1,4-naphthoquinone, 5-hydroxy- (8CI)

CAS: 481-39-0 C10 H6 O3 MW: 174.15542000

Identification

Namejuglone
IUPAC5-hydroxynaphthalene-1,4-dione
CAS Number481-39-0
EINECS207-567-5
FDA UNIIW6Q80SK9L6
Molecular FormulaC10 H6 O3
Molecular Weight174.15542000
MDL NumberMFCD00001684
Nikkaji NumberJ5.777K
Beilstein1909764
XlogP31.90 (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 SDSView
Oral/Parenteral Toxicityintravenous-dog LDLo 10 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for juglone usage levels up tonot for fragrance use.
Recommendation for juglone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

butternut bark juglans mandshurica root shell pecan seed walnut black walnut fruit walnut black walnut hull husk walnut black walnut leaf walnut black walnut nut walnut black walnut pericarp walnut black walnut plant walnut english walnut leaf walnut english walnut nut walnut english walnut testa

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)].