononuclear cell leukemia, hepatocellular adenomas and renal tubule cell adenomas. 0000002544 00000 n Other properties of hydroquinone are given in Table 1. Recent pieces of . All Rights Reserved, View All Eastman Hydroquinone USP Articles. Place water in container then bring the temperature to 15c in a boil bath then add products at this point when youre making the lotion u will need to add the other ingredients. Stir until uniform. 20grams ofhydroquinonein 20oz is liquid is 10%. Preparation, optimization and in vivo. They may also include ingredients with other therapeutic actions, such as anti-inflammatories, antibiotics, exfoliants and peels. 2017-02-16T10:10:56+01:00 Environ. The most preferred example of such an antioxidant is sodium metabisulfite. Approximate Solubilities of USP and NF Articles, methanol, 13; ethyl acetate, >10,000; hexanes, >10,000, 0.1 N hydrochloric acid, 1; 0.1 N sodium hydroxide, 1, boiling alcohol, 50; boiling chloroform, 80; acetone at 50, methanol, 3; isopropanol, 69; benzene, 2500; petroleum ether, 5000, dimethylformamide, 10; 10 N sodium hydroxide, 3.5, dimethylacetamide, 2; dimethylformamide, 3.5; dimethylsulfoxide, 3.5, 0.1 N hydrochloric acid, 2500; 0.1 N sodium hydroxide, 100, isopropyl alcohol, 4; propylene glycol, 9; methanol, 5.3, isopropyl alcohol, 1408; propylene glycol, 119; methanol, 75, alcohol solution (1 in 2), 2; diethylphthalate, <1; benzyl benzoate, <1, acetone, 100; methanol, 1000; 0.1 N hydrochloride acid, >1000, absolute alcohol, 8; methanol, 8; propylene glycol, 19, pyridine, 10; methanol, 71; acetone, 130; methylene chloride, 286; toluene, 2000; dioxane, 2000, carbon disulfide, 2 (slowly and usually incompletely), carbon disulfide, 2 (slowly and usually incompletely) olive oil, 100, methylenedichloride, 43; 4-methyl-2-pentanone, 100. The Beaver: Its Life and Impact. As utilized herein, the inhibition of the retinoid oxidation should be sufficient to prohibit browning of the composition for its shelf life, preferably greater than about six months, more preferably greater than about twelve months, and most preferably greater than about eighteen months. and our Azelaic acid (AzA) is a organic compound with the formula HOOC(CH 2) 7 COOH. Hydroquinone is an aromatic organic compound which is currently used in two main sectors: . The protective system can be an entrapment system, a single or multi-laminar system, such as by formation of vesicle, such as a liposome, or by utilizing wax, paraffin, silicone, polyethylene or any material or system which protects the retinoid from oxidation. An improvement in the color stability of the 4% hydroquinone compositions is seen at and above 2.0% magnesium ascorbyl phosphate in the 6-7 pH range. 0000000731 00000 n The toxicology of hydroquinone - relevance to occupational and environmental exposure. Crit. Dietland Muller-Schwarze, 2003, page 43 (, National Institute for Occupational Safety and Health, Additive manufacturing of ceramics from preceramic polymers, http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:31976L0768:EN:HTML, "Clear N Smooth Skin Toning Cream recalled", Skin Bleaching Drug Products for Over-the-Counter Product Use; Proposed Rule, "About the Center for Drug Evaluation and Research - Hydroquinone Studies Under The National Toxicology Program (NTP)", Campaign For Safe Cosmetics - Hydroquinone, "Skin lightening preparations and the hydroquinone controversy", https://en.wikipedia.org/w/index.php?title=Hydroquinone&oldid=1136453324, Wikipedia articles needing page number citations from October 2016, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License 3.0, The most widely used route is similar to the, A potentially significant synthesis of hydroquinone from, Hydroquinone was first obtained in 1820 by the French chemists, Pelletier and Caventou (1820) "Recherches chimiques sur les quinquinas" (Chemical investigations of quinquinas [i.e., the bark of various, This page was last edited on 30 January 2023, at 11:09. The FDA had classified hydroquinone in 1982 as a safe product - generally recognized as safe and effective (GRASE), however additional studies under the National Toxicology Program (NTP) were suggested in order to determine whether there is a risk to humans from the use of hydroquinone. : Metabolism and disposition of hydroquinone in Fischer 344 rats after oral or dermal administration. It has a white-solid appearance. Without being limited to the mechanism of this discoloration, it is believed that the discoloration may be caused at least in part by oxidation of the hydroquinone. Read our Privacy Notice. Thus, merely adding one retinoid to a hydroquinone composition would result in instability and/or discoloration, and adding hydroquinone to a retinoid product would have a similar result. A further embodiment of the invention includes a method for stabilizing a hydroquinone composition (with about 1% to about 12% hydroquinone, preferably about 2% to about 10%, more preferably about 2% to about 8%, and most preferably about 3% to about 4%) with a neutral pH of from about 5.5 to about 8.0, more preferably a pH of from about 5.5 to about 7.5, and most preferably at a pH of from about 6.0 to about 7.5, by adding a water-soluble antioxidant, preferably sulfite, including but not limited to sulfites, bisulfites, metabisulfites, their salts and their derivatives, most preferably sodium metabisulfite, and a cationic salt of acidic ascorbyl esters, preferably sodium ascorbyl phosphate, more preferably aminopropyl ascorbyl phosphate, most preferably magnesium ascorbyl phosphate. 