83-72-7 | 2-Hydroxy-1,4-naphthoquinone

Packsize	Purity	Availability	Price	Discounted Price
5g	97%	in stock	$13.00	$9.00
25g	97%	in stock	$36.00	$25.00
100g	97%	in stock	$120.00	$84.00

Description

• Catalog Number: AB48178
• Chemical Name: 2-Hydroxy-1,4-naphthoquinone
• CAS Number: 83-72-7
• Molecular Formula: C10H6O3
• Molecular Weight: 174.1528
• MDL Number: MFCD00001678
• SMILES: O=C1C=C(O)C(=O)c2c1cccc2

Computed Properties

• Complexity: 291
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• XLogP3: 0.9

Literature

• Biological evaluation of hydroxynaphthoquinones as anti-malarials.

  Malaria journal 20130101

• The effectiveness of jewelweed, Impatiens capensis, the related cultivar I. balsamina and the component, lawsone in preventing post poison ivy exposure contact dermatitis.

  Journal of ethnopharmacology 20120830

• Unexpected one-pot synthesis of highly conjugated pentacyclic diquinoid compounds.

  The Journal of organic chemistry 20120817

• Contact dermatitis to para-phenylenediamine in hair dye following sensitization to black henna tattoos - an ongoing problem.

  Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG 20120801

• Novel zinc(II) and copper(II) complexes of a Mannich base derived from lawsone: Synthesis, single crystal X-ray analysis, ab initio density functional theory calculations and vibrational analysis.

  Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20120801

• On the search for potential anti-Trypanosoma cruzi drugs: synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions.

  European journal of medicinal chemistry 20120601

• Contact blepharoconjunctivitis due to black henna--a case report.

  International journal of occupational medicine and environmental health 20120601

• Antibacterial and antifungal activity of lawsone and novel naphthoquinone derivatives.

  Medecine et maladies infectieuses 20120601

• [Tattoos - harmless decoration or health hazard?].

  Deutsche medizinische Wochenschrift (1946) 20120501

• Dermatoses secondary to Asian cultural practices.

  International journal of dermatology 20120401

• Latent fingermark development on a range of porous substrates using ninhydrin analogs--a comparison with ninhydrin and 1,8-diazofluoren.

  Journal of forensic sciences 20120301

• Quantification of p-phenylenediamine and 2-hydroxy-1,4-naphthoquinone in henna tattoos.

  Contact dermatitis 20120101

• Enhanced Raman spectrum of lawsone on Ag surface: vibrational analyses, frequency shifts, and molecular geometry.

  Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20111201

• Effect of nail polish and henna on oxygen saturation determined by pulse oximetry in healthy young adult females.

  Emergency medicine journal : EMJ 20110901

• Contact dermatitis with severe scalp swelling and upper airway compromise due to black henna hair dye.

  Pediatric emergency care 20110801

• Rapid determination of para-phenylenediamine by gas chromatography-mass spectrometry with selected ion monitoring in henna-containing cosmetic products.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110615

• Erythema multiforme caused by tattoo: a further case.

  Internal and emergency medicine 20110601

• [Henna symbolic tattoo and real dermatitis].

  Archives de pediatrie : organe officiel de la Societe francaise de pediatrie 20110601

• Synthesis and characterization of lawsone-lntercalated Zn-Al-layered double hydroxides.

  Journal of biomedical nanotechnology 20110601

• Allergic contact dermatitis to black henna.

  Acta dermatovenerologica Alpina, Pannonica, et Adriatica 20110601

• Age-related sensitization to p-phenylenediamine.

  Contact dermatitis 20110301

• Henna as a durable preoperative skin marker.

  World journal of surgery 20110201

• Henna as a durable preoperative skin marker.

  World journal of surgery 20110201

• Identifying chelators for metalloprotein inhibitors using a fragment-based approach.

  Journal of medicinal chemistry 20110127

• Contact urticaria to cosmetic and industrial dyes.

  Clinical and experimental dermatology 20110101

• Bullous allergic contact dermatitis to pure henna in a 3-year-old girl.

  Pediatric dermatology 20110101

• [A boy with a skin lesion after a henna tattoo].

  Nederlands tijdschrift voor geneeskunde 20110101

• Allergic reactions to henna-based temporary tattoos and their components.

  Immunopharmacology and immunotoxicology 20101201

• Enhanced chromate reduction by resting Escherichia coli cells in the presence of quinone redox mediators.

  Bioresource technology 20101101

• [Allergic contact dermatitis for temporary 'black henna' tattoos].

