Grundinformationen
- CAS
481-39-0- Standard-SMILES
O=C1C=CC(=O)c2c(O)cccc21- InChIKey
KQPYUDDGWXQXHS-UHFFFAOYSA-N- Summenformel
- C10H6O3
- Durchschnittliche Molmasse
- 174,15 g/mol
- Monoisotopische Masse
- 174,03169405
Überblick
Juglone is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities. It has a role as a geroprotector, a herbicide and a reactive oxygen species generator.
Namen und Bezeichner
- Bevorzugter Name
- Juglone
- IUPAC
- 5-hydroxynaphthalene-1,4-dione
- Lokaler Name
- 5-Hydroxy-1,4-naphthochinon
- Englischer Name
- 5-Hydroxy-1,4-naphthalenedione
- Summenformel
- C10H6O3
- Molmasse
- 174.15
Namen und Synonyme
juglone481-39-05-Hydroxy-1,4-naphthalenedione5-Hydroxy-1,4-naphthoquinone5-Hydroxynaphthalene-1,4-dioneRegianinNucin8-Hydroxy-1,4-naphthoquinoneC.I. Natural Brown 7C.I. 75500W6Q80SK9L6DTXSID0031504
Weitere Namen anzeigen
IuglonYuglonJuglaneJugnlon
CHEBI:15794NSC-153189NSC-622948RefChem:792551DTXCID8011504207-567-5JuglonAkhnot
Datenbank-Bezeichner
- CAS
481-39-0- PubChem CID
- 3806
- DTXSID
DTXSID0031504- ChEMBL
CHEMBL43612- ChEBI
CHEBI:15794- UNII
- W6Q80SK9L6
- EC Number
- 207-567-5
- Nikkaji
- J5.777K
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,9
- Polarare Oberfläche (TPSA)
- 54,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 280
Experimentelle und physikochemische Eigenschaften
SpringerMaterials PropertiesChemical shift
LogP
1.92
1.92
Melting Point155 °C
Physical DescriptionSolid
Collision Cross Section
131.2 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
130.8 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 161 · 161-163 °C (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.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- 10 mg/ml; · DMSO: 10 mg/ml; Ethanol: 10 mg/ml
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 79 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information1,4-Naphthalenedione, 5-hydroxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29146990
- RTECS-Nr.
- QJ5775000
- risk_code
- 25-36/37/38
- Toxizität
- LD50 oral in rat: 112mg/kg
- hazard_code
- T
- safety_code
- 22-26-36/37/39-45-37/39-28A
- hazard_class
- 6.1
- packing_group
- III
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Substances that are toxic to cells; they may be involved in immunity or may be contained in venoms. These are distinguished from CYTOSTATIC AGENTS in degree of effect. Some of them are used as CYTOTOXIC ANTIBIOTICS. The mechanism of action of many of these are as ALKYLATING AGENTS or MITOSIS MODULATORS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Substances capable of inhibiting, retarding or arresting the process of fermentation, acidification or other deterioration of foods.
Cellular LocationsCytoplasm
Anwendungen
BeschreibungJuglone (5-hydroxynapthoquinone), is found in the leaves and other parts of walnut, hickory and pecan (1,2). Juglone is synthesized from isochorismic acid (a product of the shikimic acid pathway) and 2-oxo-glutaric acid (3). In plant tissue juglone exists as a free compound or as a glycoside (3,4). Action of a glucosidase releases 1,4,5-trihydroxynapthalene, which is then oxidized to juglone (3,4).
Verwendenantineoplastic, antifungal, antioxidant, Pin 1 inhibitor
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