Juglone
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 596314

CAS#: 481-39-0

Description: Juglone is a highly selective cell-permeable, irreversible inhibitor of PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family).


Chemical Structure

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Juglone
CAS# 481-39-0

Theoretical Analysis

MedKoo Cat#: 596314
Name: Juglone
CAS#: 481-39-0
Chemical Formula: C10H6O3
Exact Mass: 174.03
Molecular Weight: 174.150
Elemental Analysis: C, 68.97; H, 3.47; O, 27.56

Price and Availability

Size Price Availability Quantity
1g USD 250 2 Weeks
5g USD 550 2 Weeks
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Synonym: Juglone; Akhnot; NSC 153189; NSC-153189; NSC153189; Regianin; NSC 622948; NSC-622948; NSC622948;

IUPAC/Chemical Name: 5-hydroxynaphthalene-1,4-dione

InChi Key: KQPYUDDGWXQXHS-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H

SMILES Code: O=C(C1=C2C=CC=C1O)C=CC2=O

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 174.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Salta M, Dennington SP, Wharton JA. Biofilm Inhibition by Novel Natural Product- and Biocide-Containing Coatings Using High-Throughput Screening. Int J Mol Sci. 2018 May 10;19(5). pii: E1434. doi: 10.3390/ijms19051434. PubMed PMID: 29748514.

2: Yang Q, Yao QS, Kuang Y, Zhang YZ, Feng LL, Zhang L, Guo L, Xie ZP, Zhang SM. Antimicrobial and cytotoxic juglones from the immature exocarps of Juglans mandshurica. Nat Prod Res. 2018 May 4:1-7. doi: 10.1080/14786419.2018.1468326. [Epub ahead of print] PubMed PMID: 29726709.

3: Wang P, Gao C, Wang W, Yao LP, Zhang J, Zhang SD, Li J, Fang SH, Fu YJ. Juglone induces apoptosis and autophagy via modulation of mitogen-activated protein kinase pathways in human hepatocellular carcinoma cells. Food Chem Toxicol. 2018 Jun;116(Pt B):40-50. doi: 10.1016/j.fct.2018.04.004. Epub 2018 Apr 6. PubMed PMID: 29627502.

4: Hönig M, Plíhalová L, Spíchal L, Grúz J, Kadlecová A, Voller J, Svobodová AR, Vostálová J, Ulrichová J, Doležal K, Strnad M. New cytokinin derivatives possess UVA and UVB photoprotective effect on human skin cells and prevent oxidative stress. Eur J Med Chem. 2018 Apr 25;150:946-957. doi: 10.1016/j.ejmech.2018.03.043. Epub 2018 Mar 21. PubMed PMID: 29604584.

5: Pektas MB, Turan O, Ozturk Bingol G, Sumlu E, Sadi G, Akar F. High-glucose causes vascular dysfunction through Akt/eNOS pathway: Reciprocal modulation by juglone and resveratrol. Can J Physiol Pharmacol. 2018 Mar 10. doi: 10.1139/cjpp-2017-0639. [Epub ahead of print] PubMed PMID: 29527953.

6: Wang S, Liao L, Wang M, Zhou H, Huang Y, Wang Z, Chen D, Ji D, Xia X, Wang Y, Liu F, Huang J, Xiong K. Pin1 Promotes Regulated Necrosis Induced by Glutamate in Rat Retinal Neurons via CAST/Calpain2 Pathway. Front Cell Neurosci. 2018 Jan 22;11:425. doi: 10.3389/fncel.2017.00425. eCollection 2017. PubMed PMID: 29403356; PubMed Central PMCID: PMC5786546.

7: Shang XF, Liu YQ, Guo X, Miao XL, Chen C, Zhang JX, Xu XS, Yang GZ, Yang CJ, Li JC, Zhang XS. Application of Sustainable Natural Resources in Agriculture: Acaricidal and Enzyme Inhibitory Activities of Naphthoquinones and Their Analogs against Psoroptes cuniculi. Sci Rep. 2018 Jan 25;8(1):1609. doi: 10.1038/s41598-018-19964-0. PubMed PMID: 29371639; PubMed Central PMCID: PMC5785474.

8: Wu X, Li M, Chen SQ, Li S, Guo F. Pin1 facilitates isoproterenol induced cardiac fibrosis and collagen deposition by promoting oxidative stress and activating the MEK1/2 ERK1/2 signal transduction pathway in rats. Int J Mol Med. 2018 Mar;41(3):1573-1583. doi: 10.3892/ijmm.2017.3354. Epub 2017 Dec 29. PubMed PMID: 29286102; PubMed Central PMCID: PMC5819929.