  Archivos argentinos de pediatria 20100801

• A well-circumscribed henna tattoo hypersensitivity reaction.

  Journal of paediatrics and child health 20100701

• 5-Hydroxy-1,4-naphthoquinone (juglone) and 2-hydroxy-1,4-naphthoquinone (lawsone) influence on jack bean urease activity: Elucidation of the difference in inhibition activity.

  Bioorganic chemistry 20100601

• Solar urticaria: photoprotection from a naphthoquinone-modified dihydroxyacetone Maillard reaction.

  Journal of the American Academy of Dermatology 20100501

• Henna tattoo: an unusual peripheral venous access difficulty.

  Journal of anesthesia 20100401

• Transient localized hypertrichosis on a temporary henna tattoo.

  Contact dermatitis 20100301

• Contact dermatitis due to temporary henna tattoos.

  Skinmed 20100101

• Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation.

  Organic & biomolecular chemistry 20091207

• Temporary henna tattoos with long-term consequences.

  The Medical journal of Australia 20091201

• Colorimetric study of effect of gamma-radiation on the color of cotton fabric colored by 'henna' dye.

  Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20091101

• Images in emergency medicine. The mark of the dragon.

  Emergency medicine journal : EMJ 20091101

• [Allergy and skin infection after use of temporary henna tattoo--case report].

  Laeknabladid 20091101

• The detection of latent fingermarks on porous surfaces using amino acid sensitive reagents: a review.

  Analytica chimica acta 20091012

• Structure-activity relationships of anthraquinones on the suppression of DNA-binding activity of the aryl hydrocarbon receptor induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.

  Journal of bioscience and bioengineering 20090301

• [Hypopigmentation and scarring reaction caused by hypersensitivity to black henna].

  Medicina clinica 20090207

• Protein glycation inhibitory activities of Lawsonia inermis and its active principles.

  Journal of enzyme inhibition and medicinal chemistry 20090201

• Allergic contact dermatitis from temporary henna tattoo.

  The Journal of dermatology 20090101

• Henna tattoo and Sweet's syndrome: a possible relation.

  European journal of dermatology : EJD 20090101

• Generalized erythema multiforme after localized allergic dermatitis from dark henna tattoo.

  Pediatric dermatology 20090101

• Localized hypertrichosis due to temporary henna tattoos: report of three cases.

  The Journal of dermatological treatment 20090101

• Can henna prevent ulceration in diabetic feet at high risk?

  Experimental diabetes research 20090101

• Catalysis reaction between sodium 1,2-naphthoquinone-4-sulfonate and hydroxyl ion using captopril as catalyzer and determination of captopril.

  Analytica chimica acta 20080926

• Images in clinical medicine. Allergic contact dermatitis from a henna tattoo.

  The New England journal of medicine 20080807

• Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.

  European journal of medicinal chemistry 20080801

• p-Phenylenediamine in black henna tattoos: a practice in need of policy in children.

  Archives of pediatrics & adolescent medicine 20080801

• [Picture of the month: henna tattooing].

  Ugeskrift for laeger 20080623

• Molluscicidal activity of 2-hydroxy-[1,4]naphthoquinone and derivatives.

  Anais da Academia Brasileira de Ciencias 20080601

• Determination of aromatic amines in hair dye and henna samples by ion-pair extraction and gas chromatography-mass spectrometry.

  Journal of pharmaceutical and biomedical analysis 20080512

• Delayed hypersensitivity reaction from black henna tattoo manifesting as severe facial swelling.

  The American journal of emergency medicine 20080501

• Topical henna for capecitabine induced hand-foot syndrome.

  Investigational new drugs 20080401

• Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors.

  Journal of medicinal chemistry 20080327

• [A black henna tattoo can cause life-long allergy to paraphenylenediamine].

  Presse medicale (Paris, France : 1983) 20080201

• [Temporary henna tattoos: Sometimes serious side effects].

  Presse medicale (Paris, France : 1983) 20080101

• Temporary localized hypertrichosis after henna pseudotattoo.

  Pediatric dermatology 20080101

• Allergic contact dermatitis due to a temporary henna tattoo, a hair dye, and a marker pen.

  Journal of investigational allergology & clinical immunology 20080101

• Determination of lawsone in henna powders by high performance thin layer chromatography.

  Journal of separation science 20071201

• Black henna tattoos: coexisting rubber and para-phenylenediamine allergy?

  Clinical and experimental dermatology 20071101

• Synthesis and anti-inflammatory activity of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives.

  Bioorganic & medicinal chemistry letters 20071015

• Henna skin reactions in the hand.

