ChemicalBook > CAS DataBase List > 5-Hydroxy-1,4-naphthalenedione

5-Hydroxy-1,4-naphthalenedione

Product Name
5-Hydroxy-1,4-naphthalenedione
CAS No.
481-39-0
Chemical Name
5-Hydroxy-1,4-naphthalenedione
Synonyms
JUGLONE;5-HYDROXY-1,4-NAPHTHOQUINONE;5-hydroxynaphthalene-1,4-dione;Nucin;Akhnot;Iuglon;Juglon;Yuglon;Juglane;Jugnlon
CBNumber
CB5447002
Molecular Formula
C10H6O3
Formula Weight
174.15
MOL File
481-39-0.mol
More
Less

5-Hydroxy-1,4-naphthalenedione Property

Melting point:
161-163 °C (lit.)
Boiling point:
265.11°C (rough estimate)
Density 
1.2346 (rough estimate)
refractive index 
1.5036 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
DMSO: 10 mg/ml; Ethanol: 10 mg/ml
pka
6.59±0.20(Predicted)
form 
Crystalline Powder
color 
Orange to brown
Water Solubility 
SOLUBLE IN HOT WATER
Sensitive 
Light Sensitive
Merck 
14,5269
BRN 
1909764
LogP
1.920
CAS DataBase Reference
481-39-0(CAS DataBase Reference)
NIST Chemistry Reference
1,4-Naphthalenedione, 5-hydroxy-(481-39-0)
EPA Substance Registry System
1,4-Naphthalenedione, 5-hydroxy- (481-39-0)
More
Less

Safety

Hazard Codes 
T
Risk Statements 
25-36/37/38
Safety Statements 
22-26-36/37/39-45-37/39-28A
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
QJ5775000
HazardClass 
6.1
PackingGroup 
III
HS Code 
29146990
Toxicity
LD50 oral in rat: 112mg/kg
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H47003
Product name
5-Hydroxy-1,4-naphthoquinone
Purity
97%
Packaging
1g
Price
$74.8
Updated
2024/03/01
Sigma-Aldrich
Product number
420120
Product name
Juglone
Packaging
250mg
Price
$82.8
Updated
2024/03/01
TCI Chemical
Product number
H0286
Product name
5-Hydroxy-1,4-naphthoquinone
Purity
>97.0%(GC)
Packaging
1g
Price
$100
Updated
2024/03/01
TCI Chemical
Product number
H0286
Product name
5-Hydroxy-1,4-naphthoquinone
Purity
>97.0%(GC)
Packaging
5g
Price
$382
Updated
2024/03/01
Alfa Aesar
Product number
H28343
Product name
5-Hydroxy-1,4-naphthoquinone, 99%
Packaging
1g
Price
$48.65
Updated
2024/03/01
More
Less

5-Hydroxy-1,4-naphthalenedione Chemical Properties,Usage,Production

Description

Juglone (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).

Description

Juglone is a natural naphthoquinone found in the black walnut (J. nigra) and other plants in the Juglandaceae family. It has allelopathic actions, suppressing growth, photosynthesis, and respiration in plants and other organisms, although some bacteria can metabolize juglone. Juglone also irreversibly inhibits peptidyl-prolyl cis/trans isomerases of the parvulin family, including human Pin1, yeast Ess1/Ptf1, and E. coli parvulin (Ki = 55.9 nM). Juglone also blocks transcription by RNA polymerases I, II, and III (IC50s = 2-7 μM) and attenuates kidney fibrosis in rats treated with unilateral ureteral obstruction, both through Pin1-independent mechanisms.

Chemical Properties

Orange to brown crystalline powder

Uses

antineoplastic, antifungal, antioxidant, Pin 1 inhibitor

Uses

Juglone (CI Natural Brown 7; CI 75500) was isolated from the husks of walnuts in 1856. Juglone occurs in walnuts as a glycoside of its reduced form, 1,4,5-trihydroxynaphthalene. Its structure is (3) Juglone is most readily synthesized by Bernthsen s method. It is a fungicide and as such finds use in the treatment of skin diseases. Its toxic properties have been made use of in catching fish. Juglone has been used to detect very small amount of nickel salts since it gives a deep violet color with such salts.

Uses

5-Hydroxy-1,4-naphthoquinone is used as a natural dye in cloth, fabrics, wool and ink. It is a coloring agent for food and cosmetics. It is involved in the synthesis of poly(hydroxyl-1,4-naphthoquinone) stabilized gold nanoparticles (AuNQ NPs), which is used for nonenzymatic electrochemical detection of glucose.

