Compound: Lawsone
SMILES: O=C1C(O)=CC(=O)c2c1cccc2
InChIKey: CSFWPUWCSPOLJW-UHFFFAOYSA-N
Synonyms: Lawsone, 83-72-7, 2-Hydroxy-1,4-naphthoquinone, 2-hydroxynaphthalene-1,4-dione, 2-Hydroxy-1,4-naphoquinone, 2-Hydroxynaphthoquinone, Henna, Mehendi, HANA, Natural Orange 6, Lawson, Mendi, 2-Hydroxy-1,4-naphthalenedione, C.I. Natural Orange 6, 1,4-Naphthalenedione, 2-hydroxy-, 4-hydroxynaphthalene-1,2-dione, 1,4-Naphthoquinone, 2-hydroxy-, C.I. 75480, NSC 8625, 2-HYDROXY-1,4-NAPTHOQUINONE, MFCD00001678, NSC 27285, 2-hydroxy-1,4-dihydronaphthalene-1,4-dione, NSC-8625, TLH4A6LV1W, CHEBI:44401, 2-hydroxy-naphthalene-1,4-dione, NSC8625, NSC-27285, 1, 2-hydroxy-, Lawsonia alba, Henna leaves, 2-Hydroxy-p-naphthoquinone, 27699-93-0, CCRIS 6248, NSC-52500, EINECS 201-496-3, UNII-TLH4A6LV1W, BRN 1565260, AI3-12099, Henna;, IMEXINE OG, Spectrum_001200, SpecPlus_000482, LAWSONE [MI], LAWSONE [MART.], Spectrum2_001506, Spectrum3_001538, Spectrum4_001697, Spectrum5_000374, HENNA (DYE), SCHEMBL16541, BSPBio_002956, KBioGR_001994, KBioSS_001680, 4-08-00-02360 (Beilstein Handbook Reference), DivK1c_006578, SCHEMBL342409, SPECTRUM1502250, 2-hydroxy-1,4-naphthaquinone, SPBio_001551, 2-hydroxyl-1,4-naphthoquinone, CHEMBL240963, NQ-6, orb1304790, DTXSID2025428, SCHEMBL11804609, SCHEMBL29350263, KBio1_001522, KBio2_001680, KBio2_004248, KBio2_006816, KBio3_002456, WVCHIGAIXREVNS-UHFFFAOYSA-N, HMS5082C19, HY-N2493, NSC27285, BBL027350, BDBM50049066, CCG-38882, EBC-44217, s3858, SBB069496, STK801825, 2-Hydroxy-1,4-naphthoquinone, 97%, AKOS000120111, DB04744, FL02351, GS-3117, SDCCGMLS-0066674.P001, UPCMLD0ENAT5883810:001, Lawsone (2-Hydroxy-1,4-naphthoquinone), NCGC00095834-01, NCGC00095834-02, NCGC00095834-03, 2-hydroxynaphthalene-1,4-dione [M+H]+, AC-34621, PD006431, ST097865, SY012958, DB-005248, CS-0022764, H0285, NS00015309, EN300-20637, F17705, F209636, SR-05000002407, Q1075492, SR-05000002407-1, Z104479394, Q 0
Theoretical properties:
molecular_formula: C10H6O3
molecular_weight: 174.15 g/mol
exact_mass: 174.031694049 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 13
topological_polar_surface_area: 54.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Lawsone is 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis. It has a role as an antifungal agent and a protective agent. It is a tautomer of a naphthalene-1,2,4-trione.", "chebi": "1,4-Naphthoquinone carrying a hydroxy function at C-2.  It is obtained from the leaves of Lawsonia inermis.", "chembl": "LAWSONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Lawsone (2-hydroxy-1,4-naphthoquinone), also known as  hennotannic acid, is a red-orange dye present in the leaves of the henna plant (Lawsonia inermis), for which it is named, as well as in the common walnut (Juglans regia) and water hyacinth (Pontederia crassipes). Humans have used henna extracts containing lawsone as hair and skin dyes for more than 5,000 years. Lawsone reacts chemically with the protein keratin in skin and hair via a Michael addition reaction, resulting in a strong permanent stain that lasts until the skin or hair is shed. Darker colored staining is due to more lawsone\u2013keratin interactions occurring, which evidently break down as the concentration of lawsone decreases and the tattoo fades. Lawsone strongly absorbs UV light, and aqueous extracts can be effective sunless tanning agents and sunscreens. Lawsone is a 1,4-naphthoquinone derivative, an analog of hydroxyquinone containing one additional ring.\nLawsone isolation from Lawsonia inermis can be difficult due to its easily biodegradable nature. Isolation involves four steps:\n\nextraction with an extraction solution, usually NaOH\ncolumn filtration using a macroporous adsorption resin\na rinse with ethanol to remove impurities, and finally\nfreeze the product to isolate the lawsone powder, usually a yellow colored dust.\nDuring the rinse, the lawsone will be the bottom as it has such a high density and the chlorophyll molecules will all be on the top of the mixture.\nLawsone is hypothesized to undergo a reaction similar to Strecker synthesis in reactions with amino acids. Recent research has been conducted on lawsone's potential applications in the forensic science field. Since lawsone shows many similarities with ninhydrin, the current reagent for latent fingerprint development, studies have been conducted to see if lawsone can be used in this field. As of now the research is inconclusive, but optimistic. Lawsone non-specifically targets primary amino acids, and displays photoluminescence with forensic light sources. It has a characteristic purple/brown coloration as opposed to the purple/blue associated with ninhydrin.\nLawsone shows promise as a reagent for fingerprint detection because of its photoluminescence maximized at 640 nm, which is high enough that it avoids background interference common for ninhydrin."}