Hydroquinone

Base Information

• Chemical Name: Hydroquinone
• CAS No.: 123-31-9
• Deprecated CAS: 57534-13-1,8027-02-9,8027-02-9
• Molecular Formula: C6H6O2
• Molecular Weight: 110.112
• Hs Code.: 29072210
• European Community (EC) Number: 204-617-8
• ICSC Number: 0166
• NSC Number: 758707,9247
• UN Number: 3077,2662
• UNII: XV74C1N1AE
• DSSTox Substance ID: DTXSID7020716
• Nikkaji Number: J2.929G
• Wikipedia: Hydroquinone
• Wikidata: Q419164,Q27102742
• NCI Thesaurus Code: C29823
• RXCUI: 5509
• Pharos Ligand ID: 8V17FMXBZ9NN
• Metabolomics Workbench ID: 38161
• ChEMBL ID: CHEMBL537
• Mol file: 123-31-9.mol

Synonyms:p-Dihydroxybenzene;Tecquinol;Benzohydroquinone;Benzoquinol;1,4-Dihydrobenzoquinone;1, 4-Dihydroxy-benzol;Idrochinone;1,4-Dihydroxy-benzeen;Diak 5;p-Hydroquinone;NCI-C55834;1, 4-Dihydroxybenzene;Benzene-1,4-diol;p-Dioxybenzene;Derma-Blanch;Hydroquinone (USP);p-Dioxobenzene;Usaf ek-356;1/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8;Tequinol;Hydrochinon (CZECH, POLISH);Quinol;Dihydroquinone;.alpha.-Hydroquinone;1,4-Diidrobenzene;Eldoquin;Eldoquin (TN);1,4-Benzenediol;Hydroquinol;p-Benzenediol;Phiaquin;4-Hydroxyphenol;1,4-Dihydroxybenzen;.beta.-Quinol;Benzene, p-dihydroxy-;Artra;Black and White Bleaching Cream;p-Hydroxyphenol;1,4-Dihydroxybenzene;Eldopaque;Hydroquinole;Tenox HQ;Hidroquinone;Arctuvin;p-dihydroxybenzene, hydroquinone;Hydroquinone,123-31-9;

Chemical Property of Hydroquinone

Chemical Property:

• Appearance/Colour: off-white powder or white needle-like crystals
• Vapor Pressure: 1 mm Hg ( 132 °C)
• Melting Point: 172-175 °C(lit.)
• Refractive Index: 1.689
• Boiling Point: 286 °C at 760 mmHg
• PKA: 10.35(at 20℃)
• Flash Point: 141.6 °C
• PSA: 40.46000
• Density: 1.275 g/cm³
• LogP: 1.09780
• Storage Temp.: Refrigerator
• Sensitive.: Air & Light Sensitive
• Solubility.: H2O: 50 mg/mL, clear
• Water Solubility.: 70 g/L (20 ºC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 110.036779430
• Heavy Atom Count: 8
• Complexity: 54.9
• Transport DOT Label: Class 9

Purity/Quality:

≥98.1005% ^*data from raw suppliers

Hydroquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-40-41-43-50-68-R68-R50-R43-R41-R40-R22
• Safety Statements: 26-36/37/39-61-S61-S36/37/39-S26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: C1=CC(=CC=C1O)O
• Recent ClinicalTrials: Prospective Evaluation of Topical Almond Oil vs Hydroquinone
• Recent EU Clinical Trials: Efficacy and safety of a 4% hydroquinone cream (Melanoderm 4%) for the treatment of melasma: a randomized controlled split-face study.
• Recent NIPH Clinical Trials: Clinical efficacy of hydroquinone in glaucoma patients with prostaglandin-induced eyelid pigmentation
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance is irritating to the skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the eyes and skin. This may result in discolouration of the conjunctiva and cornea and skin depigmentation. This substance is possibly carcinogenic to humans.
• Description: Hydroquinone (HQ) is produced by the oxidation of aniline or phenol, by the reduction of quinone, or from a reaction of acetylene and carbon monoxide. Hydroquinone occurs naturally as a glucose ether, also known as arbutin, in the leaves of many plants and in fruits, as well as one of the agents used in the defense mechanism of the bombardier beetle, family Carabidae.
• Physical properties: Colorless to pale brown, odorless, hexagonal crystals
• Uses: Use as photographic reducer and developer; as reagent in the determination of small quantities of phosphate; as antioxidant. Depigmentor hydroquinone is a pigment-lightening agent used in bleaching creams. Hydroquinone combines with oxygen very rapidly and becomes brown when exposed to air. Although it occurs naturally, the synthetic version is the one commonly used in cosmetics. Application to the skin may cause allergic reaction and increase skin sun sensitivity. Hydroquinone is potentially carcinogenic and is associated with causing ochronosis, a discoloration of the skin. The u.S. FDA has banned hydroquinone from oTC cosmetic formulations, but allows 4 percent in prescription products. Its use in cosmetics is prohibited in some european countries and in Australia. K channel agonist, antihypertensive reducing agent prevents polymerization of resin monomers lightens darkened skin, light sensitive Photographic reducer and developer; antioxidant; stabilizing agent for some polymers; intermediate in the manufacturing of some dyes and pigments; in cosmetic formulations.
• Indications: Hydroquinone interferes with the production of the pigment melanin by epidermal melanocytes through at least two mechanisms: it competitively inhibits tyrosinase, one of the principal enzymes responsible for converting tyrosine to melanin, and it selectively damages melanocytes and melanosomes (the organelles within which melanin is stored).
• Therapeutic Function: Depigmentor
• Clinical Use: Hydroquinone is applied topically to treat disorders characterized by excessive melanin in the epidermis, such as melasma. In the United States, nonprescription skin-lightening products contain hydroquinone at concentrations of 2% or less; higher concentrations are available by prescription.