Definition

ChEBI: A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 5160, 1983 DOI: 10.1021/jo00174a003
Synthetic Communications, 15, p. 1177, 1985 DOI: 10.1080/00397918508077262
Synthesis, p. 644, 1977 DOI: 10.1055/s-1977-24517

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Pharmacology

Juglone is probably best known as the allelochemical produced by black walnut. The glucoside of juglone leaches from the leaves and branches of black walnut, where it is converted to juglone in the soil. Juglone is toxic to certain plant species and also inhibits the germination of seeds (4). Thus its allelopathic activity may be the result of both phytotoxicity and a germination inhibitor. Juglone is also antifungal (1,5) and attempts to correlate its presence with disease resistance in pecan, black walnut, and hickory to several fungal pathogens have been reported (1,2,5,6). Positive correlations have been found for resistance of juvenile leaves of black walnut to anthracnose caused by Gnomia leptostyla (5) and of some Carya species to the scab pathogen Cladosporium carygenum (2). In some pecans (C. illinoensis), juglone may act as both a preformed and an induced defense factor because concentrations of juglone increase after infection by fungi (2). No correlation between juglone glycoside concentration in pecan leaves and resistance pecan to C. carygenum has been reported (6). Free juglone and the glycosides increase after infection, but these increases could not be correlated with scab resistance (6).

Purification Methods

Crystallise Juglone from *benzene/pet ether or pet ether. [Beilstein 8 III 2558, 8 IV 2368.]

