2-hydroxy-1,4-dihydronaphthalene-1,4-dione

• ChemBase ID: 75303
• Molecular Formular: C10H6O3
• Molecular Mass: 174.15284
• Monoisotopic Mass: 174.03169405
• SMILES: O=C1c2ccccc2C(=O)C=C1O
• Canonical SMILES: O=C1C=C(O)C(=O)c2c1cccc2
• InChI: InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H
• InChIKey: CSFWPUWCSPOLJW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-1,4-dihydronaphthalene-1,4-dione
• IUPAC Traditional name: 2-hydroxy-4H-naphthalene-1,4-dione; HANA; 2-hydroxy-1,4-dihydronaphthalene-1,4-dione; mehendi
• Synonyms: 2-Hydroxy-1,4-naphthoquinone; 2-hydroxynaphthalene-1,4-dione; Henna; Lawsone; Lawsone; Natural Orange 6; Hennotannic acid; C.I. 75480; Lawsone; 2-Hydroxy-1,4-naphthoquinone; 2-羟基-1,4-萘醌

Database IDs

• CAS Number: 83-72-7
• EC Number: 201-496-3
• MDL Number: MFCD00001678
• Beilstein Number: 1565260
• Merck Index: 145393
• PubChem SID: 24895653; 162040221
• PubChem CID: 6755
• CHEMBL: 240963
• Unique Ingredient Identifier: TLH4A6LV1W
• Wikipedia Title: Lawsone
• Color Index Number: 75480

CALCULATED PROPERTIES

• Acid pKa: 5.519285
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.6842885
• LogD (pH = 7.4): -0.9010882
• Log P: 0.97566026
• Molar Refractivity: 48.1506 cm^3
• Polarizability: 17.46068 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: almost insoluble in water
• Apperance: Yellow prisms
• Melting Point: 192-195 °C (dec.)(lit.); 195-196 °C (decomposition); ca 193°C dec.
• Absorption Wavelength: λmax 452 nm

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: QL8200000
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 22-36-68; 36/37/38; R36 R37 R38
• Safety Statements: 26-36/37; 26-37/39; S26 S36 S37 S39
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• LD50: 100 mg/kg
• GHS Hazard statements: H315-H319-H335; H341-H302-H319
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P281-P305+P351+P338-P301+P312-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Mechanism of Action: Inhibitor of NADPH-cytochrome C reductase

Product Information

• Purity: 97%; 98%; 98+%
• Grade: technical grade
• Impurities: 20% lawsone-3,3′-dimer
• Biological Source: Isol. from Lawsonia spp., henna and seeds of Lomatia ferruginea. Also from Impatiens spp.
• Application(s): Antineoplastic; Antispasmodic agent, fungicide, bactericide and ingredient of sunscreen preparations; Possesses antiinflammatory, analgesic and antipyretic activity
• Empirical Formula (Hill Notation): C10H6O3

DETAILS

Sigma Aldrich - 184098

Application
Lawsone (2-hydroxy-1,4-naphthoquinone) is the active ingredient of henna (Lawsonia alba), the crushed leaves of which are used as a cosmetic dye.

Sigma Aldrich - H46805

Packaging
10, 25, 100 g in glass bottle

REFERENCES

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 86A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 79D, (ir)
• Fieser, L.F., J.A.C.S., 1948, 70, 3165, (synth)
• Amorosa, M., Gazz. Chim. Ital., 1954, 84, 602, (synth)
• Org. Synth., Coll. Vol., 3, 1955, 465
• Chen, D. et al., Can. J. Biochem., 1966, 44, 1389, (biosynth)
• Baillie, A.C. et al., J.C.S.(C), 1966, 2185, (synth)
• Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1967, 1, 484
• Japan. Pat., 1971, Mitsubishi Edogawa, 71 02 977; CA, 74, 141384, (synth)
• Japan. Pat., 1971, Mitsubishi Edogawa, 71 02 978; CA, 75, 48769h, (synth)
• Chapelle, J.P., Phytochemistry, 1974, 13, 662, (isol, deriv)
• Mehendale, A.R. et al., Phytochemistry, 1975, 14, 801, (isol)
• Yano, H. et al., Chem. Pharm. Bull., 1980, 28, 1207, (cmr)
• Munday, R. et al., J. Appl. Toxicol., 1991, 11, 85, (tox)
• Ali, B.H. et al., Pharmacology, 1995, 51, 356, (pharmacol)
• Dekkers, J. et al., Acta Cryst. C, 1996, 52, 2896-2899, (cryst struct)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1719
• Zinkham, W.H. et al., Pediatrics, 1996, 7, 707, (tox)
• Ishiguro, K. et al., J. Nat. Prod., 1998, 61, 1126-1129, (deriv, isol, pmr, cmr)