0000005757 00000 n Then add it to the ingredients. Antioxidants in the hydroquinone phase are instrumental in stabilizing the color of the hydroquinone composition. [19][20], In 2006, the United States Food and Drug Administration revoked its previous approval of hydroquinone and proposed a ban on all over-the-counter preparations. A2, Designated state(s): Please sign in to view account pricing and product availability. Although about 0.01% sodium metabisulfite without magnesium ascorbyl phosphate may not color stabilize an about 4% hydroquinone composition, and about 0.5% magnesium ascorbyl phosphate without sodium metabisulfite may not either, the combination of sodium metabisulfite and magnesium ascorbyl phosphate in these percentages is effective to stabilize the color of the about 1% to about 12%, about 2% to about 10%, preferably about 2% to about 8% and more preferably about 3% to about 4% and most preferably 4% hydroquinone composition. Anyone you share the following link with will be able to read this content: Sorry, a shareable link is not currently available for this article. The solubility of sodium phenytoin in binary mixtures of ethanol +water at 298.2, 303.2, 308.2 and 313.2 K was measured. The disodium diphenolate salt of hydroquinone is used as an alternating comonomer unit in the production of the polymer PEEK. These can be burning, redness, sensitization and irritation in some patients. Hydroquinone compositions are effective but have some undesirable side effects. Thus, while cationic salts of acidic ascorbyl esters, preferably magnesium ascorbyl phosphate and aminopropyl ascorbyl phosphate, have beneficial antioxidant effects on the skin, the combination with hydroquinone in the invention results in a compatible and stable composition. Privacy Policy. Data 53, 12781282 (2008), A. %PDF-1.4 % Belhachemi, B., Makhlouf, H. & Belhachemi, M.H. [32], Hydroquinone is thought to be the active toxin in Agaricus hondensis mushrooms. Chemically, hydroquinone is designated as p-dihydroxybenzene; the empirical formula is C 6 H 6 O 2; molecular weight is 110.0. Have an order or account question? Solute (1 g) Water Boiling Water Alcohol Chloroform Ether Other Acenocoumarol 67,000 280 130 1800 Acetaminophen 20 10 1 N sodium hydroxide, 15 Acetohexamide 230 210 Acetylcysteine 5 4 Acetyldigitoxin 6100 62.5 12 >10,000 Ammonium Alum 7 0.5 Aluminum Chloride 0.9 4 Aluminum Sulfate 1 Amantadine Hydrochloride 2.5 5.1 18 polyethylene glycol 400, 70 Toxicol. Thermodyn. Hydroquinone can lose a hydrogen cation from both hydroxyl groups to form a diphenolate ion. 0000002221 00000 n Forms of retinoids have been developed wherein the retinoid is protected by a protective system. Retinoids, in particular retinoic acid, retinal, and their derivatives, isomers and analogs (such as adapalene, tazarotene and isotretoin), are beneficial for improving rough skin texture, mottled pigmentation, sallow complexion, lines and wrinkles. [Na+].OC(=O)CC(O)(CC([O-])=O)C(O)=O.OC(=O)CC(O)(CC([O-])=O)C(O)=O, SPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS, Preparations for care of the skin for chemically bleaching or whitening the skin, PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES, Medicinal preparations containing organic active ingredients, Acids; Anhydrides, halides or salts thereof, e.g. :hS-g"s2Sj Ij=x'V]gPV8tt~qkAVXi|u}5;#.pl-/4JFQ.EP3&F.qa2hI{N qBmG(z#n [GN.}aazN(~8kux9#tnYwIHFuxW v9UNj&ffNW_\\Tc""8=_"7wC>svwQy\^4gF H][QzmlOI(B@ U4[Xb0,|m0*D"/#$\u(QI)RYg\;8 Yjh fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. 0000000807 00000 n The document was not able to download due to an unknown error. Availability. Some documentation and label information may refer to the legacy brand. J. Pharm. Hydroquinone (C6H4(OH)2), also known as benzene-1,4-diol or quinol, is an aromatic organic compound, with a variety of uses in chemistry. protecting the retinoids in a protective system; mixing the hydroquinone, and the protected retinoids; and. Gravimetric method is used to measured hydroquinone solubility in water, ethanol and in water+ethanol binary mixtures at temperatures (293.15, 295.15, 298.15, 300.15, 303.15, 305.15, 308.15, 310.15 and 313.15)K. Mole fractions solubility of hydroquinone are correlated with temperature by using the Apelblat equation. 0000003430 00000 n Cookie Notice Hydroquinone[1] Idrochinone Quinol 1,4-Dihydroxybenzene p-dihydroxybenzene p-hydroxyphenol 1,4-Hydroxy benzene Identifiers CAS Number 123-31-9 Y 3D model (JSmol) Interactive image Beilstein Reference 605970 ChEBI CHEBI:17594 Y ChEMBL ChEMBL537 Y ChemSpider 764 Y DrugBank DB09526 ECHA InfoCard 100.004.199 EC Number 204-617-8 Gmelin Reference 2742 It is a reducing agent that is reversibly oxidized to semiquinone and quinone. [31], Hydroquinones are one of the two primary reagents in the defensive glands of bombardier beetles, along with hydrogen peroxide (and perhaps other compounds, depending on the species), which collect in a reservoir. The method of item 1 07 wherein the hydroquinone is present in about 4%. vz >I d50dwp?i4,H3. The solubility was increased by addition of ethanol, reached a maximum .