  Annals of plastic surgery 20071001

• The 1,4-naphthoquinone scaffold in the design of cysteine protease inhibitors.

  Bioorganic & medicinal chemistry 20070801

• Cutaneous mercury deposits after henna dye application in the arm.

  The British journal of dermatology 20070801

• An environmentally friendly electrochemical method for synthesis of benzofuranoquinone derivatives.

  Chemical & pharmaceutical bulletin 20070801

• Cytotoxicity of lawsone and cytoprotective activity of antioxidants in catalase mutant Escherichia coli.

  Toxicology 20070603

• Is black henna responsible for asthma and cross reactivity with latex?

  Journal of the European Academy of Dermatology and Venereology : JEADV 20070501

• A new henna-based medium for the differentiation of Cryptococcus neoformans.

  Journal of medical microbiology 20070401

• Apply directly to the forehead: Holmes, Nana, and hennapecia.

  FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20070401

• Para-phenylenediamine allergy from a henna tattoo.

  Archives of disease in childhood 20070301

• Henna causes life-threatening hyperbilirubinaemia in glucose-6-phosphate dehydrogenase deficiency.

  Clinical and experimental dermatology 20070301

• [Allergic contact dermatitis to temporary henna tattoos].

  Actas dermo-sifiliograficas 20070301

• Temporary henna tattoo is unsafe in atopic children.

  Acta paediatrica (Oslo, Norway : 1992) 20070301

• Allergic contact dermatitis to paraphenylendiamine in hair dye after sensitization from black henna tattoos: a report of 6 cases.

  CMAJ : Canadian Medical Association journal = journal de l'Association medicale canadienne 20070213

• Report of the IWGT working group on strategies and interpretation of regulatory in vivo tests I. Increases in micronucleated bone marrow cells in rodents that do not indicate genotoxic hazards.

  Mutation research 20070203

• Reactivity of indanedioneketene dimer with amines.

  The Journal of organic chemistry 20070119

• Structure-activity relationships in the haemolytic activity and nephrotoxicity of derivatives of 1,2- and 1,4-naphthoquinone.

  Journal of applied toxicology : JAT 20070101

• Plasma exchange as treatment for Lawsone (henna) intoxication.

  Journal of clinical apheresis 20070101

• Absorption of lawsone through human skin.

  Cutaneous and ocular toxicology 20070101

• Henna reaction.

  Journal of plastic, reconstructive & aesthetic surgery : JPRAS 20070101

• Temporary henna tattoos.

  Clinics in dermatology 20070101

• Temporary henna tattooing in siblings--an unusual chemical burn.

  Burns : journal of the International Society for Burn Injuries 20061201

• Urticaria and angioneurotic edema due to the temporary henna tattoo.

  Minerva pediatrica 20061201

• Contact dermatitis after henna skin tattooing.

  Journal of the Royal Army Medical Corps 20061201

• Inhibition of apoptosis by menadione on exposure to UVA.

  Cell biology and toxicology 20060901

• Contact dermatitis due to para-phenylenediamine (PPD) on a temporal tattoo with henna. Cross reaction to azoic dyes.

  Investigacion clinica 20060901

• Quantification of para-phenylenediamine and heavy metals in henna dye.

  Contact dermatitis 20060701

• The extent of black henna tattoo's complications are not restricted to PPD-sensitization.

  Contact dermatitis 20060701

• Allergic contact dermatitis from henna temporary tattoo.

  Journal of the European Academy of Dermatology and Venereology : JEADV 20060401

• A painful experience: black henna tattoo causing severe, bullous contact dermatitis.

  Contact dermatitis 20060401

• Effects of henna dye on oxygen saturation reading using pulse oximetry.

  Saudi medical journal 20060201

• SOM assembly of hydroxynaphthoquinone and its oxime: polymorphic X-ray structures and EPR studies.

  Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060101

• The myth of black henna.

  Skinmed 20060101

• Pseudo-tattoo dermatitis.

  Indian journal of dermatology, venereology and leprology 20060101

• Use of henna as a skin marker.

  Journal of plastic, reconstructive & aesthetic surgery : JPRAS 20060101

• [Tattoos with henna: attention; danger!].

  Revue de l'infirmiere 20060101

• Studies on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone: reactions with indole derivatives and other C-nucleophiles.

  The Journal of organic chemistry 20051028

• An unusual cause of suicide: henna (Lawsonia inermis Linn.).

  The Journal of emergency medicine 20051001

• Is patch testing for PPD routinely necessary in patients with reactions to henna tattoos?

  Contact dermatitis 20051001

• [First cool arm decoration, later burning skin finding].

