CAS 83-72-7|Natural Orange 6|2-hydroxy-4H-naphthalene-1,4-dione|Lawsone|2-hydroxy-1,4-dihydronaphthalene-1,4-dione|mehendi|2-Hydroxy-1,4-naphthoquinone|2-hydroxynaphthalene-1,4-dione|HANA|2-Hydroxy-...

General Information

Structure

Molecular Formula

C₁₀H₆O₃

Molecular Mass

174.15284

Exact Mass

174.03169405

Charge

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

Canonic Smiles

O=C1C=C(O)C(=O)c2c1cccc2

Isomeric Smiles

O=C1c2ccccc2C(=O)C=C1O

Calculated Properties

JChem

LogD (pH = 7.4)

-1.09

LogD (pH = 5.5)

0.58

Log P

0.98

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

5.32

Polar Surface Area

54.37

Polarizability

16.42

Molar Refractivity

48.15

LOG S

-2.70

Data Source

Names and Identifiers

Synonyms

Natural Orange 6Lawsone2-Hydroxy-1,4-naphthoquinone2-hydroxynaphthalene-1,4-dione2-Hydroxy-1,4-naphthoquinoneLawsoneHennotannic acidC.I. 754802-羟基-1,4-萘醌LawsoneHenna2-hydroxy-1,4-naphthalenedioneLawsonelawsone2-hydroxy-1,4-naphthoquinone2-HYDROXYNAPHTHOQUINONEHenna

IUPAC Traditional name

2-hydroxy-4H-naphthalene-1,4-dione mehendi HANA 2-hydroxy-1,4-dihydronaphthalene-1,4-dione

IUPAC name

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

Names and Identifiers

Registration numbers

MDL Number

CAS Number

Color Index Number

EC Number

Beilstein Number

PubChem SID

2489565316204022126697159

PubChem CID

6755

CHEMBL

240963CHEMBL240963

Wikipedia Title

Lawsone

Unique Ingredient Identifier

TLH4A6LV1W

Merck Index

145393

KNApSAcK Database

C00002837

PDBeChem Database

BRENDA Database

1.6.5.21.8.1.71.7.1.61.8.1.121.6.5.51.13.11.521.14.19.691.5.99.121.1.1.2521.3.1.221.1.5.34.4.1.51.6.5.101.17.3.41.18.1.21.1.5.41.1.1.B571.3.5.22.4.2.301.2.3.11.1.98.4

BKMS React Database

16284521700

Patent number

WO2007130777EP1974773

MetaboLights Database

MTBLS2096MTBLS4820MTBLS682

CHEBI ID

CHEBI:6395CHEBI:44401CHEBI:44399

BRENDA Ligand Database

ACToR Database

SABIO-RK Database

NMRShiftDB Database

Protein Data Bank

KEGG ID

SureChEMBL Database

BindingDB Database

Gmelin ID

CompTox Database

UniProt Database

Registration numbers

Properties

Physical Property

Apperance

Yellow prisms

Melting Point

195-196 °C (decomposition)

192-195 °C (dec.)(lit.)

ca 193°C dec.

Solubility

almost insoluble in water

Absorption Wavelength

λmax 452 nm

Pharmacology Properties

Mechanism of Action

Inhibitor of NADPH-cytochrome C reductase

Properties

Related Proteins

PDB Bank

2D0E

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Wikipedia

Lawsone

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.

H46805

Packaging
10, 25, 100 g in glass bottle

ChEBI

CHEBI:44401

1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.

Molecule Details

References

PubChem Literature

From Data Sources

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 79D, (ir)

• Baillie, A.C. et al., J.C.S.(C), 1966, 2185, (synth)

• Ali, B.H. et al., Pharmacology, 1995, 51, 356, (pharmacol)

• Chen, D. et al., Can. J. Biochem., 1966, 44, 1389, (biosynth)

• Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1967, 1, 484

• Chapelle, J.P., Phytochemistry, 1974, 13, 662, (isol, deriv)

• Yano, H. et al., Chem. Pharm. Bull., 1980, 28, 1207, (cmr)

• Munday, R. et al., J. Appl. Toxicol., 1991, 11, 85, (tox)

• Ishiguro, K. et al., J. Nat. Prod., 1998, 61, 1126-1129, (deriv, isol, pmr, cmr)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 86A, (nmr)