9: Senchuk MM, Dues DJ, Van Raamsdonk JM. Measuring Oxidative Stress in Caenorhabditis elegans: Paraquat and Juglone Sensitivity Assays. Bio Protoc. 2017 Jan 5;7(1). pii: e2086. doi: 10.21769/BioProtoc.2086. PubMed PMID: 29276721; PubMed Central PMCID: PMC5739066.

10: Sun GD, Huo JH, Xie RJ, Wang WM. [Dynamic variation of components in exocarp of Juglans mandshurica with browning based on UPLC-Q-TOF/MS]. Zhongguo Zhong Yao Za Zhi. 2017 Aug;42(16):3112-3120. doi: 10.19540/j.cnki.cjcmm.20170614.003. Chinese. PubMed PMID: 29171229.

11: Sobeh M, Mahmoud MF, Abdelfattah MAO, Cheng H, El-Shazly AM, Wink M. A proanthocyanidin-rich extract from Cassia abbreviata exhibits antioxidant and hepatoprotective activities in vivo. J Ethnopharmacol. 2018 Mar 1;213:38-47. doi: 10.1016/j.jep.2017.11.007. Epub 2017 Nov 7. PubMed PMID: 29126990.

12: Liu X, Chen Y, Zhang Y, Du J, Lv Y, Mo S, Liu Y, Ding F, Wu J, Li J. Juglone potentiates TRAIL induced apoptosis in human melanoma cells via activating the ROS p38 p53 pathway. Mol Med Rep. 2017 Dec;16(6):9645-9651. doi: 10.3892/mmr.2017.7806. Epub 2017 Oct 17. PubMed PMID: 29039537.

13: Durán AG, Chinchilla N, Molinillo JM, Macías FA. Influence of lipophilicity in O-acyl and O-alkyl derivatives of juglone and lawsone: a structure-activity relationship study in the search for natural herbicide models. Pest Manag Sci. 2018 Mar;74(3):682-694. doi: 10.1002/ps.4764. Epub 2017 Nov 27. PubMed PMID: 29024464.

14: Lv L, Ye M, Duan R, Yuan K, Chen J, Liang W, Zhou Z, Zhang L. Downregulation of Pin1 in human atherosclerosis and its association with vascular smooth muscle cell senescence. J Vasc Surg. 2017 Oct 3. pii: S0741-5214(17)32213-9. doi: 10.1016/j.jvs.2017.09.006. [Epub ahead of print] PubMed PMID: 28986099.

15: Arasoglu T, Derman S, Mansuroglu B, Yelkenci G, Kocyigit B, Gumus B, Acar T, Kocacaliskan I. Synthesis, characterization and antibacterial activity of juglone encapsulated PLGA nanoparticles. J Appl Microbiol. 2017 Dec;123(6):1407-1419. doi: 10.1111/jam.13601. Epub 2017 Nov 2. PubMed PMID: 28980369.

16: Ettelaie C, Collier MEW, Featherby S, Greenman J, Maraveyas A. Peptidyl-prolyl isomerase 1 (Pin1) preserves the phosphorylation state of tissue factor and prolongs its release within microvesicles. Biochim Biophys Acta. 2018 Jan;1865(1):12-24. doi: 10.1016/j.bbamcr.2017.09.016. Epub 2017 Sep 28. PubMed PMID: 28962834.

17: Nowicka B, Żądło A, Pluciński B, Kruk J, Kuczyńska P. The oxidative stress in allelopathy: Participation of prenyllipid antioxidants in the response to juglone in Chlamydomonas reinhardtii. Phytochemistry. 2017 Dec;144:171-179. doi: 10.1016/j.phytochem.2017.09.012. Epub 2017 Sep 22. PubMed PMID: 28942064.

18: Hu W, Du W, Bai S, Lv S, Chen G. Phenoloxidase, an effective bioactivity target for botanical insecticide screening from green walnut husks. Nat Prod Res. 2017 Sep 20:1-4. doi: 10.1080/14786419.2017.1380015. [Epub ahead of print] PubMed PMID: 28931324.

19: Zhi D, Wang D, Yang W, Duan Z, Zhu S, Dong J, Wang N, Wang N, Fei D, Zhang Z, Wang X, Wang M, Li H. Dianxianning improved amyloid β-induced pathological characteristics partially through DAF-2/DAF-16 insulin like pathway in transgenic C. elegans. Sci Rep. 2017 Sep 12;7(1):11408. doi: 10.1038/s41598-017-11628-9. PubMed PMID: 28900141; PubMed Central PMCID: PMC5595840.

20: Schwindl S, Kraus B, Heilmann J. Phytochemical study of Juglans regia L. leaves. Phytochemistry. 2017 Dec;144:58-70. doi: 10.1016/j.phytochem.2017.08.012. Epub 2017 Sep 8. PubMed PMID: 28888783.