juglone
1,4-naphthoquinone, 5-hydroxy- (8CI)
Identification
| Name | juglone |
| IUPAC | 5-hydroxynaphthalene-1,4-dione |
| CAS Number | 481-39-0 |
| EINECS | 207-567-5 |
| FDA UNII | W6Q80SK9L6 |
| Molecular Formula | C10 H6 O3 |
| Molecular Weight | 174.15542000 |
| MDL Number | MFCD00001684 |
| Nikkaji Number | J5.777K |
| Beilstein | 1909764 |
| XlogP3 | 1.90 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 155.00 °C. @ 760.00 mm Hg |
| Boiling Point | 385.80 °C. @ 760.00 mm Hg (est) |
| Flash Point | 394.00 °F. TCC ( 201.30 °C. ) (est) |
| logP (o/w) | 1.920 |
| Soluble in | water, 5121 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intravenous-dog LDLo 10 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for juglone usage levels up to | not for fragrance use. |
| Recommendation for juglone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
akhnot
5-
hydroxy-1,4-naftochinon
5-
hydroxy-1,4-naphthoquinone
5-
hydroxy-1,4-naphthosemiquinone
5-
hydroxynaphthalene-1,4-dione
5-
hydroxynaphthoquinone
juglon
1,4-
naphthoquinone, 5-hydroxy-
1,4-
naphthoquinone, 5-hydroxy- (8CI)
nucin
regianin
yuglon
PubMed:
Essential oil alloaromadendrene from mixed-type Cinnamomum osmophloeum leaves prolongs the lifespan in Caenorhabditis elegans.
PubMed:
Antioxidant Activity and Delayed Aging Effects of Hot Water Extract from Chamaecyparis obtusa var. formosana Leaves.
PubMed:
Seasonal variation of the main individual phenolics and juglone in walnut (Juglans regia) leaves.
PubMed:
Antimutagenic and antioxidant properties of plumbagin and other naphthoquinones.
PubMed:
Potent and specific bactericidal effect of juglone (5-hydroxy-1,4-naphthoquinone) on the fire blight pathogen Erwinia amylovora.
PubMed:
HPLC determination of phenolic acids, flavonoids and juglone in walnut leaves.
PubMed:
Monascus-fermented dioscorea enhances oxidative stress resistance via DAF-16/FOXO in Caenorhabditis elegans.
PubMed:
In vivo antioxidant activities of essential oils and their constituents from leaves of the Taiwanese Cinnamomum osmophloeum.
PubMed:
Juglone, from Juglans mandshruica Maxim, inhibits growth and induces apoptosis in human leukemia cell HL-60 through a reactive oxygen species-dependent mechanism.
PubMed:
Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone.
PubMed:
A label-free electrochemical immunosensor for direct, signal-on and sensitive pesticide detection.
PubMed:
Effects of O-methylated metabolites of quercetin on oxidative stress, thermotolerance, lifespan and bioavailability on Caenorhabditis elegans.
PubMed:
The virulence factor PEB4 (Cj0596) and the periplasmic protein Cj1289 are two structurally related SurA-like chaperones in the human pathogen Campylobacter jejuni.
PubMed:
Peptidyl-prolyl cis/trans isomerase NIMA-interacting 1 associates with insulin receptor substrate-1 and enhances insulin actions and adipogenesis.
PubMed:
Allyl isothiocyanate that induces GST and UGT expression confers oxidative stress resistance on C. elegans, as demonstrated by nematode biosensor.
PubMed:
Simultaneous detection of pro- and antioxidative effects in the variants of the deoxyribose degradation assay.
PubMed:
Caenorhabditis elegans lifespan extension caused by treatment with an orally active ROS-generator is dependent on DAF-16 and SIR-2.1.
PubMed:
Structure-activity relationships of anthraquinones on the suppression of DNA-binding activity of the aryl hydrocarbon receptor induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.
PubMed:
Feeding a ROS-generator to Caenorhabditis elegans leads to increased expression of small heat shock protein HSP-16.2 and hormesis.
PubMed:
Phenolic acids, syringaldehyde, and juglone in fruits of different cultivars of Juglans regia L.
PubMed:
Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria.
PubMed:
Proteome-level differences between auxinic-herbicide-susceptible and -resistant wild mustard (Sinapis arvensis L.).
PubMed:
Impact of dietary allelochemicals on gypsy moth (Lymantria dispar) caterpillars: importance of midgut alkalinity.
PubMed:
Comparison of the antioxidant activities of extra virgin olive oils.
PubMed:
Functional conservation of phosphorylation-specific prolyl isomerases in plants.
PubMed:
Regulation of aflatoxin production by naphthoquinones of walnut (Juglans regia).
PubMed:
Volatile components of green walnut husks.
PubMed:
Namibian chewing stick, Diospyros lycioides, contains antibacterial compounds against oral pathogens.
PubMed:
Pro- and antioxidative properties of cortical tissue preparations from human brain exhibiting NMDA-receptor characteristics.
PubMed:
Differential toxicity of juglone (5-hydroxy-1,4-naphthoquinone) and related naphthoquinones to saturniid moths.
PubMed:
Black walnut toxicosis in ten horses.
PubMed:
Chemical ecology of the luna moth : Effects of host plant on detoxification enzyme activity.
PubMed:
[Hygienic characteristics of a naphthoquinone preservative (juglone)].