Grundinformationen
- CAS
83-72-7- Standard-SMILES
O=C1C=C(O)c2ccccc2C1=O- InChIKey
CSFWPUWCSPOLJW-UHFFFAOYSA-N- Summenformel
- C10H6O3
- Durchschnittliche Molmasse
- 174,15 g/mol
- Monoisotopische Masse
- 174,03169405
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- 2-Hydroxy-1,4-naphthoquinone
- IUPAC
- 4-hydroxynaphthalene-1,2-dione
- Lokaler Name
- 2-Hydroxy-1,4-naphthochinon
- Englischer Name
- 2-Hydroxy-1,4-naphoquinone
- Summenformel
- C10H6O3
- Molmasse
- 174.15
Namen und Synonyme
Lawsone83-72-72-Hydroxy-1,4-naphthoquinone2-hydroxynaphthalene-1,4-dione2-Hydroxy-1,4-naphoquinone2-HydroxynaphthoquinoneHennaMehendiHANALawsonNatural Orange 6Mendi
Weitere Namen anzeigen
3-Hydroxy-1,4-naphthoquinone
1,4-Naphthalenedione, 2-hydroxy-4-hydroxynaphthalene-1,2-dione2-Hydroxy-1,4-naphthalenedioneC.I. Natural Orange 61,4-Naphthoquinone, 2-hydroxy-2-Hydroxy-p-naphthoquinoneC.I. 75480NSC 8625
Datenbank-Bezeichner
- CAS
83-72-7- PubChem CID
- 6755
- DTXSID
DTXSID2025428- ChEMBL
CHEMBL240963- ChEBI
CHEBI:44401- UNII
- TLH4A6LV1W
- Nikkaji
- J2.169.330H、J4.642F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,9
- Polarare Oberfläche (TPSA)
- 54,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 291
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsHair dyeing; Skin conditioning; Bulking
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
LogP1.38
Food AdditivesCosmetics -> FDA Regulatory Status of Color Additives
Physikochemische Eigenschaften
- Schmelzpunkt
- 192 · 192-195 °C (dec.)(lit.)
- Siedepunkt
- 265.11 °C · 265.11°C (rough estimate)
- Dichte
- 1.2346 · 1.2346 (rough estimate)
- Brechungsindex
- 1.5036 · 1.5036 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29146990
- RTECS-Nr.
- QL8200000
- risk_code
- 36/37/38-68-36-22
- hazard_code
- Xi,Xn
- safety_code
- 26-37/39-36/37/39-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Verwendung und Herstellung
Use Classification
Environmental transformation -> Pesticide transformation products (metabolite, successor)
Cosmetics -> Hair dyeing; Skin conditioning; Bulking
Anwendungen
HistoryLawsone (CI Natural Orange 6; CI 75420), also known as henna and isojuglone, occurs in the shrub henna (Lawsone alba). In England, the plant is known as Egyptian privet. The dye was extracted from the leaves of the plant, using sodium bicarbonate, and the extracts used to dye protein fibers an orange shade. Henna is probably the oldest cosmetic known. The ancient Egyptians used it as a hair dye and for staining fingernails. It is said that Mohammed dyed his beard with henna. Lawsone has been identified as 2-hydroxy-1,4-naphthoquinone. It has been synthesized by the Thiele acetylation of 1,4-naphthoquinone followed by hydrolysis and oxidation.
Verwendenantifungal, sunscreen, antibacterial, antineoplastic
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
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