Technology Process of Hydroquinone

There total 706 articles about Hydroquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 22.0%

phenol (108-95-2,27073-41-2) → 2,4-Dinitrophenol (51-28-5) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + hydroquinone (123-31-9,8027-02-9)

Guidance literature:

With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium dodecyl-sulfate; In acetic acid; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85902-0

Reference yield: 2.0%

phenol (108-95-2,27073-41-2) → 2,2'-dihydroxybiphenyl (1806-29-7) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + hydroquinone (123-31-9,8027-02-9)

Guidance literature:

With 3,10-di-n-butylisoalloxazine N-oxide; In acetonitrile; for 6h; Yields of byproduct given; Irradiation;

DOI:10.1039/P19900003339

Reference yield:

phenol (108-95-2,27073-41-2) → o-Phenoxyphenol (2417-10-9) + 2,2'-dihydroxybiphenyl (1806-29-7) + cis,cis-Muconic acid (1119-72-8) + 2,4'-dihydroxybiphenyl (611-62-1) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + hydroquinone (123-31-9,8027-02-9)

Guidance literature:

With sodium hydroxide; ozone; at 0 - 20 ℃; Kinetics; Mechanism; Product distribution; dependence from NaOH concn.;

DOI:10.1007/BF00965412

upstream raw materials:

piperidine

p-benzoquinone

iodobenzene

para-dichlorobenzene

Downstream raw materials:

arbutin

ethyl-trisulfane

2-(2-ethylsulfanyl-ethylsulfanyl)-ethanethiol

2,5-di-piperidin-1-yl-[1,4]benzoquinone

Refernces

• 1、 Yang, Zhiyong,Gould, Edwin S.. "Reactions of 1,4-benzoquinones with s2 reducing centers". . p. 2219 - 2223. Retrieved 2003.
• 2、 Valencia, Drochss P.,Astudillo, Pablo D.,Galano, Annia,Gonzalez, Felipe J.. "Self-decarboxylation of trichloroacetic acid redox catalyzed by trichloroacetate ions in acetonitrile solutions". . p. 318 - 325. Retrieved 2013.
• 3、 Singh, Kamini,Singh. "Kinetics and mechanistic studies of Ru(III) catalyzed oxidation of p-hydroxy benzoic acid by sodium N-chloro-p-toluene sulphonamide in acidic media". . p. 5121 - 5124. Retrieved 2014.
• 4、 Von Sonntag, Justus,Mvula, Eino,Hildenbrand, Knut,Von Sonntag, Clemens. "Photohydroxylation of 1,4-Benzoquinone in Aqueous Solution Revisited". . p. 440 - 451. Retrieved 2004.
• 5、 Maruyama et al.. "-". . p. 2470,2474. Retrieved 1973.
• 6、 Mvula, Eino,Schuchmann, Man Nien,Sonntag, Clemens von. "Reactions of phenol-OH-adduct radicals. Phenoxyl radical formation by water elimination vs. oxidation by dioxygen". . p. 264 - 268. Retrieved 2001.
• 7、 Anderson, Robert F.,Patel, Kantilal B.,Stratford, Michael R. L.. "Radical Spectra and Product Distribution following Electrophilic Attack by the OH. Radical on 4-Hydroxybenzoic Acid and Subsequent Oxidation". . p. 3177 - 3188. Retrieved 1987.
• 8、 Yatsyuk et al.. "-". . . Retrieved 1968.
• 9、 Zhang, Tianyong,Sheng, Liao,Yang, Qiusheng,Jiang, Shuang,Wang, Yanhong,Jin, Chaohui,Li, Bin. "Synthesis, characterization and catalytic reactivity of pentacoordinate iron dicarbonyl as a model of the [Fe]-hydrogenase active site". . p. 2011 - 2018. Retrieved 2015.
• 10、 Kowacz, Magdalena,Warszyński, Piotr. "Beyond esterase-like activity of serum albumin. Histidine-(nitro)phenol radical formation in conversion cascade of p-nitrophenyl acetate and the role of infrared light". . . Retrieved 2019.