• Dekkers, J. et al., Acta Cryst. C, 1996, 52, 2896-2899, (cryst struct)

• Org. Synth., Coll. Vol., 3, 1955, 465

• Zinkham, W.H. et al., Pediatrics, 1996, 7, 707, (tox)

• Fieser, L.F., J.A.C.S., 1948, 70, 3165, (synth)

• Japan. Pat., 1971, Mitsubishi Edogawa, 71 02 977; CA, 74, 141384, (synth)

• Amorosa, M., Gazz. Chim. Ital., 1954, 84, 602, (synth)

• Japan. Pat., 1971, Mitsubishi Edogawa, 71 02 978; CA, 75, 48769h, (synth)

• Mehendale, A.R. et al., Phytochemistry, 1975, 14, 801, (isol)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1719

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

2-hydroxy-4H-naphthalene-1,4-dione mehendi HANA 2-hydroxy-1,4-dihydronaphthalene-1,4-dione

IUPAC name

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

Registration numbers

MDL Number

CAS Number

Color Index Number

EC Number

Beilstein Number

PubChem SID

2489565316204022126697159

PubChem CID

6755

CHEMBL

240963CHEMBL240963

Wikipedia Title

Lawsone

Unique Ingredient Identifier

TLH4A6LV1W

Merck Index

145393

KNApSAcK Database

C00002837

PDBeChem Database

BRENDA Database

1.6.5.21.8.1.71.7.1.61.8.1.121.6.5.51.13.11.521.14.19.691.5.99.121.1.1.2521.3.1.221.1.5.34.4.1.51.6.5.101.17.3.41.18.1.21.1.5.41.1.1.B571.3.5.22.4.2.301.2.3.11.1.98.4

BKMS React Database

16284521700

Patent number

WO2007130777EP1974773

MetaboLights Database

MTBLS2096MTBLS4820MTBLS682

CHEBI ID

CHEBI:6395CHEBI:44401CHEBI:44399

BRENDA Ligand Database

ACToR Database

SABIO-RK Database

NMRShiftDB Database

Protein Data Bank

KEGG ID

SureChEMBL Database

BindingDB Database

Gmelin ID

CompTox Database

UniProt Database

Related Proteins

Molecule Details

Lawsone

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.

H46805

Packaging
10, 25, 100 g in glass bottle

ChEBI

CHEBI:44401

1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.

References

PubChem Literature

From Data Sources

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 79D, (ir)

• Baillie, A.C. et al., J.C.S.(C), 1966, 2185, (synth)

• Ali, B.H. et al., Pharmacology, 1995, 51, 356, (pharmacol)

• Chen, D. et al., Can. J. Biochem., 1966, 44, 1389, (biosynth)

• Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1967, 1, 484

• Chapelle, J.P., Phytochemistry, 1974, 13, 662, (isol, deriv)

• Yano, H. et al., Chem. Pharm. Bull., 1980, 28, 1207, (cmr)

• Munday, R. et al., J. Appl. Toxicol., 1991, 11, 85, (tox)

• Ishiguro, K. et al., J. Nat. Prod., 1998, 61, 1126-1129, (deriv, isol, pmr, cmr)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 86A, (nmr)

• Dekkers, J. et al., Acta Cryst. C, 1996, 52, 2896-2899, (cryst struct)

• Org. Synth., Coll. Vol., 3, 1955, 465

• Zinkham, W.H. et al., Pediatrics, 1996, 7, 707, (tox)

• Fieser, L.F., J.A.C.S., 1948, 70, 3165, (synth)

• Japan. Pat., 1971, Mitsubishi Edogawa, 71 02 977; CA, 74, 141384, (synth)

• Amorosa, M., Gazz. Chim. Ital., 1954, 84, 602, (synth)

• Japan. Pat., 1971, Mitsubishi Edogawa, 71 02 978; CA, 75, 48769h, (synth)

• Mehendale, A.R. et al., Phytochemistry, 1975, 14, 801, (isol)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1719

Bioactivity

PubChem BioAssay

Properties

Physical Property

Apperance

Yellow prisms

Melting Point

195-196 °C (decomposition)

192-195 °C (dec.)(lit.)

ca 193°C dec.

Solubility

almost insoluble in water

Absorption Wavelength

λmax 452 nm

Pharmacology Properties

Mechanism of Action

Inhibitor of NADPH-cytochrome C reductase

Molecule

ID:75303