5-Hydroxy-1,4-naphthalenedione Preparation Products And Raw materials

Raw materials

N-Hydroxyphthalimide

Preparation Products

More
Less

5-Hydroxy-1,4-naphthalenedione Suppliers

Americas 1 Australia 1 Belgium 1 China 209 Europe 1 France 1 Germany 3 Hungary 1 India 5 Japan 3 Poland 2 Slovakia 1 Sweden 1 Switzerland 4 United Kingdom 8 United States 31 USA 1 Global 274
Chongqing Xingcan Pharmaceutical Technology Co., Ltd.
Tel
15523000485
Email
xingcanyaoye@sina.com
Country
China
ProdList
1686
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
9371
Advantage
55
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
Advantage
61
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
Chemsky（shanghai）International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12984
Advantage
57
Record Tech (Shanghai) Co., LTD
Tel
13761627472
Fax
86-21-64965863
Email
183009664@qq.com
Country
China
ProdList
637
Advantage
62
China Langchem Inc.
Tel
0086-21-58956006
Fax
0086-21-58956100
Country
China
ProdList
7811
Advantage
57
RYSS TECH LTD
Tel
400-188-0725 +86 21 34310725 13611771617
Fax
+86 21 34311076
Country
China
ProdList
2002
Advantage
57
ShangHai YuanYe Biotechnology Co., Ltd.
Tel
021-61312847 13636370518
Fax
021-55068248
Email
shyysw007@163.com
Country
China
ProdList
4940
Advantage
60
Thermo Fisher Scientific
Tel
800-810-5118
Fax
+86-10-84193589
Email
cnchemical@thermofisher.com
Country
China
ProdList
17770
Advantage
75
Beijing innoChem Science & Technology Co.,Ltd.
Tel
400-810-7969 010-59572699
Fax
010-59572688
Email
ningzi.li@inno-chem.com.cn
Country
China
ProdList
6134
Advantage
55
Shanghai Topbiochem Technology Co., Ltd
Tel
021-58170097
Email
info@topbiochem.com
Country
China
ProdList
9478
Advantage
58
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
ProdList
9891
Advantage
58
Jiangsu Aikon Biopharmaceutical R&D co.,Ltd.
Tel
025-66099280 17798518460
Fax
(1)02557626880
Email
cfzhang@aikonchem.com
Country
China
ProdList
19915
Advantage
55
9ding chemical ( Shanghai) Limited
Tel
4009209199
Fax
86-021-52271987
Email
sales@9dingchem.com
Country
China
ProdList
22514
Advantage
55
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-6206333 18021050169
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
25003
Advantage
65
Shanghai Tauto Biotech Co., Ltd.
Tel
021-51320588
Fax
0086-21-51320502
Email
tauto@tautobiotech.com
Country
China
ProdList
3989
Advantage
66
TargetMol Chemicals Inc.
Tel
021-021-33632979 15002134094
Fax
021-33632979
Email
marketing@targetmol.com
Country
China
ProdList
7783
Advantage
58
Shanghai TaoSu Biochemical Technology Co., Ltd.
Tel
021-33632979
Fax
021-34692979
Email
info@tsbiochem.com
Country
China
ProdList
8065
Advantage
58
Chengdu Herbpurify Co.Ltd.
Tel
18302802153 18981717076
Fax
086-28-85377358
Email
2355253619@qq.com
Country
China
ProdList
1104
Advantage
58
Shanghai JONLN Reagent Co., Ltd.
Tel
400-0066400 13621662912
Fax
021-55660885
Email
422131432@qq.com
Country
China
ProdList
9978
Advantage
55
Bide Pharmatech Ltd.
Tel
400-164-7117 13681763483
Fax
+86-21-61629029
Email
product02@bidepharm.com
Country
China
ProdList
41462
Advantage
60
Sichuan Wei Keqi Biological Technology Co., Ltd.
Tel
028-81700200 18116577057
Fax
028-81705658
Email
3003855609@qq.com
Country
China
ProdList
7787
Advantage
56
Wuxi Zhongkun Biochemical Technology Co., Ltd.
Tel
0510-85629785 18013409632
Fax
051085625359
Email
sales@reading-chemicals.com
Country
China
ProdList
15178
Advantage
58
Finetech Industry Limited
Tel
027-87465837 19945049750
Fax
027-8777-2287
Email
sales@finetechnology-ind.com
Country
China
ProdList
9648
Advantage
58
Shanghai Aspire Biological Technology Co., Ltd.
Tel
021-61317773
Fax
021-61486878
Email
sales@aspirebio.com
Country
China
ProdList
2880
Advantage
58
Shanghai Xingui Biotechnology Co., Ltd.
Tel
17501653713
Email
xingui2022@126.com
Country
China
ProdList
10009
Advantage
58
Shanghai Macklin Biochemical Co.,Ltd.
Tel
15221275939 15221275939
Fax
021-50706099
Email
shenlinxing@macklin.cn
Country
China
ProdList
16166
Advantage
55
Hangzhou J&H Chemical Co., Ltd.
Tel
0571-+86-571-87396432
Fax
0571-87396431
Email
sales@jhechem.com
Country
China
ProdList
11662
Advantage
59
Shanghai Yongye Biotechnology Co., Ltd.
Tel
86-021-61559134 15921386130
Fax
021-55068248
Email
3423497944@qq.com
Country
China
ProdList
8144
Advantage
55
Chizhou Kailong Import and Export Trade Co., Ltd.
Tel
Fax
-
Email
xg01_gj@163.com
Country
China
ProdList
9484
Advantage
50
Changsha Jing Kang New Material Technology Co., Ltd.
Tel
0731-85118349 18874718518
Fax
0731-85118349
Email
ma_haihong@sina.com
Country
China
ProdList
1595
Advantage
50
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51456
Advantage
80
Wuhan ChemFaces Biochemical Co., Ltd.
Tel
18607101326 15172504745
Fax
+86-27-84254680
Email
aileen@chemfaces.com
Country
China
ProdList
6905
Advantage
55
Shanghai Synchem Pharma Co., ltd
Tel
21-619849051-1 18521059765
Email
synchempharma@aliyun.com
Country
China
ProdList
6464
Advantage
55
Henan CoreyChem Co., Ltd
Tel
0371-86658258
Fax
0371-60996044
Email
info@coreychem.com
Country
China
ProdList
10453
Advantage
58
Shanghai Qiao Chemical Science Co., Ltd
Tel
021-58892003
Email
info@qiaochem.com
Country
China
ProdList
5904
Advantage
65
Shandong Xiya Chemical Co., Ltd.
Tel
4009903999 13395398332
Fax
0539-6365991
Email
sales@xiyashiji.com
Country
China
ProdList
20806
Advantage
60
Chengdu Dianchun Technology Co., Ltd
Tel
400-1166-196 18502815961
Fax
QQ：800101999
Email
cdhxsj@163.com
Country
China
ProdList
14603
Advantage
60
Shanghai ChengShao Biological Technology Co., Ltd.
Tel
021-61847300 13341622919
Fax
021-61847300
Email
shcss01@163.com
Country
China
ProdList
4808
Advantage
58
Beijing Solarbio Science & Tecnology Co., Ltd.
Tel
010-50973130 4009686088
Email
3193328036@qq.com
Country
China
ProdList
29764
Advantage
68
Amadis Chemical Company Limited
Tel
571-89925085
Fax
0086-571-89925065
Email
sales@amadischem.com
Country
China
ProdList
131957
Advantage
58
Beijing Jin Ming Biotechnology Co., Ltd.
Tel
010-60605840 18892239720
Fax
010-60605840
Email
psaitong@jm-bio.com
Country
China
ProdList
12306
Advantage
58
Shanghai Yihe Biological Technology Co., Ltd.
Tel
17721395025
Fax
021-68882955
Email
2423903095@qq.com
Country
China
ProdList
4108
Advantage
58
More
Less