  MMW Fortschritte der Medizin 20050901

• Atopy to henna tattoos in children.

  European journal of emergency medicine : official journal of the European Society for Emergency Medicine 20050801

• Cutaneous hyperpigmentation following nonpermanent henna tattoo.

  Saudi medical journal 20050801

• A temporary henna tattoo causing hair and clothing dye allergy.

  Contact dermatitis 20050701

• Microbial fuel cell using anaerobic respiration as an anodic reaction and biomineralized manganese as a cathodic reactant.

  Environmental science & technology 20050615

• Allergic reaction with persistent hypopigmentation due to temporary tattoing with henna in a baby.

  Contact dermatitis 20050601

• [Picture of the month: contact dermatitis].

  Ugeskrift for laeger 20050411

• [Contact dermatitis due to temporary henna tattoos].

  Anales de pediatria (Barcelona, Spain : 2003) 20050301

• Determination of some organochlorine compounds in herbal colouring agent henna (Lawsonia inermis) and in tea (Thea sinensis).

  Arhiv za higijenu rada i toksikologiju 20050301

• Role of humic acid and ouinone model compounds in bromate reduction by zerovalent iron.

  Environmental science & technology 20050215

• Severe allergic contact dermatitis to paraphenylene diamine in hair dye following sensitization to black henna tattoos.

  Contact dermatitis 20050201

• A survey on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone with amino compounds.

  Molecules (Basel, Switzerland) 20050131

• In-vitro antimicrobial activity of Lawsonia inermis Linn (henna). A pilot study on the Omani henna.

  Saudi medical journal 20050101

• Cutaneous hyperpigmentation following nonpermanent henna tattoo.

  Saudi medical journal 20050101

• [Short time fun and long time allergic problems from henna tattoo].

  Duodecim; laaketieteellinen aikakauskirja 20050101

• Acute chemical colitis resulting from oral intake of henna.

  Journal of clinical gastroenterology 20050101

• [Reasons to advise against temporary henna tattoos].

  Anales del sistema sanitario de Navarra 20050101

• [Acute contact eczema from paraphenylenediamine contained in temporary henna tattoos].

  Actas dermo-sifiliograficas 20050101

• Role of oxidant stress in lawsone-induced hemolytic anemia.

  Toxicological sciences : an official journal of the Society of Toxicology 20041201

• Henna tattoos for children: a potential source of para-phenylenediamine and thiuram sensitization.

  The British journal of dermatology 20041201

• [Report on the 67th and 68th of the provisional Commission for Cosmetic Medication of the Federal Institute for Risk Assessment (BfR) from 3 and 4 December 2003 and 6 May 2004 in Berlin].

  Bundesgesundheitsblatt, Gesundheitsforschung, Gesundheitsschutz 20041101

• A new approach to patch testing patients with para-phenylenediamine allergy secondary to temporary black henna tattoos.

  Contact dermatitis 20041001

• [Allergic contact dermatitis after hair dyeing].

  Ugeskrift for laeger 20040531

• 2-Hydroxy-1,4-naphthoquinone, the natural dye of Henna, is non-genotoxic in the mouse bone marrow micronucleus test and does not produce oxidative DNA damage in Chinese hamster ovary cells.

  Mutation research 20040509

• Henna (Lawsonia inermis Linn.) induced haemolytic anaemia in siblings.

  International journal of clinical practice 20040501

• Quinones facilitate the self-assembly of the phosphorylated tubulin binding region of tau into fibrillar polymers.

  Biochemistry 20040316

• In vivo exposure of Dreissena polymorpha mussels to the quinones menadione and lawsone: menadione is more toxic to mussels than lawsone.

  Journal of applied toxicology : JAT 20040101

• Temporary henna tattooing--a risky procedure. Case report and literature review.

  Burns : journal of the International Society for Burn Injuries 20031201

• [Temporary tattooing with henna induces contact allergy to textile dyes].

  Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG 20031201

• Acute allergic contact dermatitis due to para-phenylenediamine after temporary henna painting.

  The Journal of dermatology 20031101

• Allergic contact dermatitis to henna tattoo.

  Archives of disease in childhood 20030901

• [Picture of the month: eczematous contact allergy].

  Ugeskrift for laeger 20030811

• An assessment of the genotoxicity of 2-hydroxy-1,4-naphthoquinone, the natural dye ingredient of Henna.

  Mutation research 20030606

• Henna skin reaction.

  Plastic and reconstructive surgery 20030601

• Temporary tattoo dermatitis.

  The Journal of pediatrics 20030501

• Palpebral eczema due to contact allergy to henna used as a hair dye.

  Contact dermatitis 20030401

• Black henna tattoo reaction in a person with sulfonamide and benzocaine drug allergies.

  Journal of the American Academy of Dermatology 20030201

• Cutaneous reactions to temporary tattoos.

  Dermatology online journal 20030201

• Evidence for redox cycling of lawsone (2-hydroxy-1,4-naphthoquinone) in the presence of the hypoxanthine/xanthine oxidase system.

  Journal of applied toxicology : JAT 20030101

• Trypsin inhibitory activity of Lawsonia inermis.

  Fitoterapia 20021201

• Enhanced anaerobic degradation of polymeric azo compounds by Escherichia coli in the presence of low-molecular-weight redox mediators.

  The Journal of pharmacy and pharmacology 20021101

• Fragrance sensitization caused by temporary henna tattoo.

  Contact dermatitis 20021001

• Effect of initial carbon sources on the electrochemical detection of glucose by Gluconobacter oxydans.

  Bioelectrochemistry (Amsterdam, Netherlands) 20020901

• An unusual rash.

  Archives of disease in childhood 20020801

• [Allergic reactions and hypopigmentation due to temporary tattooing with henna].

  Nederlands tijdschrift voor geneeskunde 20020713

• Hair dye and henna tattoo exposure.

  Emergency nurse : the journal of the RCN Accident and Emergency Nursing Association 20020601

• Prolonged lichenoid reaction and cross-sensitivity to para-substituted amino-compounds due to temporary henna tattoo.

  International journal of dermatology 20020501

• Effects of different quinoid redox mediators on the anaerobic reduction of azo dyes by bacteria.

  Environmental science & technology 20020401

• Identification and quantification of para-phenylenediamine in a temporary black henna tattoo.

  American journal of contact dermatitis : official journal of the American Contact Dermatitis Society 20020301

• An unexpected tattoo.

  Lancet (London, England) 20020223

• Clinicopathologic features of skin reactions to temporary tattoos and analysis of possible causes.

  Archives of dermatology 20020101

• [Allergic contact eczema caused by henna tattoo].

  Allergologia et immunopathologia 20020101

• Childhood allergic contact dermatitis from henna tattoo.

  Pediatric dermatology 20020101

• Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues.

  Bioorganic & medicinal chemistry letters 20011217

• Lead and traditional Moroccan pharmacopoeia.

  The Science of the total environment 20011203

• Triterpenoids from Lawsonia alba.

  Phytochemistry 20011201

• Henna causes life threatening haemolysis in glucose-6-phosphate dehydrogenase deficiency.

  Archives of disease in childhood 20011101

• Allergic contact dermatitis to henna.

  Allergy 20011001

• Erythema-multiforme-like eruption and depigmentation following allergic contact dermatitis from a paint-on henna tattoo, due to para-phenylenediamine contact hypersensitivity.

  Contact dermatitis 20011001

• Antipruritic and antidermatitic effect of extract and compounds of Impatiens balsamina L. in atopic dermatitis model NC mice.

  Phytotherapy research : PTR 20010901

• Temporary henna tattoos: an increasing risk of contact dermatitis.

  American journal of contact dermatitis : official journal of the American Contact Dermatitis Society 20010901

• Temporary henna tattoo reactions in children.

  International journal of dermatology 20010901

• Hypopigmentation after non-permanent henna tattoo.

  Journal of the European Academy of Dermatology and Venereology : JEADV 20010901

• Skin markings in external radiotherapy by temporary tattooing with henna: improvement of accuracy and increased patient comfort.

  International journal of radiation oncology, biology, physics 20010501

• Contact dermatitis after temporary henna tattoos--an increasing phenomenon.

  Swiss medical weekly 20010407

• IgE-mediated allergy to henna.

  Allergy 20010301

• Henna-induced hemolytic anemia and acute renal failure.

  The Turkish journal of pediatrics 20010101

• Contact allergy to henna.

  Journal of the European Academy of Dermatology and Venereology : JEADV 20010101

• Effects of plant-derived naphthoquinones on the growth of Pleurotus sajor-caju and degradation of the compounds by fungal cultures.

  Journal of basic microbiology 20010101

• Complexation equilibria and spectrophotometric determination of thorium(IV) with Lawsone.

  Annali di chimica 20010101

• Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid.

  Chemico-biological interactions 20000103

• Antiretroviral agents as inhibitors of both human immunodeficiency virus type 1 integrase and protease.

  Journal of medicinal chemistry 19960621

• Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase.

  Biochimica et biophysica acta 19951115