View Lastest Price from 5-Hydroxy-1,4-naphthalenedione manufacturers

Zibo Hangyu Biotechnology Development Co., Ltd
Product
5-Hydroxy-1,4-naphthalenedione 481-39-0
Price
US $55.00-550.00/kg
Min. Order
10kg
Purity
0.99
Supply Ability
20tons
Release date
2023-11-10
Career Henan Chemical Co
Product
5-Hydroxy-1,4-naphthalenedione 481-39-0
Price
US $2.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100g , 1kg, 5kg , 50kg
Release date
2020-01-07

481-39-0, 5-Hydroxy-1,4-naphthalenedioneRelated Search:

Menadione sodium bisulfite Chrysin 4-Hydroxybenzoic acid Hydroxy silicone oil 4-Cyanophenol Ethylparaben Glycolic acid CHLOROPHOSPHONAZO III 4-Methoxyphenol 1,4-Naphthoquinone HYDROXYAPATITE TYPE I 4-Hydroxybenzaldehyde Methylparaben 2-Hydroxy-1,4-naphthalenedione Camptothecin Series--10-hydroxycamptothecin ACETYLSHIKONIN Shikalkin ISOVALERYLSHIKONIN

  • 5-hydroxy-4-naphthalenedione
  • 5-hydroxy-4-naphthoquinone
  • 5-Hydroxynaphthoquinone
  • 8-Hydroxy-1,4-naphthalenedione
  • 8-HYDROXY-1,4-NAPHTHOQUINONE
  • 5-HYDROXY-1,4-NAPHTHALENEDIONE
  • 5-HYDROXY-1,4-NAPHTHLENEDIONE
  • 5-HYDROXY-1,4-NAPHTHOQUINONE
  • 5-HYDROXY-P-NAPHTHOQUINONE
  • JUGLONE
  • 5-hydrocy-1,4-naphthoquinone
  • Natural Brown 7.
  • JUGLONE(P)
  • JUGLONE, CRYSTALLIZED
  • 1,4-Dihydro-1,4-dioxo-5-hydroxynaphthalene
  • 5-Hydroxy-p-naphthoquinone,97%
  • 5-hydroxy-1,4-naphtoquinone
  • 5-Hydroxy-1,4-naphthoquinone ,96%
  • 5-Hydroxy-1,4-naphthoquinone,Juglone
  • 5-hydroxy-1,4-dihydronaphthalene-1,4-dione
  • 5-Hydroxy-p-naphthoquinone, 97% 1GR
  • 5-Hydroxy-p-naphthoquinone, 97% 5GR
  • Juglone(NSC 34266
  • NSC 622948)
  • 5-hydroxynaphthalene-1,4-dione
  • 5-Hydroxy-1,4-naphthoquinone 97%
  • Juglone - CAS 481-39-0 - Calbiochem
  • RARECHEM BW GC 0025
  • WALNUT EXTRACT, WATER SOLUBLE
  • 1,4-Naphthalenedione,5-hydroxy-
  • 1,4-Naphthoquinone, 5-hydroxy-
  • 1,4-Naphthoquinone, 8-hydroxy-
  • 4-Naphthalenedione,5-hydroxy-1
  • 5-Hydroxy-1,4-naftochinon
  • Juglone, 98%, from Juglans mandshurica Maxim.
  • 8-hydroxy-4-naphthoquinone
  • Akhnot
  • C.I. 75500
  • C.I. Natural Brown 7
  • c.i.75500
  • c.i.naturalbrown7
  • -Hydroxy-1,4-naphthalenedione
  • Iuglon
  • Juglane
  • Juglon
  • Jugnlon
  • NCI 2323
  • Nucin
  • Regianin
  • Yuglon
  • 5-Hydroxy-1,4-naphthoquinone&gt
  • 5-Hydroxy-1,4-naphthoquinone,99%
  • 5-Hydroxy-1,4-naphthochinon
  • 5-Hydroxy-1,4-naphthalenedione cas no.481-39-0
  • Walnut quinone
  • 5-Hydroxy-1,4-naphthalenedione(Juglone)
  • Glycerol Impurity 125
  • Juglone-RM